dimethyl 2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl]malonate | 170861-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: dimethyl 2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl]malonate
• 英文别名: Dimethyl 4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylmalonate；dimethyl 2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methyl]propanedioate
• CAS: 170861-71-9
• 化学式: C₂₄H₂₅NO₆
• 分子量: 423.466
• InChiKey: OKDCTIYZEDHHSM-UHFFFAOYSA-N

物化性质

• 熔点：
  87.9-88.5 °C
• 沸点：
  570.2±60.0 °C(Predicted)
• 密度：
  1.194±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87.9
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  dimethyl 2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl]malonate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.5h， 以72%的产率得到2-methoxycarbonyl-3-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]phenyl]propionic acid
  参考文献：
  名称：

  Isoxazolidine-3,5-dione and Noncyclic 1,3-Dicarbonyl Compounds as Hypoglycemic Agents

  摘要：

  Isoxazolidine-3,5-dione 2 (JTT-501), one of the cyclic malonic acid derivatives, was found to decrease blood glucose at an oral dose of 38 mg/kg/day in KKA(y) mice and is currently undergoing evaluation in phase II clinical trials. Further studies on a series of malonic acids and related compounds showed that the 1,3-dicarbonyl structure was important for insulin-sensitizing activity. Dimethyl malonate 10, which was selected as a successor for 2, was the optimum compound in a series of 1,3-dicarbonyl compounds and was more potent than the corresponding thiazolidine-2,4-dione 1.

  DOI：

  10.1021/jm970771m
• 作为产物：
  描述：

  4-[2-(5-甲基-2-苯基-1,3-恶唑-4-基)乙氧基]苯甲醛 在 palladium on activated charcoal 氢气 、 哌啶乙酸盐 作用下， 以 1,4-二氧六环 、 甲醇 、 甲苯 为溶剂， 反应 4.0h， 生成 dimethyl 2-[4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzyl]malonate
  参考文献：
  名称：

  Isoxazolidine-3,5-dione and Noncyclic 1,3-Dicarbonyl Compounds as Hypoglycemic Agents

  摘要：

  Isoxazolidine-3,5-dione 2 (JTT-501), one of the cyclic malonic acid derivatives, was found to decrease blood glucose at an oral dose of 38 mg/kg/day in KKA(y) mice and is currently undergoing evaluation in phase II clinical trials. Further studies on a series of malonic acids and related compounds showed that the 1,3-dicarbonyl structure was important for insulin-sensitizing activity. Dimethyl malonate 10, which was selected as a successor for 2, was the optimum compound in a series of 1,3-dicarbonyl compounds and was more potent than the corresponding thiazolidine-2,4-dione 1.

  DOI：

  10.1021/jm970771m

文献信息

• Propionic acid derivatives and applications thereof
  申请人：Japan Tobacco Inc.

  公开号：US06204277B1

  公开（公告）日：2001-03-20

  A novel propionic acid derivative of the formula (I): and a pharmaceutically acceptable salt thereof, and pharmaceutical compositions containing the derivative. The propionic acid derivative and a pharmaceutically acceptable salt thereof have superior hypoglycemic action and are expected to show hypolipidemic action and to be useful as therapeutic agents for diabetes and complications of diabetes, as well as related diseases such as hyperlipemia.

  一种具有式(I)的新型丙酸衍生物及其药学上可接受的盐，以及含有该衍生物的药物组合物。该丙酸衍生物及其药学上可接受的盐具有卓越的降血糖作用，并预期表现出降血脂作用，可作为治疗糖尿病及其并发症以及相关疾病如高脂血症的治疗剂。
• PROPIONIC ACID DERIVATIVES AND APPLICATIONS THEREOF
  申请人：Japan Tobacco Inc.

  公开号：EP0930299A1

  公开（公告）日：1999-07-21

  A novel propionic acid derivative of the formula (I): and a pharmaceutically acceptable salt thereof, and pharmaceutical compositions containing the derivative. The propionic acid derivative and a pharmaceutically acceptable salt thereof have superior hypoglycemic action and are expected to show hypolipidemic action and to be useful as therapeutic agents for diabetes and complications of diabetes, as well as related diseases such as hyperlipemia.

  一种新颖的式 (I) 丙酸衍生物： 及其药学上可接受的盐，以及含有该衍生物的药物组合物。该丙酸衍生物及其药学上可接受的盐具有卓越的降血糖作用，并有望显示出降血脂作用，可用作糖尿病和糖尿病并发症以及高脂血症等相关疾病的治疗剂。
• ISOXAZOLIDINEDIONE DERIVATIVE AND USE THEREOF
  申请人：Japan Tobacco Inc.

  公开号：EP0684242B1

  公开（公告）日：1999-05-06
• US6204277B1
  申请人：——

  公开号：US6204277B1

  公开（公告）日：2001-03-20