Synthesis of D-ring-substituted (5'R)- and (5'S)-17β-pyrazolinylandrostene epimers and comparison of their potential anticancer activities

Steroids
Zoltán IványiGyula Schneider

Abstract

Various steroidal benzylidenes were synthetized from pregnenolone with benzaldehyde and p-substituted benzaldehydes. The resulting 17β-chalconyl derivatives of pregnenolone were reacted with hydrazine hydrate in acetic acid solution. Regardless of the starting material, the ring-closure reaction afforded (in contrast with the literature data) a mixture of two steroidal pyrazoline epimers. The epimers were critical isomer pairs, which could be separated only in their acetylated form; their structures were investigated by NMR techniques. The in vitro inhibition of rat testicular C(17,20)-lyase activity and the antiproliferative effects on four human cancer cell lines were measured, and the results obtained from the two epimer series were compared.

References

Sep 27, 2005·Bioorganic & Medicinal Chemistry·Abd El-Galil E AmrMohamed M Abdalla
Mar 11, 2010·Steroids·A O Mueck, H Seeger
Jul 21, 2011·Steroids·Abid H BandayBashir A Ganaie

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Citations

Jun 15, 2014·Steroids·Anabel Romero-LópezJosé Luis Vega-Baez
Sep 12, 2013·European Journal of Medicinal Chemistry·Ning-Juan FanJin-Ming Gao
Mar 19, 2013·The Journal of Steroid Biochemistry and Molecular Biology·Eva Frank, Gyula Schneider
Sep 11, 2014·Steroids·Suzana S Jovanović-ŠantaJulijana A Petrović
Jun 4, 2013·The Journal of Steroid Biochemistry and Molecular Biology·Atul GuptaArvind S Negi
Dec 3, 2014·Bioorganic & Medicinal Chemistry·György SzalókiTheodora Calogeropoulou
Apr 23, 2020·Future Medicinal Chemistry·Ranju Bansal, Ranjit Singh
Aug 6, 2020·International Journal of Molecular Sciences·Dimitris Matiadis, Marina Sagnou
Apr 2, 2021·Steroids·Arfeen Iqbal, Tabassum Siddiqui

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