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Comprehensive structural studies of 2',3'-difluorinated nucleosides: comparison of theory, solution, and solid state.2',3'-二氟核苷的综合结构研究：理论、溶液和固态的比较。
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Synthesis of 9-(2,3-dideoxy-2,3-difluoro-beta-D-arabinofuranosyl)adenine.9-(2,3-二脱氧-2,3-二氟-β-D-阿拉伯呋喃糖基)腺嘌呤的合成
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Discovery and development of clofarabine: a nucleoside analogue for treating cancer.氯法拉滨的发现与研发：一种用于治疗癌症的核苷类似物。
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Design, synthesis, and antiviral activity of 2'-deoxy-2'-fluoro-2'-C-methylcytidine, a potent inhibitor of hepatitis C virus replication.丙型肝炎病毒复制的强效抑制剂2'-脱氧-2'-氟-2'-C-甲基胞苷的设计、合成及抗病毒活性
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Synthesis and anti-viral activity of a series of d- and l-2'-deoxy-2'-fluororibonucleosides in the subgenomic HCV replicon system.一系列d型和l型2'-脱氧-2'-氟核糖核苷在亚基因组丙型肝炎病毒复制子系统中的合成及抗病毒活性
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2'-chloro-2',3'-dideoxy-3'-fluoro-d-ribonucleosides: synthesis, stereospecificity, some chemical transformations, and conformational analysis.2'-氯-2',3'-二脱氧-3'-氟-D-核糖核苷：合成、立体专一性、一些化学转化及构象分析
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Antiviral activities and cellular toxicities of modified 2',3'-dideoxy-2',3'-didehydrocytidine analogues.修饰的2',3'-二脱氧-2',3'-二氢胞苷类似物的抗病毒活性和细胞毒性
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嘌呤2',3'-二脱氧-2',3'-二氟-D-阿拉伯呋喃糖基核苷的合成及其抗病毒活性

Synthesis and antiviral activity of purine 2',3'-dideoxy-2',3'-difluoro-D-arabinofuranosyl nucleosides.

作者信息

Sivets Grigorii G, Kalinichenko Elena N, Mikhailopulo Igor A, Detorio Mervi A, McBrayer Tami R, Whitaker Tony, Schinazi Raymond F

机构信息

Institute of Bioorganic Chemistry, National Academy of Sciences, Minsk, Belarus.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2009 May;28(5):519-36. doi: 10.1080/15257770903053979.

DOI:10.1080/15257770903053979
PMID:20183600
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7732020/
Abstract

9-(2',3'-Dideoxy-2',3'-difluoro-beta-D-arabinofuranosyl)adenine (20), 2-chloro-9-(2',3'-dideoxy-2,3-difluoro-beta-D-arabinofuranosyl)adenine (22), as well as their respective alpha-anomers 21 and 23, were synthesized by the nucleobase anion glycosylation of intermediate 5-O-benzoyl-2,3-dideoxy-2,3-difluoro-alpha-D-arabinofuranosyl bromide (13) starting from methyl 5-O-benzyl-3-deoxy-3-fluoro-alpha-D-ribofuranoside (3) and methyl 5-O-benzoyl-alpha-D-xylofuranoside (10). These compounds were evaluated as potential inhibitors of HIV-1 and hepatitis C virus in human PBM and Huh-7 Replicon cells, respectively. The adenosine analog 20 demonstrated potent activity against HIV-1 in primary human lymphocytes with no apparent cytotoxicity. Conformation of pentofuranose ring of nucleoside 20 in solution was studied by PSEUROT calculations.

摘要

9-(2',3'-二脱氧-2',3'-二氟-β-D-阿拉伯呋喃糖基)腺嘌呤(20)、2-氯-9-(2',3'-二脱氧-2,3-二氟-β-D-阿拉伯呋喃糖基)腺嘌呤(22)以及它们各自的α-异构体21和23，是从5-O-苄基-3-脱氧-3-氟-α-D-呋喃核糖苷(3)和5-O-苯甲酰基-α-D-呋喃木糖苷(10)出发，通过中间体5-O-苯甲酰基-2,3-二脱氧-2,3-二氟-α-D-阿拉伯呋喃糖基溴(13)的核碱基阴离子糖基化反应合成的。这些化合物分别在人外周血单核细胞和Huh-7复制子细胞中作为潜在的HIV-1和丙型肝炎病毒抑制剂进行了评估。腺苷类似物20在原代人淋巴细胞中表现出对HIV-1的强效活性，且无明显细胞毒性。通过PSEUROT计算研究了核苷20在溶液中戊呋喃糖环的构象。