Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives
Članak u časopisu (Recenzirana verzija)
Metapodaci
Prikaz svih podataka o dokumentuApstrakt
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 repl...acement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.
Ključne reči:
3-Oxo-α,β-unsaturated steroids / Biological activity / Carbazate esters / SemicarbazonesIzvor:
Steroids, 2019, 148, 36-46Finansiranje / projekti:
- Interakcije prirodnih proizvoda, njihovih derivata i kompleksnih jedinjenja sa proteinima i nukleinskim kiselinama (RS-MESTD-Basic Research (BR or ON)-172055)
- Modifikatori biološkog odgovora u fiziološkim i patološkim stanjima (RS-MESTD-Basic Research (BR or ON)-175011)
Napomena:
- Supplementary material: http://cherry.chem.bg.ac.rs/handle/123456789/3083
- This is peer-reviewed version of the following article: Živković, M. B.; Novaković, I. T.; Matić, I. Z.; Sladić, D. M.; Krstić, N. M. Synthesis and Preliminary Screening for the Biological Activity of Some Steroidal Δ4-Unsaturated Semicarbazone Derivatives. Steroids 2019, 148, 36–46. https://doi.org/10.1016/j.steroids.2019.04.010
DOI: 10.1016/j.steroids.2019.04.010
ISSN: 0039-128X
WoS: 000474331100005
Scopus: 2-s2.0-85065594815
Kolekcije
Institucija/grupa
Hemijski fakultet / Faculty of ChemistryTY - JOUR AU - Živković, Marijana B. AU - Novaković, Irena T. AU - Matić, Ivana Z. AU - Sladić, Dušan AU - Krstić, Natalija M. PY - 2019 UR - https://cherry.chem.bg.ac.rs/handle/123456789/3084 AB - 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. T2 - Steroids T1 - Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives VL - 148 SP - 36 EP - 46 DO - 10.1016/j.steroids.2019.04.010 ER -
@article{ author = "Živković, Marijana B. and Novaković, Irena T. and Matić, Ivana Z. and Sladić, Dušan and Krstić, Natalija M.", year = "2019", abstract = "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.", journal = "Steroids", title = "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives", volume = "148", pages = "36-46", doi = "10.1016/j.steroids.2019.04.010" }
Živković, M. B., Novaković, I. T., Matić, I. Z., Sladić, D.,& Krstić, N. M.. (2019). Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids, 148, 36-46. https://doi.org/10.1016/j.steroids.2019.04.010
Živković MB, Novaković IT, Matić IZ, Sladić D, Krstić NM. Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids. 2019;148:36-46. doi:10.1016/j.steroids.2019.04.010 .
Živković, Marijana B., Novaković, Irena T., Matić, Ivana Z., Sladić, Dušan, Krstić, Natalija M., "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives" in Steroids, 148 (2019):36-46, https://doi.org/10.1016/j.steroids.2019.04.010 . .