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[异头5-三甲基锗基-2'-脱氧尿苷的合成及其抗病毒和细胞毒性研究]

[Synthesis of anomeric 5-trimethylgermyl-2'-deoxyuridines and study of their antiviral and cytotoxic properties].

作者信息

Mel'nik S Ia, Bakhmedova A A, Nedorezova T P, Iartseva I V, Zhukova O S

出版信息

Bioorg Khim. 1985 Sep;11(9):1248-52.

PMID:2998405
Abstract

Glycosylation of silylated 5-trimethylgermyluracil with 2-deoxy-3,5-di-O-p-toluyl-alpha-D-ribofuranosylchloride in dichloroethane in the presence of SnCl4 and subsequent deacylation led to anomeric 5-trimethylgermyl-2'-deoxyuridines. The alpha-nucleoside inhibits HSV-1 replication in vitro, blocks 2'-deoxyuridine incorporation into DNA of hepatoma 22A cells and incorporation of thymidine into DNA of cancer ovarian cells as well. Treatment with 125 mg/kg X 5 days of alpha-nucleoside fails to increase the life-span of mice with leukemia P388.

摘要

在四氯化锡存在下,使甲硅烷基化的5 - 三甲基锗基尿嘧啶与2 - 脱氧 - 3,5 - 二 - O - 对甲苯甲酰基 - α - D - 呋喃核糖基氯在二氯乙烷中进行糖基化反应,随后进行脱酰基反应,得到了异头物5 - 三甲基锗基 - 2'- 脱氧尿苷。α - 核苷在体外抑制单纯疱疹病毒1型(HSV - 1)的复制,阻止2'- 脱氧尿苷掺入肝癌22A细胞的DNA以及胸苷掺入卵巢癌细胞的DNA。用125 mg/kg的α - 核苷处理5天,未能延长患白血病P388小鼠的寿命。

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1
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Bioorg Khim. 1985 Sep;11(9):1248-52.
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J Org Chem. 2013 Jun 7;78(11):5761-7. doi: 10.1021/jo400590z. Epub 2013 May 13.
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Application of germyldesulfonylation reactions to the synthesis of germanium-containing nucleoside analogues.Germyldesulfonylation反应在含锗核苷类似物合成中的应用。
Nucleosides Nucleotides Nucleic Acids. 2009 May;28(5):537-49. doi: 10.1080/15257770903054340.