ethyl 2-(2,4-dihydroxyphenyl)-1H-benzimidazole-5-carboxylate | 1350842-33-9

• 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: ethyl 2-(2,4-dihydroxyphenyl)-1H-benzimidazole-5-carboxylate
• 英文别名: ethyl 2-(2,4-dihydroxyphenyl)-3H-benzimidazole-5-carboxylate
• CAS: 1350842-33-9
• 化学式: C₁₆H₁₄N₂O₄
• 分子量: 298.298
• InChiKey: XKVFOIORTFGYOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  95.4
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-氟-3-硝基苯甲酸 在 ammonium hydroxide 、 硫酸 、 palladium 10% on activated carbon 、 甲酸铵 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 11.0h， 生成 ethyl 2-(2,4-dihydroxyphenyl)-1H-benzimidazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and evaluation of antimycobacterial activity of new benzimidazole aminoesters

  摘要：

  A total of 51 novel benzimidazoles were synthesized by a 4-step reaction starting from basic compound 4-fluoro-3-nitrobenzoic acid under relatively mild reaction conditions. The structure of the novel benzimidazoles was confirmed by mass spectra as well as H-1 NMR spectroscopic data. Out of the 51 novel synthesized compounds, 42 of them were screened for their antimycobacterial activity against Mycobacterium tuberculosis H(37)Rv strain using BacTiter-Glo (TM) Microbial Cell Viability (BTG) method. Results of activity screened using Alamar Blue method was also provided for comparison purposes. Two of the novel benzimidazoles synthesized showed moderately good activity with 1050 of less than 15 mu M. Compound 5g, ethyl 2-(4-(trifluoromethyl)phenyl)-1-(2-morpholinoethyl)-1H-benzo[d]imidazole-5-carboxylate, was found to be the most active with IC50 of 11.52 mu M. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.06.025

文献信息

• Synthesis of novel 4-(1H-benzimidazol-2-yl)benzene-1,3-diols and their cytotoxic activity against human cancer cell lines
  作者：Monika M. Karpińka、Joanna Matysiak、Andrzej Niewiadomy

  DOI：10.1007/s12272-011-1008-0

  日期：2011.10

  One-pot synthesis of new biologically active 4-(1H-benzimidazol-2-yl)benzene-l,3-diols has been developed. The compounds were prepared by the reaction of aryl-modified sulfinylbis[(2,4-dihydroxyphenyl)methanethione]s with benzene-l,2-diamines. Their structures were identified using elemental, IR, 1H-NMR, and mass spectra analyses. The developed method offers short reaction times, relatively large-scale

  新的生物活性 4-(1H-benzimidazol-2-yl)benzo-l,3-diols 的一锅合成已经开发出来。这些化合物是通过芳基修饰的亚磺酰基双[(2,4-二羟基苯基)甲硫酮]与苯-1,2-二胺反应制备的。使用元素、IR、1H-NMR 和质谱分析确定了它们的结构。所开发的方法提供了较短的反应时间、相对大规模的合成、容易和快速的产物分离以及良好的收率。测定了对 4 种人类癌细胞系：SW707（直肠）、HCV29T（膀胱）、A549（肺）和 T47D（乳腺）的体外细胞毒性。一些化合物研究的抗增殖特性比用作比较药物的顺铂更强。