Synthesis, crystal studies, anti-tuberculosis and cytotoxic studies of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives

Abstract

Series of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives were synthesized and characterized by spectral methods. Among 21 derivatives, single crystals of 3a and 3l were grown and their structural parameters were evaluated. Newly synthesized compounds were screened for anti-tubercular activity and the MIC was determined against Mycobacterium tuberculosis H37Rv by Microplate Alamar Blue Assay (MABA) method. Majority of the compounds exhibited a promising inhibition of M. tuberculosis and the molecules functionalized with electron-donating groups at C-2 carbon of benzimidazole moiety were found to be more active in inhibiting M. tuberculosis. Further, more promising compounds viz., 3b, 3i and 3l were tested for their cytotoxic activity. Compound 3l was found to display excellent activity (IC50 < 10 μg mL−1) with 100% cell lysis at 30 μg mL−1 concentration against A549 (Human lung carcinoma) and 8E5 (Human; Acute Lymphoblastic Leukemia) cell lines.