Synthesis, cytostatic, and antiviral activity of novel 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, 6-[2-(alkylsulfanyl)ethyl]-, and 6-[2-(dialkylamino)vinyl]purine nucleosides
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- 作者：Martin Kuchař ; Michal Hocek ; Radek Pohl ; Ivan Votruba ; I-hung Shih ; Eric Mabery ; Richard Mackman
- 关键词：Purines ; Nucleosides ; Conjugate additions ; Cytostatic activity
- 刊名：Bioorganic and Medicinal Chemistry
- 出版年：2008
- 出版时间：1 February 2008
- 年：2008
- 卷：16
- 期：3
- 页码：1400-1424
- 全文大小：454 K
文摘
An efficient and facile synthesis of a large series of diverse 6-[2-(dialkylamino)vinyl]-, 6-[2-(dialkylamino)ethyl]-, 6-(2-alkoxyethyl)-, and 6-[2-(alkylsulfanyl)ethyl]purine nucleosides (35 examples of both ribo- and 2′-deoxyribonucleosides) was developed. The key transformations involved conjugate nucleophilic additions of amines, alcoholates, or thiolates to Tol-protected 6-alkylylpurine or 6-vinylpurine nucleosides. 6-[(2-Dialkylamino)vinyl]- and some 6-[(2-dialkylamino)ethyl]purine ribonucleosides exerted significant cytostatic effects and some anti-HCV activity with low selectivity.