著者

小林 義郎 熊懐 稜丸 大沢 昭緒 村上 慎一 中野 隆治

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.26, no.4, pp.1247-1249, 1978-04-25 (Released:2008-03-31)

被引用文献数

31 45

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Photochemical trifluoromethylation of pyridine gave a mixture of three (trifluoromethyl) pyridines. Pyrrole and N-methylpyrrole were trifluoromethylated in α-position. Benzene gave very low yield of benzotrifluoride.

著者

小林 義郎 熊懐 稜丸 佐藤 進 原 伸祀 近見 永一

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.18, no.11, pp.2334-2339, 1970-11-25 (Released:2008-03-31)

被引用文献数

39 65

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Trifluoromethyl iodide reacts with aryl halide in the presence of copper powder to give aryltrifluoromethane derivatives in a fairly good yield. This newly observed reaction is applicable to heterocyclic halides as well as benzene derivatives. Activities of halides are in the following order of readiness : iodide>bromide>chloride. Effects of solvents and natures of copper were examined.

著者

織田 範一 小林 和弘 植田 泰誠 伊藤 磯雄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.26, no.8, pp.2578-2581, 1978-08-25 (Released:2008-03-31)

被引用文献数

1 3

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Diels-Alder reaction of 5-nitro-1, 4-naphthoquinone (1) and unsymmetrical butadienes was carried out. Reaction of 1 and 2-methyl-1, 3-butadiene gave 1, 4, 4a, 9a-tetrahydro-2-methyl-5-nitro-anthraquinone (2) and its 3-methyl analogue (3) at the ratio of 9.2 : 1. Reaction of 1 and 1, 3-pentadiene gave 1, 4, 4a, 9a-tetrahydro-1-methyl-8-nitroanthraquinone (8) and its 5-nitro analogue (9) at the ratio of 10 : 7. Their structures have been determined by aromatization to methyl-nitroanthraquinones.

著者

梅山 秀明

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.27, no.12, pp.3180-3182, 1979-12-25 (Released:2008-03-31)

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Closed shell LCAO-SCF-MO calculations were carried out for the chloride anion cryptate, which is of interest in connection with organic anion receptors and carriers. In the Cl- cryptate of [(C9H18)3(NH)2Cl]+Cl-, Cl- is encapsulated in the host molecule. Since the positions of the two protons bonded to the two nitrogens of the host molecule were not determined in the reported X-ray diffraction analyses, the positions of the two protons in the inclusion complex were decided by calculation using the ab initio molecular orbital method. A structure N+-H…Cl-…H-N+ in which Cl- is in between the two nitrogens was most stable at values of γ(NN) less than 7.0 Å. The structure N+-H…Cl-…H-N+ was most stable at γ(NN)=6.023 Å. In the most stable structure, the two protons are covalently bonded to the two nitrogens. The structure obtained by geometry optimization for the two ammonium ions and Cl- was similar to that determined by X-ray diffraction analysis.

著者

山田 幸子 大森 正幸 高山 浩明

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.27, no.12, pp.3196-3198, 1979-12-25 (Released:2008-03-31)

被引用文献数

11 14

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24, 24-Difluoro-1α, 25-dihydroxyvitamin D3 (1) has been synthesized from 24, 24-difluoro-5β-cholestane-3α, 25-diol (2) as an antimetabolic analogue of 1α, 25-dihydroxyvitamin D3 to study the role of the 24-hydroxylation in the metabolism of vitamin D3.

著者

舟越 和久 稲田 治明 浜名 政和

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.32, no.12, pp.4731-4739, 1984-12-25 (Released:2008-03-31)

参考文献数

14

被引用文献数

3 5

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Isoquinoline 2-oxide (1) reacts with cyanoacetic acid in the presence of Ac2O to afford various types of 1-substituted isoquinolines (2, 4, 6, and 7) and N-ylides (3 and 5a) depending upon the reaction conditions and processing procedures (Table I). The reaction in Ac2O gives initially α-acetoxycarbonyl-1-isoquinolineacetonitrile (2) and 2-isoquinolinio-acetoxycarbonylcyanomethylide (3), and that in Ac2O-dimethylformamide yields only 3. Products 2 and 3 are readily convertible into α-acetyl-1-isoquinolineacetonitrile (4) and 2-isoquinolinio-acetylcyanomethylide (5a), respectively, by processing involving heating. The reaction in ethanol gives ethyl α-cyano-1-isoquinolineacetate (6) and di (1-isoquinolyl) acetonitrile (7). The reaction of 1 with benzoylacetonitrile affords both the corresponding 1-substituted isoquinoline (10) and N-ylide (11). Reactions with ethyl benzoylacetate and, methyl and ethyl acetoacetates produce 1-substituted isoquinolines (12 and 14a, b) and 4-acetoxyisoquinoline (13), no ylide being formed.

著者

亀谷 哲治 川村 邦昭 津吹 政可 本多 利雄

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.33, no.11, pp.4821-4828, 1985-11-25 (Released:2008-03-31)

参考文献数

32

被引用文献数

15 20

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(-)-α-Cuparenone, (17) was synthesized from the olefinic aldehyde (9) by utilizing a rhodium-catalyzed cyclization as a key step. The optically active aldehyde (7) was prepared by employing an asymmetric [2, 3] sigmatropic rearrangement of a quaternary L-prolinol derivative. The aldehyde (7) was also converted into its antipodal form (24) in several steps.

著者

黄 永 豊田 英尚 輿石 一郎 戸井田 敏彦 今成 登志男

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.43, no.12, pp.2182-2186, 1995-12-15 (Released:2008-03-31)

参考文献数

28

被引用文献数

5 7

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Depolymerized holothurian glycosaminoglycan (DHG) produced artificially from sea cucumber has an anticoagulant and antithrombotic activity. In the present study, we attempted to determine the plasma level of DHG using a chemical procedure. A general method for determination of chondroitin sulfates by forming unsaturated disaccharides with chondroitinase digestion was difficult to apply to DHG, because it was resistant to any chondroitinase digestion. We therefore developed a highly sensitive postcolumn HPLC method for determination of intact DHG. DHG was applied to Asahipak NH2P-50, an amino-bonded column, eluted by alkaline solution and then detected with arginine under a strong alkaline condition as a postcolumn reagent. The limit of detection for DHG was 10ng. The present method was applicable to the determination of DHG in plasma after intravenous administration.

著者

樫原 宏 末宗 洋 常広 菜穂美 酒井 浄

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.9, pp.2581-2582, 1990-09-25

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The enones (II), which were obtained from dimethyl 4,5-isopropylidenedioxy-2-oxopentylphosphonate (Ia) and various aldehydes, were easily converted to 2-alkenylfurans (III) by treatment with p-TsOH in MeOH. In a similar manner, the furfuryl phosphonate (IVa) and the 3-methylfurfuryl phosphonate (IVb) were obtained from Ia and its 3-methylated analogue (Ib), respectively.

著者

Surat Laphookhieo John Keith Syers Rattana Kiattansakul Kan Chantrapromma

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.54, no.5, pp.745-747, 2006 (Released:2006-05-01)

参考文献数

12

被引用文献数

40 64

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A new prenylated xanthone, 5-O-methylcelebixanthone (1), together with six known compounds; celebixanthone (2), 1,3,7-trihydroxy-2,4-di(3-methylbut-2-enyl)xanthone (3), cochinchinone A (4), α-mangostin (5), β-mangostin (6) and cochinchinone C (7) were isolated from roots of Cratoxylum cochinchinense. Their structures were elucidated by spectroscopic methods. Compounds 2 and 4—7 showed cytotoxic activity against the human lung cancer cell line (NCI-H187) with IC50 values ranging from 0.65 to 5.2 μg/ml. Compounds 1, 2, 6 and 7 also showed antimalarial activity against Plasmodium falciparum with IC50 values of 3.2, 4.9, 7.2 and 2.6 μg/ml, respectively.

著者

Fortin Helene Tomasi Sophie Jaccard Philippe ROBIN Valerie BOUSTIE Joel

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.49, no.5, pp.619-621, 2001-05-01

参考文献数

18

被引用文献数

19

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A new coumarin identified as 5-hydroxy-6-methoxy-7-(3-methyl-but-2-enyloxy)-2H-1-benzopyran-2-one (isoobtusitin) was isolated from Psiadia dentata. This compound showed, in vitro, a moderate inhibitory activity against poliovirus and a very weak activity against (HIV), whereas it was inactive against (HSV1), (VSV), and murine tumoral cell lines (3LL, L1210).

著者

矢島 治明 小川 博 藤井 信孝 船越 奨

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.25, no.4, pp.740-747, 1977-04-25 (Released:2008-03-31)

被引用文献数

12 21

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Among various dilute sulfonic acids tested, 2 to 4N ethanesulfonic acid in acetic acid or methylenechloride was found suitable as a deprotecting reagent for the acid labile α-amino protecting groups, such as Boc and Z(OMe), which are currently removed by trifluoroacetic acid or dilute hydrochloric acid, since the deprotection occured selectively within 60 minutes at room temperature leaving intact other side chain protecting groups, such as Z, benzyl ester, S-p-methoxybenzyl and NG-p-methoxybenzenesulfonyl groups. This reagent was applied to the synthesis of three model peptides ; Met and Leu-enkephalin and endorphin.

著者

矢島 治明 木曽 良明 小川 宏 藤井 信孝 入江 寛

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.23, no.5, pp.1164-1166, 1975-05-25 (Released:2008-03-31)

被引用文献数

27 37

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Acidolytic cleavage of various protecting groups currently employed in peptide chemistry by fluorosulphonic and methanesulphonic acids was examined.

著者

木曽 良明 宇川 和子 中村 静夫 伊藤 薫 秋田 正

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.28, no.2, pp.673-676, 1980-02-25 (Released:2008-03-31)

参考文献数

18

被引用文献数

41 58

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A thioanisole-trifluoroacetic acid (TFA) system was found to deprotect Tyr (Bzl) quantitatively at 25°within 3 hr by a push-pull mechanism without O-to-C rearrangements. This new deblocking system did not completely deprotect Ser (Bzl) and Thr (Bzl), but deprotected Lys (Z) quantitatively.

著者

Nobuko Mibu Kazumi Yokomizo Marina Sano Yuuna Kawaguchi Kenta Morimoto Syunsuke Shimomura Ryo Sato Nozomi Hiraga Aya Matsunaga Jian-Rong Zhou Tomonori Ohata Hatsumi Aki Kunihiro Sumoto

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.66, no.8, pp.830-838, 2018-08-01 (Released:2018-08-01)

参考文献数

15

被引用文献数

18

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We report the preparation of new C3- and CS-symmetrical molecules constructed on a triazine (TAZ) template. Anti-herpes simplex virus type 1 (anti-HSV-1) and cytotoxic activities against Vero cells of synthesized TAZ derivatives were evaluated. The results suggested that the presence of an electron-donating group(s) on the benzene ring in benzylamine groups on the TAZ template is an important structural factor for expressing a high level of anti-HSV-1 activity and low cytotoxicity for these C3 types of TAZ derivatives. Among the tested TAZ derivatives, compounds 4f and 7h showed the highest anti HSV-1 activities (EC50=0.98 and 1.23 µM, respectively) and low cytotoxic activities to Vero cells (50% cytotoxic concentration (CC50)=292.2 and >200 µM, respectively).

著者

秋田 弘幸 古市 昭也 越地 弘子 堀越 弘毅 大石 武

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.32, no.4, pp.1342-1348, 1984-04-25 (Released:2008-03-31)

参考文献数

12

被引用文献数

6 8

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The synthesis of optically active α-hydroxy β-methyl esters V by means of microbiological reduction of the corresponding α-keto β-methyl esters IV was carried out. Methyl 3-phenyl-2-oxobutyrate 3 was found to be reduced by a variety of yeasts to the α-hydroxy β-methyl esters (7b and 8a) with (2R, 3S)-and (2R, 3R)-configurations, respectively, and by carrying out screening experiments, yeasts which give products with high optical purity were actually found.

著者

秋田 弘幸 古市 昭也 越地 弘子 堀越 弘毅 大石 武

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.32, no.4, pp.1333-1341, 1984-04-25 (Released:2008-03-31)

参考文献数

13

被引用文献数

14 17

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Microbiological asymmetric reduction of methyl 3-(2-furyl)-2-methyl-3-oxopropionate (5) by various yeasts was carried out. Four kinds of methyl 3-(2-furyl)-3-hydroxy-2-methyl propionates (6a-6d) could be obtained separately from the prochiral β-keto ester 5 by reduction with properly selected microorganisms. In particular, the desired syn-isomer 6a was obtained with high optical purity (>99% e.e.). Both the chemical yield and the optical purity of the reduction products (6a-6d) were significantly improved when fermentation was carried out on a large scale using a 30 1 jar fermentor or a 200 1 tank.

著者

秋田 弘幸 古市 昭也 越地 弘子 堀越 弘毅 大石 武

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.31, no.12, pp.4384-4390, 1983-12-25 (Released:2008-03-31)

参考文献数

13

被引用文献数

10 13

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In order to synthesize four optically active methyl 2-methylmalates (10-13), microbiological asymmetric reduction of the corresponding dimethyl 2-methyl-3-oxosuccinate (9) was carried out. The β-keto diester 9 was found to be reduced by fermenting baker's yeast (Saccharomyces cerevisiae) and Candida albicans to afford a mixture of the (2R, 3R)-isomer 10 and the (2S, 3R)-isomer 11. Although the optical purity of 10 produced by Candida albicans was reasonably high (95% e.e.), optical yields of other products were unexpectedly low. However, identification of the four possible isomers 14-17 was found to be easily carried out by means of nuclear magnetic resonance spectroscopy.

著者

秋田 弘幸 古市 昭也 越地 弘子 堀越 弘毅 大石 武

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.31, no.12, pp.4376-4383, 1983-12-25 (Released:2008-03-31)

参考文献数

19

被引用文献数

18 30

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The synthesis of optically active α-methyl β-hydroxy esters I by means of microbiological reduction of the corresponding β-keto esters II was carried out. Benzyl 2-methyl-3-oxobutyrate 1 was found to be reduced by a variety of yeasts to the α-methyl β-hydroxy esters with (2R, 3S)- and (2S, 3S)-configurations (2 and 3, respectively), and by carrying out screening experiments, yeasts which give each product with high optical purity were isolated. Moreover, the absolute configuration and the optical purity of the reduction products were found to be determinable from the 400 MHz nuclear magnetic resonance spectra of the (+)-α-methyoxy-α-trifluoromethylphenylacetyl esters of the alcohols produced.

著者

Abdel-Rahim Sayed Ibrahim Ahmed Mohamed Galal Mohammed Shamim Ahmed Gabir Salem Mossa

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.51, no.2, pp.203-206, 2003 (Released:2003-02-01)

参考文献数

24

被引用文献数

30 54

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Metabolism of 7-O-methylnaringenin (sakuranetin) by Cunninghamella elegans NRRL 1392 yielded naringenin and naringenin-4′-sulfate. C. elegans also converted 5, 3′, 4′-trihydroxy-7-methoxyflavanone into eriodictyol-4′-sulfate. Furthermore, incubation of 5, 4′-dihydroxy-7, 3′-dimethoxyflavanone with the same fungus gave homoeriodictyol (5, 7, 4′-trihydroxy-3′-methoxyflavanone) and homoeriodicytol-7-sulfate. The structures of the new metabolites were established by spectral analysis including 2D-NMR, HR-ESI-FT-MS beside hydrolysis by acid.