methyl 2-(4-bromophenyl)-1-(5-tert-butyl-1H-pyrazol-3-yl)-1H-benzimidazole-5-carboxylate | 1282480-10-7

• 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: methyl 2-(4-bromophenyl)-1-(5-tert-butyl-1H-pyrazol-3-yl)-1H-benzimidazole-5-carboxylate
• 英文别名: methyl 1-(5-tert-butyl-1H-pyrazol-3-yl)-2-(4-bromophenyl)-1H-benzo[d]imidazole-5-carboxylate；methyl 2-(4-bromophenyl)-1-(5-tert-butyl-1H-pyrazol-3-yl)benzimidazole-5-carboxylate
• CAS: 1282480-10-7
• 化学式: C₂₂H₂₁BrN₄O₂
• 分子量: 453.338
• InChiKey: WBOKGYYJQVCGCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  新戊酰基乙腈 在 一水合肼 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 methyl 2-(4-bromophenyl)-1-(5-tert-butyl-1H-pyrazol-3-yl)-1H-benzimidazole-5-carboxylate
  参考文献：
  名称：

  Synthesis of novel 1,2,5-trisubstituted benzimidazoles as potential antitumor agents

  摘要：

  Novel methyl 1-(5-tert-butyl-1H-pyrazol-3-yl)-2-(aryl)-1H-benzo[d]imidazole-5-carboxylates 11 were synthesized by following a four-step strategy involving a nucleophilic aromatic displacement (SNAr) and a solvent free approach as key steps for the formation of the desired products. Structure of intermediates and products were confirmed by X-ray diffraction as well as the tautomeric rearrangement suffered by the pyrazole moiety during the curse of the final cyclization process. Several of the obtained compounds were screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Products 11b and 11n exhibited the highest activity against a range of cancer cell lines with remarkable values in panels of Non-Small Cell Lung Cancer, Melanoma and Leukemia, with GI(50) range of 1.15-7.33 mu M and 0.167-7.59 mu M, respectively, and suitable LC50 with values greater than 100 mu M. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.06.006

文献信息

• Methyl 2-(4-bromophenyl)-1-(5-<i>tert</i>-butyl-1<i>H</i>-pyrazol-3-yl)-1<i>H</i>-benzimidazole-5-carboxylate: a hydrogen-bonded chain of edge-fused centrosymmetric rings
  作者：Edwar Cortés、Rodrigo Abonía、Justo Cobo、Christopher Glidewell

  DOI：10.1107/s0108270110052911

  日期：2011.2.15

  In the title compound, C22H21BrN4O2, the imidazole and pyrazole rings are almost orthogonal to each other, but the ester unit is effectively coplanar with the adjacent aryl rings. The molecules are linked into a chain of edge-fused centrosymmetric rings by a combination of N-H...O and C-H...pi(arene) hydrogen bonds.