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Volume 41, Issue 1
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Masakazu MAKINO, Shunsuke KAZAMA, Mamoru KAMIYA1993 Volume 41 Issue 1 Pages 1-5
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe photochemical dechlorination mechanism of 2, 3, 7, 8-, 1, 3, 6, 8- and 1, 2, 3, 4-tetrachlorodibenzo-p-dioxins(TCDDs)were theoretically studied by the parametric method 3-modified neglect of diatomic overlap (PM3-MNDO)reactivity indexes based on the frontier electron theory. The theoretical predictions were in good agreement with the experimentally postulated pathways of the photochemical dechlorimation of TCDDs.View full abstractDownload PDF (708K) -
Shoko YOKOYAMA, Junko OBATA, Tadao JUJIE, Masayuki NAKAGAKI1993 Volume 41 Issue 1 Pages 6-11
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe surface tension of aqueous solution of arachidonic acid (AA) was measured with a Du Nouy tensiometer at pH 7.80 and various temperatures, and the effect of temperature on the surface properties of AA was investigated. The value of critical micelle concentration (cmc) of AA increased and the surface tension at the cmc, γcmc, decreased as the temperature was raised from 30 to 60°C. The Langmuir constant k concerning the strength of adsorption decreased, the saturated adsorption ammount of AA, Γ∞, at the air-water interface decreased, and the area occupied by an AA molecule at the saturated adsorption, A∞, increased as the temperature was raised. The standard free energy for the adsorption, ΔGad, was of negative value, and the absolute value |ΔGad| became larger as the temperature was raised because of the negative value of the standard enthalpy change ΔHad and the positive value of the standard entropy change ΔSad. The standard free energy of micellization, ΔGm, was of negative value, and it was similarly found that |ΔGm|became larger as the temperature was raised because of the negative value of the standard enthalpy change ΔHm and the positive value of the standard entropy change ΔSm.View full abstractDownload PDF (749K) -
Hiroyuki AKITA, Isao UMEZAWA, Ikuko SAKURAI, Takeshi OISHI1993 Volume 41 Issue 1 Pages 12-15
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn ether-linked lipid-lipase aggregate was found to function as an immobilized biocatalyst. Three kinds of aggregate, I, III, and IV, obtained by sonication treatment were considered to have stacked bilayer structure of the lipid in the crystalline phase based on X-ray diffraction analysis. On the other hand, aggregate II obtained by the stirring method appeared to have an inverted micellar structure.View full abstractDownload PDF (832K) -
Hiroyuki AKITA, Isao UMEZAWA, Djadjat TISNADJAJA, Hiroko MATSUKURA, Ta ...1993 Volume 41 Issue 1 Pages 16-20
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhospholipids of a new type having ω-cyclohexyltridecyl groups were synthesized in order to investigate the influence of the structure of lipophilic part of phospholipids upon the enzymatic reaction. Enantioselective acetylation of an α-hydroxy ester was carried out in the presence of lipid-lipase aggregates bearing O-ω-cyclohexyltridecyl and O-hexadecyl groups. The chemical yield of α-acetoxy ester was improved by using lipid-lipase aggregates compared to the case of enzymatic reaction using native lipase OF-360 from Candida cylindracea. It was found that the influence of the ω-cyclohexyltridecyl group on the chemical and optical yields of α-acetoxy ester was essentially the same as that to the hexadecyl group.View full abstractDownload PDF (778K) -
Mitsunobu NAKAMURA, Shuji FUJITA, Haruo OGURA1993 Volume 41 Issue 1 Pages 21-25
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of benzyl 4, 5, 7, 8, 9-penta-O-acetyl-2-bromo- or -chloro-2, 3-dideoxy-D-glycero-β-D-galacto-2-nonulopyranosonate (2, 3) with uridine, 5-fluorouridine, and cytidine under Koenigs-Knorr reaction conditions gave the corresponding (2→5) linked disaccharide uncleoside derivatives, in yields of 32-47%. A similar reaction of 3 with inosine gave the (2→N1) linked derivative. These uncleoside analogues were converted into the final target compounds.The configuration at the anomeric position of these compounds was elucidated by means of proton and carbon unclear magnetic resonance (1H-, 13C-NMR)analysis, and consideration of the rate of hydrolysis of the (2→5) glycosidic linkage.View full abstractDownload PDF (803K) -
Mitsunobu NAKAMURA, Kazuyoshi TAKEDA, Hiroaki TAKAYANAGI, Norie ASAI, ...1993 Volume 41 Issue 1 Pages 26-30
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of methyl 4, 5, 7, 8, 9-penta-O-acetyl-3-deoxy-D-glycero-D-galacto-2-nonulopyranosonate (3) with S, S'-bis(1-phenyl-1H-tetrazol-5-yl) dithiocarbonate (4) gave methyl (1-phenyl-1H-tetrazol-5-yl 4, 5, 7, 8, 9-tetra-O-acetyl-3-deoxy-2-thio-D-glycero-β-D-galacto-2-nonulopyranosid)onate (5) and methyl (1-phenyl-5-thioxo-1H, 4H-tetrazol-4-yl4, 5, 7, 8, 9-penta-O-acetyl-2, 3-dideoxy-D-glycero-α- and -β-D-galacto-2-nonulopyranosid)onate (6, 7). The structures were elucidated by means of ultraviolet (UV), circular dichroism (CD), and 13C-nuclear magnetic resonance(13C-NMR) spectral examination, and X-ray crystal analysis. These S- and N-glycosides were applied to O-glycosylation with suitable promoters, and when palladium (II) was used as a promoter, glycosylation of 5 with 2-propanol gave the corresponding glycosides in good yield. Moreover. the S-glycoside was applied to C-glycosylations.View full abstractDownload PDF (728K) -
Takeshi IMANISHI, Yoshimi HIROKAWA, Masayuki YAMASHITA, Tetsuaki TNAKA ...1993 Volume 41 Issue 1 Pages 31-35
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1, 2, 6-Trimethyltetracyclo[5.3.1.0<2, 6&tg;.0<8, 11>]undecan-9-one (4) was prepared from 1, 5-dimethylbicyclo[3.3.0]octan-3-one (6) in fourteen steps. Its cyclopropane ring opening reaction was examined under various conditions. In all runs, 11-substituted 1, 2, 6-trimethyltricyclo[5.3.1.02, 6]undecan-9-ones 20 were obtained as major products along with 7-substituted 1, 2, 8-trimethyltricyclo[6.3.0.0<2, 6>]undecan-4-ones 21 and two other products 22 and 23.View full abstractDownload PDF (834K) -
Etsuo OHSHIMA, Toshiaki KUMAZAWA, Hiroyuki OBASE1993 Volume 41 Issue 1 Pages 36-38
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new method for effecting the formation of a carbon-carbon single bond at the 11-position of 6, 11-dihydrodibenz[b, e]oxepins was developed. The reaction of 11-methoxydibenz[b, e]oxepins with active methylene compounds proceeded in the presence of TiCl4 under mild conditions to afford the correponding 11-substituted dibenzoxepins in moderate to excellent yield. This was considered to be a vinylogous reaction of ketals with active methylene compounds. The efficacy and some applications of this method are described.View full abstractDownload PDF (537K) -
Kayoko AMIMOTO, Kazuko YOSHIKAWA, Shigenobu ARIHARA1993 Volume 41 Issue 1 Pages 39-42
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive new saponins, ilexosides XLI-XLV, were isolated from fresh leaves of Ilex rotunda, and their structures were elucidated on the basis of chemical and physicochemical evidence. Ilexoside XLI is rotundic acid 28-O-α-D-glucopyranosyl (1→6)-β-D-glucopyranoside, ilexoside XLII is 23-oxorotungenic acid 28-O-β-D-glucopyranoside, ilexoside XLIII is 30-hydroxyrotundic acid 28-O-β-D-glucopyranoside, ilexoside XLIV is 3, 28, bis-O-β-D-glucopyranosyl ilexosapogenin B (3-O-β-D-glucopyranosyl 23, 30-dihydroxyursolic acid 28-O-β-D-glucopyranoside), and ilexoside XLV is 24-hydroxyrotundioic acid 28-O-β-D-glucopyranoside.View full abstractDownload PDF (669K) -
Isao KITAGAWA, Kazuyuki HORI, Toshio TANIYAMA, Jun-Liang ZHOU, Masayuk ...1993 Volume 41 Issue 1 Pages 43-49
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the air-dried root of Glycyrrhiza uralensis, collected in the northeastern part of China, ten new oleanane-type triterpene oligoglycosides were isolated together with glycyrrhizin (1) and several known flavonoids. Among the newly isolated triterpene oligoglycosides, the chemical structures of licorice-saponin A3 (2), licorice-saponin B2 (3), and licorice-saponin C2 (4) have been determined, on the basis of chemical and physicochemical evidence, to be expressed as 30-O-β-D-glucopyranosylglycyrrhizm, 11-deoxo-glycyrrhizin, and 3-O-[β-D-glucuronopyranosyl(1→2)-β-D-glucuronopyranosyl]oleana-11, 13(18)-dien-30-oic acid, respectively. During the course of these studies, facile conversions from glycyrrhizn (1) to licorice-saponins A3 (2), B2 (3), and C2 (4) have been accomplished.View full abstractDownload PDF (1107K) -
Toshikazu MATSUOKA, Kazunobu HARANO, Toshihiro UEMURA, Takuzo HISANO1993 Volume 41 Issue 1 Pages 50-54
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of N'-thiobenzoyl -N, N-dimethylformamidine (I) with electron-dificient dienophiles was investigated.The reaction of I with N-substituted maleimides (II) afforded exo and endo 1 : 1 cycloadducts (III). The stereochemistry was determined by analysis of 1H-nuclear magnetic resonance (1H-NMR) spectral data based on the modified neglect of diatomic overlap (MNDO) optimized structures. An equilibrium was observed between the starting materials (I and II) and 1 : 1 cycloadducts (III). The reaction of I with II in the presence of acetic acid afforded thiazine derivatives(IV), through elimination of dimethylamine from the primary cycloadduct (III). The reactions of I with several electron-deficient dienophiles were also examined. The reaction behavior is discussed in terms of frontier molecular orbital (FMO) theory and kinetic factors.View full abstractDownload PDF (747K) -
Hiroyuki AKITA, Isao UMEZAWA, Michika TAKANO, Chiiko OHYAMA, Hiroko MA ...1993 Volume 41 Issue 1 Pages 55-63
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of (±) methyl 4, 5-trans-epoxy-2E-hexenoate (2) with aromatic nucleophiles having an electrondonating group in the presence of BF3·Et2O gave the 4, 5-anti-5-hydroxy-4- or/and 2, 5-anti-5-hydroxy-2-substituted products. The 5-acetates of the 4, 5-anti-4-substitution products were subjected to enantioselective hydrolysis with lipase to provide the optically acitive 4, 5-disubstituted 2-hexenoate derivatives.View full abstractDownload PDF (1352K) -
Takehiko SANO, Miyuki HIROSE, Yoshie HORIGUCHI, Fumiyuki KIUCHI, Yoshi ...1993 Volume 41 Issue 1 Pages 64-72
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe photocycloaddition reaction of the dioxopyrroline 1 to cyclic trimethylsilyloxy olefins was examined. The addition of 3-trimethylsilyloxy-1H-indene and 4-trimethylsilyloxy-1, 2-dihydronaphthalene occurred in a regio- and stereoselective manner to give the cis-anti-cis cyclobutanes 3 and 4, respectively. The stereochemical result supported the stereo-selection rule which states that the photocycloaddition of a very polar dioxopyrroline-olefin pair proceeds in an s+s manner via f favored O-endo-π-complex transition. On the other hand, the addition of 1-trimethylsilyloxy-cyclopentene and 1-trimethylsilyloxycyclohexene occurred less stereoselectively, proceeding predominantly in an s+a manner to give the adducts 5a, b, 6a, b, 7a, b, and 12. The results are consistent with the prediction of the stereo-selection rule obtained by assuming that these dioxopyrroline-olefin pairs are polar. The latter cases demonstrate that an incresed steric hindrance around the olefin moiety affects the polarity of enone-olefin pair in the transition state.View full abstractDownload PDF (1196K) -
Yuko TAKEMURA, Motoharu JU-ICHI, Tomoko KUROZUMI, Miki AZUMA, Chihiro ...1993 Volume 41 Issue 1 Pages 73-76
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour binary coumarins, namely citrumarin-A (1), -B (2), -C (3), and -D (4), were isolated from root of Citrus hassaku and/or Swingle Citrumelo, and their structures were elucidated by spectroscopic methods.View full abstractDownload PDF (584K) -
Kayoko AMIMOTO, Kazuko YOSHIKAWA, Shigenobu ARIHARA1993 Volume 41 Issue 1 Pages 77-80
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSix new saponins, ilexosides XLVI-LI, were isolated from fresh leaves of Ilex rotunda, and their structures were elucidated on the basis of chemical and physicochemical evidence. Ilexosides XLVI, XLVII, L and LI are 3, 28-bisglycosides of ilexosapogenin A, spathodic acid, bredemolic acid, and siaresinokic acid, respectively. Ilexosides XLVIII and XLIX are 3, 28-bisglycosides of hederagenin.View full abstractDownload PDF (659K) -
Takao SAKAMOTO, Chisato SATOH, Yoshinori KONDO, Hiroshi YAMANAKA1993 Volume 41 Issue 1 Pages 81-86
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPyrrolo[2, 3-d]pyrimidines and pyrrolo[3, 2-d]pyrimidines were synthesized in high yields by the palladiumcatalyzed reaction of 4-acetylamino-5-bromopyrimidines and 5-acetylamino-4-iodopyrimidines with (Z)-1-ethoxy-2-(tributylstannyl)ethene followed by cyclization under acidic conditions.View full abstractDownload PDF (966K) -
Masaru KOBAYASHI, Madala M MRISHNA, Bodepudi HARIBABU, Vallurupalli AN ...1993 Volume 41 Issue 1 Pages 87-89
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new marine polyhydroxysterols, 23-demethylgorgost-7-ene-3β, 5α, 6β-triol (4a) and (24S)-ergostane-3β, 5α, 6β, 7β, 15β-pentol (6), were isolated from soft corals(Sinularia sp. and Lobophytum crassum, respectively) collected off the Andaman and Nicobar Islands, Indian Ocean. (24S)-Ergost-5-ene-3β, 7α-diol (1), a known synthetic compound, was isolated from Sclerophytum sp. soft coral of the same region. The structures of 4a and 6 were derived by comparison of the 1H- and 13C-NMR data with those of reference compounds having the same partial structures. The previous assignments of C-1 and C-2 of 3β, 5α, 6β-trihydroxysterol were reversed.View full abstractDownload PDF (619K) -
Setsuo SAITO, Shigeya SUMITA, Koki ICHINOSE, Yasuhiko KANDA1993 Volume 41 Issue 1 Pages 90-96
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen acetylated pyranose-1, 2-(ethyl orthyl orthoacetates) were hydrolyzed in acidic solvents, the ring-opening of the orthoacetate rings was influenced by the axial or equatorial OAc group at C-4 on the pyranoses; on acid-catalyzed hydrolysis, 3, 4, 6-tri-O-acetyl-α-D-glactopyranose- (8) and methyl 3, 4-di-O-acetyl-α-D-galacturonatopyranose-1, 2-(ethyl orthoacetate) (16) having an axial OAc group at C-4 on the pyranose rings gave 1, 3, 4, 6-tetra-O-acetyl-α-D-galactopyranose (9) and methyl 1, 3, 4-tri-O-acetyl-α-D-galacturonatopyranose (23), respectively, whereas 3, 4, 6-tri-O-acetyl-α-D-glucopyranose- (10) and methyl 3, 4-di-O-acetyl-α-D-glucuronatopyranose-1, 2-(ethyl orthoacetate) (22)having an equatorial OAc group at C-4 on the pyranose rings gave 2, 3, 4, 6-tetra-O-acetyl-D-glucopyranose (11) and methyl 2, 3, 4-tri-O-acetyl-D-glucuronatopyranose (24), respectively. On the acid-catalyzed hydrolysis, 3, 4-di-O-acetyl-β-L-arabinopyranose-1, 2-(ethyl orthoacetate) (34) having an axial OAc group at C-4 on the pyranose ring gave a mixture of 1, 3, 4-tri-O-acetyl-β-L- (35) and 2, 3, 4-tri-O-acetyl-L-arabinopyranose (36). These selectivities of ring-opening of the 1, 2-(orthoacetates) were considered to have resulted from the differences of the conformers fo the 1, 2-(orthoacids)intermediates derived from the 1, 2-(othoacetates) and the orientation of the acetyl groups at C-4 on the pyranose rings.View full abstractDownload PDF (864K) -
Masashi ETO, Kazunobu HARANO, Tomohiro OYA, Takuzo HISANO1993 Volume 41 Issue 1 Pages 97-107
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe cycloaddition behavior of 2, 5-bis(methoxycarbonyl)-3, 4-diphenylcyclopentadienone (Ia) toward allylic alcohols(II) was investigated. The exo [4+2]π cycloadducts were transformed into hydrophthalide derivatives via intramolecular addition of the alcohol group to the strained bridged carbonyl. The endo [4+2]π cycloadducts underwent transesterification with the bridgehead methoxycarbonyl group to give the lactone derivatives. The structures of the products were determined on the basis of the 1H- and 13C-NMR spectral data and X-ray analyses. The reactivity of Ia toward allylic alcohols is discussed in terms of frontier molecular orbital (FMO) theory.View full abstractDownload PDF (1330K) -
Toshihisa OGAWA, Atsuro NAKAZATO, Katsuharu TSUCHIDA, Katsuo HATAYAMA1993 Volume 41 Issue 1 Pages 108-116
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of a new series of dihydropyridines containing a nitrooxy mojety at the 3-ester position is described.The antihypertensive activity of the compounds was examined and compared with that of nifedipine; some of them were relatively potent. The structure-activity relationship is also discussed.View full abstractDownload PDF (1110K) -
Toyoo NAKAYAMA, Seizo TAIRA, Masato IKEDA, Hiroshi ASHIZAWA, Minoru OD ...1993 Volume 41 Issue 1 Pages 117-125
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy developing 6-amidino-2-naphthyl 4-guanidinobenzoate (I, FUT-175) as a basic structure, its various derivatives were synthesized and their inhibitory activities on trypsin, plasmin, kallikrein, thrombin, C1^- and C1s^- as well as on complement-mediated hemolysis were examined. The protective effect of these compounds on complement-mediated Forssman shock was also examined in guinea pigs. 6-Amidino-2-naphthyl 4-[(4, 5-dihydro-1H-imidazol-2-yl)amino]-benzoate (41, FUT-187) was found to be a suitable compound for oral administration with anti-complement activity superior to that of compound I.View full abstractDownload PDF (1001K) -
Tetsuo OKADA, Kiyoshi EZUMI, Masumi YAMAKAWA, Hisao SATO, Teruji TSUJI ...1993 Volume 41 Issue 1 Pages 126-131
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSQuantitative structure-activity relationships (QSAR) of various 7-(3-substituted-azetidin-1-yl)-1-cyclopropyl-6, 8-difluoro-1, 4-dihydro-4-oxoquinoline-3-carboxylic acids, 14-25, were studied to clarify the structural requirements for 3-substituted azetidines to potentiate antibacterial activity. A good parabolic relationship seemed to exist between the relative mean antibacterial activity indices against five representative gram-negative bacteria, GNM, and the calculated hydrophobic parameters, CLOG P, of these molecules. The CLOG P value of the most potent derivative was predicted to be around 2.3. On the other hand, against five representative gram-positive bacteria, the relative mean antibacterial activity indices, GPM, remained high and rather constant regardless of structural variation in the azetidine moiety. In order to confirm these findings, the QSAR analysis was extended with success to the quinolonecarboxylic acids, 26-34, which bear various substituted pyrrolidine, piperazine and piperidine derivatives instead of azetidines. The findings showed that the introduction of any amide substituent group to these heterocyclic amine moieties would lead to marked decrease in GNM, whereas incorporation of some amino substituent groups at a position two or three carbons remote from the N-1 position resulted in great enhancement of GNM. As azetidine quinolones exhibited somewhat low in vivo antibacterial activities, possibly reflecting their lesser bioavailability, we finally selected 3-amino-4-methoxypyrrolidine as one of the most promising C-7 substituent groups based on our QSAR analysis.View full abstractDownload PDF (780K) -
Tetsuo OKADA, Hisao SATO, Teruji TSUJI, Tadahiko TSUSHIMA, Hiroshi NAK ...1993 Volume 41 Issue 1 Pages 132-138
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new series of quinolone derivatives 3a-I bearing 3-amino-4-methoxypyrrolidines of different configurations and chirality were synthesized and their antibacterial activities as well as some of their toxicological properties were examined. As predicted by our previous quantitative structure-activity relationships (QSAR) analysis of C-7 heterocyclic amine substituted quinolonecarboxylic acid antibacterial agents, these pyrrolidine derivatives showed higher in vitro and in vivo antibacterial activities against both gram-positive and gram-negative bacteria than the analogs bearing various 3-substituted azetidines. Furthermore, the amino and methoxy substituent groups on the pyrrolidine ring exhibited strong configurational and chiral effects on the in vitro and in vivo antibacterial activities of these compounds : (1) cis compounds showed higher antibacterial activities against most of the pathogens examined : (2) N-methylation of the 3-amino group on the pyrrolidine ring lowered in vitro but not in vivo antibacterial activities, particularly leading to superior in vivo anti-pseudomonal activity; (3) the (3'S, 4'R)-derivative showed substantially higher activity that the (3'R, 4'S)-one. These findings led to the selection of compound 3k for further evaluation as it possessed the highest in vivo antibacterial activity and no cytotoxicity.View full abstractDownload PDF (994K) -
Atsushi KUNO, Kiyotaka KATSUTA, Hiroyoshi SAKAI, Mitsuru OHKUBO, Yoshi ...1993 Volume 41 Issue 1 Pages 139-147
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNovel 4-arylpyrimidine derivatives, bearing an amino moiety in the C-5 or C-6 position of the pyrimidine ring, were synthesized and tested for anti-anoxic (AA) activity in mice. Among them, 6, 7-dihydro-6-[2-(dimethylamino)-ethyl]-4-(3-nitrophenyl-2-phenyl-5H-pyrrolo[3, 4-d]pyrimidine-5-one (2a, FR 75469) and 6-methyl-5-(4-methyl-piperazin-1-ylmethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine (4c, FR 72707) had comparable potency 10-100mg/kg, i.p. and p.o.)to that of 6-methyl-5-(4-methylpiperazin-1-ylcarbonyl)-4-(3-nitrophenyl)-2-phenylpyrimidine (FK 360).These were also effective on anti-lipid peroxidation (ALP) assay and arachidonate-induced cerebral edema in rats.Structure-activiity relationship in regard to AA activity of this series of compounds are discussed. Three-dimensional molecular electrostatic potentials (3D-MEP) around the nitrogeneous basic moiety of FK 360 and 5-acetyl-6-(2-dimethylaminoethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine (5f) were compared, and both electrostatic potential maps were similar.View full abstractDownload PDF (1033K) -
Takehiko YAMANE, Takuji HASHIZUME, Katsuji YAMASHITA, Eisaku KONISHI, ...1993 Volume 41 Issue 1 Pages 148-155
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs a part of our studies on the syntheses of benzoxazinorifamycin derivatives, 3'-hydroxy-5'-aminobenzoxazino-rifamycin derivatives were synthesized, and tested for their antimicrobial activities. The antimicrobial activites of these compounds against gram-positive and gram-negative bacteria were almost identical to those of rifampicin (RFP) and rifabutain (RFB), however, antimicrobial activities against Mycobacterium tuberculosis were superior to RFP, while being similar to RFB. 3'-Hydroxy-5'-(4-alkyl-1-piperazinyl)benzoxazinorifamycin derivatives also had in vitro potent activities against Mycobacterium avium complex (MAC). Their minimal inhibitory concentration values against MAC were 2-256 times greater than RFP and RFB. Their in vivo efficacies against M. tuberculosis and MAC, after oral administration to mice, were superior to RFP and RFB, except for RFB against M. tuberculosis activity in vivo.Although they were absorbed from the gastrointestinal tract, theri plasma levels were lower than that of RFP. Among these 5'-(4-alkyl-1-piperazinyl) derivatives, 3'-hydroxy-5'-(4-isobutyl-1-piperazinyl)benzoxazinorifamycin, compound 19 (KRM-1648), was selected as the most promising and its preliminary pharmacokinetic characteristics in mice were investigated, Compound 19 was distributed much more in tissues, especially in spleen and lung, than in plasma and had a long elimination time from tissues.View full abstractDownload PDF (1015K) -
Atsushi KUNO, Hiroyoshi SAKAI, Yoshie SUGIYAMA, Hisashi TAKASUGI1993 Volume 41 Issue 1 Pages 156-162
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn a search for new cerebral protective agents, a series of 4-(3- or 4-nitrophenyl)-6-phenylpyridines (or pyridazines) and 2-(3-nitrophenyl)-6-phenylpyridines, possessing an amino moiety at the C-3 position of the pyridine(or pyridazine) ring, were synthesized through the corresponding novel 1, 4-dihydro derivatives and tested for anti-anoxic (AA) activity in mice. Four compounds (2c, 2f, 3a, 4a) possessed significant AA activity at a dose of 32 mg/kg, i.p. These results suggest that four-atom linkages between the C-3 position of the pyridine (or pyridazine)ring and the nitrogeneous basic moiety also seems to be a prerequisite for the expression of AA activity.View full abstractDownload PDF (1063K) -
Atsushi KUNO, Hiroyoshi SAKAI, Mitsuru OHKUBO, Hisashi TAKASUGI1993 Volume 41 Issue 1 Pages 163-170
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNovel 4-(3-nitrophenyl)pyridine and 4-(3-nitrophenyl)pyrimidine derivatives, possessing three-atom linkages between basic nitrogen and at the C-5 (or C-3) position of the pyrimidine (or pyridine) ring, were synthesized and tested for anti-anoxic (AA) activity in mice. Among them, 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-(pyrrolidinomethylcarbonyl-amino)pyrimidine (10f) had the most potent AA activity (3.2 mg/kg, i.p.). Three-dimensional molecular electrostatic potentials (3D-MEP) around the nitrogeneous basic moiety of 6-methyl-5-(4-methylpiperazin-1-ylcarbonyl)-4-(3-nitrophenyl)-2-phenylpyrimidine (FK 360) and 10f were compared. The negative zone of 10f is broader and deeper and positioned somewhat differently to that of FK 360, although there is a co-occupied spacial area in part.View full abstractDownload PDF (1042K) -
Takayasu KITAGAWA, Rikio IKENISHI, Nobuo CHOMEI, Susumu TAKADA1993 Volume 41 Issue 1 Pages 171-177
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe partition equilibrium of 2-(5-methylthien-3-yl)-2, 5-dihydro-3H-pyrazolo[4, 3-c]quinolin-3-one (S-135) in n-octanol (n-OcOH)-water system was studied. S-135, which was developed as a drug for activating depressed brain function, could be easily partitioned into n-OcOH from water with a coefficient (p) of about 40 as the ratio of the concentration in the organic phase to the aqueous phase. In alkaline solution above pH 11, S-135 with a pKa, value of 9.44 decreased the parition ratio up to about 5 with an increase in nuextractable sodium salt dissociated in the aqueous phase. When extracted in more alkaline solution above pH 13, the distribution increased to p=15, in spite of the fact that sodium salt alone was present. The distribution ratio increased as the concentrations of n-OcOH and NaOH increased in the mixed solvent system of n-OcOH, n-hexane and aqueous alkaline solution. The acid-base equilibrium in n-OcOH and the partition equilibrium between n-OcOH and the strongly alkaline system were examined to determine the species extracted in n-OcOH. The extracted species of S-135 was not a monosodium salt but a complex salt associated with both the solvent molecule and NaOH. The salt isolated from the 5 N NaOH solution containing NaOH in its structure differed in physico-chemical character from the monosodium salt, thus supporting the validity of the partition equilibrium.View full abstractDownload PDF (960K) -
Baoliang CUI, Motoyuki NAKAMURA, Junei KINJO, Toshihiro NOHARA1993 Volume 41 Issue 1 Pages 178-182
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStudy on the constituents of Astragali Semen, the seeds of Astragalus complanatus R. BR. (Leguminosae), led to the identification of nine known flavonoids (1, 4, 6-12) and characterization of three new flavonol glycosides (2, 3, 5)as rhamnocitrin 3-O-β-D-apiofuranosyl(1→2)-β-D-glucopyranoside, 3-O-β-D-apiofuranosyl(1→2)-β-D-glucopyranosyl rhamonocitrin 4'-O-β-D-glucopyranoside and 3-O-β-D-apiofuranosyl(1→2)-β-D-glucopyranosyl kaempferol 4'-O-β-D-glucopyranoside, respectively. The occurrence of methyl dihydrophaseate (13), roseoside (14), blumenol C glucoside(15), (±)-3-oxo-α-ionyl glucoside (16a, 16b), tuberonic acid glucoside (17), benzylalcohol-O-α-L-arabiopyranosyl(1→6)-β-D-glucopyranoside (18), piceid (19) and deoxyrhaponticin (20) were also disclosed.View full abstractDownload PDF (757K) -
Tsutomu NAKANISHI, Keishi TANAKA, Hiroko MURATA, Midori SOMEKAWA, Akir ...1993 Volume 41 Issue 1 Pages 183-186
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree isomeric pairs of ursolic acid (1, 3, and 5) and oleanolic acid (2, 4, and 6) glycosides were isolated as predominant constituents from seeds of Patrinia scabiosaefolia FISCHER (Valerianaceae). Based on chemical and spectral evidence, their structures were established to be 3-O-[α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl] ursolic acid(1) and oleanolic acid (2), 3-O-[β-D-glucopyranosyl-(1→3)-α-L-arabinopyranosyl] ursolic acid (3) and oleanolic acid(4), and 3-O-{α-L-rhamonopyranosyl-(1→2)-[β-D-glucopyranosyl-(1→3)]-α-L-arabinopyranosyl} ursolic acid (5) and oleanolic acid (6), respectively. Glycosides 1, 5, and new compounds and named as patrinia-glycosides A-I, B-I, and B-II, respectively. Glycoside 3 is a known but is the first naturally occurring product. Ursolic acid glycosides were first found from this plant specimen.View full abstractDownload PDF (773K) -
Hiroki TERADA, Midori KOKUMAI, Takao KONOSHIMA, Mutsuo KOZUKA, Mitsuma ...1993 Volume 41 Issue 1 Pages 187-190
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo search for possible antiumor promoters, we carried out an investigation of the leaves of Amorpha fruticosa L. (Leguminosae). The novel spironone type rotenoid, amorphispironone (1), isolated together with four known rotenoids, tephrosin (2), amorphigenin (3), 12a-hydroxyamorphigenin (4) and 12a-hydroxydalpanol (5). Some of these compounds were inhibitors of Epstein-Barr virus early antigen activation induced by 12-O-tetradecanoylphorbol-13-acetate. The structure of 1 was derermined from 2D-NMR spectral data and difference NOE experiments.Amorphispironone (1) was also converted to know rotenoids in order to confirm the proposed structure.View full abstractDownload PDF (655K) -
Yoshiaki KAWASHIMA, Taro IWAMOTO, Toshiyuki NIWA, Hirofumi TAKEUCHI, T ...1993 Volume 41 Issue 1 Pages 191-195
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe size of ibuprofen microspheres fabricated by the o/w emulsion solvent diffusion method was controlled by adjusting the pH (1.0-5.0) in an aqueous dispersion phase. As the pH decreased, the diameter of the microspheres decreased, while drug entrapment efficiency and yield of microspheres remained unchanged. In the present system, the size of microspheres increased via coalescence and fusion of the oil emulsion droplets before solidification of the droplets occurred. At a lower pH, the solvent (ethanol) diffiusion rate from the oil droplets to the squeous phase was accelerated, and the drug and polymer solved in the oil droplets were rapidly deposited, forming a rigid outer-shell on the surface of the droplets to prevent the coalescence and fusion. These accelerations of solvent diffusion and rapid solidification were attributed to that the hydrogen bonding between drug and solvent, and the solubility of drug in the droplets were reduced in the strongly acidic (low pH) aqueous medium.View full abstractDownload PDF (960K) -
Ryuzo ISHINO, Hisakazu SUNADA1993 Volume 41 Issue 1 Pages 196-200
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to elucidate individually the influence of drug solubility and the matrix structure on the drug release rate from a wax matrix tablet, the intrinsic dissolution rates of drugs and the release rates of several matrix tablets consisting of various proportions of drug and hydrogenated castor oil were measured for five drugs differing in solubility. From the theoretical modification of Higuchi's equation, the boundary retreat rate of the matrix tablet was expressed with two parameters : one parameter was a constant consisting of three physical quantities (diffusivity, solubility and density), and the other was the tortuosity representing the matrix structure. As the constant term in the modified Higuchi's equation was related to the intrinsic dissolution rate constant for every drig, it was found to be an index of the drug solubility in the matrix system. From this study, therefore, it is clear that boundary retreat rate constant, namely, the drug release rate constant form the matrix tablet, was in proportion to the solubility and in inverse proportion to the square root of tortuosity. The relation between the tortuosity and the void space (porosity) was well expressed by the proposed equation derived on the basis of the free volume theory (H. Yasuda and C. E. Lamaze, J. Polymer Sic., Part A-2, 9, 1537 (1971)). It was found that the tortuosity in the matrix tablets varied with the drug species even though the porosity was the same, and also the dependency of tortuosity on porosity varied. Further, it was determined that the dependency of tortuosity on porosity could be controlled by the addition of other materials.View full abstractDownload PDF (680K) -
Novel α-Mannoside Synthesis Promoted by the Combination of Trimethylsilyl Chloride and Zinc TriflateHiroshi SUSAKI, Kunio HIGASHI1993 Volume 41 Issue 1 Pages 201-204
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSα-Mannosides were obtained in good yields and with good selectivity directly form benzyl-protected mannopyranosyl p-nitrobenzoate or acetate using a trimethylsilyl chloride-zinc triflate catalyst system.View full abstractDownload PDF (627K) -
Chihiro ITO, Tomohisa ONO, Emiko TANAKA, Yuko TAKEMURA, Toshimi NAKATA ...1993 Volume 41 Issue 1 Pages 205-207
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPummeloquinone (1), the third example of a coumarin-naphthoquinone dimer from a natural source, was isolated form the roots of several hybrid seedlings resulting from a cross of May pummelo x Marsh grapefruit (Rutaceae) grown in an orchard at Okitsu, Shizuoka, and its structure was elucidated by chamical and spectrometric methods. Synthesis of 1 was also achieved by Diels-Alder reaction between trans-dehydroosthol (3) and 2-methoxy-1, 4-benzoquinone followed by 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone (DDQ) oxidation.View full abstractDownload PDF (506K) -
Kazuo YANADA, Tetsuo NAGANO, Masaaki HIROBE1993 Volume 41 Issue 1 Pages 208-210
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactivities of the model complexes, [Fe4S4(SPh)4]2- (1) and [Fe2S2(SPh)4]2- (2), of nonheme iron-sulfur proteins were compared. Complex 1 catalyzed the oxidation of benzenethiol to diphenyl disulfide with the reduction of dioxygen to H2O. Complex 2 did not catalyze it, but the reaction proceeded after an induction period during which complex 2 was converted to complex 1. In addition, complex 1 catalyzed the reduction of 1, 4-dinitrobenzene to N -(4-nitrophenyl)hydroxylamine (21 %) and 4-nitroaniline (16 %) with the oxidation of benzenethiol to diphenyl disulfide, but complex 2 induced mainly the displacement of nitro group to phenylthio group to give 1-nitro-4-(phenylthio)benzene (92 %). It was revealed that the reactivities of complex 1 complex 2 are quite different.View full abstractDownload PDF (431K) -
Kazuo NAGASAWA, Yukako HIGUCHI, Keiichi ITO, Mamoru IMANARI, Naoyuki F ...1993 Volume 41 Issue 1 Pages 211-213
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSO-NMR at natural abundance was, for the first time, employed so effectively for the characterization between comarins (I) and chromones (2) .View full abstractDownload PDF (425K) -
Masayuki YOSHIKAWA, Shoko HATAKEYAMA, Yasuhiro INOUE, Johji YAMAHARA1993 Volume 41 Issue 1 Pages 214-216
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive new amino acid-sesquiterpene adducts, saussureamines A, B, C, D, and E, were isolated from Chinese Saussureae Radix, the dried root of Saussurea lappa CLARKE, together with a new lignan glycoside, (-)-massoniresinol 4"-O-β-D-glucopyranoside. Their structures were determined on the basis of chemical and physicochemical evidence. Among of these compounds. saussureamines A, B, C showed anti-ulcer effect on HCl / ethanol-induced lesions in rats, and saussureamine A also exhibited a inhibitory activiity on stress-induced ulcer formation in mice. During the course of these studies, facile conversion from sesquiterpene having an α-methylene γ-lactone function to amino acid-sesquiterpene adduct has been accomplished by means of Michael type addition reaction.View full abstractDownload PDF (559K) -
Takeaki NAITO, Yuko HONDA, Okiko MIYATA, Ichiya NINOMIYA1993 Volume 41 Issue 1 Pages 217-219
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new stereoselective route to isoanantine (1) and anantine (2) has been developed by the combination of three key steps : thiyl radical addition-cyclization of dienylamide, construction of the substituted imidazole, and stereoselective construction on the E-benzylidene moiety.View full abstractDownload PDF (439K) -
Takashi ITOH, Kazuhiro NAGATA, Mamiko OKADA, Akio OHSAWA1993 Volume 41 Issue 1 Pages 220-222
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVicarious nucleophilic substitution of pyridinium 1-dicyanomethylides with 1-chloromethyl phenyl sulfone gave corresponding 4-substituted derivatives. The dicyanomethylene group was readily eliminated via radical reaction to afford 4-phenylsulfonylmethylpyridines.View full abstractDownload PDF (395K) -
Satsuki OKUYAMA, Hajime KAMACHI, Toshikazu OKI1993 Volume 41 Issue 1 Pages 223-225
Published: January 15, 1993
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe sterically hindered alanine-amide bond of pradimicin A (PRM A, 1__-) was successfully cleaved via less hindered primary amide ((11)___-)by treatment with NOBF4 in eight steps to afford practical yield of 4'-N-Cbz-pradimic acid ((13)___-), which is a useful intermediate for the synthesis of alanine-exchanged derivatives.View full abstractDownload PDF (418K)
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