Ethyl 4-chloro-6-(4-methoxyanilino)pyrimidine-5-carboxylate | 768376-33-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: Ethyl 4-chloro-6-(4-methoxyanilino)pyrimidine-5-carboxylate
• CAS: 768376-33-6
• 化学式: C₁₄H₁₄ClN₃O₃
• 分子量: 307.736
• InChiKey: QXNQIWJSUPMSDL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  73.3
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 4-chloro-6-(4-methoxyanilino)pyrimidine-5-carboxylate 、 C.I.酸性橙108 以 乙醇 为溶剂， 生成 ethyl 4-(2-hydroxyethyl)amino-6-(4-methoxyphenyl)aminopyrimidine-5-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
• 作为产物：
  描述：

  在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以64%的产率得到Ethyl 4-chloro-6-(4-methoxyanilino)pyrimidine-5-carboxylate
  参考文献：
  名称：

  Chhabria, Mahesh T.; Shishoo, Chamanlal J.; Vaghela, Dilip K., Arzneimittel-Forschung/Drug Research, 2009, vol. 59, # 7, p. 350 - 356

  摘要：

  DOI：

文献信息

• Chhabria, Mahesh T.; Shishoo, Chamanlal J.; Vaghela, Dilip K., Arzneimittel-Forschung/Drug Research, 2009, vol. 59, # 7, p. 350 - 356
  作者：Chhabria, Mahesh T.、Shishoo, Chamanlal J.、Vaghela, Dilip K.、Patel, Shailesh M.、Satia, Milan C.

  DOI：——

  日期：——
• 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.