Design and stereoselective synthesis of novel isosteviol-fused pyrazolines and pyrazoles as potential anticancer agents

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• 作者：Song-Lin Zhu ; Ya Wu ; Cong-Jun Liu ; Chang-Yong Wei ; Jing-Chao Tao ; Hong-Min Liu
• 关键词：Isosteviol ; Stereoselective synthesis ; Pyrazoline ; Pyrazole ; Cytotoxicity
• 刊名：European Journal of Medicinal Chemistry
• 出版年：2013
• 出版时间：July, 2013
• 年：2013
• 卷：65
• 期：Complete
• 页码：70-82
• 全文大小：766 K

文摘

Two series of novel isosteviol-fused pyrazoline and pyrazole derivatives were facilely synthesized via intramolecular 1,3-dipolar cycloaddition and condensation reaction, respectively. All compounds were characterized by NMR, IR and HRMS spectra. The stereochemistry of compounds 9b, 10, 11a and 11v were further confirmed by X-ray crystallographic analysis. The antiproliferative activities of the structurally related pyrazoline and pyrazole derivatives were tested in?vitro on four human malignant cell lines (SGC 7901, A549, Raji and HeLa): Our results revealed that isosteviol-fused pyrazole derivatives exhibited noteworthy cytotoxic activities. Among them, 2,4-di-Cl-phenylpyrazole derivative 11t displayed better cytotoxities with IC₅₀ values: 2.71, 3.18, 1.09 and 13.52?¦ÌM against SGC 7901, A549, Raji and HeLa, respectively, compared to cisplatin (IC₅₀ values: 7.56, 17.78, 17.32 and 14.31?¦ÌM, respectively).