(R)-2-amino-N-(4-(((2S,5R)-5-((R)-hydroxy(phenyl)methyl)pyrrolidin-2-yl)methyl)phenyl)-4,5,6,7-tetrahydrobenzo[d]thiazole-4-carboxamide | 1190389-25-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-amino-N-(4-(((2S,5R)-5-((R)-hydroxy(phenyl)methyl)pyrrolidin-2-yl)methyl)phenyl)-4,5,6,7-tetrahydrobenzo[d]thiazole-4-carboxamide
• 英文别名: (4R)-2-amino-N-[4-[[(2S,5R)-5-[(R)-hydroxy(phenyl)methyl]pyrrolidin-2-yl]methyl]phenyl]-4,5,6,7-tetrahydro-1,3-benzothiazole-4-carboxamide
• CAS: 1190389-25-3
• 化学式: C₂₆H₃₀N₄O₂S
• 分子量: 462.616
• InChiKey: JCWSKAVOGRUMKE-FBHSLPMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  129
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-溴-2-氧-环己酮甲酸乙酯 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 、 三氟乙酸 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 (R)-2-amino-N-(4-(((2S,5R)-5-((R)-hydroxy(phenyl)methyl)pyrrolidin-2-yl)methyl)phenyl)-4,5,6,7-tetrahydrobenzo[d]thiazole-4-carboxamide
  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