Click chemistry-based synthesis and anticancer activity evaluation of novel C-14 1,2,3-triazole dehydroabietic acid hybrids
2017-09-29
发表期刊EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY (IF:6.0[JCR-2023],6.1[5-Year])
ISSN0223-5234
卷号138页码:1042-1052
发表状态已发表
DOI10.1016/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.
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