2-(2-bromoacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide | 1001020-10-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: 2-(2-bromoacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide
• 英文别名: 2-[(2-bromoacetyl)amino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide
• CAS: 1001020-10-5
• 化学式: C₁₁H₁₃BrN₂O₂S
• 分子量: 317.206
• InChiKey: ITHFJIMYHSRWDA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  100
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(2-bromoacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.42h， 以41%的产率得到2-{2-[4-(2-hydroxy-ethyl)-3-trifluoromethylpyrazol-1-yl]-acetylamino}-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxamide
  参考文献：
  名称：

  WO2008/3452

  摘要：

  公开号：
• 作为产物：
  描述：

  溴乙酰溴 、 2-氨基-4,5,6,7-四氢苯并[b]噻吩-3-甲酰胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以94%的产率得到2-(2-bromoacetamido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide
  参考文献：
  名称：

  A novel series of positive modulators of the AMPA receptor: Discovery and structure based hit-to-lead studies

  摘要：

  Starting from an HTS derived hit 1, application of biostructural data facilitated rapid optimization to lead 22, a novel AMPA receptor modulator. This is the first demonstration of how structure based drug design can be exploited in an optimization program for a glutamate receptor.

  DOI：

  10.1016/j.bmcl.2010.07.138

文献信息

• Heterocyclic Derivatives
  申请人：Gillen Kevin James

  公开号：US20080255086A1

  公开（公告）日：2008-10-16

  The present invention relates to a heterocyclic derivative according to formula I wherein the variables are defined as in the specification, or to a pharmaceutically acceptable salt or solvate thereof. The present invention also relates to a pharmaceutical composition comprising said heterocyclic derivatives and to their use in therapy, for instance in the treatment or prevention of psychiatric diseases where an enhancement of synaptic responses mediated by AMPA receptors is required, including schizophrenia, depression and Alzheimer's disease.

  本发明涉及式I的杂环衍生物，其中变量如规范中所定义，或其药学上可接受的盐或溶剂。本发明还涉及包含上述杂环衍生物的制药组合物，以及它们在治疗中的使用，例如在需要增强由AMPA受体介导的突触反应的精神疾病的治疗或预防中，包括精神分裂症、抑郁症和阿尔茨海默病。
• Heterocyclic derivatives
  申请人：N.V. Organon

  公开号：US07820707B2

  公开（公告）日：2010-10-26

  The present invention relates to a heterocyclic derivative according to formula I wherein the variables are defined as in the specification, or to a pharmaceutically acceptable salt or solvate thereof. The present invention also relates to a pharmaceutical composition comprising said heterocyclic derivatives and to their use in therapy, for instance in the treatment or prevention of psychiatric diseases where an enhancement of synaptic responses mediated by AMPA receptors is required, including schizophrenia, depression and Alzheimer's disease.

  本发明涉及一种杂环衍生物，其化学式为I，其中变量如规范中所定义，或其药学上可接受的盐或溶剂。本发明还涉及一种含有该杂环衍生物的制药组合物，以及它们在治疗中的用途，例如在需要增强由AMPA受体介导的突触反应的精神疾病的治疗或预防中，包括精神分裂症、抑郁症和阿尔茨海默病。
• A novel series of positive modulators of the AMPA receptor: Structure-based lead optimization
  作者：Craig Jamieson、Robert A. Campbell、Iain A. Cumming、Kevin J. Gillen、Jonathan Gillespie、Bert Kazemier、Michael Kiczun、Yvonne Lamont、Amanda J. Lyons、John K.F. Maclean、Frederic Martin、Elizabeth M. Moir、John A. Morrow、John Pantling、Zoran Rankovic、Lynn Smith

  DOI：10.1016/j.bmcl.2010.08.063

  日期：2010.10

  Starting from lead compound 1, we demonstrate how X-ray structural data can be used to understand SAR and expediently optimize bioavailability in a novel series of AMPA receptor modulators, furnishing 5 with improved bioavailability and robust in vivo activity. (C) 2010 Elsevier Ltd. All rights reserved.
• PYRAZOLEALKANAMIDE SUBSTITUTED THIOPHENES AS AMPA POTENTIATORS
  申请人：N.V. Organon

  公开号：EP2041124A1

  公开（公告）日：2009-04-01
• US7820707B2
  申请人：——

  公开号：US7820707B2

  公开（公告）日：2010-10-26