title: 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.
authors.affiliation: Department of Chemistry, Karnatak University, Dharwad 580 003, India.
authors.forename: Veerendra Kumar A
authors.initials: VK
authors.lastname: Kalalbandi
authors.affiliation: Department of Chemistry, Karnatak University, Dharwad 580 003, India. Electronic address: jseetharam@yahoo.com.
authors.forename: J
authors.initials: J
authors.lastname: Seetharamappa
authors.affiliation: Department of Chemistry, Karnatak University, Dharwad 580 003, India.
authors.forename: Umesha
authors.initials: U
authors.lastname: Katrahalli
authors.affiliation: Department of Microbiology, Maratha Mandal's NGH Institute of Dental Sciences and Research Centre, Belgaum 590 010, India.
authors.forename: Kishore G
authors.initials: KG
authors.lastname: Bhat
mesh_terms: D000995:Antitubercular Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D003603:Cytotoxins / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D006801:Humans; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects*; D013329:Structure-Activity Relationship; D014407:Tumor Cells, Cultured
chemical_list: D000995:Antitubercular Agents; D003603:Cytotoxins
keywords: 1H-benzimidazoles; Anti-tuberculosis; Crystal structure; Cytotoxic activity