4-Chloro-2-phenyl-6-p-tolylamino-pyrimidine-5-carboxylic acid ethyl ester | 90832-88-5

• 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: 4-Chloro-2-phenyl-6-p-tolylamino-pyrimidine-5-carboxylic acid ethyl ester
• 英文别名: ethyl 4-chloro-6-(4-methylanilino)-2-phenylpyrimidine-5-carboxylate
• CAS: 90832-88-5
• 化学式: C₂₀H₁₈ClN₃O₂
• 分子量: 367.835
• InChiKey: WRRLBVQIMYZRIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.03
• 重原子数：
  26.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  64.11
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  C.I.酸性橙108 、 4-Chloro-2-phenyl-6-p-tolylamino-pyrimidine-5-carboxylic acid ethyl ester 以 乙醇 为溶剂， 生成 Ethyl 4-(2-hydroxyethylamino)-6-(4-methylanilino)-2-phenylpyrimidine-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， 生成 4-Chloro-2-phenyl-6-p-tolylamino-pyrimidine-5-carboxylic acid ethyl ester
  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

• Heterocyclization of functionalized ketene acetals: Synthesis of pyrimidines vinylamidine intermediates
  作者：C.J. Shishoo、M.B. Devani、V.S. Bhadti、S. Ananthan、G.V. Ullas

  DOI：10.1016/s0040-4039(01)80137-4

  日期：1984.1

  Stable N-(carbethoxycyanovinyl)amidines have been isolated from the reaction of benzamidine with carbethoxycyanoketene S,N-acetals and have been found to cyclize to 4-chloro-, 4-amino- and 4-hydroxypyrimidines depending upon the cyclizing agent employed.

  从苯甲idine与碳乙氧基氰基酮S，N-乙缩醛的反应中已经分离出稳定的N-（乙氧基氰基乙烯基）am，并发现根据所使用的环化剂，环化成4-氯-，4-氨基-和4-羟基嘧啶。
• SHISHOO, C. J.;DEVANI, M. B.;BHADTI, V. S.;ANANTHAN, S.;ULLAS, G. V., TETRAHEDRON LETT., 1984, 25, N 12, 1291-1292
  作者：SHISHOO, C. J.、DEVANI, M. B.、BHADTI, V. S.、ANANTHAN, S.、ULLAS, G. V.

  DOI：——

  日期：——