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Synthesis and preliminary screening for the biological activity of some steroidal Δ4-unsaturated semicarbazone derivatives
- Source :
- Steroids
- Publication Year :
- 2019
- Publisher :
- Elsevier, 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. 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]
- Subjects :
- medicine.medical_treatment
Clinical Biochemistry
Hydrazone
030209 endocrinology & metabolism
Biochemistry
Medicinal chemistry
Steroid
HeLa
03 medical and health sciences
chemistry.chemical_compound
0302 clinical medicine
Endocrinology
medicine
Ethyl chloroacetate
Molecular Biology
Semicarbazone
3-Oxo-α,β-unsaturated steroids
Pharmacology
chemistry.chemical_classification
Semicarbazones
Ethanol
biology
Biological activity
Organic Chemistry
Carbazate esters
biology.organism_classification
In vitro
3. Good health
chemistry
030220 oncology & carcinogenesis
Subjects
Details
- Database :
- OpenAIRE
- Journal :
- Steroids
- Accession number :
- edsair.doi.dedup.....b8cf90058aa093b0330ce7e9ea603e40