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A series of 4′-acylamino modified Δ 1,4 -pregnadien-21 E -benzylidene-3,20-dione derivatives ( 6a – v ) was synthesized from the commercially available progesterone ( 1 ). These title compounds were evaluated for their toxicity against brine shrimp ( Artemia salina ) and cytotoxic activities against two human cancer cell lines (HeLa and MCF-7). The results revealed that compound 6f exhibited promising in vitro cytotoxic activity to the two cancer cell lines and the nature of acylamino functional group in the benzylidene moiety had a significant influence on cytotoxicity. [ABSTRACT FROM AUTHOR]

Using progesterone as the starting material, we synthesized a series of steroidal derivatives possessing a D-ring substituted benzamidothiazole. All of the final structures were reported and identified by NMR and HRMS spectrometry for the first time. The antiproliferative activity of the synthesized compounds against PC-3 (human prostate cancer cell line) and SKOV-3 (ovarian cancer cells) were investigated. The preliminary results showed that compounds 8b , 8d and 8g possessed moderate antiproliferative activities. [ABSTRACT FROM AUTHOR]

The synthesis of steroidal derivatives containing [1,2,4]triazolo[1,5-a]pyrimidine derived from progesterone is described. The Claisen condensations of Δ1,4-pregnadien-3,20-dione and 4-chloro-Δ1,4-pregnadien-3,20-dione with dimethyl oxalate afforded 21-methoxalylpregn-1,4-diene-3,20-dione and 4-chloro-21-methoxalylpregn-1,4-diene-3,20-dione, respectively. Furthermore, the reactions of these compounds with 3-amino-1,2,4-triazole yielded the corresponding [1,2,4]triazolo[1,5-a]pyrimidine derivatives. The newly synthesised compounds were evaluated in vitro by means of sulforhodamine B assays for antiproliferative activity against HeLa and MCF-7 cells. [ABSTRACT FROM AUTHOR]

Abstract: Fourteen novel steroidal C-17 pyrazolinyl derivatives 9a–g and 10a–g were synthesized from commercially available progesterone and tested for their cytotoxic activity against brine shrimp (Artemia salina) and three human cancer cell lines (NCI-H460, HeLa, and HepG2). Some of these synthetic compounds exhibited significant cytotoxic activity, and treatment of HeLa cells with compound 10b resulted in the cell population arrest in the S phase. A structure–activity relationship was discussed. [Copyright &y& Elsevier]

Highlights: [•] Fourteen novel 21E-benzylidene steroidal derivatives were synthesized. [•] Cytotoxicities against brine shrimps and LLC cells of these compounds were evaluated. [•] Most compounds showed marked toxic activity against brine shrimps. [Copyright &y& Elsevier]