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Volume 35, Issue 8
Displaying 1-50 of 66 articles from this issue
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HIDEO KUBODERA, HIDEAKI UMEYAMA1987 Volume 35 Issue 8 Pages 3087-3104
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSTo describe electrostatic potentials, new sets of fractional point charges are presented for medium-sized neurotransmitters; dopamine, gamma-aminobutyric acid (GABA) and acetylcholine. The charge set consists of the original STO-3G Mulliken net atomic charges and new additional charges. The new additional charge sets were determined to correct electrostatic potential (ESP) values on the van der Waals molecular surface based upon Mulliken net atomic charges from STO-3G calculation.
The additional charge sets were obtained first for a variety of small molecules (water, ammonia, methane, ethane, benzene, formic acid anion, acetic acid, methylammonium, trimethylammonium, tetramethylammonium, and methyl acetate). Lone-pair regions of oxygen and nitrogen atoms showed remarkable improvement. The new additional charge sets were transferred as they were to Mulliken net atomic charge sets of the larger neurotransmitter molecules.
The present method is useful for large molecules of the types often considered in the fields of biological and pharmaceutical sciences; the approach gives approximately the same qualities to classical fractional point charge ESP's as can be obtained with complex ab initio calculations.View full abstractDownload PDF (2541K) -
TOSHIYUKI ESAKI1987 Volume 35 Issue 8 Pages 3105-3111
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe antibacterial potencies of phenols were analyzed by using empirical and theoretical quantitative structure-activity relationships equations which take account of the influence of ionization. The lowest unoccupied molecular orbital energy term of the neutral form related to the drug-receptor interaction process always had a negative coefficient and was highly significant, while the hydrophobic term related to the drug transport process also made a significant contribution to the potency. The equilibrium model-based equation with one aqueous, one nonaqueous, and one receptor compartments gave the best result in analysis of the antibacterial assay data at pH 7.4. However, in general, the highest correlation was obtained from the neutral form-based Hansch equation, and the distribution coefficient-based Hansch equation offered the most helpful information for the design of drugs with selective antibacterial activity. The mechanism of antibacterial action of phenols is also discussed from the frontier electronic standpoint, and a drug receptor interaction model of the charge-transfer type is proposed.View full abstractDownload PDF (1115K) -
HIROSHI SUEMUNE, YUKAKO MIZUHARA, HIROYUKI AKITA, TAKESHI OISHI, KIYOS ...1987 Volume 35 Issue 8 Pages 3112-3118
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSAsymmetric synthesis of platelet-activating factor (PAF) and its enantiomer by using biocatalysts was studied. Microbial reduction of the pro-chiral α-ketoester (3) afforded (+) -4 (> 99% ee), which could be converted to (+) -and (-) -batyl alcohol (12), a key synthetic intermediate for PAF. Compound (-) -4 (96% ee), with the requisite configuration for the synthesis of natural PAF, could also be obtained by enzyme-catalyzed enantioselective hydrolysis of (±) -15.View full abstractDownload PDF (1160K) -
HIROSHI YAMANAKA, TAKAO SAKAMOTO, SUMIKO NISHIMURA, MATAICHI SAGI1987 Volume 35 Issue 8 Pages 3119-3126
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe site-selectivity in the modified Reissert-Henze reaction of 5-substituted, and 4, 5-disubstituted pyrimidine 1-oxides with trimethylsilyl cyanide was examined. The reaction of 5-substituted 4-methoxypyrimidine 1-oxides with trimethylsilyl cyanide gave exclusively 2-pyrimidine-carbonitriles in good yields without exception. On the other hand, the other 5-substituted and 4, 5-disubstituted pyrimidine 1-oxides gave mainly 6-pyrimidinecarbonitriles.View full abstractDownload PDF (1140K) -
GEN-ICHIRO NONAKA, MAKOTO ISHIMATSU, TAKASHI TANAKA, ITSUO NISHIOKA, M ...1987 Volume 35 Issue 8 Pages 3127-3131
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSTogether with 6-O-and 2, 3, 4, 6-tetra-O-galloylglucoses, two unusual gallotannins possessing an α-glucopyranose core have been isolated from the rhizomes of Nuphar japonicum DC. (Nymphaeaceae), and their structures have been established as 1, 2, 4-tri-O-galloyl-α-D-glucose (3) and 1, 2, 3, 4, 6-penta-O-galloyl-α-D-glucose (6) on the basis of chemical and spectroscopic evidence.View full abstractDownload PDF (781K) -
TAKASHI YAMAGISHI, MAKOTO NISHIZAWA, MITSUHIKO IKURA, KUNIO HIKICHI, G ...1987 Volume 35 Issue 8 Pages 3132-3138
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSFour new laxative constituents, rheinosides A, B, C and D, were isolated from commercial rhubarb (Rhei Rhizoma). On the basis of high-resolution nuclear magnetic resonance spectral data and chemical correlation with rhein, the structures were characterized as stereoisomers of 8-O-β-D-glucosyl-10-hydroxy-10-C-β-D-glucosyl rhein-9-anthrone (rheinosides A and B), and 8-O-β-D-glucosyl-10-C-β-D-glucosyl rhein-9-anthrone (rheinosides C and D).View full abstractDownload PDF (1099K) -
HIROKI TAKAHATA, ENG-CHI WANG, TOMOKO NAKAJIMA, TAKAO YAMAZAKI1987 Volume 35 Issue 8 Pages 3139-3145
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSKetene-S, N-acetals reacted with isothiocyanates to give β-aminothiocarbonyl-α-methylthioen-amines, which were transformed into enaminonitriles by carbon-carbon bond formation with malononitriles. Treatment of the enaminonitriles with base afforded pyridine-2-thiones. In addition, bis-lithio-ketene-S, N-acetals, generated from the enaminonitriles and n-BuLi, reacted with alkyl halides to give 3-alkylpyridine-2-thiones.View full abstractDownload PDF (801K) -
MASANORI SOMEI, YOSHIHIRO SAIDA, TETSUO FUNAMOTO, TOSHIHARU OHTA1987 Volume 35 Issue 8 Pages 3146-3154
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA simple four-step synthetic method for 7-iodo-, 7-bromo-and 7-chloroindole was established with high overall yield starting from 2, 3-dihydroindole. Several 7-substituted indoles carrying a carbon side chain and 7-methoxyindole were also synthesized.View full abstractDownload PDF (1779K) -
MIYOJI HANAOKA, SIN KYU KIM, SHUN-ICHIRO SAKURAI, YUKO SATO, CHISATO M ...1987 Volume 35 Issue 8 Pages 3155-3165
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSOn treatment with an acid, 8-alkyl-8, 14-cycloberbines (9) afforded the N-unsubstituted spirobenzylisoquinolines (10, 11, and 12) through regioselective C8-N bond cleavage in contrast to the 8-unsubstituted 8, 14-cycloberbine (9d), which gave the benzindenoazepine (19, R = H) through regioselective C14-N bond cleavage. Reduction of 9 with NaBH4 or LiAlH (OBut) 3 yielded stereoselectively the alcohol (20 or 21, respectively) as the main product. Acidic treatment of the isomeric alcohols (20 and 21) effected regioselective C8-N bond cleavage, resulting in the N-unsubstituted spirobenzylisoquinolines (22-26).View full abstractDownload PDF (1431K) -
JYOJI KURITA, KUNIYOSHI IWATA, TAKASHI TSUCHIYA1987 Volume 35 Issue 8 Pages 3166-3174
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESS3-Azatricyclo [4.1.0.02.5] hept-3-ene derivatives prepared from pyridines via five steps were found to be useful synthons for fully unsaturated monocyclic seven-membered heterocyclic rings. Photolysis of the 7-oxa derivatives 15 resulted in valence isomerization with ring opening to give the 1, 4-oxazepines (19), which are the first examples of fully conjugated 1, 4-oxazepines. Similarly, the 7-aza derivatives 16, upon irradiation, afforded the novel 1H-1, 4-diazepines (20).
The 2, 7-dimethyl-1, 4-oxazepine (19c) and 2, 7-dimethyl-1, 4-diazepine (20c) underwent thermal ring conversion, giving rise to the 1, 3-oxazepine (22) and 1, 3-diazepine (24), respectively.View full abstractDownload PDF (1395K) -
HIROYUKI SAWANISHI, KAYOKO TAJIMA, TAKASHI TSUCHIYA1987 Volume 35 Issue 8 Pages 3175-3181
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSPhotolysis of 4-azidopyridines (7a-e) in the presence of methoxide ions resulted in ring expansion to give 5-methoxy-6H-1, 4-diazepines (10a-e), presumably via the azirine intermediates 8 derived from the initially formed singlet pyridylnitrenes. Treatment of the 6H-1, 4-diazepine (10a) with benzoyl chloride, acetyl chloride, or ethyl chloroformate in pyridine afforded the corresponding 1-acyl-1H-1, 4-diazepines (21a-c), whose structures were confirmed by means of thermal and photochemical reactions.View full abstractDownload PDF (1209K) -
HARUKI SASHIDA, AKIRA FUJII, TAKASHI TSUCHIYA1987 Volume 35 Issue 8 Pages 3182-3189
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSIrradiation of the 4-azidoquinolines (7a-d) in a 1 : 1 mixture of methanol and dioxane containing sodium methoxide resulted in ring expansion to form the unstable fully unsaturated 1H-1, 4-benzodiazepines (9a-d), which were tautomerized to the stable 3H-1, 4-benzodiazepines (10a-d) by further treatment with sodium methoxide. Acetylation of the 3H-diazepines (10a and 10d) resulted in tautomerization to afford the 1-acetyl compounds 13a and 13d, which are the first isolated examples of 1H-1, 4-benzodiazepines. From these fully unsaturated diazepines (10 and 13), the 2, 3-dihydro-1H-1, 4-benzodiazepines (14-18) and their 5-oxo derivatives (19 and 20) were prepared.View full abstractDownload PDF (1307K) -
YUICHI HASHIMOTO, HIROYUKI KAGECHIKA, EMIKO KAWACHI, KOICHI SHUDO1987 Volume 35 Issue 8 Pages 3190-3194
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSNew-type inducers of differentiation of human promyelocytic leukemia cells HL-60, i.e., 4- (5, 6, 7, 8-tetrahydro-5, 5, 8, 8-tetramethyl-2-naphthalenylcarbamoyl) benzoic acid (Am 80) and (E) -4- [3- (3, 5-di-tert-butylphenyl) -3-oxo-l-propenyl] benzoic acid (Ch 55), suppress c-myc expression as all-trans-retinoic acid (RA) does. The decreased level of c-myc expression was detected within 5-14 h after the start of treatment, and preceded morphological differentiation and functional differentiation measured in terms of nitroblue tetrazolium (NBT) reduction. Treatment of HL-60 cells with 0.1 μm Am 80, Ch 55 or RA for 96 h caused more than 90% suppression of c-myc expression and around 10-fold increase in the percentage of NBT-positive cells.View full abstractDownload PDF (1954K) -
HIROSHI HARADA, YOSHIHIRO MATSUSHITA, MITSUAKI YODO, MASUHISA NAKAMURA ...1987 Volume 35 Issue 8 Pages 3195-3214
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESS2, 3-Dihydrobenzofuran derivatives having various sulfamoyl groups at the 5-position were synthesized and tested for oral diuretic and saluretic activities in rats and mice. Intraperitoneal uricosuric activity was also tested by a clearance method using oxonate-treated rats. Structureactivity relationships are presented. The 6, 7-dichloro-5-N, N-disubstituted sulfamoyl-2, 3-dihydro-benzofuran-2-carboxylic acids (9ab, ac, 13a and b) having lower alkyl substituents showed the most potent diuretic and saluretic activities among the compounds synthesized. Hyperuricosuric activity was observed in 6, 7-dichloro-2, 3-dihydrobenzofuran-2-carboxylic acids and 2-hydroxymethyl-6, 7-dichloro-2, 3-dihydrobenzofurans having a 5-sulfamoyl group, with relatively small substituents (9aa-ac, af, ak, al, an, ao and 16a-c). The saluretic activity of 9ab showed a high-ceiling profile. Examination of the enantiomers of 9ab revealed that the (-) -enantiomer is responsible for most of the diuretic and saluretic activities, while the (+) -enantiomer is responsible for most of the uricosuric activity.View full abstractDownload PDF (2830K) -
HIROSHI HARADA, YOSHIHIRO MATSUSHITA, MITSUAKI YODO, MASUHISA NAKAMURA ...1987 Volume 35 Issue 8 Pages 3215-3226
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESS2, 3-Dihydrobenzofuran-2-carboxylic acids substituted with electronegative nitro, acyl and sulfamoyl groups at the 4-position were synthesized and tested for oral diuretic and saluretic activities in rats and mice. The intraperitoneal uricosuric activity was also tested by a clearance method using oxonate-treated rats. The 4-nitro compounds (11b, 12b, 13b and 14b) showed more potent saluretic activity than the corresponding 5-nitro compounds (7b, 18b, 19b and 20). Although the 5-acyl compounds were reported to show potent saluretic activities, the 4-acyl compounds (41a and b) had much lower activities. On the other hand, the saluretic activities of the 4-sulfamoyl compounds (22a-e) were as potent as those of the 5-sulfamoyl compounds reported previously. Uricosuric activity was found in 14b and 22a.View full abstractDownload PDF (2012K) -
MIKIO HONJO, TOKUMI MARUYAMA, MITZUYO HORIKAWA, JAN BALZARINI, ERIK De ...1987 Volume 35 Issue 8 Pages 3227-3234
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSTreatment of lithiated 2', 3', 5'-tri-Ο-protected uridine and 6-chloropurine ribonucleoside with diethyl chlorophosphate, followed by deblocking (and amination) and hydrolysis, provided 5-and 6-phosphonouridine (IV and VII), and 8-phosphonoadenosine (Xb), respectively. The Arbuzov reaction of 2', 3', 5'-tri-Ο-protected 4-chloro-2 (1H) -pyrimidinone ribonucleoside and triethyl phosphite afforded the diethyl 4-phosphonate derivative (XII). Compounds IV, VII and Xb, and their respective diethyl esters (IIb and VIb) and monoethyl ester (Xa) were inactive in vitro as antiviral and cytostatic agents, but the diethyl 8-phosphonate derivative (IXb) of 6-chloro-9- (β-D-ribofuranosyl) purine (VIIIa) showed some antiviral and cytostatic activities, which were comparable in all respects to those of VIIIa.View full abstractDownload PDF (1533K) -
IKUO ADACHI, TERUO YAMAMORI, YOSHIHARU HIRAMATSU, KATSUNORI SAKAI, HAT ...1987 Volume 35 Issue 8 Pages 3235-3252
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA series of 4-aryl-4, 7-dihydropyrazolo [3, 4-b] pyridine-5-carboxylate derivatives (72-149) was prepared and the compounds were tested for Ca-blocking activity in isolated guinea pig portal vein, antihypertensive activity in spontaneously hypertensive rats, and coronary vasodilating effect in isolated guinea pig heart. A number of derivatives had potent antihypertensive and coronary vasodilating activities. The structure-activity relationships of the series indicated that a 3-cyclopentyl or 3-cyclohexyl substituent and a hydrophobic 5-ester moiety with moderate bulkiness were effective for increasing the pharmacological potencies.View full abstractDownload PDF (2512K) -
HIROYUKI NATE, YASUO SEKINE, KUNIYUKI ODA, KEIICHI AOE, HIDEO NAKAI, H ...1987 Volume 35 Issue 8 Pages 3253-3261
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe carba (2) and oxa analogues (3) of 2- (phenylpiperazinylalkoxyphenyl) thiazolidine-3-carboxamide (1, Y=O) and-thiocarboxamide (1, Y=S) were synthesized and tested for cardiotonic activity. These analogues (2 and 3) were prepared from the aldehydes (4) through several intermediates (7, 10, and 13). In a series of the N-methylcarboxamides, positive inotropic activity in anesthetized dogs decreased in the following order : the thiazolidine (1a) >>oxazolidine (3a) >pyrrolidine (2a). In the corresponding thiocarboxamide series, however, the oxazolidine (3b) was the most potent, followed by the thiazolidine (1b) and the pyrrolidine (2c).View full abstractDownload PDF (1353K) -
YUTAKA SAIGA, IKUO IIJIMA, AKIHIKO ISHIDA, TOSHIKAZU MIYAGISHIMA, KEIS ...1987 Volume 35 Issue 8 Pages 3262-3269
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA large number of alkyl 1, 2, 3, 4-tetrahydro-β-carboline-2-carbodithioates (2 and 5) with 3-hydroxycarbonyl and 3-hydroxymethyl groups were synthesized and tested for hepatoprotective activity against CCl4-induced liver damage in mice. Structure-activity relationships were investigated. Lengthening of the alkyl group in 2 and 5 tends to adversely affect the activity. Both enantiomers of the methyl derivatives (2a and 5a), the most potent compounds in this series, were synthesized, and no difference in hepatoprotective activity was observed. Apparent neighboring group participation was observed in the treatment of 5a with base or acid, giving the cyclized product (6) or the rearranged products (7, 8, and 9).View full abstractDownload PDF (1153K) -
HIROSHI OHTAKA, TOSHIRO KANAZAWA, KEIZO ITO, GORO TSUKAMOTO1987 Volume 35 Issue 8 Pages 3270-3275
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA series of 1-benzyl-4-diphenylmethylpiperazines was prepared and tested for cerebral vasodilating activity. Among the compounds with stronger potency and longer-lasting action than papaverine, the most potent analog 19 (KB-2796) was selected for further study. Some pharmacological properties of 19 are presented.View full abstractDownload PDF (643K) -
KAZUO OGAWA, TADAFUMI TERADA, YOSHIYUKI MURANAKA, TOSHIHIRO HAMAKAWA, ...1987 Volume 35 Issue 8 Pages 3276-3283
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESStrans-and cis-2-Diazo-1- (4-alkylcyclohexyl) -1-ethanones were reacted with arenesulfonic acids to afford the corresponding 2- (4-alkylcyclohexyl) -2-oxoethyl arenesulfonates. The esteraseinhibitory activity and hypolipidemic effect of the arenesulfonates were examined, and it was found that in most cases, the trans-isomers were more active than the corresponding cis-isomers.
Stereoselective syntheses of several biologically potent trans-isomers (trans-3) were also developed.View full abstractDownload PDF (1137K) -
YUTAKA SAIGA, IKUO IIJIMA, AKIHIKO ISHIDA, TOSHIKAZU MIYAGISHIMA, KOIC ...1987 Volume 35 Issue 8 Pages 3284-3291
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSDithiocarbamates of various substituted tetrahydro-β-carbolines were synthesized and tested for hepatoprotective activity against carbon tetrachloride (CCl4) -induced liver damage in mice. Structure-activity relationships were investigated. Some neighboring group participation of the 3-substituent with the dithiocarbamate group appeared to be important for the manifestation of activity. The compounds (1a, 2a, and 3i) with hydrophilic substituents at the 3 poisition exhibited significant activity. Substitution at the 9 position of the 3-carboxylic acid (1a) lowered the activity.View full abstractDownload PDF (1193K) -
TAKEHIKO FUKUNAGA, IKUKO KAJIKAWA, KOICHI NISHIYA, YOSHIKUNI WATANABE, ...1987 Volume 35 Issue 8 Pages 3292-3297
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSFour new flavonoid glycosides, 2'-hydroxy-3, 4', 6'-trimethoxychalcone-4-Ο-glucoside (VII), 2'-hydroxy-4', 6'-dimethoxychalcone-4-Ο- [apiosyl (1→2)] glucoside (VIII), (2R) -5, 7-dimethoxyflavanone-4'-Ο-glucoside (IX) and (2S) -3', 5, 7-trimethoxyflavanone-4'-Ο-glucoside (X), and a known flavonoid glucoside, 2'-hydroxy-4', 6'-dimethoxychalcone-4-Ο-glucoside (VI), were isolated from the twigs and leaves of Viscum album L. (Loranthaceae). These structures were established on the basis of the spectral and chemical data. β-Amyrin acetate, oleanolic acid, betulinic acid, phytosterol, phytosterol-β-D-glucoside and syringin were also isolated.View full abstractDownload PDF (852K) -
SHIN-ICHI UEHARA, ICHIRO YASUDA, KAZUYUKI AKIYAMA, HIROSHI MORITA, KOI ...1987 Volume 35 Issue 8 Pages 3298-3304
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSFive diarylheptanoids including two new compounds were isolated from the rhizomes of Curcuma xanthorrhiza (Zingiberaceae). The structures of the new compounds were determined to be octahydrocurcumin ((3S, 5S) -1, 7-bis (4-hydroxy-3-methoxyphenyl) -heptane-3, 5-diol) (Ia) and (1ξ) -1-hydroxy-1, 7-bis (4-hydroxy-3-methoxyphenyl) -6-heptene-3, 5-dione (II) on the basis of spectral and chemical evidence.
The absolute configurations of Ia and a new similar diarylheptanoid, (3R, 5R) -1- (4-hydroxyphenyl) -7-phenylheptane-3, 5-diol (VIa), isolated from the rhizomes of Alpinia officinarum (Zingiberaceae), were established by application of the exciton chirality rule.View full abstractDownload PDF (1098K) -
KAZUO KOIKE, TAICHI OHMOTO1987 Volume 35 Issue 8 Pages 3305-3308
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSTwo new β-carboline dimeric alkaloids, (±) -picrasidine G (1) and (±) -picrasidine-S (2), have been isolated from the root bark of Picrasma quassioides BENNET (Simaroubaceae). The structures were determined on the basis of spectral analysis.View full abstractDownload PDF (469K) -
HIROMI KOBAYASHI, HIROKO OGUCHI, NOBUO TAKIZAWA, TOSHIO MIYASE, AKIRA ...1987 Volume 35 Issue 8 Pages 3309-3314
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSFour new phenylethanoid glycosides, tubulosides A (II), B (VI), C (VII) and D (VIII), have been isolated from Cistanche tubulosa (SCHRENK) HOOK. f. (Orobanchaceae), together with four known phenylethanoid glycosides, echinacoside (I), acteoside (III), acteoside isomer (IV) and 2'-acetylacteoside (V). The structures of II, VI, VII and VIII were established on the basis of chemical evidence and spectral data. Compounds VII and VIII possess a triacetylrhamnosyl moiety as the terminal sugar.View full abstractDownload PDF (1019K) -
MASAO HATTORI, SUMITRA HADA, YUKIO KAWATA, YASUHIRO TEZUKA, TOHRU KIKU ...1987 Volume 35 Issue 8 Pages 3315-3322
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSSeveral new tetrahydrofuran lignans, named fragransins A2 (II), B1 (IV), B2 (V), B3 (VI), C1 (VII), C2 (VIII), C3a (IX) and C3b (X) were isolated from the methanolic extract of the aril of Myristica fragrans HOUTT. (Myristicaceae), along with nectandrin B (I) and verrucosin (III). The structures of these compounds were elucidated by spectroscopic methods.View full abstractDownload PDF (1164K) -
TADATO TANI, TADAHISA KATSUKI, YUKO OKAZAKI, SHIGERU ARICHI1987 Volume 35 Issue 8 Pages 3323-3328
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe concentrations and distributions of nine elements and three saikosaponins in Bupleurum falcatum root cultivated in Japan were histochemically examined by means of an electron microprobe X-ray microanalyzer (EXMA), inductively coupled plasma spectrometry (ICP) and high-performance liquid chromatography. Point and line analyses by semi-quantitative EXMA coupled with quantitative ICP proved to be a convenient and selective method for histochemical analysis of the tissue-specific distributions of the elements in plant roots. The present histochemical examination showed that aluminum and manganese along with three saikosaponins a, c and d occur exclusively in the outermost peripheral layer, consisting of a cork layer and pericycle, of the root, and that phosphorus occurs in the innermost xylem layer at a high concentration.View full abstractDownload PDF (2846K) -
TSUKASA HAMADA, MASANA KADOWAKI, NORIO AWATA1987 Volume 35 Issue 8 Pages 3329-3335
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA radioreceptor assay (RRA) for the quantitative determination of a new antiallergic agent, 1- (2-ethoxyethyl) -2- (4-methyl-1-homopiperazinyl) benzimidazole difumarate (KB-2413), has been developed. This RRA method, based upon competitive binding of [3H] mepyramine and KB-2413 to histamine H1 receptors in guinea pig cerebellum, allows the simple, sensitive and reproducible determination of KB-2413 in plasma. The determination limit was 0.1 ng (as free base) /ml and the standard curve was linear over the range of 0.1 to 5.0 ng/ml. The intra-and inter-assay coefficients of variation for the determination of KB-2413 were 5.2-11.1 % and 3.4-5.6%, respectively. The active metabolites, 1- (2-ethoxyethyl) -2- (1-homopiperazinyl) benzimidazole and 1- (2-ethoxyethyl) -5-hydroxy-2- (4-methyl-1-homopiperazinyl) benzimidazole, cross-reacted to the extents of 28.6 and 21.1 %, respectively. However, plasma levels obtained by the RRA method and the gas chromatographic method for the intact drug were well correlated in guinea pigs after oral administration of KB-2413.View full abstractDownload PDF (1123K) -
HIROSHI HOSODA, WATARU TAKASAKI, REIKO TSUKAMOTO, TOSHIO NAMBARA1987 Volume 35 Issue 8 Pages 3336-3342
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe sensitivities of colorimetric testosterone enzyme immunoassays using alkaline phosphatase (AP), β-galactosidase (β-GAL) and horseradish peroxidase (HRP) as labels were compared. Enzyme labeling of testosterone was carried out by the N-succinimidyl ester method at an appropriate molar ratio of steroid to enzyme. In the competitive immunoassay, the bound and free enzyme-labeled antigens were separated by a double antibody method and the enzymic activity of the immune precipitate was determined by spectrophotometric methods. The AP activity was measured in four ways, using p-nitrophenyl phosphate, phenolphthalein monophosphate, phenyl phosphate, and nicotinamide adenine dinucleotide phosphate (NADP) as substrates. In the cases of β-GAL and HRP, o-nitrophenyl β-D-galactopyranoside and 3, 3', 5, 5'-tetramethylbenzidine were used, respectively. A dose-response curve with a satisfactory sensitivity was obtained in each testosterone assay system by the use of a minimum amount of the enzyme-labeled antigen at an appropriate dilution of anti-testosterone antiserum (Ka =2 × 1010M-1). The amount of testosterone needed to displace 50% of the bound label ranged from 9 to 90 pg. It was found that the highest sensitivity was obtained by the use of HRP, with AP next and β-GAL third; the former two sensitivities were each comparable to that of the corresponding fluorimetric assay.View full abstractDownload PDF (1179K) -
SHIGERU TABATA, KENTARO TANAKA1987 Volume 35 Issue 8 Pages 3343-3352
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSOral administration to rats of Fe (II) complexes produced by yeast in FeCl3-added wine resulted in effective intestinal absorption of Fe and incorporation of Fe into hemoglobin. The physicochemical properties of an Fe (II) complex showing the highest Fe absorption (designated B1-c) were studied. In paper electrophoresis, inorganic Fe salts migrated to the cathode, while B1-c was detected as a single spot consisting of Fe (II) and saccharides which moved to the anode in the pH range of 2-5.6. When methanol was added to an aqueous solution of B1-c, Fe was precipitated at alcohol contents over 50%. When incubated at 25 °C, Fe (II) in an aqueous solution of B1-c was more stable to oxidation than that in an inorganic Fe (II) salt solution. In the B1-c solution, more than 70% of Fe was maintained in the soluble Fe (II) form at pH 5.5, 7 and 10 even after 18d of incubation. Just after adjustment of an aqueous B1-c solution to pH 11, 90% of Fe in the B1-c solution was soluble. Linear regression analysis of the data on B1-c showed a close correlation between the Fe solubility at the rat small intestinal pH (assumed to be 7.5) and the Fe absorption in the rat after oral administration. The results of infrared spectrometry, elementary analysis and colorimetry suggested that the ligand of B1-c was an oligosaccharide having a carboxyl group and with a molecular weight of around 1500.View full abstractDownload PDF (1288K) -
NAOHITO OHNO, HISAMI SHINOHARA, TOSHIRO YADOMAE1987 Volume 35 Issue 8 Pages 3353-3363
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSSclerotinia sclerotiorum IFO 9395 strain produces “sclerotia” on agar media. The immunomodulating activities of the non-dialyzable fraction of hot water extract of sclerotia (TSHW) grown on six kinds of agar media (i.e., malt (M), potato-sucrose (PS), potato-dextrose (P), YpSs (Y), Leonian-yeast extract (L) and malt-yeast extract (MY)) were comparatively studied. The sclerotial formation was strongly affected by the composition of the media. The yield was the highest on PS agar (26.8 g as average dry weight of sclerotia per 100 agar plates), and the lowest on MY agar. However, the yield, composition (protein ca. 30%, carbohydrate ca. 60%, phosphate (<0.4%)), carbohydrate components (glucose and mannose in a molar ratio of 1.0 : ca. 0.5) and amino acid composition of TSHW were similar on all the media. The results of methylation analysis indicated that all the TSHW preparations possessed quite similar branched β-1, 3-glucan structures. These TSHW preparations showed various immunomodulating effects (mitogenic, polyclonal B-cell activating (PBA), reticuloendothelial system (RES) -activating, and antitumor activities). Antitumor and RES activation activities of TSHW were quite similar regardless of the difference of culture media, while mitogenic and PBA activities varied somewhat. These results suggest that the sclerotia contained immunomodulating material (s), the production of which was affected, in part, by the composition of the culture media.View full abstractDownload PDF (1629K) -
KIYOMI KIKUGAWA, KUMIKO TAGUCHI, TEPPEI MARUYAMA1987 Volume 35 Issue 8 Pages 3364-3369
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe reaction of yeast ribonucleic acid (RNA) with malonaldehyde. a product of lipid oxidation, at pH 4 and 37 C produced modified RNA with absorption at 325 nm and fluorescence. The fluorescence intensity was extremely low as compared with that of bovine serum albumin modified similarly. Torula yeast transfer RNA (tRNA), calf thymus deoxyribonucleic acid (DNA). polycytidylic acid (polyC) and polyadenylic acid (polyA) underwent similar modification. The modification took place at cytosine, adenine and probably guanine residues. The absorption maximum at 325 nm may he due to the modified cytosine and adenine residues, which form 1 : 3 adducts with a methylene cyclopropane ring and a six-membered ring (Nair et al., J. Am. Chem. Soc., 106, 3370 (1984)). These modifications did not produce any significant fluorescence. The present data are inconsistent with those of Reiss et al. (Biochcm. Blophys. Res. Commun., 48. 921 (1972)), who reported that the modification of nucleic acids with malonaldehyde produced fluorescent cross-links due to conjugated Schiff bases.View full abstractDownload PDF (963K) -
HIRAKU ONISHI, TAKEO KAWAGUCHI, TSUNEJI NAGAI1987 Volume 35 Issue 8 Pages 3370-3374
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESS3'- (7-Carboxyheptanoyl) -5-fluoro-2'-deoxyuridine (C6-FUdR) was conjugated to decylenediamine-dextran T70 (T70-C10) or poly-L-lysine (PLL) by using 1-ethyl-3- (3-dimethylaminopropyl) -carbodiimide hydrochloride (EDC). Drug release patterns from the conjugates between C6-FUdR and T70-C10 (T70-C10-C6-FUdR) or PLL (PLL-C6-FUdR) by enzymatic and nonenzymatic processes were investigated at neutral and weakly acidic pHs. Under the nonenzymatic conditions, 5-fluoro-2'-deoxyuridine (FUdR) was released slowly only at neutral pH. This property is similar to that of C6-FUdR. Gradual drug release was observed enzymatically from T70-C10-C6-FUdR at both pHs, while PLL-C6-FUdR did not show enzymatic drug release. However, after the treatment of PLL-C6-FUdR with trypsin, FUdR was released enzymatically from the products; in this case, the release rate of FUdR was faster at neutral pH than at the weakly acidic pH. However, the release of FUdR by enzymatic processing was much slower from these conjugates than from C6-FUdR.View full abstractDownload PDF (800K) -
SHOJI FUKUSHIMA, MIKA NISHIDA, MASAHIRO NAKANO1987 Volume 35 Issue 8 Pages 3375-3381
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSW/O/W type double emulsions stable for a long time were prepared by two-step emulsification procedures using an oily lymphographic agent, Lipiodol Ultra-Fluid, and a derivative of hydrogenated castor oil (HCO-10) as an oil phase. The yield of W/O/W type double emulsions was about 90%. Although the yield was not lowered by vigorous dispersion with a homogenizer, the size of oil droplets was decreased and the release rate of cytarabine was enhanced. Neither the concentration of cytarabine in, nor the volume of, the inner aqueous phase affected the release pattern of cytarabine from W/O/W type double emulsions. The release rate of 5-fluorouracil (5-FU) from the W/O/W type double emulsion was so fast that the release was completed within 1 h. The release of cytarabine and glucose was sustained and peplomycin was hardly released from the W/O/W type double emulsion. W/O type emulsions or W/O/W type double emulsions prepared in this study might be suitable as carriers of drugs such as peplomycin.View full abstractDownload PDF (3879K) -
SHINJI YAMASHITA, HIDETAKA SAITOH, KENJI ABE, KUNIO NAKANISHI, MIKIO M ...1987 Volume 35 Issue 8 Pages 3382-3389
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe effects of buffer components, glucose and sodium, on the passive transfer of sulfanilic acid (SA) and sulfaguanidine (SG) across isolated rat jejunal membranes were investigated, together with their effects on the transmural potential difference. (PD) and the membrane resistance (Rm). Glucose or sodium exclusion from bathing solutions significantly increased the mucosal-to-serosal transfer of both drugs. Glucose exclusion caused an irreversible reduction in PD, and the active transfer of L-phenylalanine (L-Phe) was also inhibited. However, effects of sodium exclusion on PD and the transfer of SA were reversible. The addition of phloridzin (Phl) to the mucosal solution induced the effect similar to that of glucose exclusion. In contrast, Rm was not significantly altered by the exclusion of glucose or the addition of Phl. It is clear that environmental conditions which reduce the active transport activity of the membrane enhance the membrane permeability to drugs.View full abstractDownload PDF (1255K) -
MASAYUKI YAMADA, YOSHIAKI UDA1987 Volume 35 Issue 8 Pages 3390-3398
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSMolsidomine, which is effective in treating angina pectoris, was poorly absorbed through the skin from a simple solution in oleic acid or propylene glycol, and its bioavailability was below 1% in rats. However, molsidomine was efficiently absorbed from a two-component system consisting of oleic acid and propylene glycol. Maximum absorption enhancement was observed in the two-component system containing 10% oleic acid; the bioavailability was about 95% within 6h. Remarkable percutaneous absorption enhancement was also observed in the presence of linoleic acid when a series of unsaturated straight fatty acids with different carbon numbers were substituted for oleic acid. Lauric acid was the most effective in the series of saturated straight fatty acids. Effective percutaneous absorption enhancement also occurred with lauryl alcohol and oleyl alcohol, but little enhancement was observed with any fatty acid ester or sodium oleate. The two-component system is also effective for some water-soluble drugs and poorly water-soluble drugs, besides molsidomine.View full abstractDownload PDF (1300K) -
MASAYUKI YAMADA, YOSHIAKI UDA, YUSUKE TANIGAWARA1987 Volume 35 Issue 8 Pages 3399-3406
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe mechanism of percutaneous absorption of molsidomine, enhanced by a two-component system consisting of oleic acid and propylene glycol, was studied in vitro and in vitro in rats. About 10-20% of the oleic acid was absorbed from the skin independently of the oleic acid-propylene glycol ratio. In contrast, about 95% of molsidomine and propylene glycol were transdermally absorbed from the two-component system containing 10% oleic acid in 6 h. The permeability (percent of dose) of molsidomine through the excised rat skin was comparable to that of propylene glycol (both about 80% in 24h). These results suggest that the molsidomine and propylene glycol permeated simultaneously through rat skin. Our proposed mechanism of percutaneous absorption of molsidomine assumes that oleic acid and propylene glycol penetrate into the stratum corneum and improve the permeability of the skin by dissolving hard lipoidal components, and then molsidomine, dissolved in the propylene glycol, passes through the modified stratum corneum.View full abstractDownload PDF (3344K) -
MASAYUKI YAMADA, YUSUKE TANIGAWARA1987 Volume 35 Issue 8 Pages 3407-3412
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA basic investigation aimed at developing a membrane-controlled transdermal therapeutic system was carried out. The drug used was molsidomine with oleic acid and propylene glycol as the absorption enhancer and the vehicle, respectively. It was concluded that a microporous polyethylene membrane was most suitable for release control. A desirable pattern of the molsidomine plasma concentration versus time curve could be obtained by controlling the amounts of the three components, molsidomine, oleic acid, and propylene glycol in the device. Furthermore, the plasma concentration of molsidomine was well sustained by adding polyethyleneglycol 400 to the oleic acid-propylene glycol solution.View full abstractDownload PDF (792K) -
KYOKO KOIZUMI, YASUYO OKADA, YOKO KUBOTA, TOSHIKO UTAMURA1987 Volume 35 Issue 8 Pages 3413-3418
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe inclusion complex-forming ability of three glucosyl-cyclodextrins (CDs), 6-Ο-α-D-glucosyl-α-CD (G-α-CD), 6-Ο-α-D-glucosyl-β-CD (G-β-CD), and 6A, 6D-di-Ο-α-D-glucosyl-β-CD (2G-β-CD) with slightly soluble or insoluble drugs in aqueous solution and in the solid state was studied by the solubility method, ultraviolet spectroscopy, and differential scanning calorimetry. These glucosyl-CDs were capable of forming inclusion complexes with compounds which can form complexes with the parent CDs. The enhancement of solubility of poorly water-soluble drugs by glucosyl-β-CDs was much more marked than that by β-CD. The hemolytic activity of glucosyl-CD was lower than that of each parent CD. The estriol-glucosyl-β-CD complex may be practically applicable to injectable preparations because of its high water-solubility and low hemolytic activity.View full abstractDownload PDF (831K) -
HAJIMU YAMAMOTO, YOSHIKI NAKAMURA, MITSUAKI NAGASAKA, HAJIME ASAI1987 Volume 35 Issue 8 Pages 3419-3424
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe pharmacological actions of the optical isomers of cis-2, 3-dihydro-3- (4-methylpiperazinylmethyl) -2-phenyl-1, 5-benzothiazepin-4 (5H) -one (BTM) were studied and compared. Antiacetylcholine activity determined by the Magnus method was higher but antihistamine activity was lower with the (-) -compound than with the (+) -compound; the (±) -compound showed intermediate activities. The antiulcer action and antisecretory action in pylorus-ligated rats as well as the antistress ulcer action in mice were more potent with the (-) -compound than the (+) -compound. The optical isomers showed similar local anesthetic action, when tested by using the corneal reflex in guinea pigs. Analgesic action, tested by the acetic acid-induced writhing method, was observed with the (+) -compound, but not the (±) - or (-) -compound. The (+) -compound showed the strongest acute toxicity in mice, followed by the (±) - and the (-) -compounds in that order. These results suggest the presence of multiple targets for the various pharmacological activities. The (-) - compound appears to be more promising as an antiulcer agent, since the antiulcer effect was greater and the toxicity was milder as compared with (+) -compound.View full abstractDownload PDF (785K) -
HIROSHI TSUCHIHASHI, TAKAFUMI NAGATOMO1987 Volume 35 Issue 8 Pages 3425-3432
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe characteristics of the high-and low-affinity binding sites for 125I-iodocyanopindolol (125I-ICYP) in rat cerebral cortex membrane were examined. The Scatchard plots of 125I-ICYP binding were biphasic in the absence of antagonists as well as in the presence of non-selective antagonists (d-, dl- and l-propranolol) and selective antagonists. Two of the latter (atenolol and practolol) are β1-selective antagonists and two others (butoxamine and ICI-118551) are β2-selective antagonists.The β2-selective antagonists showed more potent action on the high-affinity sites than on the low-affinity sites, while the β1-selective antagonists had a more potent effect on the low-affinity sites. These results were consistent with those obtained from pharmacological experiments, and suggest that the high- and low-affinity sites in the biphasic Scatchard plots correspond to β2-and β1-adrenoceptors, respectively.
By means of this approach, the relative percentages of the two receptor subtypes in rat brain (cerebral cortex), lung, heart, and spleen were calculated (ratios of β1 : β2-adrenoceptors) to be brain 89 : 11, lung 28 : 72, heart 92 : 8, and spleen 59 : 41. The absolute capacities of β-adrenoceptors per g wet weight in these tissues were 10-14 pmol/g tissue except for heart (approx. 2.4 pmol/g tissue).View full abstractDownload PDF (1030K) -
Adsorption Behavior of Ammonia and Trimethylamine in Pores of Oxygen Plasma Treated Activated CarbonSEIKI TANADA, SHOZO TSUTSUI, KEITO BOKI, TAKEO NAKAMURA1987 Volume 35 Issue 8 Pages 3433-3437
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe adsorption characteristics of ammonia and trimethylamine into pores of oxygen plasma treated activated carbon (PT-AC) were investigated in terms of adsorption isotherms, desorption isotherms, and isosteric differential heats of adsorption. The acid functional group concentration of PT-AC was increased 4 times as compared with that of raw activated carbon (R-AC). The surface area and pore volume of PT-AC were about the same as those of R-AC, but the adsorption capacity for ammonia was remarkably increased over that of R-AC. The adsorption capacity for trimethylamine was about the same as that of R-AC. The adsorption of ammonia and trimethylamine on PT-AC was found to be physical adsorption from the desorption isotherms. In the initial stage of adsorption, the isosteric differential heat of adsorption of ammonia on PT-AC was approximately twice that on R-AC. It seems that the amount of ammonia adsorbed on activated carbon is greatly increased by oxygen plasma treatment, probably because acid functional groups produced in the pores attract ammonia in the initial stage of adsorption. It is concluded that PT-AC is a characteristic adsorbent having a remarkably increased adsorption capacity for ammonia, which is a small and weakly basic molecule.View full abstractDownload PDF (652K) -
HIROSHI YOSHINO, YUTAKA TSUCHIYA, ISAO SAITO, MASAHIKO TSUJII1987 Volume 35 Issue 8 Pages 3438-3441
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSΟ-Benzyltyrosine was rapidly deprotected without formation of 3-benzyltyrosine by treatment with trifluoroacetic acid containing pentamethylbenzene. This method was also found to be useful in the deprotection of Nε-benzyloxycarbonyllysine [Lys (Z)] and NG-4-methoxy-2, 3, 6-trimethylbenzenesulfonylarginine [Arg (Mtr)]. The new deprotecting method was successfully applied to the synthesis of kyotorphin (Tyr-Arg).View full abstractDownload PDF (529K) -
TADASHI HASHIMOTO, YOSHIKI UCHIDA, KEIKO OKIMURA, KATSURO KUROSAWA1987 Volume 35 Issue 8 Pages 3442-3446
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSNine neurokinin B (NKB) related octapeptide analogs, substituted with Arg for His3, or Gly, D-Trp, D-Ala or D-Phe for Phe6, or Gly for Val7, or D-Trp or D-Ala for Gly8 in the original sequence, were synthesized by the solid-phase method. The biological activity of the synthetic analogs was assayed on isolated guinea-pig ileum and rat duodenum. None of the analogs possessed agonistic activity. In the guinea-pig ileum assay, [Arg3, Gly6, D-Ala8] - and [Arg3, Gly6, D-Trp8] -NKB (3-10) were found to act as fairly potent antagonists against NKB, but showed no antagonistic effect against substance P (SP) or neurokinin A (NKA). [Arg3, D-Ala6, D-Trp8] -and [Arg3, D-Trp6, 8, Gly7] -NKB (3-10) showed antagonistic activities against NKB and SP, and NKB, SP and NKA, respectively, in the ileum assay, while the latter acted as an antagonist against NKB, but not against SP or NKA in the rat duodenum assay.View full abstractDownload PDF (768K) -
NOBUTAKA FUJII, AKIRA OTAKA, OSAMU IKEMURA, MIKA HATANO, AKIRA OKAMACH ...1987 Volume 35 Issue 8 Pages 3447-3452
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSThe use of trimethylsilyl trifluoromethanesulfonate as a peptide deprotecting reagent was examined, together with the role of soft bases employed. A new deprotecting procedure based on the hard acid principle is presented.View full abstractDownload PDF (894K) -
TAKAO YAMAZAKI, KATSUHIDE MATOBA, TOSHIYUKI ITOOKA, MASARU CHINTANI, T ...1987 Volume 35 Issue 8 Pages 3453-3459
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSCyclohexane-1, 3-dicarboxylic anhydrides (IVa-c), prepared from isophthalic acids in several steps, were treated with diethyl magnesiomalonate and triethylamine to give 3-di (ethoxycarbonyl) -acetylcyclohexanecarboxylic acids (Va-c) in good yields. Compounds Va-c were converted into methyl 3-acetylcyclohexanecarboxylates (VIa-c) by decarboxylation and esterification. Cyclization of VIa-c to bicyclo [3.3.1] nonane-2, 4-diones (I) was performed by refluxing a mixture of VI and potassium hydride in xylene. In the case of VIb, two products (Id and Ie) were obtained. Compounds Ic and Ie were hydrolyzed to Ib and Ig, respectively, by treatment with p-toluenesulfonic acid in acetone and phosphorus tribromide. The 7α-hydroxy β-diketone (If) was obtained from Ib-triketal in three steps via reduction of Ib-2, 4-diketal with lithium aluminum hydride. The keto-enol equilibrium of these β-diketones (Ia-f) and 9-substituted bicyclo [3.3.1] -nonane-2, 4-diones (Xa-b) in deuteriochloroform is also described.View full abstractDownload PDF (1168K) -
KOOHEI NOZAWA, SHUN-ICHI UDAGAWA, SHOICHI NAKAJIMA, KEN-ICHI KAWAI1987 Volume 35 Issue 8 Pages 3460-3463
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSIn the course of a search for metabolites related to emestrin (2) from Emericells striata, a new compound designated emestrin B (1) was isolated, together with shamixanthone, from the mycelial acetone extract. Shamixanthone is a compound related to emericellin, which had previously been isolated from the mycelium of the above fungus. The structure of emestrin B (1), including its absolute configuration, was established on the basis of the spectroscopic investigations. Emestrin B (1) is an epitrithio derivative corresponding to the antifungal macrocyclic epidithiodioxopiperazine, emestrin (2).View full abstractDownload PDF (515K) -
OSAMU NAKAGUCHI, KEIJI HEMMI, YOICHI SHIOKAWA, MASASHI HASHIMOTO, TAKA ...1987 Volume 35 Issue 8 Pages 3464-3466
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESSA nocardicin derivative was prepared from penicillin G, confirming that nocardicins have the same configuration as penicillins at C-3 of the β-lactam ring.View full abstractDownload PDF (374K) -
KYOKO TAKAHASHI, KEIKO USAMI, TAMAMI TAKAHASHI, TOMOKO OKADA, MASUO MO ...1987 Volume 35 Issue 8 Pages 3467-3469
Published: August 25, 1987
Released on J-STAGE: October 19, 2009
JOURNAL FREE ACCESS14α-Methylcholesterol was synthesized from lanosterol via 19 steps in 1-2% overall yield.View full abstractDownload PDF (485K)