ethyl 7-[(2-chlorophenyl)amino]-2,3-dihydroimidazo[1,2-c]pyrimidine-8-carboxylate | 1189029-15-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: ethyl 7-[(2-chlorophenyl)amino]-2,3-dihydroimidazo[1,2-c]pyrimidine-8-carboxylate
• 英文别名: ethyl 7-(2-chloroanilino)-2,3-dihydroimidazo[1,2-c]pyrimidine-8-carboxylate
• CAS: 1189029-15-9
• 化学式: C₁₅H₁₅ClN₄O₂
• 分子量: 318.763
• InChiKey: AARSIRSPEKSDHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.28
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  66.29
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  Ethyl 4-(2-chloroanilino)-6-(2-hydroxyethylamino)pyrimidine-5-carboxylate 在 三氯氧磷 作用下， 以 甲苯 为溶剂， 以45%的产率得到ethyl 7-[(2-chlorophenyl)amino]-2,3-dihydroimidazo[1,2-c]pyrimidine-8-carboxylate
  参考文献：
  名称：

  Design, synthesis and antimycobacterial activity of some novel imidazo[1,2-c]pyrimidines

  摘要：

  Tuberculosis, due to its relentless nature, is now a major public health threat. The concomitant resurgence of TB with the MDR- or XDR-TB and HIV/AIDS pandemic has exposed the frailties of the current drug armatorium. Based on isosteric replacement and good 3D structural similarity between PA-824, a novel anti mycobacterial agent undergoing clinical trials, and imidazo[1,2-c]pyrimidines, we have designed novel imidazo[1,2-c]pyrimidines. The designed molecules were synthesized by nucleophilic displacement of chloro group of various substituted 4-chloropyrimidines by ethanolamine followed by cyclisation of these 4-(2-hydroxyethyl)aminopyrimidines to imidazo[1,2-c]pyrimidines in good yield. All the compounds were screened for their antimycobacterial activity on Mycobacterium tuberculosis H37Rv strain by 1% proportion method. Some of the synthesized compounds exhibited potent antimycobacterial activity with MIC values in the range of 2-20 mu g/mL. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.04.002

文献信息

• Design, synthesis and antimycobacterial activity of some novel imidazo[1,2-c]pyrimidines
  作者：Mahesh T. Chhabria、Mitesh H. Jani

  DOI：10.1016/j.ejmech.2009.04.002

  日期：2009.10

  Tuberculosis, due to its relentless nature, is now a major public health threat. The concomitant resurgence of TB with the MDR- or XDR-TB and HIV/AIDS pandemic has exposed the frailties of the current drug armatorium. Based on isosteric replacement and good 3D structural similarity between PA-824, a novel anti mycobacterial agent undergoing clinical trials, and imidazo[1,2-c]pyrimidines, we have designed novel imidazo[1,2-c]pyrimidines. The designed molecules were synthesized by nucleophilic displacement of chloro group of various substituted 4-chloropyrimidines by ethanolamine followed by cyclisation of these 4-(2-hydroxyethyl)aminopyrimidines to imidazo[1,2-c]pyrimidines in good yield. All the compounds were screened for their antimycobacterial activity on Mycobacterium tuberculosis H37Rv strain by 1% proportion method. Some of the synthesized compounds exhibited potent antimycobacterial activity with MIC values in the range of 2-20 mu g/mL. (C) 2009 Elsevier Masson SAS. All rights reserved.