SYNTHESIS AND ANTI-HIV ACTIVITY OF NOVEL 2′-Deoxy-2′-β-Fluoro-THREOSYL NUCLEOSIDE PHOSPHONIC ACID ANALOGUES

被引：4
|
作者：
Kim, Seyeon [1 ]
Hong, Joon Hee [1 ]
机构：
[1] Chosun Univ, Coll Pharm, Project Team BK 21, Kwangju 501759, South Korea
来源：
NUCLEOSIDES NUCLEOTIDES & NUCLEIC ACIDS | 2015年 / 34卷 / 12期
关键词：
Anti-HIV agents; 2-deoxy-2-fluoro-threose-phosphonic acid analogue; Vorbruggen reaction; VIRUS; GS-9148; DNA;
D O I：
10.1080/15257770.2015.1076840
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Novel 2-deoxy-2--fluoro-threose purine phosphonic acid analogues were designed and racemically synthesized from 2-propanone-1,3-diacetate. Condensation successfully proceeded from a glycosyl donor 9 under Vorbruggen conditions. Cross-metathesis of vinyl analogues 13 and 23 with diethyl vinylphosphonate yielded the desired nucleoside phosphonate analogues 14 and 24, respectively. Ammonolysis and hydrolysis of phosphonates yielded the nucleoside phosphonic acid analogues 16, 19, 26, and 29. The synthesized nucleoside analogues were subjected to antiviral screening against human immunodeficiency virus (HIV)-1. Adenine analogue 18 exhibited weak in vitro activities against human immunodeficiency virus (HIV)-1.
引用
收藏
页码：815 / 833
页数：19
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