ethyl 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazole-4-carboxylate | 1558057-24-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: ethyl 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazole-4-carboxylate
• 英文别名: ethyl 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[d][1,3]thiazole-4-carboxylate
• CAS: 1558057-24-1
• 化学式: C₁₁H₁₆N₂O₂S
• 分子量: 240.326
• InChiKey: LJWZQEXNEUKCLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  65.21
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazole-4-carboxylate 在 4-二甲氨基吡啶 、 水 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 tert-butyl (2S,5R)-2-(4-((R)-2-((tert-butoxycarbonyl)amino)-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazole-4-carboxamido)benzyl)-5-((R)-hydroxy(phenyl)methyl)pyrrolidine-1-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Conformationally Restricted Acetanilides as Potent and Selective β₃Adrenergic Receptor Agonists for the Treatment of Overactive Bladder

  摘要：

  A series of conformationally restricted acetanilides were synthesized and evaluated as beta(3)-adrenergic receptor agonists (beta(3)-AR) for the treatment of overactive bladder (OAB). Optimization studies identified a five-membered ring as the preferred conformational lock of the acetanilide. Further optimization of both the aromatic and thiazole regions led to compounds such as 19 and 29, which have a good balance of potency and selectivity. These compounds have significantly reduced intrinsic clearance compared to our initial series of pyridylethanolamine beta(3)-AR agonists and thus have improved unbound drug exposures. Both analogues demonstrated dose dependent beta(3)-AR mediated responses in a rat bladder hyperactivity model.

  DOI：

  10.1021/jm4017224
• 作为产物：
  描述：

  2-氧代环庚烷甲酸乙酯 在 溴 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 0.5h， 生成 ethyl 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[d]thiazole-4-carboxylate
  参考文献：
  名称：

  Design, Synthesis, and Evaluation of Conformationally Restricted Acetanilides as Potent and Selective β₃Adrenergic Receptor Agonists for the Treatment of Overactive Bladder

  摘要：

  A series of conformationally restricted acetanilides were synthesized and evaluated as beta(3)-adrenergic receptor agonists (beta(3)-AR) for the treatment of overactive bladder (OAB). Optimization studies identified a five-membered ring as the preferred conformational lock of the acetanilide. Further optimization of both the aromatic and thiazole regions led to compounds such as 19 and 29, which have a good balance of potency and selectivity. These compounds have significantly reduced intrinsic clearance compared to our initial series of pyridylethanolamine beta(3)-AR agonists and thus have improved unbound drug exposures. Both analogues demonstrated dose dependent beta(3)-AR mediated responses in a rat bladder hyperactivity model.

  DOI：

  10.1021/jm4017224