Synthesis of (2'S,3'S)-9-(4'-phosphono-4',4'-difluoro-2',3'methanobutyl)guanine and its enantiomer. Evaluation of the inhibitory activity for purine nucleoside phosphorylase

被引：30

作者：

Yokomatsu, T

Sato, M

Abe, H

Suemune, K

Matsumoto, K

Kihara, T

Soeda, S

Shimeno, H

Shibuya, S

机构：

[1] TOKYO UNIV PHARM & LIFE SCI,SCH PHARM,HACHIOJI,TOKYO 19203,JAPAN

[2] TAISHO PHARMACEUT CO LTD,RES CTR,OMIYA,SAITAMA 330,JAPAN

[3] FUKUOKA UNIV,SCH PHARMACEUT SCI,JONAN KU,FUKUOKA 81480,JAPAN

来源：

TETRAHEDRON | 1997年 / 53卷 / 33期

关键词：

D O I：

10.1016/S0040-4020(97)00704-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Conformationally constrained analogues 2a and ent-2a of 9-(difluorophosphonopentyl)guanines 1, a multi-substrate analogue inhibitor of PNP, were prepared from optically active trans-1-(diethoxyphosphinyl)difluromethy-2-hydroxymethylcyclopropanes (+)-6 and (-)-6, Enzymatic double resolution was applied to obtain (+)-6 and (-)-6 with high enantiomeric purity. Inhibitory activity of 2a and ent-2a were found to be 2400-fold less potent than 1. (C) 1997 Elsevier Science Ltd.

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页码：11297 / 11306

页数：10

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