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

被引：18
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
收藏
页码：5541 / 5543
页数：3
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