((Z)-C-(4-(2,2-Dimethylpropanoyl)phenyl)-N-methoxycarbonimidoyl)4-(2,2-dimethylpropanoyl)benzoate | 139681-18-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ((Z)-C-(4-(2,2-Dimethylpropanoyl)phenyl)-N-methoxycarbonimidoyl)4-(2,2-dimethylpropanoyl)benzoate
• 英文别名: [(Z)-C-[4-(2,2-dimethylpropanoyl)phenyl]-N-methoxycarbonimidoyl] 4-(2,2-dimethylpropanoyl)benzoate
• CAS: 139681-18-8
• 化学式: C₂₅H₂₉NO₅
• 分子量: 423.509
• InChiKey: YXIAKADBIZQTQI-ROMGYVFFSA-N

物化性质

• 沸点：
  544.1±60.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  82
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ((Z)-C-(4-(2,2-Dimethylpropanoyl)phenyl)-N-methoxycarbonimidoyl)4-(2,2-dimethylpropanoyl)benzoate 在 dimethyl sulfide borane 、 (R)-2-甲基-CBS-恶唑硼烷 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以80%的产率得到4-(1-hydroxy-2,2-dimethylpropyl)benzoic acid anhydride with -4-(1-hydroxy-2,2-dimethylpropyl)-N-methoxybenzenecarboximidic acid
  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 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 1.5h， 生成 ((Z)-C-(4-(2,2-Dimethylpropanoyl)phenyl)-N-methoxycarbonimidoyl)4-(2,2-dimethylpropanoyl)benzoate
  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

• Process for preparing substituted N-oxy-imidic acid derivatives
  申请人：Sandoz Ltd.

  公开号：US05319123A1

  公开（公告）日：1994-06-07

  N-oxy substituted imidic acid derivative of the formula ##STR1## where R.sub.1, R.sub.2 and R.sub.3 are alkyl and aryl substituents, which are useful as antidiabetic and hypolipidemic agents are prepared by the following procedure: ##STR2## where X is chlorine, bromine, or iodine, and R.sub.1 ' is the same as R.sub.1 but with any hydroxy or carboxy groups present protected by a hydroxy or carboxy protecting group and, when R.sub.1 ' is a protected hydroxy or carboxy substituent, deprotecting the substituent.

  化学式为##STR1##的N-氧代取代的咪唑酸衍生物，其中R.sub.1、R.sub.2和R.sub.3是烷基和芳基取代基，可用作抗糖尿病和降脂药物，制备方法如下：##STR2##其中X为氯、溴或碘，R.sub.1'与R.sub.1相同，但任何羟基或羧基取代基都被羟基或羧基保护基保护，当R.sub.1'是保护的羟基或羧基取代基时，脱保护取代基。
• 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.