SYNTHESIS, CHARACTERIZATION AND CYTOTOXICITY OF MANNICH BASES OF 2-SUBSTITUTED BENZIMIDAZOLE DERIVATIVES AGAINST SK-N-MC CELL LINE
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2-(4-fluorophenyl)-1H-benzimidazole was synthesized with o-phenylenediamine and 4-fluoro benzoic acid in presence of polyphosphoric acid. The Mannich reaction of 2-phenyl benzimidazole, substituted benzylamine, ethanol and formaldehyde yielded N-benzyl-1-(2-(4-fluorophenyl)-1H-benzo[d]imidazol-1-yl) methanamine derivatives, which was treated with hydroxybenzotriazole (HOBT), 1-Ethyl-3-(3-dimethylaminopropyl) carbodiimide (EDCI), N, N-Diiso propylethylamine (DIPEA), and adamantane 1-carboxylic acid in dimethylformamide to produced substituted (3r, 5r, 7r)-N-Benzyl-N-((2-4-fluorophenyl-1H-benzo[d]imidazole-1-yl) methyl) adamantane-1-carboxamide (3A1-3J1) derivatives. Ten Mannich bases of substituted (3r,5r,7r)-N-Benzyl-N-((2-(4-fluorophenyl)-1H-benzo[d]imidazol-1-yl) methyl) adamantane-1-carboxamide were synthesized, characterized on the basis of IR, 1H NMR, 13C NMR and mass spectroscopic analysis and evaluated for in vitro cytotoxicity. The in vitro cytotoxicity study showed that the compound 3C1 has less cytotoxicity while, 3H1 had potent cytotoxicity. Hence compound 3C1 can be considered less active whereas compound 3H1 can be considered more active. The other synthesized compounds exhibited medium level of cytotoxicity.
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