4-(2,2-Dimethyl-propionyl)-N-(2-hydroxy-ethyl)-benzamide | 1027022-75-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2,2-Dimethyl-propionyl)-N-(2-hydroxy-ethyl)-benzamide
• 英文别名: 4-(2,2-dimethylpropanoyl)-N-(2-hydroxyethyl)benzamide
• CAS: 1027022-75-8
• 化学式: C₁₄H₁₉NO₃
• 分子量: 249.31
• InChiKey: OEQHLEAWXDQEDI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2,2-Dimethyl-propionyl)-N-(2-hydroxy-ethyl)-benzamide 在 氯化亚砜 作用下， 反应 1.0h， 生成 4-(2,2-dimethyl-1-oxopropyl)-N-(2-chloroethyl)benzamide
  参考文献：
  名称：

  Hypoglycemic Prodrugs of 4-(2,2-Dimethyl-1-oxopropyl)benzoic Acid

  摘要：

  SAH 51-641 (1) is a potent hypoglycemic agent, which acts by inhibiting hepatic gluconeogenesis. It is a prodrug of 4-(2,2-dimethyl-1-oxopropyl)benzoic acid (2) and 4-(2,2-dimethyl-1-hydroxy propyl)benzoic acid (3), which sequester coenzyme A (CoA) in the mitochondria, and inhibits medium-chain acyltransferase. 1-3 and 4-tert-butylbenzoic acid all cause testicular degeneration in rats at pharmacologically active doses. 14b (FOX 988) is a prodrug of 3, which is metabolized in the liver at a rate sufficient enough to have hypoglycemic potency (an ED50 of 65 mu mol/kg, 28 mg/kg/day, for glucose lowering), yet by avoiding significant escape of the metabolite 3 to the systemic circulation, it avoids the testicular toxicity at doses up to 1500 mu mol/kg/day. 14b was selected for clinical studies.

  DOI：

  10.1021/jm980438y
• 作为产物：
  描述：

  4-Pivaloyl-benzoesaeure 在 sodium hydroxide 、 氯化亚砜 作用下， 以 丙酮 为溶剂， 反应 1.5h， 生成 4-(2,2-Dimethyl-propionyl)-N-(2-hydroxy-ethyl)-benzamide
  参考文献：
  名称：

  Hypoglycemic Prodrugs of 4-(2,2-Dimethyl-1-oxopropyl)benzoic Acid

  摘要：

  SAH 51-641 (1) is a potent hypoglycemic agent, which acts by inhibiting hepatic gluconeogenesis. It is a prodrug of 4-(2,2-dimethyl-1-oxopropyl)benzoic acid (2) and 4-(2,2-dimethyl-1-hydroxy propyl)benzoic acid (3), which sequester coenzyme A (CoA) in the mitochondria, and inhibits medium-chain acyltransferase. 1-3 and 4-tert-butylbenzoic acid all cause testicular degeneration in rats at pharmacologically active doses. 14b (FOX 988) is a prodrug of 3, which is metabolized in the liver at a rate sufficient enough to have hypoglycemic potency (an ED50 of 65 mu mol/kg, 28 mg/kg/day, for glucose lowering), yet by avoiding significant escape of the metabolite 3 to the systemic circulation, it avoids the testicular toxicity at doses up to 1500 mu mol/kg/day. 14b was selected for clinical studies.

  DOI：

  10.1021/jm980438y

文献信息

• Hypoglycemic Prodrugs of 4-(2,2-Dimethyl-1-oxopropyl)benzoic Acid
  作者：Thomas D. Aicher、Gregory R. Bebernitz、Philip A. Bell、Leonard J. Brand、Jeremy G. Dain、Rhonda Deems、William S. Fillers、James E. Foley、Douglas C. Knorr、Jeffrey Nadelson、Dario A. Otero、Ronald Simpson、Robert J. Strohschein、Douglas A. Young

  DOI：10.1021/jm980438y

  日期：1999.1.1

  SAH 51-641 (1) is a potent hypoglycemic agent, which acts by inhibiting hepatic gluconeogenesis. It is a prodrug of 4-(2,2-dimethyl-1-oxopropyl)benzoic acid (2) and 4-(2,2-dimethyl-1-hydroxy propyl)benzoic acid (3), which sequester coenzyme A (CoA) in the mitochondria, and inhibits medium-chain acyltransferase. 1-3 and 4-tert-butylbenzoic acid all cause testicular degeneration in rats at pharmacologically active doses. 14b (FOX 988) is a prodrug of 3, which is metabolized in the liver at a rate sufficient enough to have hypoglycemic potency (an ED50 of 65 mu mol/kg, 28 mg/kg/day, for glucose lowering), yet by avoiding significant escape of the metabolite 3 to the systemic circulation, it avoids the testicular toxicity at doses up to 1500 mu mol/kg/day. 14b was selected for clinical studies.