Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase

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• 作者：Kim ; Hea Ok ; Yoo ; Su Jeong ; Ahn ; Hee Sung ; Choi ; Won Jun ; Moon ; Hyung Ryong ; Lee ; Kang Man ; Chun ; Moon Woo ; et. al.
• 关键词：S-Adenosylhomocysteine hydrolase ; Antiviral ; Electrophilic fluorination ; Carbocyclic nucleosides
• 刊名：Bioorganic and Medicinal Chemistry Letters
• 出版年：2004
• 期刊代码：10_0960894x
• 类别：ch
• 出版时间：May 3, 2004
• 卷：14
• 期：9
• 页码：2091-2093
• 文件大小：255 K

摘要

Fluoro-DHCeA (4) was efficiently synthesized from d-cyclopentenone derivative 5 using electrophilic fluorination as a key step. Fluoro-DHCeA (4) was found to be as potent as DHCeA (3), but exhibited irreversible inhibition of enzyme unlike DHCeA (3) showing reversible inhibition. From this study, 4^′-hydroxymethyl groups of neplanocin A and fluoro-neplanocin A played an important role in binding to the active site of the enzyme.