Ceric ammonium nitrate-promoted oxidative coupling reaction for the synthesis and evaluation of a series of anti-tumor amide anhydrovinblastine analogs

doi:10.1016/j.bmcl.2011.10.114

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	Ceric ammonium nitrate-promoted oxidative coupling reaction for the synthesis and evaluation of a series of anti-tumor amide anhydrovinblastine analogs
	Song, Weibin 2; Lei, Min1 ; Zhao, Kun 1; Hu, Lingjun 1; Meng, Yuhui 1; Guo, Dean1 ; Liu, Xuan 1; Hu, Lihong 1,2
刊名	BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
	2012
卷号	22 期号:1 页码:387-390
关键词	Ceric ammonium nitrate (CAN) Amide anhydrovinblastine analogs Oxidative coupling Structure-activity relationship (SAR) Cytotoxicity
ISSN号	0960-894X
DOI	10.1016/j.bmcl.2011.10.114
文献子类	Article
英文摘要	A new, practical and efficient method for the synthesis of anhydrovinblastine AVBL (1f) by oxidative coupling of vindoline and catharanthine in the presence of ceric ammonium nitrate (CAN) was developed. Under the optimized reaction conditions, we synthesized a new series of amide anhydrovinblastine analogs substituted at the vindoline moiety of C-23 site and, evaluated for their proliferation inhibition against HeLa cell. The aryl-substituted derivatives showed loss of potency, while alkyl-substituted derivatives retained some of its cytotoxic potency. The iso-butylamide compound 10b and 2-furancorboxamide compound 18b displayed a similar cytotoxic potency compared to the positive control AVBL. (C) 2011 Elsevier Ltd. All rights reserved.
资助项目	Chinese National Science Technology[2009ZX09301-001] ; Chinese National Science Technology[2009ZX09102-022] ; National Natural Science Foundation of China[90713046] ; National Natural Science Foundation of China[30925040] ; CAS Foundation[KSCX2-YW-R-179]
WOS关键词	DIMERIC CATHARANTHUS ALKALOIDS ; VINBLASTINE-TYPE ALKALOIDS ; VINCA ALKALOIDS ; BIOLOGICAL EVALUATION ; BISINDOLE ALKALOIDS ; BIOGENETIC APPROACH ; SOLID TUMORS ; DERIVATIVES ; VINDOLINE ; (+)-VINBLASTINE
WOS研究方向	Pharmacology & Pharmacy ; Chemistry
语种	英语
出版者	PERGAMON-ELSEVIER SCIENCE LTD
WOS记录号	WOS:000298636700074
内容类型	期刊论文
源URL	[http://119.78.100.183/handle/2S10ELR8/278280]
专题	上海中药现代化研究中心
通讯作者	Liu, Xuan
作者单位	1.Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai Res Ctr Modernizat Tradit Chinese Med, Shanghai 201203, Peoples R China; 2.E China Univ Sci & Technol, Sch Pharm, Shanghai 200237, Peoples R China
推荐引用方式 GB/T 7714	Song, Weibin,Lei, Min,Zhao, Kun,et al. Ceric ammonium nitrate-promoted oxidative coupling reaction for the synthesis and evaluation of a series of anti-tumor amide anhydrovinblastine analogs[J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,2012,22(1):387-390.
APA	Song, Weibin.,Lei, Min.,Zhao, Kun.,Hu, Lingjun.,Meng, Yuhui.,...&Hu, Lihong.(2012).Ceric ammonium nitrate-promoted oxidative coupling reaction for the synthesis and evaluation of a series of anti-tumor amide anhydrovinblastine analogs.BIOORGANIC & MEDICINAL CHEMISTRY LETTERS,22(1),387-390.
MLA	Song, Weibin,et al."Ceric ammonium nitrate-promoted oxidative coupling reaction for the synthesis and evaluation of a series of anti-tumor amide anhydrovinblastine analogs".BIOORGANIC & MEDICINAL CHEMISTRY LETTERS 22.1(2012):387-390.