Design, synthesis, and biological evaluation of fluoroneplanocin A as the novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase

被引：61

作者：

Jeong, LS ^{[1
]}

Yoo, SJ

Lee, KM

Koo, MJ

Choi, WJ

Kim, HO

Moon, HR

Lee, MY

Park, JG

Lee, SK

Chun, MW

机构：

[1] Ewha Womans Univ, Coll Pharm, Med Chem Lab, Seoul 120750, South Korea

[2] Seoul Natl Univ, Div Chem & Mol Engn, Seoul 151742, South Korea

[3] Seoul Natl Univ, Coll Pharm, Seoul 151, South Korea

来源：

JOURNAL OF MEDICINAL CHEMISTRY | 2003年 / 46卷 / 02期

关键词：

D O I：

10.1021/jm025557z

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Fluoroneplanocin A (12) was designed as a novel mechanism-based inhibitor of S-adenosylhomocysteine hydrolase (SAH) and efficiently synthesized via an electrophilic vinyl fluorination reaction (n-BuLi, N-fluorobenzenesulfonimide at -78 degreesC). Fluoroneplanocin A exhibited 2-fold more potent SAH inhibitory activity than the parent neplanocin A. A new mechanism of irreversible inhibition discovered in this work might provide new alternatives in the design of a different class of antiviral agents operating via SAH inhibition.

引用

页码：201 / 203

页数：3

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