4-CF3-ezetimibe analogs: design, synthesis, and biological evaluation of cholesterol absorption inhibitions

被引：19

作者：

Liu, Yingle ^{[1
]}

Chen, Jun-Ling ^{[1
]}

Wang, Gai-Hong ^{[3
]}

Sun, Peng ^{[3
]}

Huang, Heyao ^{[3
]}

Qing, Feng-Ling ^{[1
,2
]}

机构：

[1] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[3] Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China

来源：

TETRAHEDRON LETTERS | 2013年 / 54卷 / 40期

基金：

中国国家自然科学基金;

关键词：

Ezetimibe; Cholesterol; beta-Lactam; Trifluoromethyl; Asymmetric hydrogention; BETA-AMINO-ACID; STEREOSELECTIVE-SYNTHESIS; EZETIMIBE; CONVENIENT; DISCOVERY; FLUORINE; RING; CYCLIZATION; REDUCTION; ALCOHOLS;

D O I：

10.1016/j.tetlet.2013.08.027

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

On the purpose of looking for better cholesterol absorption inhibitors, several trifluoromethyl substituted ezetimibe analogs 1a-d were designed and synthesized. The key steps in the synthesis of these optically pure trans-4-CF3-beta-lactams include chiral auxiliary induced asymmetric hydrogenation and substrate controlled stereoselective alkylation. The inhibitory activities of these target compounds were evaluated on the cholesterol absorption in Caco-2 cells. The result showed that the inhibitory activity of compound 1a was comparable to ezetimibe. (C) 2013 Elsevier Ltd. All rights reserved.

引用

页码：5541 / 5543

页数：3

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