Synthesis of novel hydrazone and azole functionalized pyrazolo[3,4-b]pyridine derivatives as promising anticancer agents

[Display omitted] A series of novel pyrazolo[3,4-b]pyridine based target compounds were synthesized starting from the key intermediate ethyl 2-(3-amino-6-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl)acetate 5 on reaction with hydrazine hydrate followed by reaction with different aldehydes, acid...

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Published in:Bioorganic & medicinal chemistry letters 2016-09, Vol.26 (18), p.4427-4432
Main Authors: Nagender, P., Naresh Kumar, R., Malla Reddy, G., Krishna Swaroop, D., Poornachandra, Y., Ganesh Kumar, C., Narsaiah, B.
Format: Article
Language:English
Subjects:
1,2,4-Triazole
Anticancer activity
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - pharmacology
Azoles - chemistry
Cell Line, Tumor
Drug Screening Assays, Antitumor
Humans
Hydrazones - chemistry
Oxadiazole
Pyrazoles - chemistry
Pyrazolo[3,4-b]pyridine
Pyridines - chemistry
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Summary:[Display omitted] A series of novel pyrazolo[3,4-b]pyridine based target compounds were synthesized starting from the key intermediate ethyl 2-(3-amino-6-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-1-yl)acetate 5 on reaction with hydrazine hydrate followed by reaction with different aldehydes, acid chlorides and isothiocyanates to form hydrazones 7, oxadiazoles 8, 1,2,4 triazoles 10 and thiadiazoles 11 respectively in high yield. All the final compounds were screened for anticancer activity against four human cancer cell lines. Among them, 1,2,4 triazole derivatives showed promising activity and compound 10d is identified as a lead molecule.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2016.08.006