4,5-Diaryl-3-aminopyrazole Derivatives as Analogs of Combretastatin A-4: Synthesis and Biological Evaluation

被引：20

作者：

Liu, Tao ^{[1
]}

Cui, Rong ^{[1
,2
]}

Chen, Jing ^{[1
]}

Zhang, Jun ^{[3
]}

He, Qiaojun ^{[3
]}

Yang, Bo ^{[3
]}

Hu, Yongzhou ^{[1
]}

机构：

[1] Zhejiang Univ, Coll Pharmaceut Sci, ZJU ENS Joint Lab Med Chem, Hangzhou 310058, Zhejiang, Peoples R China

[2] JinHua Coll Vocat & Technol, Jinhua, Peoples R China

[3] Zhejiang Univ, Coll Pharmaceut Sci, Inst Pharmacol & Toxicol, Hangzhou 310058, Zhejiang, Peoples R China

来源：

ARCHIV DER PHARMAZIE | 2011年 / 344卷 / 05期

关键词：

Antitumor agents; Combretastatin A-4 analogs; Cytotoxicity; 4,5-Diaryl-3-aminopyrazole derivatives; CIS-RESTRICTED ANALOGS; ANTITUMOR AGENTS; ANTINEOPLASTIC AGENTS; TUBULIN; COLCHICINE; DESIGN; INHIBITORS; BINDING; GROWTH;

D O I：

10.1002/ardp.201000069

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of cis-restricted 4,5-diaryl-3-aminopyrazole derivatives were synthesized and tested for their cytotoxic activity in vitro against five human cancer cell lines (K562, ECA-109, A549, SMMC-7721, and PC-3). Compounds 5a, 5b, 5d, and 6b showed potent cytotoxicity against all tested cell lines. Primary mechanism research on compound 5a indicated that it was a potent inhibitor of tubulin polymerization, arresting cell cycle in G(2)/M phase. The docking research showed the conformation of 5a overlaps well with CA-4 in the crystallized protein complex, suggesting the 4,5-diaryl-3-aminopyrazoles were good mimics of CA-4.

引用

页码：279 / 286

页数：8

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[21] Design and synthesis of novel enhanced water soluble hydroxyethyl analogs of combretastatin A-4 [J].

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