Synthesis and preliminary screening for the biological activity of some steroidal Δ 4 -unsaturated semicarbazone derivatives
- 1. Center for Chemistry, Institute of Chemistry, Technology and Metallurgy, University of Belgrade, Studentski trg 12-16, P. O. Box 473, 11001 Belgrade, Republic of Serbia;
- 2. Institute for Oncology and Radiology of Serbia, *Department for Diagnostic Radiology, Belgrade, Serbia
- 3. Faculty of Chemistry, University of Belgrade, Studentski trg 12-16, P. O. Box 158, 11001 Belgrade, Republic of Serbia
Description
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
Notes
Files
Synthesis and preliminary screening for the biological activity of some steroidal... 10.1016@j.steroids.2019.04.010.pdf
Files
(1.2 MB)
Name | Size | Download all |
---|---|---|
md5:c02ce9f80c4befdb39d7afacbbe290bc
|
1.2 MB | Preview Download |
Additional details
Related works
- Is part of
- 0039-128X (ISSN)
Funding
- Biological response modifiers in physiological and pathological conditions 175011
- Ministry of Education, Science and Technological Development
- Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids 172055
- Ministry of Education, Science and Technological Development