(S)-1-(4-{2-[N-tert-butoxycarbonyl-N-(2-hydroxy-3-phenoxypropyl)amino]ethyl}phenyl)-3-phenylthiourea | 202740-29-2

• 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: (S)-1-(4-{2-[N-tert-butoxycarbonyl-N-(2-hydroxy-3-phenoxypropyl)amino]ethyl}phenyl)-3-phenylthiourea
• 英文别名: tert-butyl N-[(2S)-2-hydroxy-3-phenoxypropyl]-N-[2-[4-(phenylcarbamothioylamino)phenyl]ethyl]carbamate
• CAS: 202740-29-2
• 化学式: C₂₉H₃₅N₃O₄S
• 分子量: 521.681
• InChiKey: NPKHYHJWLMCUJQ-VWLOTQADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  37
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-1-(4-{2-[N-tert-butoxycarbonyl-N-(2-hydroxy-3-phenoxypropyl)amino]ethyl}phenyl)-3-phenylthiourea 在 盐酸 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 0.5h， 以57%的产率得到(S)-1-(4-{2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl}phenyl)-3-phenylthiourea hydrochloride
  参考文献：
  名称：

  Discovery of novel thiourea 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, we prepared a novel series of phenoxypropanolamine derivatives containing the thiourea moiety and evaluated their biological activities at human beta 3-, beta 2-, and beta 1-ARs. Among these compounds, 4-nitrophenylthiourea (18i) and 3-methoxyphenylthiourea (18k) derivatives were found to exhibit potent agonistic activity at the b3-AR, with EC(50) values of 0.10 and 0.16 mu M, respectively, and no agonistic activity for either the beta 1-or beta 2-AR. In addition, they showed significant hypoglycemic activity in a rodent diabetic model. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.031
• 作为产物：
  描述：

  硫代异氰酸苯酯 、 tert-butyl (S)-N-[2-(4-aminophenyl)ethyl]-N-(2-hydroxy-3-phenoxy)propylcarbamate 以 氯仿 为溶剂， 反应 15.0h， 以52%的产率得到(S)-1-(4-{2-[N-tert-butoxycarbonyl-N-(2-hydroxy-3-phenoxypropyl)amino]ethyl}phenyl)-3-phenylthiourea
  参考文献：
  名称：

  Discovery of novel thiourea 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, we prepared a novel series of phenoxypropanolamine derivatives containing the thiourea moiety and evaluated their biological activities at human beta 3-, beta 2-, and beta 1-ARs. Among these compounds, 4-nitrophenylthiourea (18i) and 3-methoxyphenylthiourea (18k) derivatives were found to exhibit potent agonistic activity at the b3-AR, with EC(50) values of 0.10 and 0.16 mu M, respectively, and no agonistic activity for either the beta 1-or beta 2-AR. In addition, they showed significant hypoglycemic activity in a rodent diabetic model. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.031