[2-(4-Amino-phenyl)-ethyl]-{(S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenoxy]-2-hydroxy-propyl}-carbamic acid tert-butyl ester | 159182-39-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: [2-(4-Amino-phenyl)-ethyl]-{(S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenoxy]-2-hydroxy-propyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-(4-aminophenyl)ethyl]-N-[(2S)-3-[4-[tert-butyl(dimethyl)silyl]oxyphenoxy]-2-hydroxypropyl]carbamate
• CAS: 159182-39-5
• 化学式: C₂₈H₄₄N₂O₅Si
• 分子量: 516.753
• InChiKey: MBJNROLBSGMCEP-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  94.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [2-(4-Amino-phenyl)-ethyl]-{(S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenoxy]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 在 palladium dihydroxide 吡啶 、 氢气 作用下， 以 甲醇 为溶剂， 生成 {2-[4-(4-Amino-benzenesulfonylamino)-phenyl]-ethyl}-{(S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenoxy]-2-hydroxy-propyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Discovery of L-755,507: A subnanomolar human β3 adrenergic receptor agonist

  摘要：

  A study of 4-acylaminobenzenesulfonamides in a cloned human beta(3) adrenergic receptor assay resulted in the discovery of n-hexylurea, L-755,507 (22). This 0.43 nM beta(3) agonist, which is > 440-fold selective over both beta(1) and beta(2) binding, is among the most potent human beta(3) agonists reported to date. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00170-x
• 作为产物：
  描述：

  2-(4-氨基苯)乙胺 以 四氢呋喃 为溶剂， 生成 [2-(4-Amino-phenyl)-ethyl]-{(S)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenoxy]-2-hydroxy-propyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Potent, selective benzenesulfonamide agonists of the human β3 adrenergic receptor

  摘要：

  A cloned human beta(3) adrenergic receptor assay was used to identify phenoxypropanolamine agonist 1. SAR studies led to the identification of benzenesulfonamide derivative 20, a 6.3 nM beta(3) agonist which shows 30-fold selectivity for beta(3) agonist activity over beta(1) and beta(2) receptor binding. Further refinement of this lead provided 4-bromo derivative 39, a subnanomolar agonist with 660-fold and 230-fold selectivity over beta(1) and beta(2), respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00169-3

文献信息

• 3-Pyridyloxypropanolamine agonists of the β3 adrenergic receptor with improved pharmacokinetic properties
  作者：Ann E Weber、Hyun O Ok、Raul F Alvaro、Mari R Candelore、Margaret A Cascieri、Shuet-Hing L Chiu、Liping Deng、Michael J Forrest、Gary J Hom、Jennifer E Hutchins、John Kao、D.Euan MacIntyre、Robert J Mathvink、Debra McLoughlin、Randall R Miller、Ronald C Newbold、Timothy V Olah、Emma R Parmee、Leroy Perkins、Ralph A Stearns、Catherine D Strader、John Szumiloski、Yui S Tang、Laurie Tota、Pasquale P Vicario、Matthew J Wyvratt、Michael H Fisher

  DOI：10.1016/s0960-894x(98)00381-3

  日期：1998.8

  Pyridyloxypropanolamines L-749,372 (8, beta(3) EC50 = 3.6 nM) and L-750,355 (29, beta(3) EC50 = 13 nM) are selective partial agonists of the human receptor, with 33% and 49% activation, respectively. Both stimulate lipolysis in rhesus monkeys (ED50 = 2 and 0.8 mg/kg, respectively), with minimal effects on heart rate. Oral bioavailability in dogs, 41% for L-749,372 and 47% for L-750,355, is improved relative to phenol analogs. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Potent, selective benzenesulfonamide agonists of the human β3 adrenergic receptor
  作者：Ann E. Weber、Robert J. Mathvink、Leroy Perkins、Jennifer E. Hutchins、Mari R. Candelore、Laurie Tota、Catherine D. Strader、Matthew J. Wyvratt、Michael H. Fisher

  DOI：10.1016/s0960-894x(98)00169-3

  日期：1998.5

  A cloned human beta(3) adrenergic receptor assay was used to identify phenoxypropanolamine agonist 1. SAR studies led to the identification of benzenesulfonamide derivative 20, a 6.3 nM beta(3) agonist which shows 30-fold selectivity for beta(3) agonist activity over beta(1) and beta(2) receptor binding. Further refinement of this lead provided 4-bromo derivative 39, a subnanomolar agonist with 660-fold and 230-fold selectivity over beta(1) and beta(2), respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Discovery of L-755,507: A subnanomolar human β3 adrenergic receptor agonist
  作者：Emma R. Parmee、Hyun O. Ok、Mari R. Candelore、Laurie Tota、Liping Deng、Catherine D. Strader、Matthew J. Wyvratt、Michael H. Fisher、Ann E. Weber

  DOI：10.1016/s0960-894x(98)00170-x

  日期：1998.5

  A study of 4-acylaminobenzenesulfonamides in a cloned human beta(3) adrenergic receptor assay resulted in the discovery of n-hexylurea, L-755,507 (22). This 0.43 nM beta(3) agonist, which is > 440-fold selective over both beta(1) and beta(2) binding, is among the most potent human beta(3) agonists reported to date. (C) 1998 Elsevier Science Ltd. All rights reserved.