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

---

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

---

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

---

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

---

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

---

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

---

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

---

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.

著者

今井 欣一 丸本 龍二 小林 邦夫 吉岡 義夫 戸田 準 本庄 美喜男

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.19, no.3, pp.576-586, 1971-03-25 (Released:2008-03-31)

被引用文献数

11 19

---

Ring closure of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide (AICA-riboside) with phenyl isothiocyanate afforded 2-mercaptoinosine (I) in good yield. Similarly, the ring closure of AICA-riboside 5'-phosphate (AICAR) led to the formation of 2-mercaptoinosine 5'-phosphate (II). Various 2-substituted inosine 5'-phosphates were prepared from I and II or starting with AICA-riboside. It was found that 2-furfuryl-thioinosine 5'-phosphate possessed a flavor enhancing activity of about 17-times that of inosine 5'-phosphate. The chemical structure-flavor enhancing activity relationship was presented.

著者

松田 彰 野本 裕二 上田 亨

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.1, pp.183-192, 1979-01-25 (Released:2008-03-31)

被引用文献数

16 31

---

A facile displacement of a methylsulfonyl group in adenosines with cyanide ion is described. Treatment of protected 8-methylsulfonyladenosines with sodium cyanide in dimethylformamide gave the 8-cyanoadenosines. The conversion of the cyano group to the methyl imidate, methoxycarbonyl, carbamoyl, and carboxylic acid, respectively, was achieved. Similar reaction was carried out with 2-methylsulfonyladenosines to give the 2-cyanoadenosines and their derivatives. The nuclear magnetic resonance (NMR) and circular dichroism (CD) spectra of these 2-and 8-substituted adenosines are given. The 8-substituted adenosines possess syn-conformations while the 2-substituted derivatives prefer to possess anti-conformations, as confirmed by the CD and NMR spectra.

著者

松田 彰 篠崎 操 宮坂 貞 町田 治彦 畔蒜 藤一

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.4, pp.1766-1769, 1985-04-25 (Released:2008-03-31)

参考文献数

24

被引用文献数

19 30

---

Reaction of 2-iodoadenosine (2) with terminal alkynes in the presence of bis (triphenylphosphine) palladium dichloride and cuprous iodide in triethylamine and N, N, -dimethylformamide gave 2-alkynyl-adenosines (3a-h) in excellent yields. Several compounds showed high activity as inhibitors in rat passive cutaneous anaphylaxis (PCA) reaction. Among them, 2-(3-hydroxypropynyl)- and 2-(3-hydroxybutynyl)-adenosines (3d, f) are much more potent than disodium cromoglycate (DSCG).

著者

松田 彰 佐藤 和恵 宮坂 貞 上田 亨

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.5, pp.2048-2051, 1984-05-25 (Released:2008-03-31)

参考文献数

8

被引用文献数

4 4

---

2-Aminomethylinosine (1), a one-carbon extended homolog of an exocyclic amino group of guanosine, was synthesized from guanosine by the use of a newly developed protection and deprotection method. Introduction of a methoxy group into the 6-position of 2-benzenesulfonyl-purine riboside facilitated a nucleophilic substitution with cyanide to afford 2-cyano-6-methoxypurine riboside (11) which was subsequently hydrogenated and demethylated with trimethylsilyl iodide to afford 1.

著者

坂田 紳二 米井 清志郎 吉野 宏

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.30, no.7, pp.2583-2585, 1982-07-25 (Released:2008-03-31)

参考文献数

11

被引用文献数

7 10

---

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

菊川 清見 市野 元信

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.21, no.5, pp.1151-1155, 1973-05-25 (Released:2008-03-31)

被引用文献数

8 14

著者

林 清五郎 植木 寛 原野 誠子 小宮 順子 井山 駿 原野 一誠 宮田 勝昭 新形 邦宏 米村 嘉郎

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.12, no.11, pp.1271-1276, 1964-11-25 (Released:2008-03-31)

被引用文献数

2 3

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Dimethanesulphonylthioalkanes and analogous compounds were synthesized by the reaction of corresponding sodium thiosulphonate and appropriate dibromide to test the carcinostatic activity compaed with Myleran. It was found that some of these compounds inhibited pronouncedly the growth of the solid tumor produced by Ehrlich ascites carcinoma cells.

著者

田之口 真理子 加島 竜彦 雑賀 英之 井上 大志 有本 正生 山口 秀夫

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.37, no.1, pp.68-72, 1989-01-25 (Released:2008-03-31)

参考文献数

31

被引用文献数

11 16

---

Two new lignans, hernolactone (1) and fernandin (2), isolated from the seeds of Hernandia ovigera L. were synthesized in recemic forms. Firstly, (±)-1 was obtained by utilizing the conjugate addition reaction of 4 with butenolide followed by alkylation with trimethoxybenzyl bromide and subsequent removal of the protecting groups. Synthesis of 2 was pursued using the corresponding 4-phenyl-1, 2-dihydronaphthalene lactone(18). The cleavage of the lactone moiety of 18 afforded an unsaturated hydroxy acid (22). Subsequent hydrogenation of 22 followed by acidification with concetrated hydrochloric acid gave isopicrobernanadin (21), leaving the 2, 3-trans, 3, 4-cis hydroxy acid (23), which was lactonized by means of N, N-dicyclohexylcarbodiimide to afford (±)-2.

著者

田之口 真理子 細野 江津子 北岡 真由子 有本 正生 山口 秀夫

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.39, no.7, pp.1873-1876, 1991-07-25 (Released:2008-03-31)

参考文献数

10

被引用文献数

8 11

---

Two kinds of lignans were isolated from the seeds of Hernandia ovigera L. in addition to the nine lignans previously reported. One was confirmed as (-)-dimethylmatairesinol (11) and the other was identified as 5'-methoxypodorhizol (14) by comparison with the anthentic sample. An attempt at the cyclization of 14 afforded two compounds which were determined to be isohernandin (15) and an isomer of 15, 2-hydroxymethy 1-5, 6-methylenedioxy-7-methoxy-4-(3', 4', 5'-trimethoxyphenyl)-1, 2, 3, 4-tetrahydronaphthoic acid lactone (16).

著者

山口 秀夫 有本 正生 中島 淳二 田之口 眞理子 深田 能成

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.34, no.5, pp.2056-2060, 1986-05-25 (Released:2008-03-31)

参考文献数

16

被引用文献数

10 11

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Epipodophyllotoxin (EPT) and podophyllotoxin (PT) were prepared from desoxypodophyllotoxin (DPT), obtained from the seeds of Hernandia ovigera L. (Hernandiaceae) EPT was obtaind together with dehydrodesoxypodophyllotoxin (I) by a radical bromination of DPT with N-bromosuccinimide (NBS) followed by hydrolysis of the resultant 1-bromo-DPT, which was confirmed to be a mixture of 1α- and 1β-bromo compounds (7 : 3). EPT was oxidized with pyridinium chlorochromate to give podophyllotoxone (IV). The stereoselective reduction of IV to afford PT was examined with a variety of reagents, and borane-tert-butylamine complex was found to be effective.

著者

山口 秀夫 中島 淳二 有本 正生 田之口 真理子 石田 寿昌 井上 正敏

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.5, pp.1754-1760, 1984-05-25 (Released:2008-03-31)

参考文献数

18

被引用文献数

2 5

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Two kinds of 4-aryltetralin type lignans, β-peltatin-A methyl ether (I-A) and β-peltatin-B methyl ether (I-B), were synthesized from desoxypodophyllotoxin (DPT), which is available in large quantities from the seeds of Hernandia ovigera L. (Hernandiaceae). The syntheses were achieved via demethylene-DPT (IV), 8-bromo-demethylene-DPT (V) and 8-bromo-DPT (VI). Methylenation of V was carried out successfully by using cesium fluoride and methylene iodide in DMF. Compound I-B was readily obtained by the reaction of VI with cuprous iodide and sodium methoxide in the presence of pyridine. Synthesis of I-A was only achieved by the reaction of lithiated VI with nitrobenzene at-100°C in the presence of tetramethylethylene diamine, and I-A was obtained in low yield, together with I-B.

著者

山口 秀夫 有本 正生 田之口 眞理子 石田 寿昌 井上 正敏

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.30, no.9, pp.3212-3218, 1982-09-25 (Released:2008-03-31)

参考文献数

22

被引用文献数

12 21

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Two kinds of lignans were isolated from the seeds of Hernandia ovigera L. (Hernandiaceae) besides the previously reported desoxypodophyllotoxin (DPT), desoxypicropodophyllin, bursehernin and podorhizol, and the structures of the lignans were clarified. One, C23H24O8, named hernandin, was identified as 5-methoxy-desoxypodophyllotoxin (I) by both chemical and X-ray crystallographic methods. The other, C22H18O7, was obtained by purification of a previously isolated impure substance, mp 270-275°C. This compound was identified as 1, 2, 3, 4-dehydrodesoxypodophyllotoxin (II). This is the first report of the natural occurrence of II in plants.