5-(4-氯-苯氧基甲基)-2-(4-氯-苯基)-噻唑烷 | 1026566-55-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-(4-氯-苯氧基甲基)-2-(4-氯-苯基)-噻唑烷
• 英文名称: 5-(4-Chloro-phenoxymethyl)-2-(4-chloro-phenyl)-thiazolidine
• 英文别名: 5-[(4-Chlorophenoxy)methyl]-2-(4-chlorophenyl)-1,3-thiazolidine
• CAS: 1026566-55-1
• 化学式: C₁₆H₁₅Cl₂NOS
• 分子量: 340.273
• InChiKey: NIWYANXBBMBXSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  46.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  乙酰氯 、 5-(4-氯-苯氧基甲基)-2-(4-氯-苯基)-噻唑烷 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 1-[(2R,5S)-5-(4-Chloro-phenoxymethyl)-2-(4-chloro-phenyl)-thiazolidin-3-yl]-ethanone 、 1-[(2R,5R)-5-(4-Chloro-phenoxymethyl)-2-(4-chloro-phenyl)-thiazolidin-3-yl]-ethanone
  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
• 作为产物：
  描述：

  1-氨基-3-(4-氯苯氧基)-2-丙醇 在 ammonium hydroxide 、 sodium hydroxide 、 偶氮二甲酸二异丙酯 、 三苯基膦 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h， 生成 5-(4-氯-苯氧基甲基)-2-(4-氯-苯基)-噻唑烷
  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

• 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.