Click chemistry-based synthesis and anticancer activity evaluation of novel C-14 1,2,3-triazole dehydroabietic acid hybrids

doi:10.1016/j.ejmech.2017.07.049

	Click chemistry-based synthesis and anticancer activity evaluation of novel C-14 1,2,3-triazole dehydroabietic acid hybrids
	Hou, Wei 1; Luo, Zhi 2; Zhang, Guanjun 3; Cao, Danhui 1; Li, Di 1; Ruan, Haoqiang 1; Ruan, Benfang Helen 1; Su, Lin 1; Xu, Hongtao4,5
	2017-09-29
发表期刊	EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (IF:6.0[JCR-2023],6.1[5-Year])
ISSN	0223-5234
卷号	138 页码:1042-1052
发表状态	已发表
DOI	10.1016/j.ejmech.2017.07.049
摘要	A concise and efficient synthetic approach has been established to readily access a series of novel C-14 1,2,3-triazole-tethered dehydroabietic acid derivatives in moderate to high yields. In vitro anti proliferative activity evaluation indicated that most of the hybrids exhibited potent inhibitory activities in a variety of cancer cell lines with low micromolar to submicromolar IC50 values. Further studies demonstrated that some of these analogues such as 20, 21, and 24 were also effective against adriamycin-resistant MCF-7 clone at low concentrations in a dose-dependent manner. Notably, the most potent compound 24, which possesses a 3-(tert-butoxycarbonylamino)phenyl-substituted triazole moiety, not only exhibited obviously improved IC50 values ranging from 0.7 to 1.2 mu M against a panel of tested cancer cells, but also showed very weak cytotoxicity on normal cells. Preliminary mechanism studies indicated that compound 24 could induce apoptosis in MDA-MB-231 cells and was worth developing into a novel natural product-like anticancer lead by proper structure modification. (C) 2017 Elsevier Masson SAS. All rights reserved.
关键词	Terpenoids Dehydroabietic acid Cancer 1,2,3-triazole Synthesis Click chemistry Drug resistance
收录类别	SCI ; IC
语种	英语
资助项目	Open Foundation of the State Key Laboratory of Drug Research, China[SIMM1601KF-05]
WOS研究方向	Pharmacology & Pharmacy
WOS类目	Chemistry, Medicinal
WOS记录号	WOS:000411297000080
出版者	ELSEVIER FRANCE-EDITIONS SCIENTIFIQUES MEDICALES ELSEVIER
WOS关键词	NATURAL-PRODUCTS ; IN-VITRO ; DERIVATIVES ; TRIPTOLIDE ; DESIGN ; RING ; TRIPTONIDE ; ANALOGS ; COMPLEX
原始文献类型	Article
引用统计	被引频次：53[WOS] [WOS记录] [WOS相关记录]
文献类型	期刊论文
条目标识符	https://kms.shanghaitech.edu.cn/handle/2MSLDSTB/4630
专题	免疫化学研究所_特聘教授组_抗体化学实验室免疫化学研究所_特聘教授组_抗体设计学实验室
通讯作者	Su, Lin; Xu, Hongtao
作者单位	1.Zhejiang Univ Technol, Coll Pharmaceut Sci, Collaborat Innovat Ctr Yangtza River Delta Reg Gr, Hangzhou 310014, Zhejiang, Peoples R China 2.Shanghai Evergene Biotech Co Ltd, Shanghai 201499, Peoples R China 3.Tianjin Univ Sci & Technol, Coll Chem Engn & Mat Sci, Tianjin 300457, Peoples R China 4.ShanghaiTech Univ, Shanghai Inst Adv Immunochem Studies, Shanghai 201210, Peoples R China 5.Chinese Acad Sci, Shanghai Inst Mat Med, State Key Lab Drug Res, Shanghai 201203, Peoples R China
通讯作者单位	免疫化学研究所
推荐引用方式 GB/T 7714	Hou, Wei,Luo, Zhi,Zhang, Guanjun,et al. Click chemistry-based synthesis and anticancer activity evaluation of novel C-14 1,2,3-triazole dehydroabietic acid hybrids[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,2017,138:1042-1052.
APA	Hou, Wei.,Luo, Zhi.,Zhang, Guanjun.,Cao, Danhui.,Li, Di.,...&Xu, Hongtao.(2017).Click chemistry-based synthesis and anticancer activity evaluation of novel C-14 1,2,3-triazole dehydroabietic acid hybrids.EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY,138,1042-1052.
MLA	Hou, Wei,et al."Click chemistry-based synthesis and anticancer activity evaluation of novel C-14 1,2,3-triazole dehydroabietic acid hybrids".EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY 138(2017):1042-1052.