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 rep...lacement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.
This is peer-reviewed version of the 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 Δ 4-unsaturated semicarbazone derivatives,
Steroids (2019), doi: https://doi.org/10.1016/j.steroids.2019.04.010
TY - JOUR
AU - Živković, Marijana B.
AU - Novaković, Irena
AU - Matić, Ivana Z.
AU - Sladić, Dušan
AU - Krstić, Natalija
PY - 2019
UR - http://cer.ihtm.bg.ac.rs/handle/123456789/2948
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.
PB - Elsevier BV
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 and Matić, Ivana Z. and Sladić, Dušan and Krstić, Natalija",
year = "2019",
url = "http://cer.ihtm.bg.ac.rs/handle/123456789/2948",
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.",
publisher = "Elsevier BV",
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 MB, Novaković I, Matić IZ, Sladić D, Krstić N. Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. Steroids. 2019;148:36-46
Živković, M. B., Novaković, I., Matić, I. Z., Sladić, D.,& Krstić, N. (2019). Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives.
SteroidsElsevier BV., 148, 36-46.
https://doi.org/10.1016/j.steroids.2019.04.010
Živković Marijana B., Novaković Irena, Matić Ivana Z., Sladić Dušan, Krstić Natalija, "Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives" 148 (2019):36-46,
https://doi.org/10.1016/j.steroids.2019.04.010 .
