Fluoroanalogues of anti-cytomegalovirus agent cyclopropavir: synthesis and antiviral activity of (E)- and (Z)-9-{[2,2-bis(hydroxymethyl)-3-fluorocyclopropylidene]methyl}-adenines and guanines.
Fluoroanalogues of anti-cytomegalovirus agent cyclopropavir: synthesis and antiviral activity of (E)- and (Z)-9-{[2,2-bis(hydroxymethyl)-3-fluorocyclopropylidene]methyl}-adenines and guanines.
复制标题
抗巨细胞病毒剂环丙帕韦的氟类似物：(E)-和(Z)-9-{[2,2-双(羟甲基)-3-氟亚环丙基]甲基}-腺嘌呤和鸟嘌呤的合成和抗病毒活性。
DOI：
10.1080/15257770701257210
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发表时间：
2007
期刊：
影响因子：
--
通讯作者：
Drach,JohnC
中科院分区：
文献类型：
--
作者：
Zhou,Shaoman;Zemlicka,Jiri;Kern,EarlR;Drach,JohnC
Synthesis of fluorinated cyclopropavir analogues13a,13b,14a, and14bis described starting from alkene15. Addition of carbene derived from dibromofluoromethane gave bromofluoro cyclopropane16. Reduction (compound17) followed by desilylation gave intermediate18, which was transformed to 2-nitrophenylselenenyl derivative19. Oxidation to selenoxide20was followed by β-elimination to afford methylenecyclopropane21. Addition of bromine provided compound22for alkylation-elimination of adenine and 2-amino-6-chloropurine. The resultant E,Z isomeric mixtures of methylenecyclopropanes23a+24aand23c+24cwere resolved and the individual isomers were deprotected to give adenine analogues13aand14aas well as compounds13cand14c. Hydrolytic dechlorination of13cand14cfurnished guanine analogues13band14b. The only significant antiviral effects were observed with analogue13aagainst HCMV and14aagainst VZV in cytopathic inhibition assays.
