(S)-4'-(2-{N-benzyl-N-[3-(4-benzyloxyphenoxy)-2-hydroxypropyl]amino}ethyl)-2-(1-naphthyl)acetanilide | 1160619-72-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (S)-4'-(2-{N-benzyl-N-[3-(4-benzyloxyphenoxy)-2-hydroxypropyl]amino}ethyl)-2-(1-naphthyl)acetanilide
• 英文别名: N-[4-[2-[benzyl-[(2S)-2-hydroxy-3-(4-phenylmethoxyphenoxy)propyl]amino]ethyl]phenyl]-2-naphthalen-1-ylacetamide
• CAS: 1160619-72-6
• 化学式: C₄₃H₄₂N₂O₄
• 分子量: 650.817
• InChiKey: NRFMYEHRBNJCIX-KDXMTYKHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  49
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  71
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-4'-(2-{N-benzyl-N-[3-(4-benzyloxyphenoxy)-2-hydroxypropyl]amino}ethyl)-2-(1-naphthyl)acetanilide 在 palladium 10% on activated carbon 、 氢气 、 盐酸 作用下， 以 乙醇 、 甲醇 、 乙酸乙酯 为溶剂， 反应 15.0h， 以43%的产率得到(S)-4'-(2-{[2-hydroxy-3-(4-hydroxyphenoxy)propyl]amino}ethyl)-2-(1-naphthyl)acetanilide hydrochloride
  参考文献：
  名称：

  Discovery of novel acetanilide derivatives as potent and selective β3-adrenergic receptor agonists

  摘要：

  In the search for potent and selective human beta 3-adrenergic receptor (AR) agonists as potential drugs for the treatment of obesity and noninsulin-dependent (type II) diabetes a novel series of acetanilide-based analogues were prepared and their biological activities were evaluated at the human beta 3-, beta 2-, and beta 1-ARs. Among these compounds, 2-pyridylacetanilide (2f), pyrimidin-2-ylacetanilide (2u), and pyrazin-2-ylacetanilide (2v) derivatives exhibited potent agonistic activity at the beta 3-AR with functional selectivity over the beta 1- and beta 2-ARs. In particular, compound 2u was found to be the most potent and selective beta 3-AR agonist with an EC(50) value of 0.11 mu M and no agonistic activity for either the beta 1 - or beta 2-AR. In addition, 2f, 2u, and 2v showed significant hypoglycemic activity in a rodent diabetic model. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.022
• 作为产物：
  描述：

  萘-1-基乙酰氯 、 (S)-1-{N-[2-(4-aminophenyl)ethyl]-N-benzylamino}-3-(4-benzyloxyphenoxy)-2-propanol 在 三乙胺 作用下， 以 氯仿 为溶剂， 以51%的产率得到(S)-4'-(2-{N-benzyl-N-[3-(4-benzyloxyphenoxy)-2-hydroxypropyl]amino}ethyl)-2-(1-naphthyl)acetanilide
  参考文献：
  名称：

  Discovery of novel acetanilide derivatives as potent and selective β3-adrenergic receptor agonists

  摘要：

  In the search for potent and selective human beta 3-adrenergic receptor (AR) agonists as potential drugs for the treatment of obesity and noninsulin-dependent (type II) diabetes a novel series of acetanilide-based analogues were prepared and their biological activities were evaluated at the human beta 3-, beta 2-, and beta 1-ARs. Among these compounds, 2-pyridylacetanilide (2f), pyrimidin-2-ylacetanilide (2u), and pyrazin-2-ylacetanilide (2v) derivatives exhibited potent agonistic activity at the beta 3-AR with functional selectivity over the beta 1- and beta 2-ARs. In particular, compound 2u was found to be the most potent and selective beta 3-AR agonist with an EC(50) value of 0.11 mu M and no agonistic activity for either the beta 1 - or beta 2-AR. In addition, 2f, 2u, and 2v showed significant hypoglycemic activity in a rodent diabetic model. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.022

文献信息

• Discovery of novel acetanilide derivatives as potent and selective β3-adrenergic receptor agonists
  作者：Tatsuya Maruyama、Kenichi Onda、Masahiko Hayakawa、Tetsuo Matsui、Toshiyuki Takasu、Mitsuaki Ohta

  DOI：10.1016/j.ejmech.2009.01.022

  日期：2009.6

  In the search for potent and selective human beta 3-adrenergic receptor (AR) agonists as potential drugs for the treatment of obesity and noninsulin-dependent (type II) diabetes a novel series of acetanilide-based analogues were prepared and their biological activities were evaluated at the human beta 3-, beta 2-, and beta 1-ARs. Among these compounds, 2-pyridylacetanilide (2f), pyrimidin-2-ylacetanilide (2u), and pyrazin-2-ylacetanilide (2v) derivatives exhibited potent agonistic activity at the beta 3-AR with functional selectivity over the beta 1- and beta 2-ARs. In particular, compound 2u was found to be the most potent and selective beta 3-AR agonist with an EC(50) value of 0.11 mu M and no agonistic activity for either the beta 1 - or beta 2-AR. In addition, 2f, 2u, and 2v showed significant hypoglycemic activity in a rodent diabetic model. (C) 2009 Elsevier Masson SAS. All rights reserved.