1-[(2E)-3-苯基丙-2-烯酰基]-1H-苯并咪唑衍生物的合成、晶体研究、抗结核及细胞毒性研究
Synthesis, crystal studies, anti-tuberculosis and cytotoxic studies of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives.
作者信息
Kalalbandi Veerendra Kumar A, Seetharamappa J, Katrahalli Umesha, Bhat Kishore G
机构信息
Department of Chemistry, Karnatak University, Dharwad 580 003, India.
Department of Chemistry, Karnatak University, Dharwad 580 003, India.
出版信息
Eur J Med Chem. 2014 May 22;79:194-202. doi: 10.1016/j.ejmech.2014.04.017. Epub 2014 Apr 5.
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.
合成了一系列1-[(2E)-3-苯基丙-2-烯酰基]-1H-苯并咪唑衍生物，并通过光谱方法对其进行了表征。在21种衍生物中，培养出了3a和3l的单晶，并评估了它们的结构参数。通过微孔板阿拉玛蓝测定法（MABA）对新合成的化合物进行抗结核活性筛选，并测定其对结核分枝杆菌H37Rv的最低抑菌浓度（MIC）。大多数化合物对结核分枝杆菌表现出有前景的抑制作用，并且发现苯并咪唑部分C-2碳上带有供电子基团的分子在抑制结核分枝杆菌方面更具活性。此外，对更有前景的化合物3b、3i和3l进行了细胞毒性活性测试。发现化合物3l对A549（人肺癌）和8E5（人急性淋巴细胞白血病）细胞系表现出优异的活性（IC50 < 10 μg mL(-1)），在30 μg mL(-1)浓度下细胞裂解率为100%。
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