(R)-toluene-4-sulfonic acid 2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl ester | 364080-73-9

• 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)-toluene-4-sulfonic acid 2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl ester
• 英文别名: [(2R)-2-[tert-butyl(dimethyl)silyl]oxy-2-(6-chloropyridin-3-yl)ethyl] 4-methylbenzenesulfonate
• CAS: 364080-73-9
• 化学式: C₂₀H₂₈ClNO₄SSi
• 分子量: 442.051
• InChiKey: WCTMANXEFWNSIX-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  73.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-toluene-4-sulfonic acid 2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl ester 在 吡啶 、 palladium on activated charcoal 、 四丁基氟化铵 、 ammonium formate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 、 1,2-二氯乙烷 为溶剂， 反应 48.0h， 生成 N-cyclohexyl-N'-[4-[2-[[(2R)-2-hydroxy-2-(3-pyridinyl)ethyl]amino]-2-methylpropyl]phenyl]-sulfamide
  参考文献：
  名称：

  Potent and selective, sulfamide-based human β3-adrenergic receptor agonists

  摘要：

  A series of sulfamide-based analogs related to L-796568 were prepared and evaluated for their biological activity at the human beta(3)-adrenergic receptor (AR). This modification allows for a significant reduction in molecular weight, while maintaining single-digit nanomolar potencies at the beta(3)-AR and high selectivities versus the beta(1)- or beta(2)-AR. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.03.089
• 作为产物：
  描述：

  (R)-Toluene-4-sulfonic acid 2-(6-chloro-pyridin-3-yl)-2-hydroxy-ethyl ester 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 18.0h， 生成 (R)-toluene-4-sulfonic acid 2-(tert-butyl-dimethyl-silanyloxy)-2-(6-chloro-pyridin-3-yl)-ethyl ester
  参考文献：
  名称：

  Sulfamide derivatives useful as beta3 agonists and pharmaceutical uses thereof

  摘要：

  公式（I）的磺胺化合物被描述，并且它们被用于治疗依赖于与β-肾上腺素受体相关的信号通路的疾病，例如肥胖症、糖尿病、高血压、胃肠道低动力或高动力以及心血管疾病。

  公开号：

  EP1236723A1

文献信息

• The Synthesis of Two Potent β-3 Adrenergic Receptor Agonists
  作者：Paul A. Bradley、Robert J. Carroll、Yann C. Lecouturier、Robert Moore、Pierre Noeureuil、Bhairavi Patel、Jonathan Snow、Simon Wheeler

  DOI：10.1021/op1001462

  日期：2010.11.19

  This contribution describes the initial preparation of two potent β-3 receptor agonists 1 and 2. Subsequent scale up of these two compounds was required for further evaluation and proceeded via a common key amine intermediate 24. Synthesis of this key intermediate by way of a Ritter reaction was a vital step in the sequence. Enantioselective Noyori hydrogenation reactions gave access to the chiral

  该贡献描述了两种有效的β-3受体激动剂1和2的初始制备。随后需要进一步放大这两种化合物的规模，以进行进一步评估，并通过常见的关键胺中间体24进行。通过Ritter反应合成该关键中间体是该过程中至关重要的一步。对映选择性的Noyori氢化反应使获得制备目标化合物所必需的手性环氧化物接近。已开发出一种在敏感的异恶唑单元存在下使2氯吡啶基选择性脱卤的化学方法，以提供对1的访问。
• Beta3 agonists and uses thereof
  申请人：——

  公开号：US20020128247A1

  公开（公告）日：2002-09-12

  Sulfamide compounds having formula (I) are described as well as their use in the treatment of diseases dependent on the signaling pathways associated with &bgr;-adrenergic receptors, such as obesity, diabetes, hypertension, gastrointestinal hypo- or hyper-motility and cardiovascular diseases. 1

  化学式为(I)的磺胺化合物被描述，并且它们在治疗依赖与β-肾上腺素受体相关的信号通路的疾病中的用途也被描述，例如肥胖症、糖尿病、高血压、胃肠道低动力或高动力和心血管疾病。
• β3 agonists and uses thereof
  申请人：Dow Robert L.

  公开号：US06939867B2

  公开（公告）日：2005-09-06

  Sulfamide compounds having formula (I) are described as well as their use in the treatment of diseases dependent on the signaling pathways associated with β-adrenergic receptors, such as obesity, diabetes, hypertension, gastrointestinal hypo- or hyper-motility and cardiovascular diseases

  本文描述了具有公式（I）的磺酰胺化合物，以及它们在治疗依赖于与β肾上腺素受体相关的信号通路的疾病中的应用，例如肥胖症、糖尿病、高血压、胃肠道低动力或高动力和心血管疾病。
• Sulfamide derivatives useful as beta3 agonists and pharmaceutical uses thereof
  申请人：Pfizer Products Inc.

  公开号：EP1236723A1

  公开（公告）日：2002-09-04

  Sulfamide compounds having formula (I) are described as well as their use in the treatment of diseases dependent on the signaling pathways associated with β-adrenergic receptors, such as obesity, diabetes, hypertension, gastrointestinal hypo- or hyper-motility and cardiovascular diseases.

  公式（I）的磺胺化合物被描述，并且它们被用于治疗依赖于与β-肾上腺素受体相关的信号通路的疾病，例如肥胖症、糖尿病、高血压、胃肠道低动力或高动力以及心血管疾病。
• Potent and selective, sulfamide-based human β3-adrenergic receptor agonists
  作者：Robert L. Dow、Ernest S. Paight、Steven R. Schneider、John R. Hadcock、Diane M. Hargrove、Kelly A. Martin、Tristan S. Maurer、Nancy A. Nardone、David A. Tess、Paul DaSilva-Jardine

  DOI：10.1016/j.bmcl.2004.03.089

  日期：2004.6

  A series of sulfamide-based analogs related to L-796568 were prepared and evaluated for their biological activity at the human beta(3)-adrenergic receptor (AR). This modification allows for a significant reduction in molecular weight, while maintaining single-digit nanomolar potencies at the beta(3)-AR and high selectivities versus the beta(1)- or beta(2)-AR. (C) 2004 Elsevier Ltd. All rights reserved.