Synthesis and Conformation of Novel 4′-Fluorinated 5′-Deoxythreosyl Phosphonic Acid Nucleosides as Antiviral Agents

被引：8

作者：

Kang, Lien ^{[1
]}

Kim, Eunae ^{[1
]}

Choi, Eun Joo ^{[1
]}

Yoo, Jin Cheol ^{[1
]}

Lee, Wonjae ^{[1
]}

Hong, Joon Hee ^{[1
]}

机构：

[1] Chosun Univ, Coll Pharm, BK Project Team Coll 21, Kwangju 501759, South Korea

来源：

BULLETIN OF THE KOREAN CHEMICAL SOCIETY | 2012年 / 33卷 / 12期

基金：

新加坡国家研究基金会;

关键词：

Antiviral agent; 4 '-Fluorinated nucleoside; Deoxythreosyl nucleoside; Phosphonic acid nucleoside; AIDS-RELATED-COMPLEX; ANTI-HIV AGENTS; CARBOCYCLIC NUCLEOSIDES; CLAISEN REARRANGEMENT; ASYMMETRIC-SYNTHESIS; CROSS-METATHESIS; ANALOGS; VIRUS; DERIVATIVES; METABOLISM;

D O I：

10.5012/bkcs.2012.33.12.4007

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Efficient synthetic route to novel 4'-fluorinated 5'-deoxythreosyl phosphonic acid nucleosides was described from glyceraldehyde using Horner-Emmons reaction in the presence of triethyl alpha-fluorophosphonoacetate. Glycosylation reaction of nucleosidic bases with glycosly donor 14 gave the nucleosides which were further phosphonated and hydrolyzed to reach desired nucleoside analogues. Synthesized nucleoside analogues 18, 21, 25 and 28 were tested for anti-HIV activity as well as cytotoxicity. Adenine derivatives 18 and 21 showed significant anti-HIV activity up to 100 mu M.

引用

页码：4007 / 4014

页数：8

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