Cytotoxic Activity of Flavone Analogues

Afroze Alam, U Farooq, Kamlesh Kumar Naik, Rashmi Singh, Vachaspati Dubey, Monika Verma, B D Tripathi, Vinod Kumar

Abstract


The flavonoids are polyphenolic compounds and universally present as constituents of flowering plants, particularly of food plants. The flavonoids are phenyl substituted chroman (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C), also shared by the tocopherols, with a phenyl (the aromatic ring B), substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. Various analogues of 3-methylflavones were synthesised, purified and characterised by UV, IR, 1HNMR and mass spectrometry .All the synthesised
compounds were evaluated for their cytotoxic activity by MTT assay against HeLa cell line. Most of the compounds show moderate activity, whereas the compounds like FA-04.FA-20,FA-10 and FA-13 have shown good activity having IC50 value 22.00,25.49.26.24 and 26.35 μg/ml respectively, in comparison
to standard molecule Cisplastin had IC50 value 6- 12.5 μg/ml . Thus it appears the presence of 3- methyl group in the flavone nucleus significantly influences the log ‘P’ value of all the twenty test compounds.

The prominent activity the of above compounds is probably because of 3-methyl and N, N-dimethyl amino substitution on 4’- position of flavonoid nucleus.


Keywords


Benzopyrone, Cytotoxic activity, Flavonoids, HeLa cell line, log ‘P’ value, MTT assay

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