(E)-1-(5,6-dimethyl-1H-benzo[d]imidazol-1-yl)-3-phenylprop-2-en-1-one | 1609007-30-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (E)-1-(5,6-dimethyl-1H-benzo[d]imidazol-1-yl)-3-phenylprop-2-en-1-one
• 英文别名: (2E)-1-(5,6-dimethyl-1H-benzimidazol-1-yl)-3-phenylprop-2-en-1-one；(E)-1-(5,6-dimethylbenzimidazol-1-yl)-3-phenylprop-2-en-1-one
• CAS: 1609007-30-8
• 化学式: C₁₈H₁₆N₂O
• 分子量: 276.338
• InChiKey: UTNQALXYULKBRJ-CMDGGOBGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 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：

  反式肉桂醛 、 5,6-二甲基苯并咪唑 在 二叔丁基过氧化物 作用下， 以 乙酸乙酯 为溶剂， 反应 15.0h， 以50%的产率得到(E)-1-(5,6-dimethyl-1H-benzo[d]imidazol-1-yl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Metal-free cross-dehydrogenative coupling of benzimidazoles with aldehydes to N-acylbenzimidazoles

  摘要：

  A novel and direct cross-dehydrogenative coupling (CDC) between benzimidazoles with aldehydes promoted by di-tert-butyl peroxide (DTBP) was developed. The reactions generated the corresponding N-acylbenzimidazoles in good yields under metal-free conditions. This method has broad substrate scope and high efficiency. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.07.009

文献信息

• 1-[(2E)-3-Phenylprop-2-enoyl]-1H-benzimidazoles as anticancer agents: synthesis, crystal structure analysis and binding studies of the most potent anticancer molecule with serum albumin
  作者：Veerendra Kumar A. Kalalbandi、J. Seetharamappa

  DOI：10.1039/c5md00293a

  日期：——

  The anticancer activity of 1H-benzimidazoles was studied against NCI 60 cell panel. Compound3fshowed antitumor activity with good to moderate selectivity ratio. Mechanism of interaction of3fwith protein was studied by spectral methods.

  1-苯并咪唑类化合物在NCI 60细胞系中的抗癌活性进行了研究。化合物3f表现出良好至中等的抗肿瘤活性选择性比。通过光谱方法研究了3f与蛋白质的相互作用机制。
• 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.