1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-ethanone | 873693-15-3

• 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: 1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-ethanone
• 英文别名: 1-[2-[2-(dimethylamino)ethyl]-1-benzothiophen-3-yl]ethanone
• CAS: 873693-15-3
• 化学式: C₁₄H₁₇NOS
• 分子量: 247.361
• InChiKey: IVVXCRRTXPKDOZ-UHFFFAOYSA-N

物化性质

• 沸点：
  387.0±37.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-ethanone 在 肼 作用下， 以 乙醇 为溶剂， 生成
  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：

  [2-(3-bromo-benzo[b]thiophen-2-yl)-ethyl]dimethyl-amine hydrobromide 在 正丁基锂 、 sodium hydroxide 作用下， 以 水 为溶剂， 生成 1-[2-(2-dimethylamino-ethyl)-benzo[b]thiophen-3-yl]-ethanone
  参考文献：
  名称：

  NBI-75043的化学开发。使用流动反应器规避分批限制的金属-卤素交换反应

  摘要：

  介绍了NBI-75043的发现路线和后续的放大路线。当发现传统的批处理化学方法限制了关键反应的规模时，设计并优化了流动反应器以提供另一种生产方法。

  DOI：

  10.1021/op800071m

文献信息

• Sleep inducing compounds and methods relating thereto
  申请人：Beaton Graham

  公开号：US20060014797A1

  公开（公告）日：2006-01-19

  Compounds having the following structure (I): including stereoisomers, prodrugs, and pharmaceutically acceptable salts, esters and solvates thereof, wherein R 1 , R 2 , R 3a , R 3b , L 1 , L 2 and n are as defined herein. Such compounds generally function as H 1 receptor ligands, and thus have utility as sleep inducing agents. Pharmaceutical compositions containing a compound of structure (I), as well as methods relating to the use thereof, are also disclosed.

  具有以下结构（I）的化合物，包括立体异构体、前药、以及其药用可接受的盐、酯和溶剂合物，其中R1、R2、R3a、R3b、L1、L2和n如本文所定义。这些化合物通常作为H1受体配体发挥作用，因此具有作为催眠药的用途。还披露了含有结构（I）化合物的药物组合物，以及与其使用相关的方法。
• Characterization of Novel Selective H₁-Antihistamines for Clinical Evaluation in the Treatment of Insomnia
  作者：Wilna J. Moree、Bin-Feng Li、Florence Jovic、Timothy Coon、Jinghua Yu、Raymond S. Gross、Fabio Tucci、Dragan Marinkovic、Said Zamani-Kord、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：10.1021/jm900933k

  日期：2009.9.10

  Analogues of the known H-1-antihistamine R-dimethindene were profiled as potential agents for the treatment of insomnia. Several highly selective compounds were efficacious in rodent sleep models. On the basis of overall profile, indene 1d and benzothiophene 2a had pharmacokinetic properties suitable for evaluation in night time dosing. Compound 2a did not show an in vivo cardiovascular effect from weak hERG channel inhibition.
• US7393865B2
  申请人：——

  公开号：US7393865B2

  公开（公告）日：2008-07-01
• [EN] SLEEP-INDUCING COMPOUNDS AND METHODS RELATED THERETO<br/>[FR] COMPOSES SOMNIFERES ET PROCEDES ASSOCIES
  申请人：NEUROCRINE BIOSCIENCES INC

  公开号：WO2006019497A2

  公开（公告）日：2006-02-23

  Compounds having the following structure (I): including stereoisomers, prodrugs, and pharmaceutically acceptable salts, esters and solvates thereof, wherein R1, R2, R3a, R3b, L1, L2 and n are as defined herein. Such compounds generally function as H1 receptor ligands, and thus have utility as sleep inducing agents. Pharmaceutical compositions containing a compound of structure (I), as well as methods relating to the use thereof, are also disclosed.
• 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.