1 0 0 0 OA Synthesis of Aristeromycin Analogs
- 著者
- 丸本 龍二 吉岡 義夫 古川 純康 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.24, no.11, pp.2624-2628, 1976-11-25 (Released:2008-03-31)
- 被引用文献数
- 8 9
Reaction of aristeromycin (I) with acetyl bromide in acetonitrile, followed by treatment with hydrobromic acid afforded 3'β-bromo-3'-deoxyaristeromycin hydrobromide (V) and 2'β-bromo-2'-deoxyaristeromycin hydrobromide (VI). Catalytic reduction of V and VI with palladium on charcoal gave 3'-deoxyaristeromycin (X) and 2'-deoxyaristeromycin (XI), respectively. Treatment of V with sodium alkoxide yielded 2', 3'-anhydroaristeromycin (IV). Two carbocyclic analogs (XII and XV) of inosine and 6-mercaptopurine ribonucleoside, 8-bromoaristeromycin (XVI) and 8-hydroxyaristeromycin (XVII) were also prepared.
- 著者
- 丸本 龍二 吉岡 義夫 宮下 修 島 俊介 今井 欣一 川添 勝義 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.23, no.4, pp.759-774, 1975-04-25 (Released:2008-03-31)
- 被引用文献数
- 23 40
A large scale preparation of 2-haloadenosines (1) was attained by acetylation of 2-haloinosines (3), followed by chlorination and amination. 2-Alkoxyadenosines (5) were prepared in fairly good yields by protection of both 2'- and 3'-hydroxyl groups of 2-chloroadenosine (1a) or 2-chloroinosine (3a), followed by substitution of the chlorine atom with alkoxy group. In the reaction of 1a with sodium alkoxide, there were obtained some oligomers of 5, of which the structures were elucidated. The reaction of 5-amino-4-cyano-1-β-D-ribofuranosylimidazole with carbon disulfide afforded 2, 6-di-mercapto-9-β-D-ribofuranosylpurine (15), which was converted to 2-mercaptoadenosine (14e) and its S-substituted derivatives. 2-Phenylaminoadenosine (29e) was prepared with comparative ease via 2-phenylamino-2', 3', 5'-tri-O-acetylinosine (32), the synthesis of which was effected by acetylation of 2-phenylaminoinosine (30) with acetylchloride in acetic acid. Many 2-substituted adenosines including O-substituted 2-hydroxyadenosines, S-substituted 2-mercaptoadenosines, N2-substituted 2-aminoadenosines, 2-alkyl- and -aryl-adenosines were prepared, among which several compounds were found to have a remarkable coronary vasodilating potency. Compound (29e) showed not only a strong potency, but also a longer duration of the effect than that of 1a. The structure-coronary vasodilating activity relationship was also discussed.
- 著者
- 野村 容朗 吉岡 義夫 南 功
- 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.4, pp.899-906, 1979-04-25 (Released:2008-03-31)
- 被引用文献数
- 7 13
Addition of 5-fluorouracil (1) to the double bond of 2, 3-dihydrofuran (3) without using any catalyst progressed smoothly at an elevated temperature and afforded an equilibrium mixture of 1-(tetrahydro-2-furyl)-5-fluorouracil (5) and 1, 3-bis (tetrahydro-2-furyl)-5-fluorouracil (7). By choosing favourable reaction conditions, each of these compounds was obtained in high yield. Thermal decomposition of 7 gave an equimolar mixture of 3 and 5. At a higher temperature, 5 underwent thermal reaction to yield 1 and 3. Study of the present addition reaction was extended to other 5-substituted uracils (8, R=-H, -CH3, -Cl, -Br, -COOCH3, -CONH2, -CN) which furnished the corresponding 1-(tetrahydro-2-furyl)-and 1, 3-bis (tetrahydro-2-furyl)-derivatives (9-15, 18-23) with high yields. A very small amount of 3-(tetrahydro-2-furyl)-5-substituted uracils (6, 16, 17) by-produced in the reactions was isolated and the structures unequivocally identified.
- 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.