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

Само за регистроване кориснике
2019
Аутори
Živković, Marijana B.
Novaković, Irena
Matić, Ivana Z.
Sladić, Dušan
Krstić, Natalija
Чланак у часопису (Објављена верзија)
,
Elsevier BV
Метаподаци
Приказ свих података о документу
Апстракт
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.

Кључне речи:
3-Oxo-α,β-unsaturated steroids / Semicarbazones / Carbazate esters / Biological activity
Извор:
Steroids, 2019, 148, 36-46
Издавач:
  • Elsevier
Финансирање / пројекти:
  • Интеракције природних производа, њихових деривата и комплексних једињења са протеинима и нуклеинским киселинама (RS-172055)
  • Модификатори биолошког одговора у физиолошким и патолошким стањима (RS-175011)
Напомена:
  • The peer-reviewed version: http://cer.ihtm.bg.ac.rs/handle/123456789/2948

DOI: 10.1016/j.steroids.2019.04.010

ISSN: 0039-128X

WoS: 000474331100005

Scopus: 2-s2.0-85065594815
[ Google Scholar ]
4
2
URI
https://cer.ihtm.bg.ac.rs/handle/123456789/2947
Колекције
  • Radovi istraživača / Researchers' publications
Институција/група
IHTM
TY  - 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/123456789/2947
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 . .

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