rac-2-(3-(1-(1H-imidazol-1-yl)ethyl)benzo[b]thiophen-2-yl)-N,N-dimethylethanamine | 1226789-97-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: rac-2-(3-(1-(1H-imidazol-1-yl)ethyl)benzo[b]thiophen-2-yl)-N,N-dimethylethanamine
• 英文别名: 2-[3-(1-imidazol-1-ylethyl)-1-benzothiophen-2-yl]-N,N-dimethylethanamine
• CAS: 1226789-97-4
• 化学式: C₁₇H₂₁N₃S
• 分子量: 299.44
• InChiKey: MSPFRPWEGPBFTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  rac-2-(3-(1-(1H-imidazol-1-yl)ethyl)benzo[b]thiophen-2-yl)-N,N-dimethylethanamine 在 chiral HPLC 作用下， 生成 、 (R)-2-(3-(1-(1H-imidazol-1-yl)ethyl)benzo[b]thiophen-2-yl)-N,N-dimethylethan-1-amine
  参考文献：
  名称：

  Novel benzothiophene H1-antihistamines for the treatment of insomnia

  摘要：

  SAR of lead benzothiophene H-1-antihistamine 2 was explored to identify backup candidates with suitable pharmacokinetic profiles for an insomnia program. Several potent and selective H-1-antihistamines with a range of projected half-lives in humans were identified. Compound 16d had a suitable human half-life as demonstrated in a human microdose study, but variability in pharmacokinetic profile, attributed to metabolic clearance, prevented further development of this compound. Compound 28b demonstrated lower predicted clearance in preclinical studies, and may represent a more suitable backup compound. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.134
• 作为产物：
  描述：

  聚合甲醛 、 在 sodium cyanoborohydride 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 rac-2-(3-(1-(1H-imidazol-1-yl)ethyl)benzo[b]thiophen-2-yl)-N,N-dimethylethanamine
  参考文献：
  名称：

  Novel benzothiophene H1-antihistamines for the treatment of insomnia

  摘要：

  SAR of lead benzothiophene H-1-antihistamine 2 was explored to identify backup candidates with suitable pharmacokinetic profiles for an insomnia program. Several potent and selective H-1-antihistamines with a range of projected half-lives in humans were identified. Compound 16d had a suitable human half-life as demonstrated in a human microdose study, but variability in pharmacokinetic profile, attributed to metabolic clearance, prevented further development of this compound. Compound 28b demonstrated lower predicted clearance in preclinical studies, and may represent a more suitable backup compound. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.01.134

文献信息

• Novel benzothiophene H1-antihistamines for the treatment of insomnia
  作者：Wilna J. Moree、Florence Jovic、Timothy Coon、Jinghua Yu、Bin-Feng Li、Fabio C. Tucci、Dragan Marinkovic、Raymond S. Gross、Siobhan Malany、Margaret J. Bradbury、Lisa M. Hernandez、Zhihong O’Brien、Jianyun Wen、Hua Wang、Samuel R.J. Hoare、Robert E. Petroski、Aida Sacaan、Ajay Madan、Paul D. Crowe、Graham Beaton

  DOI：10.1016/j.bmcl.2010.01.134

  日期：2010.4

  SAR of lead benzothiophene H-1-antihistamine 2 was explored to identify backup candidates with suitable pharmacokinetic profiles for an insomnia program. Several potent and selective H-1-antihistamines with a range of projected half-lives in humans were identified. Compound 16d had a suitable human half-life as demonstrated in a human microdose study, but variability in pharmacokinetic profile, attributed to metabolic clearance, prevented further development of this compound. Compound 28b demonstrated lower predicted clearance in preclinical studies, and may represent a more suitable backup compound. (C) 2010 Elsevier Ltd. All rights reserved.