著者

落合 正仁 藤田 榮一 有本 正生 山口 秀夫

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.33, no.3, pp.989-997, 1985-03-25

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Oxidative cyclization of hydroxy allylsilanes utilizing the combination of a hypervalent organoiodine compound and a Lewis acid was studied. The allylsilanes 4,prepared from the γ-lactones 1 via conversion to the bis (trimethylsilylmethyl) carbinols 3,on treatment with iodosyl-benzene in the presence of boron trifluoride-etherate in an ethereal solution, afforded the 6-membered β-methylene cyclic ethers 13a and 13b in good yields. Similar treatment of the allylsilanes 8a and 8b gave the 5-membered cyclic ethers 13a and 13b. On the other hand, oxidative cyclization of the carboxylic acid 12 gave a poor yield of the lactone 21 and the major product was found to be the rearranged γ-keto acid 22. Regioselectivity in the iodine (III)-mediated cyclization of 8a is discussed.

著者

加島 竜彦 田ノ口 真理子 有本 正生 山口 秀夫

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.39, no.1, pp.192-194, 1991-01-25

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(±)-Desoxypodophyllotoxin (2), a chief component of the seeds of Hernandia ovigera L., and (±)-β-peltatin-A methyl ether (3), an analogous phenyltetralin lignan, which have 2,3-trans, 3,4-cis configuration were synthesized according to the method developed for the synthesis of hernandin (1). The syntheses were pursued using the corresponding 4-phenyl-1,2-dihydronaphthalene lactones (9 and 10) followed by cleavage of the lactone moiety to give the unsaturated hydroxy acids (11 and 12). Subsequent hydrogenation and ring closure by means of p-toluenesulfonic acid afforded both 2,3-trans, 3,4-cis and 2,3-cis, 3,4-cis ligans (2 and 13 or 3 and 14), which were isolated by preparative thin layer chromatography.

著者

平島 昭司 堀越 正美 中西 義信 平井 洋 関水 和久 水野 伝一 名取 俊二

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.35, no.2, pp.877-881, 1987-02-25

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We previously reported the purification of eukaryotic transcription factor S-II and its phosphorylated form S-H' from Ehrlich ascites tumor cells. In this work, we modified the previous purification procedure to make it quicker and simpler. By this improved procedure, involving a different solubilization method, and improved buffer solutions and centrifugation processes, S-II could be purified to homogeneity from 1 kg of frozen cells in about 10 d instead of 1 month. The purity, specific activity and total yield of S-II purified by the new method were comparable to those obtained by using the previous method.

著者

三橋 博 佐々木 希吉 清水 譲

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.11, no.11, pp.1452-1455, 1963-11-25

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The whole plant of Perugularia extensa N. E. Br. was proved to contain a glycoside mixture which showed strong Keller-Kiliani reaction, suggesting the presence of a 2-deoxy-sugars in the sugar part. The sugar fraction obtained by acid hydrolysis was found to contain D-cymarose, D-sarmentose, L-oleandrose, and D-glucose by a paper chromatographic comparison with authentic specimens. Uzarigenin and a new glycoside (m.p. 244〜248°) were found.

著者

渡辺 正純 豊田 満里子 今田 伊助 森本 浩

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.22, no.1, pp.176-182, 1974-01-25

被引用文献数

1

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Urinary metabolites from rabbits dosed with phylloquinone and dl-α-tocopheryl acetate were examined. We found that phylloquinone was excreted as conjugate forms of 2-methyl-3-(5'-carboxy-3'-methyl-2'-pentenyl)-1,4-naphthoquinone and 2-methyl-3-(3'-carboxybutyl)-1,4-naphthoquinone, and dl-α-tocopheryl acetate was excreted mainly as the conjugate form of 2,3,5-trimethyl-6-(5'-carboxy-3'-hydroxy-3'-methylpentyl)-1,4-benzoquinone lactone and in small amounts, as the conjugate form of 2,3,5-trimethyl-6-(3'-carboxybutyl)-1,4-benzoquinone.

著者

関屋 実 鈴木 次郎 柿谷 芳宏

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.18, no.6, pp.1233-1238, 1970-06-25

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Reaction for preparation of a new series of 5-acylaminooxazole-4-carboxamides has been found. 5-Acetamidooxazole-4-carboxamides were obtained by heating 2-acylamino-2-cyanoacetamides with acetic anhydride in the presence of perchloric acid. Analogous 5-form-amido derivatives were also obtained by heating the same substrates with a mixture of formic acid and acetic anhydride in the presence of hydrochloric acid. Trials for synthesis of oxazolo [5,4-d] pyrimidine-7-ol from the 5-acylaminooxazole-4-carboxamide obtained were also successful in some cases by means of heating with potassium bicarbonate solution.

著者

中島 恵美 横川 弘一 市村 藤雄 倉田 孝一 木戸 日出喜 山口 成良 山名 月中

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.35, no.2, pp.718-725, 1987-02-25

被引用文献数

4

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The disposition characteristics of biperiden were investigated in rats, rabbits, beagles, and humans, and a physiologically based pharmacokinetic model was established by using the hepatic intrinsic clearance of unbound drug concentration and the tissue-to-plasma unbound concentration ratios. Protein-binding parameters and blood-to-plasma concentration ratios were determined, and linear parameters were obtained in beagles and humans over a wide concentration range. The hepatic intrinsic clearance of humans was predicted from the animal data. The coincidence of each tissue-to-plasma Unbound concentration ratio between rats and rabbits was confirmed in the steady state, and the mean tissue-to-plasma unbound concentration ratios were used for the prediction of the plasma concentration-time courses of beagles and humans. The predicted lines fitted the observed plasma concentrations of beagles and a patient well after a single intravenous injection and repeated intramuscular administrations, respectively.

著者

崎谷 陽子 赤田 良信 河野 貞子 宮内 芳子

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.27, no.5, pp.1125-1129, 1979-05-25

被引用文献数

9

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A method was established by which glycyrrhizin and glycyrrhetinic acid present in plasma can be extracted with methanol and then separated and determined quantitatively within 10 min by means of high-speed liquid chromatography. Using this method, glycyrrhizin and glycyrrhetinic acid added to the plasma were recovered to satisfactory extents. An in situ recirculating perfusion technique showed that G is absorbed in rat small intestine in an apparent first-order process. There was no detectable amount of glycyrrhetinic acid in the blood after bolus injection of glycyrrhizin into the portal vein, althouth glycyrrhetinic acid was present in a detectable amount in the blood after oral administration. Since it is water-soluble and has a high molecular weight, glycyrrhizin is probably absorbed in the small intestine in the form of glycyrrhetinic acid. With the decline of glycyrrhetinic acid in the blood, there was a rise in the blood level of a substance which exhibited the same chromatographic behavior as glycyrrhizin. This substance appears to be a glucuronic acid conjugate formed as a metabolite of glycyrrhetinic acid, although it is not clear whether it is a mono-or diglucuronic acid conjugate or a mixture of the two. Glycyrrhizin injected into the portal vein was eliminated from the blood only slowly.

著者

森田 岩男 国本 克俊 津田 正己 但田 信一 黄瀬 正博 木村 喜代史

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.35, no.10, pp.4144-4154, 1987-10-25

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A series of 1,4-dihydropyridine-5-cyclic phosphonate derivatives, designed as analogues of 1,4-dihydropyridine-3,5-dicarboxylate calcium antagonists, was synthesized and examined for antihypertensive activity. Several compounds were proved to have activities superior or comparable to that of nifedipine in lowering blood pressure in normotensive and spontaneously hypertensive rats (SHR). Among these compounds, methyl 2,6-dimethyl-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-4(2-nitrophenyl)-1,4-dihydropyridine-3-carboxylate (31, DHP-218) was approximately 7 times more active than nifedipine in SHR and was selected for further development and clinical evaluation. The structure-activity relationships are discussed.

著者

森田 岩男 津田 正己 黄瀬 正博 杉山 信

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.36, no.3, pp.1139-1142, 1988-03-25

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Attempts were made to improve the synthesis of methyl 2,6-dimethyl-4-(2-nitrophenyl)-5-(2-oxo-1,3,2-dioxaphosphorinan-2-yl)-1,4-dihydropyridine-3-carboxylate (DHP-218), a new calcium antagonist. 2-Acetonyl-2-oxo-1,3,2-dioxaphosphosphorinane (5a), the key intermediate, was prepared from the allenylphosphonate (2) via the enaminophosphonate (4) in a good yield. Subsequently, the Knoevenagel condensation using 5a and the imine (6a) gave the benzylideneacetonylphosphonate (7a) in a good yield without the use of the Horner-Emons reaction. This condensation also gave good results for other acetonylphopshonates. The final step gave DHP-218 in a good yield through a modified Hantzsch synthesis with the use of a dehydrating agent. The overall yield was increased from 1.7% to 22%.

著者

瀬川 純 数野 憲二 松岡 正人 白波瀬 一朗 尾崎 正邦 松田 真人 冨井 由文 北野 正彦 黄瀬 正博

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.43, no.1, pp.63-70, 1995-01-15

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A seried of 1,8-disubstituted 6-fluoro-4-oxo-7-piperazinyl-4H-[1,3]thiazeto[3,2-a]quinoline-3-carboxylic acid derivatives was prepared and evaluated for antibacterial activity. In the 7-piperazinyl series, addition of a fluorine at C-8,which increased the in vitro activity for the 1-hydrogen and 1-methyl analogues and decreased it for the 1-phenyl analogue, improved the in vivo activity of all the analogues. Introduction of a methoxy group at C-8 of the 1-methyl-7-piperazinyl analogue also improved its in vivo antibacterial activity. The effect of 8-substituents on the in vitro and in vivo antibacterial activity of the 1-methyl-7-(4-methyl-1-piperazinyl) series is also discussed.

著者

小林 資正 田中 淳一 香取 岳人 北川 勲

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.38, no.11, pp.2960-2966, 1990-11-25

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Following the characterization of swinholide A (1), the major cytotoxic dimeric macrolide, three new congeneric dimeric macrolides, named swinholide B (2), swinholide C (3), and isoswinholide A (10), have been isolated from the Okinawa marine sponge Theonella swinhoei. The structures of these dimeric macrolides have been elucidated on the basis of chemical and physiocochemical evidence. These dimeric macrolides were shown to exhiit potent cytotoxicities toward KB cell lines.

著者

小湊 潔

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.17, no.11, pp.2198-2200, 1969-11-25

被引用文献数

1

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In the previous paper, scordinin A_1 was isolated from boiled garlic, and it was seemed as the biological active component in garlic. In this paper the constituents of scordinin A_1 were described from the hydrolysis products of scordinin A_1. By acid hydrolysis of scordinin A_1,fructuronic acid was detected, and by garlic enzyme allyl mercaptan was proved. And by hydrolysis with barium hydroxide, one kind of peptide, scormin, was isolated. From the above results, the author presumed that allyl thiofructuronic acid combined with scormin to form scordinin A_1,and on the chemical structure of scormin will be discussed in Part III in this series.

著者

西部 三省 木下 英弘 武田 秀勝 岡野 五郎

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.38, no.6, pp.1763-1765, 1990-06-25

被引用文献数

16

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Ten phenolic compounds, isofraxidin (1), (+)-syringaresinol-di-O-β-D-glucoside (2), syringin (3), chlorogenic acid (4), isofraxidin-7-O-β-D-glucoside (5), 2,6-dimethoxy-p-benzoquinone (6), (+)-pinoresinol-O-β-D-glucoside (7), (+)-syringaresinol-O-β-D-glucoside (8), (+)-pinoresinol-di-O-β-D-glucoside (9), and (+)-medioresinol-di-O-β-D-glucoside (10), were isolated from the stem bark of Acanthopanax senticosus HARMS and identified, respectively.The aquenous extract of the stem bark exhibited a prolonging effect on the exercise time to exhaustion in chronic swimming stressed rats. The effect on the exercise time in the chronic swimming stressed rats was respectively tested for compounds 2 and 4,which are major constituents of the stem bark. As a result, it was indicated that compound 2 is the compound responsible for part of the pharmacological effect which the aqueous extract of the stem bark showed.

著者

Harinantenaina Liva Tanaka Michi Takaoka Shigeru ODA Munehiro MOGAMI Orie UCHIDA Masayuki ASAKAWA Yoshinori

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.54, no.7, pp.1017-1021, 2006-07-01

被引用文献数

4 150

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Bioguided fractionation of the methanol extract of Momordica charantia dried gourds led to the isolation of three new cucurbitane triterpenoids (1-3), together with eight known compounds (4-11). The aglycone of momordicoside I was isolated from the ether soluble fraction in a high amount. The structures of the metabolites were established on the basis of one and two dimensional NMR spectroscopic evidence, X-ray analysis, and comparison with the reported data in the literature. A number of phytochemicals have been isolated from Momordica charantia but the constituents responsible for the hypoglycaemic/antihyperglycaemic activities have not been determined. Therefore, in order to evaluate the contribution of the cucurbitane triterpenoids of the ether fraction of M. charantia methanol extract to in vivo anti-diabetic effects, the major compounds, 5β,19-epoxy-3β,25-dihydroxycucurbita-6,23(E)-diene (4), and 3β,7β,25-trihydroxycucurbita-5,23(E)-dien-19-al(5) have been tested and have shown blood hypoglycaemic effects in the diabetes-induced male ddY mice strain at 400 mg/kg. The two aglycones of charantin did not show any hypoglycaemic effects. Our finding is the first demonstration that major pure cucurbutanoid compounds of M. charantia have in vivo hypoglycaemic effects.

著者

MINH DUC Nguyen THOI NHAM Nguyen 笠井 良次 伊藤 優子 山崎 和男 田中 治

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.41, no.11, pp.2010-2014, 1993-11-15

被引用文献数

6

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From rhizomes and roots of Panax vietnamensis HA et GRUSHV., Araliaceae, commonly known as Vietnamese Ginseng, two new acetylated saponins named vina-ginsenoside-R1 (13) and vina-ginsenoside-R2 (15) were isolated. On the basis of chemical and spectral data, 13 was formulated as monoacetyl 24(S)-pseudo-ginsenoside-F_<11> and 15 was proved to be monoacetyl majonoside-R2.Besides the two new saponins and β-sitosteryl-3-O-β-D-glucopyranoside, sixteen known saponins were also isolated and identified. Dammarane saponins : ginsenoside-Rh_1 and 20(R)-ginsenoside-Rh_1 (1), ginsenosides-Rg_1 (2), -Re (3), -Rd(6), -Rb_3 (7), -Rb_2 (8), -Rb_1 (9), pseudo-ginsenoside-RS_1 (=monoacetyl ginsenoside-Re, 4), notoginsenosides-R1 (5) and -Fa (10). Ocotillol-type saponins : pseudo-ginsenoside-RT_4 (11), 24(S)-pseudo-ginsenoside-F_<11> (12), majonosides-R1 (16) and -R2 (14). Oleanolic acid saponins : ginsenoside-Ro (=chikusetsusaponin V, 17) and hemsloside-Ma3 (18), a saponin previously isolated from a cucurbitaceous plant, Hemsleya macrosperma C. Y. WU.Despite having large horizontally elongated rhizomes, the underground part of this plant contains mainly dammarane saponins and a small amount of oleanolic acid saponins. In addition, the yield of ocotillol-type saponins, especially majonoside-R2,is surprisingly very high (more than 5% and ca. half of the total yield of saponin). This characteristic saponin composition has made Vietnamese Ginseng an interesting species among Panax spp.

著者

西出 喜代治 山村 真理子 小堀 武夫 常本 大英 近藤 聖 佐藤 清

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.36, no.7, pp.2354-2361, 1988-07-25

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The syntheses and the antibacterial activities of new 3-dimethoxyphosphinylmethyl and 3-dihydroxyphosphinylmethyl cephalosporins I-(Z), II-(Z), III-(Z) and III-(E), possessing the chloromethylene or methoxyimino substituent at the α-position to the 7-(2-aminothiazol-4-yl)acetamido or 7-(thiazol-4-yl)acetamido moiety of the cephem nucleus, are described. The key steps of these syntheses were the Michaelis-Arbusov reaction of the 3-halomethylcephem 1 with trimethyl phosphite and the dealkylation reactions of both the dimethoxyphosphinyl group and the p-methoxybenzyl ester of 7a, b-(Z) by treatment with bromotrimethylsilane to afford 9a, b-(Z).

著者

坂田 紳二 米井 清志郎 吉野 宏

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.30, no.7, pp.2583-2585, 1982-07-25

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A new method for the synthesis of 2-substituted 6-methylpurine ribosides from guanosine is described. Reaction of N (2), O (2'), O (3'), O (5')-tetraacetyl-O (6)-p-toluenesulfonylguanosine with carbanion from ethylacetoacetate gave the 6-ethoxycarbonylmethyl derivative, which was further converted to 2-amino-6-methylpurine riboside by deacetylation and decarboxylation. Replacement of the amino group of the compound by the fluoro group was achieved by the Schiemann reaction. The fluoro group could easily be replaced by several nucleophiles. As a result, 2-methylthio-, and 2-dimethylamino-6-methyl-9-β-D-ribofuranosylpurines could be effectively prepared.

著者

Gao Jiang-Jing Min Byung-Sun Ahn Eun-Mi NAKAMURA Norio LEE Hyeong-Kyu HATTORI Masao

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.50, no.6, pp.837-840, 2002-06-01

被引用文献数

6 119

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Three new lanostante-type triterpene aldehydes, named lucialdehydes A-C (1-3), were isolated from the fruiting bodies of Ganoderma lucidum, together with ganodermanonol (4), ganodermadiol (5), ganodermanondiol (6), ganodermanontriol (7), ganoderic acid A (8), ganoderic acid B8 (9), and ganoderic acid C1 (10). The structures of the new triterpenes were determined as (24E)-3β-hydroxy-5α-lanosta-7,9(11),24-trien-26-al (1), (24E)-3,7-dioxo-5α-lanosta-8,24-dien-26-al (2), and (24E)-3β-hydroxy-7-oxo-5α-lanosta-8,24-dien-26-al (3), respectively, by spectroscopic means. The cytotoxicity of the compounds isolated from the ganoderma mushroom was tested in vitro against Lewis lung carcinoma (LLC), T-47D, Sarcoma 180, and Meth-A tumor cell lines. Lucialdehydes B, C (2, 3), ganodermanonol (4) and ganodermanondiol (6) showed cytotoxic effects on tested tumor cells. Of the compounds, lucialdehyde C (3) exhibited the most potent cytotoxicity against LLC, T-47D, Sarcoma 180, and Meth-A tumor cells with ED_<50> values of 10.7, 4.7, 7.1, and 3.8 /μg/ml, respectively.

著者

Maeda Takuya Manabe Yuki Yamamoto Masashi YOSHIDA Munehiro OKAZAKI Kiyo NAGAMUNE Hideaki KOURAI Hiroki

出版者

公益社団法人日本薬学会

雑誌

Chemical & pharmaceutical bulletin (ISSN:00092363)

巻号頁・発行日

vol.47, no.7, pp.1020-1023, 1999-07-15

被引用文献数

18

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Potent new biocides against both bacteria and fungi, 4,4'-(1,6-hexamethylenedioxydicarbonyl)bis(1-alkylpyridinium iodide)s (4DOCBP-6,n) (alkyl chain length, n=8,10,12,14,16 and 18) were synthesized. 4DOCBP-6,n is bis-quaternary ammonium compound (bis-QAC) and has a symmetrical dimeric structure which is composed of two alkylpyridinium iodides connected with a hexamethylenedioxydicarbonyl chain. 4DOCBP-6,10 and 4DOCBP-6,12 exhibited wide and effective antimicrobial spectra, compared with those of typical bactericides, N-dodecylpyridinium iodides (P-12) and benzyldimethyldodecylammonium chloride (BAC), or a popularly-used fungicide, 2-(4-thiazolyl)benzimidazole (TBZ). Their superior properties would be due to the unique dimeric structure which contains two active moieties in a molecule.