(S)-1-(4-bromophenyl)-3-(4-{2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl}phenyl)thiourea hydrochloride | 202740-66-7

• 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-bromophenyl)-3-(4-{2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl}phenyl)thiourea hydrochloride
• 英文别名: 1-(4-bromophenyl)-3-[4-[2-[[(2S)-2-hydroxy-3-phenoxypropyl]amino]ethyl]phenyl]thiourea;hydrochloride
• CAS: 202740-66-7
• 化学式: C₂₄H₂₆BrN₃O₂S*ClH
• 分子量: 536.92
• InChiKey: YSIZCQWAOAZASM-FTBISJDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.25
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  97.6
• 氢给体数：
  5
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (S)-1-(4-{2-[N-tert-butoxycarbonyl-N-(2-hydroxy-3-phenoxypropyl)amino]ethyl}phenyl)-3-(4-bromophenyl)thiourea 在 盐酸 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 反应 0.5h， 以63%的产率得到(S)-1-(4-bromophenyl)-3-(4-{2-[(2-hydroxy-3-phenoxypropyl)amino]ethyl}phenyl)thiourea 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

文献信息

• Discovery of novel thiourea derivatives as potent and selective β3-adrenergic receptor agonists
  作者：Tatsuya Maruyama、Norio Seki、Kenichi Onda、Takayuki Suzuki、Souichirou Kawazoe、Masahiko Hayakawa、Tetsuo Matsui、Toshiyuki Takasu、Mitsuaki Ohta

  DOI：10.1016/j.bmc.2009.06.031

  日期：2009.8

  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.