ethyl 5-(5-methyl-7-phenylisoxazolo[4,5-d]pyrimidin-3-yl)[1,3,4]oxadiazole-2-carboxylate | 1093747-84-2

• 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 5-(5-methyl-7-phenylisoxazolo[4,5-d]pyrimidin-3-yl)[1,3,4]oxadiazole-2-carboxylate
• 英文别名: Ethyl 5-(5-methyl-7-phenyl-[1,2]oxazolo[4,5-d]pyrimidin-3-yl)-1,3,4-oxadiazole-2-carboxylate
• CAS: 1093747-84-2
• 化学式: C₁₇H₁₃N₅O₄
• 分子量: 351.321
• InChiKey: YQKODZWPTWZMDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  117
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 5-(5-methyl-7-phenylisoxazolo[4,5-d]pyrimidin-3-yl)[1,3,4]oxadiazole-2-carboxylate 、 苄胺 以 四氢呋喃 为溶剂， 反应 2.0h， 以77.76%的产率得到N-benzyl-5-(5-methyl-7-phenyl-[1,2]oxazolo[4,5-d]pyrimidin-3-yl)-1,3,4-oxadiazole-2-carboxamide
  参考文献：
  名称：

  Synthesis and pharmacological screening of derivatives of isoxazolo[4,5-d]pyrimidine

  摘要：

  A number of derivatives of isoxazolo[4,5-d]pyrimidine were prepared with structures similar to that of purine. Condensation of the hydrazide of 4-amino-5-benzoylisoxazolo-3-carboxylic acid 2 with ethyloxalyl chloride followed by cyclization gave 3-oxdiazolo-[1,3,4]-4-amino-5-benzoylisoxazole 7 which, upon cyclization with acetonitrile followed by reactions with different amines, gave derivatives of isoxazolo[4,5-d]pyrimidine 9 and 10d-g. Compounds 8g and 10f were tested for their effects on the immune response in the mouse model. Both compounds significantly inhibited the humoral immune response in vivo to sheep erythrocytes at a dose of 100 jig, whereas in the delayed type hypersensitivity assay a suppressive activity was shown only by compound 10f. In addition, compound 8g inhibited and compound 10f stimulated the proliferative response of mouse splenocytes to concanavalin A. The results indicated that compound 10f was a universal inhibitor of the immune response, while compound 8g selectively suppressed the humoral immune response. (C) 2008 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2008.01.035
• 作为产物：
  描述：

  ethyl 5-(4-amino-5-benzoylisoxazol-3-yl)[1,3,4]oxadiazole-2-carboxylate 、 乙腈 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 150.0h， 以84.11%的产率得到ethyl 5-(5-methyl-7-phenylisoxazolo[4,5-d]pyrimidin-3-yl)[1,3,4]oxadiazole-2-carboxylate
  参考文献：
  名称：

  Synthesis and pharmacological screening of derivatives of isoxazolo[4,5-d]pyrimidine

  摘要：

  A number of derivatives of isoxazolo[4,5-d]pyrimidine were prepared with structures similar to that of purine. Condensation of the hydrazide of 4-amino-5-benzoylisoxazolo-3-carboxylic acid 2 with ethyloxalyl chloride followed by cyclization gave 3-oxdiazolo-[1,3,4]-4-amino-5-benzoylisoxazole 7 which, upon cyclization with acetonitrile followed by reactions with different amines, gave derivatives of isoxazolo[4,5-d]pyrimidine 9 and 10d-g. Compounds 8g and 10f were tested for their effects on the immune response in the mouse model. Both compounds significantly inhibited the humoral immune response in vivo to sheep erythrocytes at a dose of 100 jig, whereas in the delayed type hypersensitivity assay a suppressive activity was shown only by compound 10f. In addition, compound 8g inhibited and compound 10f stimulated the proliferative response of mouse splenocytes to concanavalin A. The results indicated that compound 10f was a universal inhibitor of the immune response, while compound 8g selectively suppressed the humoral immune response. (C) 2008 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2008.01.035