4-(5-bromothiophen-2-yl)-N,N-dimethylbenzamide | 857334-83-9

• 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: 4-(5-bromothiophen-2-yl)-N,N-dimethylbenzamide
• 英文别名: 4-(5-bromo-thiophen-2-yl)-N,N-dimethyl-benzamide
• CAS: 857334-83-9
• 化学式: C₁₃H₁₂BrNOS
• 分子量: 310.214
• InChiKey: QUSZQTKCRWUCTP-UHFFFAOYSA-N

物化性质

• 沸点：
  418.9±35.0 °C(Predicted)
• 密度：
  1.438±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  48.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(5-bromothiophen-2-yl)-N,N-dimethylbenzamide 、 (S)-螺[1-氮杂双环[2.2.2]辛烷-3,5'-恶唑啉]-2'-酮 在 copper(l) iodide 、 potassium carbonate 、 乙二胺 作用下， 以 1,4-二氧六环 为溶剂， 以47%的产率得到4-[5-((R)-5-1-aza-bicyclo[2.2.2]oct-3-yl-2-oxo-oxazolidin-3-yl)-thiophen-2-yl]-N,N-dimethyl-benzamide
  参考文献：
  名称：

  WO2006/65209

  摘要：

  公开号：
• 作为产物：
  描述：

  4-(5-溴噻吩-2-基)苯甲酸 在 吡啶 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 生成 4-(5-bromothiophen-2-yl)-N,N-dimethylbenzamide
  参考文献：
  名称：

  Diarylthiophenes as inhibitors of the pore-forming protein perforin

  摘要：

  Evolution from a furan-containing high-throughput screen (HTS) hit (1) resulted in isobenzofuran-1(3H)-one (2) as a potent inhibitor of the function of both isolated perforin protein and perforin delivered in situ by intact KHYG-1 NK cells. In the current study, structure-activity relationship (SAR) development towards a novel series of diarylthiophene analogues has continued through the use of substituted-benzene and -pyridyl moieties as bioisosteres for 2-thioxoimidazolidin-4-one (A) on a thiophene (B) -isobenzofuranone (C) scaffold. The resulting compounds were tested for their ability to inhibit perforin lytic activity in vitro. Carboxamide (23) shows a 4-fold increase over (2) in lytic activity against isolated perforin and provides good rationale for continued development within this class. (C) 2015 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license.

  DOI：

  10.1016/j.bmcl.2015.12.003

文献信息

• [EN] NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS<br/>[FR] LIGANDS DU RECEPTEUR A L'ACETYLCHOLINE NICOTINIQUE
  申请人：ASTRAZENECA AB

  公开号：WO2005061510A1

  公开（公告）日：2005-07-07

  Acetylcholine receptor ligands of formula (I), wherein D, Ar1, E and Ar2 are as described in the specification, diastereoisomers, enantiomers, pharmaceutically-acceptable salts, methods of making, pharmaceutical compositions containing and methods for using the same.

  乙酰胆碱受体配体的化学式（I），其中D、Ar1、E和Ar2如规范中所述，对映异构体，对映体，药用盐，制备方法，含有该化合物的药物组合物以及使用该化合物的方法。
• Nicotinic Acetylcholine Receptor Ligands
  申请人：Ernst Glen

  公开号：US20070249588A1

  公开（公告）日：2007-10-25

  Acetylcholine receptor ligands of formula (I), wherein D, Ar1, E and Ar2 are as described in the specification, diastereoisomers, enantiomers, pharmaceutically-acceptable salts, methods of making, pharmaceutical compositions containing and methods for using the same.

  公式（I）的乙酰胆碱受体配体，其中D，Ar1，E和Ar2如规范所述，对映异构体，对映体，药学上可接受的盐，制备方法，包含制剂和使用方法的药物组合物。
• NICOTINIC ACETYLCHOLINE RECEPTOR LIGANDS
  申请人：AstraZeneca AB

  公开号：EP1699801A1

  公开（公告）日：2006-09-13
• Diarylthiophenes as inhibitors of the pore-forming protein perforin
  作者：Christian K. Miller、Kristiina M. Huttunen、William A. Denny、Jagdish K. Jaiswal、Annette Ciccone、Kylie A. Browne、Joseph A. Trapani、Julie A. Spicer

  DOI：10.1016/j.bmcl.2015.12.003

  日期：2016.1

  Evolution from a furan-containing high-throughput screen (HTS) hit (1) resulted in isobenzofuran-1(3H)-one (2) as a potent inhibitor of the function of both isolated perforin protein and perforin delivered in situ by intact KHYG-1 NK cells. In the current study, structure-activity relationship (SAR) development towards a novel series of diarylthiophene analogues has continued through the use of substituted-benzene and -pyridyl moieties as bioisosteres for 2-thioxoimidazolidin-4-one (A) on a thiophene (B) -isobenzofuranone (C) scaffold. The resulting compounds were tested for their ability to inhibit perforin lytic activity in vitro. Carboxamide (23) shows a 4-fold increase over (2) in lytic activity against isolated perforin and provides good rationale for continued development within this class. (C) 2015 The Authors. Published by Elsevier Ltd. This is an open access article under the CC BY license.
• WO2006/65209
  申请人：——

  公开号：——

  公开（公告）日：——