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.
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收藏
页码：201 / 203
页数：3
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