Concise synthesis and antitumor activity of Bengamide E and its analogs

被引：15

作者：

Zhang, Wenxuan ^{[1
]}

Liang, Qingzhao ^{[1
]}

Li, Hui ^{[1
]}

Meng, Xiangbao ^{[1
]}

Li, Zhongjun ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, Dept Biol Chem, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

来源：

TETRAHEDRON | 2013年 / 69卷 / 02期

基金：

中国国家自然科学基金;

关键词：

Bengamide E; Carbohydrate; Stereoselective reduction; Antitumor activity; BIOLOGICAL EVALUATION; CHIRAL AUXILIARIES; AMINO-ACIDS; STEREOCHEMISTRY; CYCLOADDITION; ALDEHYDES; DESIGN; ROUTE;

D O I：

10.1016/j.tet.2012.11.004

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Bengamide E (1a) and C-2 epimer (1b), free hydroxyl analogs (1c) and (1d), and shorter chain analog (1e) were synthesized by utilizing (2R,3S,4R)-2,3,4-tris(benzyloxy)hex-5-enal (2a) as the chiral building block. Preliminary biological studies revealed that only compound 1c showed slightly weaker activity than Bengamide E (1a) against MDA-MB-453 human breast carcinoma cells, MCF-7 human breast cancer cells and HCT-116 colon cancer cells, with the others being inactive. These results suggest that the correct stereochemistry at C-2, the alkylation on C-2 hydroxyl group, as well as the length of the carbon chain of Bengamide E are critical for structural recognition and binding to the target(s). (C) 2012 Elsevier Ltd. All rights reserved.

引用

页码：664 / 672

页数：9

共 42 条

[1] NOVEL SPONGE-DERIVED AMINO-ACIDS .5. STRUCTURES, STEREOCHEMISTRY, AND SYNTHESIS OF SEVERAL NEW HETEROCYCLES [J].