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Paper | Regular issue | Vol 94, No. 8, 2017, pp.1554-1565
Published online, 20th June, 2017
DOI: 10.3987/COM-17-13750
Synthesis of 17β-N-Phenylpyrazolyl Steroidal Derivatives and Their Inhibitory Effect on Cell Proliferation

Ning-Juan Fan,* Yuan-Feng Li, Qiu-Rui He, Shuang Liang, and Jiang-Jiang Tang*

*Biochemistry and Molecular Biology Research Platform, College of Life Science, Northwest A&F University, Yangling, Shaanxi 712100, China


The synthesis of several 17β-N-phenylpyrazolyl derivatives steroid derived from progesterone are described. The Claisen condensations of ∆1, 4-pregnadien-3,20-dione (1) and 4-chloro-∆1,4-pregnadiene-3,20-dione (2) with dimethyl oxalate afforded 21-methoxalylpregna-1,4-diene-3,20-dione (3) and 4-chloro-21-methoxalylpregna-1,4-diene-3,20-dione (4), respectively. Furthermore, the reactions of 3 and 4 with substituted phenylhydrazines yielded 5'-pyrazolyl derivatives as main products, and the 5'-pyrazolyl isomers 6a-k (and 7a-k) were isolated from the crude reaction mixture (3'-pyrazolyl regioisomers as minor products). The newly synthetized compounds were evaluated in vitro by means of SRB assays for antiproliferative activity against HepG-2 (hepatoma), HeLa (cervix adenocarcinoma) and MCF-7 (breast adenocarcinoma). The preliminary results showed that compounds 6d, 6i and 7d possessed moderate antiproliferative activities.