Facile synthesis and antiproliferative activity of new 3-cyanopyridines.

BACKGROUND

Pyridines have been reported to possess various pharmacological activities.

RESULTS

Sodium 3-oxo-3-(2-oxo-2-chromen-3-yl)prop-1-en-1-olate () and sodium 3-oxo-3-(3-oxo-3-benzo[f]chromen-2-yl)prop-1-en-1-olate () were prepared and reacted with 2-cyano-'-(1-aryl(heteryl)ethylidene)acetohydrazides to produce 2-oxo-1,2-dihydropyridine-3-carbonitrile derivatives and , respectively, in good yields. Also, reacted with sodium (2-oxocyclopentylidene)methanolate ( or sodium (2-oxocyclohexylidene) methanolate ) to yield 2-oxo-tetrahydro-1-cyclopenta[b]pyridine-3-carbonitriles and 2-oxo-hexahydroquinoline-3-carbonitriles , respectively. The mechanisms that account for the formation of the products are discussed. Additionally, the structures of all the newly synthesized products are confirmed, based on elemental analysis and spectral data. Several of the newly synthesized compounds are evaluated for their antitumor activity against HEPG2 and their structure activity relationship (SAR) was studied.

CONCLUSIONS

The results revealed that the pyridine derivatives and (IC = 1.46, 7.08 µM, respectively) have promising antitumor activity against liver carcinoma cell line (HEPG2), compared to the reference drug, doxorubicin.