diethyl (4-methylcyclohexanecarbonyl)succinate | 220203-28-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: diethyl (4-methylcyclohexanecarbonyl)succinate
• 英文别名: Diethyl 2-(4-methylcyclohexanecarbonyl)pentanedioate
• CAS: 220203-28-1
• 化学式: C₁₇H₂₈O₅
• 分子量: 312.406
• InChiKey: ZXXBMDDCBVZRTE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  diethyl (4-methylcyclohexanecarbonyl)succinate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以1.07 g的产率得到2-(4-Methyl-cyclohexanecarbonyl)-pentanedioic acid
  参考文献：
  名称：

  4-(trans-4-Methylcyclohexyl)-4-Oxobutyric Acid (JTT-608). A New Class of Antidiabetic Agent

  摘要：

  During an investigation of drugs for improving the beta-cell response to glucose, we found that 4-cyclohexyl-4-oxobutyric acid selectively improved glucose-stimulated insulin release and glucose tolerance in both normal and diabetic rats. A series of 4-cycloalkyl-4-oxobutyric acids and related compounds were synthesized and evaluated for their effects on the glucose tolerance test and fasting euglycemia. This study elucidated the structural requirements for drug activity and determined th at the optimum compound was 4-(trans-4-methylcyclohexyl)-4-oxobutyric acid 7 (JTT-608). This compound improved glucose tolerance from an oral dose of 3 mg/kg and did not change fasting euglycemia even at an oral dose of 30 mg/kg. Selective improvement of glucose-induced insulin secretion was observed in studies using neonatal streptozotocin rats (nSTZ rats) and perfused pancreases isolated from nSTZ rats.

  DOI：

  10.1021/jm9804228
• 作为产物：
  描述：

  4-methylcyclohexanecarbonyl chloride 在 正丁基锂 、 potassium tert-butylate 作用下， 反应 3.5h， 生成 diethyl (4-methylcyclohexanecarbonyl)succinate
  参考文献：
  名称：

  4-(trans-4-Methylcyclohexyl)-4-Oxobutyric Acid (JTT-608). A New Class of Antidiabetic Agent

  摘要：

  During an investigation of drugs for improving the beta-cell response to glucose, we found that 4-cyclohexyl-4-oxobutyric acid selectively improved glucose-stimulated insulin release and glucose tolerance in both normal and diabetic rats. A series of 4-cycloalkyl-4-oxobutyric acids and related compounds were synthesized and evaluated for their effects on the glucose tolerance test and fasting euglycemia. This study elucidated the structural requirements for drug activity and determined th at the optimum compound was 4-(trans-4-methylcyclohexyl)-4-oxobutyric acid 7 (JTT-608). This compound improved glucose tolerance from an oral dose of 3 mg/kg and did not change fasting euglycemia even at an oral dose of 30 mg/kg. Selective improvement of glucose-induced insulin secretion was observed in studies using neonatal streptozotocin rats (nSTZ rats) and perfused pancreases isolated from nSTZ rats.

  DOI：

  10.1021/jm9804228

文献信息

• 4-(<i>trans</i>-4-Methylcyclohexyl)-4-Oxobutyric Acid (JTT-608). A New Class of Antidiabetic Agent
  作者：Hisashi Shinkai、Hidekazu Ozeki、Takahisa Motomura、Takeshi Ohta、Noboru Furukawa、Itsuo Uchida

  DOI：10.1021/jm9804228

  日期：1998.12.1

  During an investigation of drugs for improving the beta-cell response to glucose, we found that 4-cyclohexyl-4-oxobutyric acid selectively improved glucose-stimulated insulin release and glucose tolerance in both normal and diabetic rats. A series of 4-cycloalkyl-4-oxobutyric acids and related compounds were synthesized and evaluated for their effects on the glucose tolerance test and fasting euglycemia. This study elucidated the structural requirements for drug activity and determined th at the optimum compound was 4-(trans-4-methylcyclohexyl)-4-oxobutyric acid 7 (JTT-608). This compound improved glucose tolerance from an oral dose of 3 mg/kg and did not change fasting euglycemia even at an oral dose of 30 mg/kg. Selective improvement of glucose-induced insulin secretion was observed in studies using neonatal streptozotocin rats (nSTZ rats) and perfused pancreases isolated from nSTZ rats.