ethyl 5,7-dimethoxyimidazo<1,2-a>pyrimidine-2-carboxylate | 156756-46-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1，2-a]嘧啶
• 英文名称: ethyl 5,7-dimethoxyimidazo<1,2-a>pyrimidine-2-carboxylate
• 英文别名: Ethyl 5,7-dimethoxyimidazo[1,2-a]pyrimidine-2-carboxylate
• CAS: 156756-46-6
• 化学式: C₁₁H₁₃N₃O₄
• 分子量: 251.242
• InChiKey: DIHNZQAJBKHYGY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  75
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 5,7-dimethoxyimidazo<1,2-a>pyrimidine-2-carboxylate 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 以45%的产率得到5,7-dimethoxyimidazo<1,2-a>pyrimidine-2-carboxamide
  参考文献：
  名称：

  Research on heterocyclic compounds. XXXII. Synthesis and cyclooxygenase-independent antiinflammatory and analgesic activity of imidazo[1,2-a]pyrimidine derivatives

  摘要：

  The synthesis of a group of imidazo[1,2-a]pyrimidine-2-carboxylic esters, acids and amides is described. The structures of the new compounds are supported by H-1- and C-13-NMR spectra. These compounds were tested in vivo for their antiinflammatory and analgesic activities as well as for their ulcerogenic action. The ester 5b, the acid 6c and the amide 7a showed antiinflammatory action in the rat paw edema (similar to 1/3 x indomethacin), while almost all compounds displayed significant analgesic activity in the acetic acid writhing test, particularly the 5-chloro-7 methyl derivatives 5a, 6a and 7a (similar to 1/5 x indomethacin). All new compounds were found to be lacking in inhibitory activity on cyclooxygenase in vitro.

  DOI：

  10.1016/0223-5234(94)90097-3
• 作为产物：
  描述：

  2-氨基-4,6-二甲氧基嘧啶 、 3-溴丙酮酸乙酯 以 乙醇 为溶剂， 反应 8.0h， 以8.8%的产率得到ethyl 5,7-dimethoxyimidazo<1,2-a>pyrimidine-2-carboxylate
  参考文献：
  名称：

  Research on heterocyclic compounds. XXXII. Synthesis and cyclooxygenase-independent antiinflammatory and analgesic activity of imidazo[1,2-a]pyrimidine derivatives

  摘要：

  The synthesis of a group of imidazo[1,2-a]pyrimidine-2-carboxylic esters, acids and amides is described. The structures of the new compounds are supported by H-1- and C-13-NMR spectra. These compounds were tested in vivo for their antiinflammatory and analgesic activities as well as for their ulcerogenic action. The ester 5b, the acid 6c and the amide 7a showed antiinflammatory action in the rat paw edema (similar to 1/3 x indomethacin), while almost all compounds displayed significant analgesic activity in the acetic acid writhing test, particularly the 5-chloro-7 methyl derivatives 5a, 6a and 7a (similar to 1/5 x indomethacin). All new compounds were found to be lacking in inhibitory activity on cyclooxygenase in vitro.

  DOI：

  10.1016/0223-5234(94)90097-3

文献信息

• Research on heterocyclic compounds. XXXII. Synthesis and cyclooxygenase-independent antiinflammatory and analgesic activity of imidazo[1,2-a]pyrimidine derivatives
  作者：E Abignente、A Sacchi、S Laneri、F Rossi、M D'Amico、L Berrino、V Calderaro、C Parrillo

  DOI：10.1016/0223-5234(94)90097-3

  日期：1994.1

  The synthesis of a group of imidazo[1,2-a]pyrimidine-2-carboxylic esters, acids and amides is described. The structures of the new compounds are supported by H-1- and C-13-NMR spectra. These compounds were tested in vivo for their antiinflammatory and analgesic activities as well as for their ulcerogenic action. The ester 5b, the acid 6c and the amide 7a showed antiinflammatory action in the rat paw edema (similar to 1/3 x indomethacin), while almost all compounds displayed significant analgesic activity in the acetic acid writhing test, particularly the 5-chloro-7 methyl derivatives 5a, 6a and 7a (similar to 1/5 x indomethacin). All new compounds were found to be lacking in inhibitory activity on cyclooxygenase in vitro.