1. Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives.
- Author
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Živković, Marijana B., Novaković, Irena T., Matić, Ivana Z., Sladić, Dušan M., and Krstić, Natalija M.
- Subjects
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HELA cells , *CARBONYL group , *ETHANOL , *ISOMERS , *HYDRAZONE derivatives , *CANCER cells , *CELL lines - Abstract
• The synthesis of new steroidal mono- and bis(semicarbazones) was performed. • The new carbazate esters were obtained. • The structures were determined by IR, NMR, HRMS and elemental analysis. • The antimicrobial and cytotoxic activities of the compounds were tested. • The replacement of C S with C O in steroidal hydrazone decrease biological activity. Eleven new steroidal mono- and bis(semicarbazones) 2a – e, 4d and 3a – e have been prepared starting from various 3-oxo-α,β-unsaturated steroids. Mono-semicarbazones 2a – e were further subjected to ethyl chloroacetate in boiling absolute ethanol but, instead of expected intramolecular cyclocondensation reaction products, the new carbazate esters 5a - e were obtained. The structures of all synthesized compounds and identification of each E / Z isomer were deduced by elemental analysis, HRMS, NMR, and IR spectroscopy. Preliminary screening for the cytotoxic activity in vitro of the new compounds has been conducted against three cancer cell lines, K562, Jurkat and HeLa cells. HeLa cells were the most sensitive while K562 cells were the least sensitive to the cytotoxic action of the novel steroid derivatives. Compounds 2e , 3c and 5e were found to have the best but still moderate cytotoxic effects. All tested compounds showed very weak antimicrobial activities. These results demonstrate that the replacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity. [ABSTRACT FROM AUTHOR]
- Published
- 2019
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