Faculty of Chemistry Repository - Cherry
University of Belgrade - Faculty of Chemistry
    • English
    • Српски
    • Српски (Serbia)
  • English 
    • English
    • Serbian (Cyrillic)
    • Serbian (Latin)
  • Login
View Item 
  •   Cherry
  • Hemijski fakultet
  • Publikacije
  • View Item
  •   Cherry
  • Hemijski fakultet
  • Publikacije
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives

Authorized Users Only
2019
Authors
Živković, Marijana B.
Novaković, Irena T.
Matić, Ivana Z.
Sladić, Dušan
Krstić, Natalija M.
Article (Published version)
Metadata
Show full item record
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 repl...acement of thioxo group with carbonyl group in steroidal hydrazone derivatives resulted in decrease in their biological activity.

Keywords:
3-Oxo-α,β-unsaturated steroids / Biological activity / Carbazate esters / Semicarbazones
Source:
Steroids, 2019, 148, 36-46
Publisher:
  • 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:
  • Supplementary material: https://cherry.chem.bg.ac.rs/handle/123456789/3083
  • Peer-reviewed manuscript: https://cherry.chem.bg.ac.rs/handle/123456789/3084

DOI: 10.1016/j.steroids.2019.04.010

ISSN: 0039-128X

WoS: 000474331100005

Scopus: 2-s2.0-85065594815
[ Google Scholar ]
3
2
URI
http://www.sciencedirect.com/science/article/pii/S0039128X19300893
https://cherry.chem.bg.ac.rs/handle/123456789/3082
Collections
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - JOUR
AU  - Živković, Marijana B.
AU  - Novaković, Irena T.
AU  - Matić, Ivana Z.
AU  - Sladić, Dušan
AU  - Krstić, Natalija M.
PY  - 2019
UR  - http://www.sciencedirect.com/science/article/pii/S0039128X19300893
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/3082
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 . .

DSpace software copyright © 2002-2015  DuraSpace
About CHERRY - CHEmistry RepositoRY | Send Feedback

re3dataOpenAIRERCUB
 

 

All of DSpaceInstitutions/communitiesAuthorsTitlesSubjectsThis institutionAuthorsTitlesSubjects

Statistics

View Usage Statistics

DSpace software copyright © 2002-2015  DuraSpace
About CHERRY - CHEmistry RepositoRY | Send Feedback

re3dataOpenAIRERCUB