Reaction of pregnenolone with cyanoacetylhydrazine: Novel synthesis of hydrazide–hydrazone, pyrazole, pyridine, thiazole, thiophene derivatives and their cytotoxicity evaluations

[Display omitted] ► Synthesis of pyrazole, thiophene and thiazole derivatives of pregnenolone. ► Structures of the newly synthesized products were confirmed. ► Anti-tumor evaluations of the newly synthesized products against cancer cell lines. ► Some of the new pregnenolone derivatives showed high c...

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Bibliographic Details
Published in:Steroids 2012-12, Vol.77 (14), p.1551-1559
Main Authors: Mohareb, Rafat M., Al-Omran, Fatima
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Biological and medical sciences
Cell Line, Tumor
Cytotoxicity
Drug Screening Assays, Antitumor
Fundamental and applied biological sciences. Psychology
Humans
Hydrazide–hydrazone
Hydrazines - chemistry
Hydrazones - chemical synthesis
Hydrazones - pharmacology
Nitriles - chemistry
Pregnenolone
Pregnenolone - chemistry
Pyrazole
Pyrazoles - chemical synthesis
Pyrazoles - pharmacology
Pyridines - chemical synthesis
Pyridines - pharmacology
Thiazole
Thiazoles - chemical synthesis
Thiazoles - pharmacology
Thiophene
Thiophenes - chemical synthesis
Thiophenes - pharmacology
Vertebrates: endocrinology
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Summary:[Display omitted] ► Synthesis of pyrazole, thiophene and thiazole derivatives of pregnenolone. ► Structures of the newly synthesized products were confirmed. ► Anti-tumor evaluations of the newly synthesized products against cancer cell lines. ► Some of the new pregnenolone derivatives showed high cytotoxicity. Pregnenolone (1) was used as a template to develop new anticancer compounds. Ring D modification of 1 through its reaction with cyanoacetylhydrazine (2) gave the hydrazide–hydrazone derivative 3. The latter compound underwent heterocyclization reactions to give the pyrazole, pyridine, thiazole and thiophene derivatives of pregnenolone. The cytotoxicity of the newly synthesized heterocyclic steroids against three human tumor cell lines namely breast adenocarcinoma (MCF-7), non-small cell lung cancer (NCI-H460) and CNS cancer (SF-268) were studied. Some of tested compounds were found to exhibit much higher inhibitory effects towards the three tumor cell lines than the reference drug, doxorubicin.
ISSN:0039-128X
1878-5867
DOI:10.1016/j.steroids.2012.09.007