2-((pyridin-2-yl)aminomethyl)-1H-benzo[d]imidazole-5-carboxylic acid | 1262201-35-3

• 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: 2-((pyridin-2-yl)aminomethyl)-1H-benzo[d]imidazole-5-carboxylic acid
• 英文别名: 2-[(pyridin-2-ylamino)methyl]-3H-benzimidazole-5-carboxylic acid
• CAS: 1262201-35-3
• 化学式: C₁₄H₁₂N₄O₂
• 分子量: 268.275
• InChiKey: IZHSVXYKRCKRGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  90.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氨基吡啶 、 2-(chloromethyl)-1H-benzo[d]imidazole-5-carboxylic acid hydrochloride 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以60%的产率得到2-((pyridin-2-yl)aminomethyl)-1H-benzo[d]imidazole-5-carboxylic acid
  参考文献：
  名称：

  Synthesis and antitumor activity of novel benzimidazole-5-carboxylic acid derivatives and their transition metal complexes as topoisomerease II inhibitors

  摘要：

  N-Aminomethyl-1H-benzimidazole-5-carboxylic acid derivatives 2-5 and the ligand, 1-(5 (or 6-)-carboxy-1H-benzimidazol-2-ylmethyl)pyridinium chloride (6; H2L1) have been synthesized. New benzimidazole complexes 7-9 of the ligand 6; H2L1 with Cu2+ Co-2 and Zn2+ were prepared. The growth-inhibitory against a panel of 21 human cancer cell lines of the synthesized compounds 1-9 was studied. Compounds 6-9 showed potent growth-inhibitory activity against the studied cell lines. The correlation coefficients according to COMPARE analysis of the National Cancer Institute screening protocol showed that the pattern of the growth-inhibitory effect of the compounds 6-9 was similar to that of etoposide and doxorubicin but different from that of SN-38 and cisplatin. The topoisomerase II inhibitory activity of the tested compounds 6-9 was studied. Compounds 6 and 8 inhibited topoisomerase II activity at 10 times lower concentration than etoposide in relaxation assay. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.09.023

文献信息

• Synthesis and antitumor activity of novel benzimidazole-5-carboxylic acid derivatives and their transition metal complexes as topoisomerease II inhibitors
  作者：Shadia A. Galal、Khaled H. Hegab、Ahmed M. Hashem、Nabil S. Youssef

  DOI：10.1016/j.ejmech.2010.09.023

  日期：2010.12

  N-Aminomethyl-1H-benzimidazole-5-carboxylic acid derivatives 2-5 and the ligand, 1-(5 (or 6-)-carboxy-1H-benzimidazol-2-ylmethyl)pyridinium chloride (6; H2L1) have been synthesized. New benzimidazole complexes 7-9 of the ligand 6; H2L1 with Cu2+ Co-2 and Zn2+ were prepared. The growth-inhibitory against a panel of 21 human cancer cell lines of the synthesized compounds 1-9 was studied. Compounds 6-9 showed potent growth-inhibitory activity against the studied cell lines. The correlation coefficients according to COMPARE analysis of the National Cancer Institute screening protocol showed that the pattern of the growth-inhibitory effect of the compounds 6-9 was similar to that of etoposide and doxorubicin but different from that of SN-38 and cisplatin. The topoisomerase II inhibitory activity of the tested compounds 6-9 was studied. Compounds 6 and 8 inhibited topoisomerase II activity at 10 times lower concentration than etoposide in relaxation assay. (C) 2010 Elsevier Masson SAS. All rights reserved.