dimethyl [4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene]-malonate | 209530-90-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: dimethyl [4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene]-malonate
• 英文别名: dimethyl 2-[[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]methylidene]propanedioate
• CAS: 209530-90-5
• 化学式: C₂₄H₂₃NO₆
• 分子量: 421.45
• InChiKey: CQWUYGSSXCELKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 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 [4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene]-malonate 在 palladium on activated charcoal sodium hydroxide 、 氢气 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 为溶剂， 反应 1.5h， 生成 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 、 丙二酸二甲酯 在 哌啶乙酸盐 作用下， 以 甲苯 为溶剂， 反应 4.0h， 以60%的产率得到dimethyl [4-[2-(5-methyl-2-phenyl-4-oxazolyl)ethoxy]benzylidene]-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

• Production method of isoxazolidinedione compound
  申请人：JAPAN TOBACCO, INC.

  公开号：US20020188133A1

  公开（公告）日：2002-12-12

  The present invention relates to a novel method for producing a compound of the formula [11] 1 wherein R is an optionally substituted aromatic hydrocarbon group, an optionally substituted alicyclic hydrocarbon group, an optionally substituted heterocyclic group or an optionally substituted condensed heterocyclic group, which is useful as a therapeutic agent for diabetes. The method of the present invention is an industrially utilizable method that enables efficient production of the objective compound [11] from &bgr;-methyl L-aspartate via an important intermediate compound [6] 2 wherein R is as defined above, at high yield.

  本发明涉及一种新的方法，用于生产化合物的公式[11]1，其中R是一种可选取的取代芳香族烃基、可选取的取代脂环烃基、可选取的取代杂环基或可选取的取代紧缩杂环基，该化合物可用作治疗糖尿病的治疗剂。本发明的方法是一种工业上可利用的方法，能够高产地从&bgr;-甲基L-天冬氨酸经由重要的中间化合物[6]2，其中R如上所定义，高效地生产目标化合物[11]。
• PRODUCTION METHOD OF ISOXAZOLIDINEDIONE COMPOUND
  申请人：Ando Koji

  公开号：US20050159466A1

  公开（公告）日：2005-07-21

  The present invention relates to a novel method for producing a compound of the formula [11] wherein R is an optionally substituted aromatic hydrocarbon group, an optionally substituted alicyclic hydrocarbon group, an optionally substituted heterocyclic group or an optionally substituted condensed heterocyclic group, which is useful as a therapeutic agent for diabetes. The method of the present invention is an industrially utilizable method that enables efficient production of the objective compound [11] from β-methyl L-aspartate via an important intermediate compound [6] wherein R is as defined above, at high yield.

  本发明涉及一种新型制备化合物的方法，该化合物的化学式为[11]，其中R为可选取的取代芳香族碳氢基团、可选取的取代脂环烃基团、可选取的取代杂环基团或可选取的取代紧缩杂环基团，该化合物可用作糖尿病治疗剂。本发明的方法是一种工业上可利用的方法，能够以高产率从β-甲基L-天冬氨酸经由重要的中间化合物[6]，制备所需的化合物[11]。
• Process for producing isoxazolidinedione compound
  申请人：Japan Tobacco Inc.

  公开号：US06248897B1

  公开（公告）日：2001-06-19

  The present invention relates to a novel method for producing a compound of the formula [11] wherein R is an optionally substituted aromatic hydrocarbon group, an optionally substituted alicyclic hydrocarbon group, an optionally substituted heterocyclic group or an optionally substituted condensed heterocyclic group, which is useful as a therapeutic agent for diabetes. The method of the present invention is an industrially utilizable method that enables efficient production of the objective compound [11] from &bgr;-methyl L-aspartate via an important intermediate compound [6] wherein R is as defined above, at high yield.

  本发明涉及一种新的制备化合物的方法，该化合物的化学式为[11]，其中R是一个可选取代的芳香族碳氢基团、可选取代的脂环烃基团、可选取代的杂环基团或可选取代的紧缩杂环基团，该化合物可用作治疗糖尿病的治疗剂。本发明的方法是一种可工业化利用的方法，可以高效地从&bgr;-甲基L-天冬氨酸经过重要的中间化合物[6]（其中R如上所述）高产地制备目标化合物[11]。
• 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。
• US6204277B1
  申请人：——

  公开号：US6204277B1

  公开（公告）日：2001-03-20