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学科主题: 药学
题名:
Concise synthesis and antitumor activity of Bengamide E and its analogs
作者: Zhang, Wenxuan; Liang, Qingzhao; Li, Hui; Meng, Xiangbao; Li, Zhongjun
关键词: Bengamide E ; Carbohydrate ; Stereoselective reduction ; Antitumor activity
刊名: TETRAHEDRON
发表日期: 2013-01-14
DOI: 10.1016/j.tet2012.11.004
卷: 69, 期:2, 页:664-672
收录类别: SCI ; IC ; CCR
文章类型: Article
WOS标题词: Science & Technology
类目[WOS]: Chemistry, Organic
研究领域[WOS]: Chemistry
关键词[WOS]: CHIRAL AUXILIARIES ; METHIONINE AMINOPEPTIDASES ; STEREOSELECTIVE-SYNTHESIS ; BIOLOGICAL EVALUATION ; AMINO-ACIDS ; D-XYLOSE ; STEREOCHEMISTRY ; ROUTE ; CYCLOADDITION ; DERIVATIVES
英文摘要:

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.

语种: 英语
所属项目编号: 21072017 ; 2012CB822100
项目资助者: National Natural Science Foundation of China (NSFC) ; National Basic Research Program of China
WOS记录号: WOS:000314371800034
Citation statistics:
内容类型: 期刊论文
URI标识: http://ir.bjmu.edu.cn/handle/400002259/68191
Appears in Collections:北京大学药学院_化学生物学系_期刊论文

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作者单位: Peking Univ, Sch Pharmaceut Sci, Dept Biol Chem, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

Recommended Citation:
Zhang, Wenxuan,Liang, Qingzhao,Li, Hui,et al. Concise synthesis and antitumor activity of Bengamide E and its analogs[J]. TETRAHEDRON,2013,69(2):664-672.
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