Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives
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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.
Keywords:
3-Oxo-α,β-unsaturated steroids / Semicarbazones / Carbazate esters / Biological activitySource:
Steroids, 2019, 148, 36-46Publisher:
- Elsevier
Funding / projects:
- Interactions of natural products, their derivatives and coordination compounds with proteins and nucleic acids (RS-172055)
- Biological response modifiers in physiological and pathological conditions (RS-175011)
Note:
- 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
- http://cer.ihtm.bg.ac.rs/handle/123456789/2947
DOI: 10.1016/j.steroids.2019.04.010
ISSN: 0039-128X
WoS: 000474331100005
Scopus: 2-s2.0-85065594815
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IHTMTY - JOUR AU - Živković, Marijana B. AU - Novaković, Irena AU - Matić, Ivana Z. AU - Sladić, Dušan AU - Krstić, Natalija PY - 2019 UR - https://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 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", 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", 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., Matić, I. Z., Sladić, D.,& Krstić, N.. (2019). Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives. in Steroids Elsevier., 148, 36-46. https://doi.org/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. in Steroids. 2019;148:36-46. doi: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" in Steroids, 148 (2019):36-46, https://doi.org/10.1016/j.steroids.2019.04.010 . .