Novel and efficient synthesis of 22-alkynyl-13,24(23)-cyclo-18,21-dinorchol-22-en-20(23)-one analogues

Wang, Cunde; Liu, Lanhai; Xu, Hangxian; Zhang, Zonglei; Wang, Xingbin; Liu, Hui

doi:10.1016/j.steroids.2011.01.005

Cited by 10 publications

(1 citation statement)

References 18 publications

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“…Some studies in recent past have showed that synthetic steroids with α, β-unsaturated ketone core gave the potency against human cancer cell lines [16][17][18]. Thus, with this institution, an attempt of synthesizing some derivatives from compounds with α, β-unsaturated ketone core was made, and subsequently, in vitro anticancer activity of the synthesized compounds was carried out using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay [13][14][15].…”

Section: In Vitro Cytotoxicity (Mtt Assay)mentioning

confidence: 99%

Steroidal dihydrocarbothioic acid amido pyrazoles: synthesis, characterization, cytotoxicity and genotoxicity studies

2015

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A new series of steroidal dihydrocarbothioic acid amido pyrazole analogues were synthesized, and after characterization, evaluation for cytotoxicity, comet assay and western blotting was carried out. The synthesis of these analogues is convenient and involves two steps, i.e. aldol condensation as first step followed by nucleophilic addition of thiosemicarbazide across α, β-unsaturated carbonyl as a later step. Quantitative yields of more than 80 % are obtained in both the steps. After characterization by IR, (1)H NMR, (13)C NMR, MS and analytical data, all the compounds of both series were tested for cytotoxic activity against a panel of different human cancer cell lines by MTT assay, during which compound 3e, 3f, 4e, 4f and 4h are very potent especially against HepG2 and MCF-7 cancer cell lines. Cell cycle analysis depicted the cell death in S-phase while as annexin V-FITC/PI analysis showed that compounds effectively induce apoptosis. Apoptotic degradation of DNA of MCF-7 cells in the presence of different steroidal derivatives was analysed by agarose gel electrophoresis and visualized by ethidium bromide staining (comet assay). In western blotting analysis, the relative expressions of relevant apoptotic markers depicted an apoptosis by steroidal dihydropyrazole in MCF-7 cancer cells.

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