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嘧啶脱氧核糖核苷的单氟和二氟类似物对人类免疫缺陷病毒（HIV-1）的合成及抗病毒活性

Synthesis and antiviral activity of monofluoro and difluoro analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1).

作者信息

Martin J A, Bushnell D J, Duncan I B, Dunsdon S J, Hall M J, Machin P J, Merrett J H, Parkes K E, Roberts N A, Thomas G J

机构信息

Research Division, Roche Products Limited, Welwyn Garden City, Hertfordshire, England.

出版信息

J Med Chem. 1990 Aug;33(8):2137-45. doi: 10.1021/jm00170a015.

DOI:10.1021/jm00170a015
PMID:2165161
Abstract

A range of 2'-fluoro and 2',3'-difluoro analogues of pyrimidine deoxyribonucleosides have been synthesized and evaluated against human immunodeficiency virus (HIV-1) in a human lymphoblastoid cell line. Among these compounds, 1-(2,3-dideoxy-2-fluoro-beta-D-threopentofuranosyl)cytosine (12), 2',3'-didehydro-2',3'-dideoxy-2'-fluorocytidine (35), 1-(2,3-dideoxy-2,3-difluoro-beta-D-arabinofuranosyl)cytosine (41), and 3'-deoxy-2',3'-didehydro-2'-fluorothymidine (45) were found to have significant antiviral activity, with IC50 values of 0.65, 10, 10, and 100 microM, respectively. The structure-activity relationships are discussed.

摘要

已经合成了一系列嘧啶脱氧核糖核苷的2'-氟和2',3'-二氟类似物，并在人淋巴母细胞系中针对人类免疫缺陷病毒（HIV-1）进行了评估。在这些化合物中，发现1-(2,3-二脱氧-2-氟-β-D-苏型戊呋喃糖基)胞嘧啶（12）、2',3'-二脱氢-2',3'-二脱氧-2'-氟胞苷（35）、1-(2,3-二脱氧-2,3-二氟-β-D-阿拉伯呋喃糖基)胞嘧啶（41）和3'-脱氧-2',3'-二脱氢-2'-氟胸苷（45）具有显著的抗病毒活性，其IC50值分别为0.65、10、10和100微摩尔。讨论了构效关系。

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