(2S,7aR)-2-(4-Chloro-phenoxymethyl)-7a-(3,4-dichloro-phenyl)-tetrahydro-pyrrolo[2,1-b]oxazol-5-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (2S,7aR)-2-(4-Chloro-phenoxymethyl)-7a-(3,4-dichloro-phenyl)-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
• 英文别名: Sdzpgu693；(2S,7aR)-2-[(4-chlorophenoxy)methyl]-7a-(3,4-dichlorophenyl)-2,3,6,7-tetrahydropyrrolo[2,1-b][1,3]oxazol-5-one
• 化学式: C₁₉H₁₆Cl₃NO₃
• 分子量: 412.7
• InChiKey: AUDZPOJILZPYBI-HNAYVOBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(3,4-二氯苯基)-4-氧代丁酸 、 (S)-2-hydroxy-3-(p-chlorophenoxy)propylamine 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 16.0h， 以24%的产率得到(2S,7aR)-2-(4-Chloro-phenoxymethyl)-7a-(3,4-dichloro-phenyl)-tetrahydro-pyrrolo[2,1-b]oxazol-5-one
  参考文献：
  名称：

  Substituted Tetrahydropyrrolo[2,1-b]oxazol-5(6H)-ones and Tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones as Hypoglycemic Agents

  摘要：

  A series of substituted tetrahydropyrrolo[2,1-b]oxazol-5(6H)-one and tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones was synthesized from amino alcohols or amino thiols and keto acids. A pharmacological model based on the results obtained with these compounds led to the synthesis and evaluation of a series of isoxazoles and other monocyclic compounds. These were evaluated for their ability to enhance glucose utilization in cultured L6 myocytes. The in vivo hypoglycemic efficacy and potency of these compounds were evaluated in a model of type 2 diabetes mellitus (non-insulin-dependent diabetes mellitus), the ob/ob mouse. 25a(2S) (SDZ PGU 693) was selected for further pharmacological studies.

  DOI：

  10.1021/jm9803121

文献信息

• Bicyclic oxazole and thiazole substituted ethers
  申请人：Novartis AG

  公开号：EP0702015B1

  公开（公告）日：1997-09-24
• JPH08109183A
  申请人：——

  公开号：JPH08109183A

  公开（公告）日：1996-04-30
• Substituted Tetrahydropyrrolo[2,1-<i>b</i>]oxazol-5(6<i>H</i>)-ones and Tetrahydropyrrolo[2,1-<i>b</i>]thiazol-5(6<i>H</i>)-ones as Hypoglycemic Agents
  作者：Thomas D. Aicher、Bork Balkan、Philip A. Bell、Leonard J. Brand、S. H. Cheon、Rhonda O. Deems、Jay B. Fell、William S. Fillers、James D. Fraser、Jiaping Gao、Douglas C. Knorr、Gerald G. Kahle、Christina L. Leone、Jeffrey Nadelson、Ronald Simpson、Howard C. Smith

  DOI：10.1021/jm9803121

  日期：1998.11.1

  A series of substituted tetrahydropyrrolo[2,1-b]oxazol-5(6H)-one and tetrahydropyrrolo[2,1-b]thiazol-5(6H)-ones was synthesized from amino alcohols or amino thiols and keto acids. A pharmacological model based on the results obtained with these compounds led to the synthesis and evaluation of a series of isoxazoles and other monocyclic compounds. These were evaluated for their ability to enhance glucose utilization in cultured L6 myocytes. The in vivo hypoglycemic efficacy and potency of these compounds were evaluated in a model of type 2 diabetes mellitus (non-insulin-dependent diabetes mellitus), the ob/ob mouse. 25a(2S) (SDZ PGU 693) was selected for further pharmacological studies.