(E)-3-phenyl-1-(2-(p-tolyl)-1H-benzo[d]imidazol-1-yl)prop-2-en-1-one | 1609007-39-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: (E)-3-phenyl-1-(2-(p-tolyl)-1H-benzo[d]imidazol-1-yl)prop-2-en-1-one
• 英文别名: (E)-3-phenyl-1-[2-(p-tolyl)benzimidazol-1-yl]prop-2-en-1-one；(E)-1-[2-(4-methylphenyl)benzimidazol-1-yl]-3-phenylprop-2-en-1-one
• CAS: 1609007-39-7
• 化学式: C₂₃H₁₈N₂O
• 分子量: 338.409
• InChiKey: CDJOKNJBELEQJB-DTQAZKPQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  34.9
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-甲基苯)苯并咪唑 、 3-苯基-2-丙烯酰氯 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 以82%的产率得到(E)-3-phenyl-1-(2-(p-tolyl)-1H-benzo[d]imidazol-1-yl)prop-2-en-1-one
  参考文献：
  名称：

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

  摘要：

  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 mu g mL(-1)) with 100% cell lysis at 30 mu g mL(-1) concentration against A549 (Human lung carcinoma) and 8E5 (Human; Acute Lymphoblastic Leukemia) cell lines. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.04.017

文献信息

• Synthesis, crystal studies, anti-tuberculosis and cytotoxic studies of 1-[(2E)-3-phenylprop-2-enoyl]-1H-benzimidazole derivatives
  作者：Veerendra Kumar A. Kalalbandi、J. Seetharamappa、Umesha Katrahalli、Kishore G. Bhat

  DOI：10.1016/j.ejmech.2014.04.017

  日期：2014.5

  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 mu g mL(-1)) with 100% cell lysis at 30 mu g mL(-1) concentration against A549 (Human lung carcinoma) and 8E5 (Human; Acute Lymphoblastic Leukemia) cell lines. (c) 2014 Elsevier Masson SAS. All rights reserved.