tert-butyl (S)-N-{2-hydroxy-3-[4-(methoxymethoxy)phenoxy]propyl}-N-[2-(4-nitrophenyl)-ethyl]carbamate | 1160619-88-4

• 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: tert-butyl (S)-N-{2-hydroxy-3-[4-(methoxymethoxy)phenoxy]propyl}-N-[2-(4-nitrophenyl)-ethyl]carbamate
• 英文别名: tert-butyl N-[(2S)-2-hydroxy-3-[4-(methoxymethoxy)phenoxy]propyl]-N-[2-(4-nitrophenyl)ethyl]carbamate
• CAS: 1160619-88-4
• 化学式: C₂₄H₃₂N₂O₈
• 分子量: 476.527
• InChiKey: ZPKIGGSNVVVVHG-FQEVSTJZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  123
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  tert-butyl (S)-N-{2-hydroxy-3-[4-(methoxymethoxy)phenoxy]propyl}-N-[2-(4-nitrophenyl)-ethyl]carbamate 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以99%的产率得到tert-butyl (S)-N-[2-(4-aminophenyl)ethyl]-N-{2-hydroxy-3-[4-(methoxymethoxy)phenoxy]-propyl}carbamate
  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：

  二碳酸二叔丁酯 、 (S)-1-[4-(methoxymethoxy)phenoxy]-3-[2-(4-nitrophenyl)ethylamino]-2-propanol 以 四氢呋喃 为溶剂， 反应 1.0h， 以96%的产率得到tert-butyl (S)-N-{2-hydroxy-3-[4-(methoxymethoxy)phenoxy]propyl}-N-[2-(4-nitrophenyl)-ethyl]carbamate
  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