(2S)-1-Amino-3-(4-hydroxy-phenoxy)-propan-2-ol | 208459-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (2S)-1-Amino-3-(4-hydroxy-phenoxy)-propan-2-ol
• 英文别名: 4-((2S)-3-Amino-2-hydroxy-propoxy)-phenol；4-[(2S)-3-amino-2-hydroxypropoxy]phenol
• CAS: 208459-22-7
• 化学式: C₉H₁₃NO₃
• 分子量: 183.207
• InChiKey: XJWKQIRILGLHPJ-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  75.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-{4-[2-(1-benzyl-piperdin-4-ylamino)-4-oxo-4H-thiazol-5-ylidenemethyl]-phenyl}-piperidin-4-one 、 (2S)-1-Amino-3-(4-hydroxy-phenoxy)-propan-2-ol 生成 2-(1-Benzyl-piperidin-4-ylamino)-5-(4-{(2s)-4-[2-hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-piperidin-1-yl}-benzylidene)-thiazol-4-one
  参考文献：
  名称：

  2-substituted thiazolidinones as beta-3 adrenergic receptor agonists

  摘要：

  本发明提供了具有以下结构的I式化合物：其中A、X、Y、Z、R1、R2、R3、R4、R5和R6如前所定义，或其药学上可接受的盐，可用于治疗或抑制与胰岛素抵抗或高血糖相关的代谢性疾病（通常与肥胖或葡萄糖不耐症相关），动脉粥样硬化、胃肠道疾病、神经遗传性炎症和频繁排尿；特别适用于治疗或抑制2型糖尿病。

  公开号：

  US06410734B1
• 作为产物：
  描述：

  (S)-4-(2,3-epoxypropoxy)phenol 在 palladium on activated charcoal 甲酸铵 作用下， 以 甲醇 为溶剂， 生成 (2S)-1-Amino-3-(4-hydroxy-phenoxy)-propan-2-ol
  参考文献：
  名称：

  2,4-thiazolidinediones as potent and selective human β3 agonists

  摘要：

  Methylsulfonamide substituted 2,4-thiazolidinedione 22c is a potent (EC50 = 0.01 muM, IA = 1.19) and selective (more than 110-fold over beta (1) and beta (2) agonist activity) beta (3) agonist. This compound has also been proven to be active and selective in an in vivo mode. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00063-4

文献信息

• N-(4-sulfonylaryl)Cyclylamine 2-hydroxyethylamines as beta-3 adrenergic receptor agonists
  申请人：American Home Products Corporation

  公开号：US20020028797A1

  公开（公告）日：2002-03-07

  This invention provides compounds of Formula I having the structure 1 wherein R 1 , R 2 , R 3 , R 4 , W, X, and Y are as defined hereinbefore or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.

  这项发明提供了具有结构1的化合物，其中R1、R2、R3、R4、W、X和Y如前文所定义，或其药用盐，这些化合物可用于治疗与胰岛素抵抗或高血糖相关的代谢紊乱。
• 2-substituted thiazolidinones as beta-3 adrenergic receptor agonists
  申请人：Wyeth

  公开号：US06410734B1

  公开（公告）日：2002-06-25

  This invention provides compounds of Formula I having the structure wherein: A, X, Y, Z, R1, R2, R3, R4, R5, and R6 are as defined hereinbefore or a pharmaceutically acceptable salt thereof, which are useful in treating or inhibiting metabolic disorders related to insulin resistance or hyperglycemia (typically associated with obesity or glucose intolerance), atherosclerosis, gastrointestinal disorders, neurogenetic inflammation, and frequent urination; and are particularly useful in the treatment or inhibition of type II diabetes.

  该发明提供了具有以下结构的I型化合物，其中：A、X、Y、Z、R1、R2、R3、R4、R5和R6如前所定义或其药学上可接受的盐，可用于治疗或抑制与胰岛素抵抗或高血糖相关的代谢障碍（通常与肥胖或葡萄糖不耐受有关）、动脉粥样硬化、胃肠道障碍、神经遗传性炎症和频繁排尿；并且特别适用于治疗或抑制2型糖尿病。
• New oxadiazolidinedione derivatives as potent and selective human β3 agonists
  作者：Baihua Hu、Michael Malamas、John Ellingboe、Elwood Largis、Stella Han、Ruth Mulvey、Jeff Tillett

  DOI：10.1016/s0960-894x(01)00147-0

  日期：2001.4

  investigation into the development of potent and selective human beta3 agonists, a series of thiazolidinedione analogues was prepared and evaluated for their biological activity on the human beta3-adrenergic receptor. The oxadiazolidinedione derivative 17 was found to be the most potent and selective compound in this study, with an EC50 value of 0.02 microM at the beta3 receptor, 259-fold selectivity over the beta1

  作为我们对有效和选择性人β3激动剂开发的调查的一部分，制备了一系列噻唑烷二酮类似物，并评估了其对人β3肾上腺素受体的生物学活性。在本研究中发现恶二唑烷二酮衍生物17是最有效和最具选择性的化合物，在beta3受体上的EC50值为0.02 microM，在beta1受体上的选择性是259倍，在beta2受体上的选择性是745倍。
• Cyclamine sulfonamides as beta-3 adrenergic receptor agonists
  申请人：American Home Products Corporation

  公开号：US20020022605A1

  公开（公告）日：2002-02-21

  This invention provides compounds of Formula I having the structure 1 wherein R 1 , R 2 , R 3 , W, X, and Z are as defined hereinbefore or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.

  本发明提供了具有结构1的化合物，其中R1、R2、R3、W、X和Z如前所定义，或其药学上可接受的盐，这些化合物可用于治疗与胰岛素抵抗或高血糖相关的代谢性疾病。
• Cyclylamine sulfonamides as beta-3 adrenergic receptor agonists
  申请人：Wyeth

  公开号：US20030027797A1

  公开（公告）日：2003-02-06

  This invention provides compounds of Formula I having the structure 1 wherein R 1 , R 2 , R 3 , W, X, and Z are as defined hereinbefore or a pharmaceutically acceptable salt thereof, which are useful in treating metabolic disorders related to insulin resistance or hyperglycemia.

  本发明提供具有结构1的化合物，其中R1，R2，R3，W，X和Z如前所定义，或其药学上可接受的盐，用于治疗与胰岛素抵抗或高血糖相关的代谢性疾病。