ethyl 5-(4-amino-5-benzoylisoxazol-3-yl)[1,3,4]oxadiazole-2-carboxylate | 1093747-70-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 5-(4-amino-5-benzoylisoxazol-3-yl)[1,3,4]oxadiazole-2-carboxylate
• 英文别名: Ethyl 5-(4-amino-5-benzoyl-1,2-oxazol-3-yl)-1,3,4-oxadiazole-2-carboxylate
• CAS: 1093747-70-6
• 化学式: C₁₅H₁₂N₄O₅
• 分子量: 328.284
• InChiKey: LMNCWPVCUQEUIF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  134
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  ethyl 5-(4-amino-5-benzoylisoxazol-3-yl)[1,3,4]oxadiazole-2-carboxylate 、 苄胺 以 乙醇 为溶剂， 以86%的产率得到5-(4-amino-5-benzoyl-1,2-oxazol-3-yl)-N-benzyl-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 {2-[(4-amino-5-benzoylisoxazol-3-yl)carbonyl]hydrazine}(oxo)acetate 在 氯化亚砜 作用下， 以 1,4-二氧六环 为溶剂， 反应 15.0h， 以67.9%的产率得到ethyl 5-(4-amino-5-benzoylisoxazol-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