4-氨基-5-苯甲酰基-1,2-恶唑-3-甲酰胺 | 76390-64-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-氨基-5-苯甲酰基-1,2-恶唑-3-甲酰胺
• 英文名称: 4-amino-5-benzoylisoxazolo-3-carboxamide
• 英文别名: 4-amino-5-benzoylisoxazole-3-carboxamide；4-amino-5-benzoyl-1,2-oxazole-3-carboxamide
• CAS: 76390-64-2
• 化学式: C₁₁H₉N₃O₃
• mdl: MFCD03034430
• 分子量: 231.211
• InChiKey: PEPVENQAOITVSR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-氨基-5-苯甲酰基-1,2-恶唑-3-甲酰胺 在 一水合肼 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 反应 6.0h， 以81.3%的产率得到4-amino-5-benzoylisoxazole-3-carbohydrazide
  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：

  Cyan(phenacyloxyimino)acetamid 在 lithium hydroxide 作用下， 以 水 为溶剂， 反应 16.0h， 以46%的产率得到4-氨基-5-苯甲酰基-1,2-恶唑-3-甲酰胺
  参考文献：
  名称：

  Gewald, Karl; Bellmann, Peter; Jaensch, Hans-Joachim, Liebigs Annalen der Chemie, 1980, # 10, p. 1623 - 1629

  摘要：

  DOI：

文献信息

• Synthesis and pharmacological screening of derivatives of isoxazolo[4,3-d]pyrimidine and isoxazolo[4,5-d]pyrimidine
  作者：Edwin Wagner、Kamal Al-Kadasi、Lilianna Becan、Wanda Sawka-Dobrowolska

  DOI：10.1002/jhet.373

  日期：——

  A number of derivatives of isoxazolo[4,3-d]pyrimidine and isoxazolo[4,5-d]pyrimidine were prepared with potential anticancer activity. Condensation of 4-amino-5-benzoyl-isoxazolo-3-carboxylic acid hydrazide with ethyl orthoformate and then with different amines gave a series of 3-benzoyl-7-oxo-7H-isoxazolo[4,3-d]pyrimidin-6-yl-aryliden-formamidine. A series of 5-aminomethyl-7-phenyl-isoxazolo[4,5-

  制备了许多具有潜在抗癌活性的异恶唑并[4,3- d ]嘧啶和异恶唑并[4,5- d ]嘧啶的衍生物。缩合的与4-氨基-5-苯甲酰基异恶唑-3-羧酸酰肼原甲酸乙酯，然后与不同的胺反应，得到一系列的3-苯甲酰基-7-氧代-7 H-异恶唑并[4,3 - d ]嘧啶-6-基-芳基-甲form。一系列5-氨基甲基-7-苯基-异恶唑并[4，5 - d ]嘧啶-3-羧酰胺得自4-氨基-5-苯甲酰基异恶唑-3-羧酰胺与乙腈，氯乙腈与气态氯化氢。测试了其中一些化合物的细胞毒性活性。J.杂环化​​学。（2010）。
• Wagner; Opolski; Wietrzyk, Polish Journal of Chemistry, 2003, vol. 77, # 8, p. 1001 - 1006
  作者：Wagner、Opolski、Wietrzyk

  DOI：——

  日期：——
• Chattopadhyay, Gautam; Saha, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 9, p. 861 - 864
  作者：Chattopadhyay, Gautam、Saha

  DOI：——

  日期：——
• Wagner; Poreba; Jakowicz, Il Farmaco, 1995, vol. 50, # 3, p. 183 - 187
  作者：Wagner、Poreba、Jakowicz、Balicka、Rutkowska、Kedzierska-Gozdzik、Szelag

  DOI：——

  日期：——
• Synthesis of isoxazolo[4,5-e][1,4]diazepin-5-ones from 5-acyl-4-(haloacetylamino)isoxazoles
  作者：Victor P. Kislyi、Evgenia B. Danilova、Victor V. Semenov

  DOI：10.1016/j.mencom.2012.03.011

  日期：2012.3

  Treatment of 5-benzoyl-4-(iodoacetylamino)isoxazoles with alcoholic ammonia leads to isoxazolo[4,5-e][1,4]diazepin-5-ones, whereas the analogous chloroacetylamino derivatives are converted into a mixture of the deacylated 4-aminoisoxazoles and isoxazolo[4,5-d]pyrimidines.