Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
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Volume 50, Issue 8
Displaying 1-30 of 30 articles from this issue
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Regular Articles
  • New Steroidal Alkaloids from Fritillaria imperialis and Their Cholinesterase Inhibiting Activities
    Atta-ur-Rahman, Muhammad Nadeem Akhtar, Muhammad Iqbal Choudhary, Yos ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1013-1016
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1013
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    Two new cevanine steroidal alkaloids, impericine (1) and forticine (2) along with known bases delavine (3), persicanidine A (4), and imperialine (5) were isolated from the bulbs of Fritillaria imperialis. The structures of impericine (1) [(20R,22S,25S)-5α-cevanin-23-ene-3β,6β,16β-triol] and forticine (2) [(20S,22S,25S)-5α-cevanine-3β,6β-diol] were determined with the help of spectroscopic studies. These steroidal bases showed anti-acetylcholinesterase and anti-butyrylcholinesterase inhibitory activity.
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  • NMR Study on the Low-Affinity Interaction of Human Serum Albumin with Diclofenac Sodium
    Zhu-Sheng Ji, Cong-Gang Li, Xi-An Mao, Mai-Li Liu, Ji-Ming Hu
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1017-1021
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1017
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    The low-affinity interaction between human serum albumin (HSA) and Diclofenac sodium (DCF) was studied using NMR techniques. Both 13C-NMR chemical shift and linewidth show that the dichlorophenyl ring in DCF molecule plays a primary role in its interaction with HSA. Langmuir adsorption isotherm was applied to evaluate the association constant K and the number of binding sites n of the drug/HSA complex through 1H-NMR spin-lattice relaxation measurement. The results indicate that Langmuir isotherm can perfectly explain the capacity of low-affinity binding of proteins for the ligands.
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  • Crystal Structure of the Alcoholates and the Ansolvate of PNU-97018, an Angiotensin II Receptor Antagonist
    Hiroaki Ishii, Kentaro Yamaguchi, Hiroko Seki, Shigeru Sakamoto, Yuich ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1022-1027
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1022
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    The title compound, PNU-97018 {systemic name: 2-butyl-3,6,7,8,9,11-hexahydro-6,9-dimethyl-3-{[2′-(2H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl}-6,9-ethano-4H-imidazo[4,5-d]-pyridazino[1,2-a]pyridazin-4-one} is a newly developed angiotensin II receptor antagonist. The compound and its methanolate and ethanolate were characterized by X-ray crystallography and thermal analysis. The methanolate and ethanolate crystals have an almost identical molecular conformation and crystal packing. In both alcoholates, each alcohol molecule is fixed to the compound with a molar ratio of 1 : 1 by a hydrogen bond between the hydroxyl group of the alcohol molecule and the tetrazole group of the compound. The hydroxyl group of each alcohol molecule further links with the imidazole ring of the neighboring compound by hydrogen bond to form a hydrogen-bond network in both alcoholates. A tunnel-like structure that includes alcohol molecules is formed in each alcoholate. The ansolvate crystal showed completely different thermal and X-ray crystallographic characteristics from the alcoholates, where the compound molecules were directly linked by hydrogen bonds between the tetrazole group of a molecule and the imidazole ring of the neighboring molecule. The position of the hydrogen atom in the tetrazole ring was different between the ansolvate and alcoholates. Unlike alcoholates, a layer structure stacked on the b—c plane was observed in the ansolvate crystal. It was concluded that the molecular conformation and the arrangement of the compound molecules were largely different between ansolvate and alcoholate crystals.
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  • A New Synthetic Route towards the Mono-O-protected Anti-conformationally Constrained Pyrimidine Acyclic Nucleoside
    Chi-Tsan Liu, Tsu-Chiang Tu, Ling-Yih Hsu
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1028-1030
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1028
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    Novel synthetic approach to mono-O-protected anti-conformationally constrained pyrimidine acyclic nucleoside was attained from the coupling of lithiated 2,4-dimethoxy-6-methylpyrimidine with 1-benzyloxy-3-(tert-butyldiphenylsilyloxy)propan-2-one, followed by the sequential reactions of methylthiomethylation, cyclization, hydroxylation, and dealkylation.
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  • Pregnane and Pregnane Glycosides from the Malagasy Plant, Cynanchum aphyllum
    Tripetch Kanchanapoom, Ryoji Kasai, Kazuhiro Ohtani, Marta Andriantsif ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1031-1034
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1031
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    A new 8,14-seco-pregnane type of steroid called cynaphyllogenin and its eight glycosides, cynaphyllosides A—H, were isolated from the aerial parts of Cynanchum aphyllum. The structures of these compounds were elucidated based on chemical and spectroscopic evidence.
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  • Iridoids and Anthraquinones from the Malaysian Medicinal Plant, Saprosma scortechinii (Rubiaceae)
    Sui-Kiong Ling, Akiko Komorita, Takashi Tanaka, Toshihiro Fujioka, Kun ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1035-1040
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1035
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    A further investigation of the leaves and stems of Saprosma scortechinii afforded 13 compounds, of which 10 are new compounds. These were elucidated as the bis-iridoid glucosides, saprosmosides G (1) and H (2), the iridoid glucoside, 6-O-epi-acetylscandoside (3), and the anthraquinones, 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone (4), 1-methoxy-3-hydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-β-primeveroside (5), 1,3-dihydroxy-2-carbomethoxy-9,10-anthraquinone 3-O-β-primeveroside (6), 1,3,6-trihydroxy-2-methoxymethyl-9,10-anthraquinone (7), 1-methoxy-3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (8), 1,3,6-trihydroxy-2-hydroxymethyl-9,10-anthraquinone 3-O-β-primeveroside (9), and 3,6-dihydroxy-2-hydroxymethyl-9,10-anthraquinone (10). Structure assignments for all compounds were established by means of mass and NMR spectroscopies, chemical methods, and comparison with published data. The new anthraquinones were derivatives of munjistin and lucidin.
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  • Studies on the Constituents of Lonicera Species. XVII. New Iridoid Glycosides of the Stems and Leaves of Lonicera japonica THUNB
    Koichi Machida, Hiromi Sasaki, Takeyoshi Iijima, Masao Kikuchi
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1041-1044
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1041
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    Four new iridoid glycosides, named L-phenylalaninosecologanin (1), 7-O-(4-β-D-glucopyranosyloxy-3-methoxybenzoyl)secologanolic acid (2), 6′-O-(7α-hydroxyswerosyloxy)loganin (3) and (Z)-aldosecologanin (5), were isolated, together with a known one, newly named (E)-aldosecologanin (4), from the stems and leaves of Lonicera japonica. Their structures were established on the basis of chemical and spectral data.
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  • New Farnesane-Type Sesquiterpenes, Hedychiols A and B 8,9-Diacetate, and Inhibitors of Degranulation in RBL-2H3 Cells from the Rhizome of Hedychium coronarium
    Toshio Morikawa, Hisashi Matsuda, Yasuko Sakamoto, Kazuho Ueda, Masayu ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1045-1049
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1045
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    Two new farnesane-type sesquiterpenes, hedychiols A and B 8,9-diacetate, were isolated from the methanolic extract of the fresh rhizome of Hedychium coronarium KOEN. cultivated in Japan. Their stereostructures were elucidated on the basis of chemical and physicochemical evidence. The inhibitory effects of isolated constituents on the release of β-hexosaminidase from RBL-2H3 cells were examined, and hedychilactone A and coronarin D were found to show the inhibitory activity.
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  • Synthetic Studies on Selective Type 4 Phosphodiesterase (PDE 4) Inhibitors. 1. Structure–Activity Relationships and Pharmacological Evaluation of 1,8-Naphthyridin-2(1H)-one Derivatives
    Kazuhisa Takayama, Masahiro Iwata, Hiroyuki Hisamichi, Yoshinori Okamo ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1050-1059
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1050
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    In order to develop novel and orally active phosphodiesterase (PDE) 4 inhibitors, random screening was performed using our chemical library to find YM-10335 possessing the 1,8-naphthyridin-2(1H)-one skeleton which is a completely different structure from rolipram. In this report, the syntheses and structure–activity relationships of the YM-10335 derivatives were described. Some compounds showed selective inhibitory activities for PDE 4 derived from human peripheral blood cells and no effect on the other PDE types (1, 2, 3, 5). The inhibition of the tumor necrosis factor-alpha (TNF-α) release in vitro and the carrageenan-induced pleurisy in rats were also described.
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  • Scandium(III) Trifluoromethanesulfonate Catalyzed Aromatic Nitration with Inorganic Nitrates and Acetic Anhydride
    Atsushi Kawada, Shigemitsu Takeda, Kazumi Yamashita, Hitoshi Abe, Taka ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1060-1065
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1060
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    The rare earth metal(III) trifluoromethanesulfonate (rare earth metal(III) triflate, RE(OTf)3) was found to be an efficient catalyst for aromatic nitration with carboxylic anhydride–inorganic nitrate as the nitrating agent. In the presence of a catalytic amount of RE(OTf)3, the nitration of substituted benzenes proceeded to afford the corresponding nitrobenzenes. Especially, scandium(III) trifluoromethanesulfonate (scandium(III) triflate, Sc(OTf)3) is the most active catalyst among our tested Lewis acids. It was also found that acetic anhydride–Al(NO3)·9H2O is the most active nitrating agent in this system.
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  • Asymmetric Synthesis of a Selective Endothelin A Receptor Antagonist
    Yoshiaki Kato, Kenji Niiyama, Hideki Jona, Shigemitsu Okada, Atsushi A ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1066-1072
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1066
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    An asymmetric synthesis of a selective endothelin A receptor antagonist 1b is described. Asymmetric conjugate addition of aryllithium derived from 18 to the chiral oxazoline 17 followed by hydrolysis afforded 15 in 96% ee via purification as (S)-(−)-1-phenylethylamine salt. Pd(OAc)2/dppf (1,1′-bis(diphenylphosphino)ferrocene) catalyzed carbonylation followed by chemoselective addition of aryllithium derived from 23 which gave ketone 24. Diastereoselective reduction of the ketone with catecholborane followed by concomitant activation of the resulting alcohol and cyclization gave the late intermediate 26. Introduction of amino moiety on the pyridine ring by imidoyl rearrangement followed by deprotection and purification by crystallization furnished the enantiomerically pure target molecule 1b in 8% overall yield from 16.
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  • Structure–Activity Relationships of 6-Nitroquinazolines: Dual-Acting Compounds with Inhibitory Activities toward both TNF-α Production and T Cell Proliferation
    Masanori Tobe, Yoshiaki Isobe, Hideyuki Tomizawa, Takahiro Nagasaki, F ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1073-1080
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1073
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    We synthesized various 6-nitroquinazolines by modifying the structure of compound 1 and evaluated their inhibitory activities toward both TNF-α production and T cell proliferation responses. The presence of the unsubstituted piperazine ring at the C(7)-position was required for both inhibitory activities. In this series of compounds, 5d and 5f, containing the 4-fluorophenyl and 3,4-difluorophenyl moiety, respectively, at the C(4)-position, showed the suppressing effects toward both responses with low cell growth inhibition. Furthermore, the oral administration of these compounds mentioned above at doses of 30 and 100 mg/kg also resulted in significant inhibition of TNF-α production induced by LPS in vivo.
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  • Synthesis of Optically Active Homocysteine from Methionine and Its Use in Preparing Four Stereoisomers of Cystathionine
    Tadashi Shiraiwa, Kazuo Nakagawa, Norito Kanemoto, Tomohiro Kinda, Hir ...
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1081-1085
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1081
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    In order to synthesize four stereoisomers of cystathionine (CYT), D- and L-homocysteines (D- and L-Hcy) were synthesized from methionine (Met) by a facile procedure. L-Met was reacted with dichloroacetic acid in concentrated hydrochloric acid under reflux to give (4S)-1,3-thiazane-2,4-dicarboxylic acid hydrochloride [(4S)-TDC·HCl]. L-Hcy was obtained by treatment of (4S)-TDC·HCl with hydroxylamine. D-Hcy was also synthesized from D-Met via (4R)-TDC·HCl intermediate. The obtained D- and L-Hcy were condensed with (R)- and (S)-2-amino-3-chloropropanoic acid hydrochlorides under alkaline conditions to give four stereoisomers of CYT.
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  • Regulation of Lithospermic Acid B and Shikonin Production in Lithospermum erythrorhizon Cell Suspension Cultures
    Hirobumi Yamamoto, Ping Zhao, Kazufumi Yazaki, Kenichiro Inoue
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1086-1090
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1086
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    Cell suspension cultures of Lithospermum erythrorhizon produced a large amount of lithospermic acid B, a caffeic acid tetramer, as well as shikonin derivatives (each ca. 10% of dry wt.) when cultured in shikonin production medium M-9. Various culture factors for increasing the production of lithospermic acid B were investigated. Lithospermic acid B production was inhibited by 2, 4-D or NH4+, whereas it was stimulated by Cu2+. These regulatory patterns were similar to those for the production of shikonin derivatives in these cell cultures, suggestive of close relations and similar metabolic regulation between the production of these compounds. Cultivation under light illumination, however, showed that these metabolisms were independently regulated. In particular, blue light showed a stimulatory effect on lithospermic acid B production, while shikonin production was strongly inhibited, indicative of an effective condition for lithospermic acid B production.
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  • Isolation and Structure Determination of Six Glucocerebrosides from the Starfish Luidia maculata
    Satoshi Kawatake, Kazufumi Nakamura, Masanori Inagaki, Ryuichi Higuchi
    Article type: Regular Article
    Subject area: [not specified]
    2002 Volume 50 Issue 8 Pages 1091-1096
    Published: 2002
    Released on J-STAGE: August 01, 2002
    DOIhttps://doi.org/10.1248/cpb.50.1091
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    Two new glucocerebrosides, luidiacerebroside A (2) and B (6), were isolated from the cerebroside molecular species obtained from the less polar fraction of the CHCl3/MeOH extract of the starfish Luidia maculata using HPLC. Four known cerebrosides, CE-2b (1), astrocerebroside B (3), acanthacerebroside B (4), and CE-3-2 (5) have also been isolated and characterized. The structures of these cerebrosides were determined on the basis of chemical and spectroscopic evidence. Mass spectrometry of dimethyl disulfide derivatives was useful for the determination of the double-bond position in the long-chain base.
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