5-溴-3-乙基-2-甲基-1-苯并噻吩 | 501901-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 5-溴-3-乙基-2-甲基-1-苯并噻吩
• 英文名称: 5-bromo-3-ethyl-2-methylbenzo[b]thiophene
• 英文别名: 5-Bromo-3-ethyl-2-methyl-1-benzothiophene
• CAS: 501901-98-0
• 化学式: C₁₁H₁₁BrS
• 分子量: 255.178
• InChiKey: VZNRYLCNHFEOQJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  28.2
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  5-溴-3-乙基-2-甲基-1-苯并噻吩 、 (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 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 (R)-3'-(3-ethyl-2-methylbenzo[b]thiophen-5-yl)spiro[1-azabicyclo[2.2.2]octane-3,5'-oxazolidin]-2'-one
  参考文献：
  名称：

  (R)-3‘-(3-Methylbenzo[b]thiophen-5-yl)spiro[1-azabicyclo[2,2,2]octane-3,5‘-oxazolidin]-2‘-one, a Novel and Potent α7 Nicotinic Acetylcholine Receptor Partial Agonist Displays Cognitive Enhancing Properties

  摘要：

  Recent studies have suggested that the alpha 7 nicotinic acetylcholine receptors play important roles in learning and memory. Herein, we describe our research of the structure-activity relationships (SAR) in a series of (S)-spiro[1-azabicyclo[2.2.2]octane-3,5'-oxazolidin]-2'-ones bearing various bicyclic moieties to discover novel alpha 7 receptor agonists. Through a number of SAR studies on the series, we have found out that inhibition of CYP 2D6 isozyme, which was a primary obstacle for the previously identified compound, was avoidable by the introduction of bicyclic moieties. Chemical optimization of the series led to the identification of a novel and potent alpha 7 nicotinic acetylcholine receptor partial agonist 23. This compound not only possessed high binding affinity (K-i) 3 nmol/L) toward the alpha 7 receptor but also showed agonistic activity even at a concentration of 0.1 mu mol/L. In addition, compound 23 improved cognition in several rat models, which might suggest the potential of the alpha 7 receptor partial agonist for the treatment of neurological disorders including cognitive dysfunction.

  DOI：

  10.1021/jm060249c
• 作为产物：
  描述：

  5-bromo-2-methylbenzothiophene 在 三氯化铝 、 一水合肼 作用下， 以 二氯甲烷 、 乙二醇 为溶剂， 反应 9.0h， 生成 5-溴-3-乙基-2-甲基-1-苯并噻吩
  参考文献：
  名称：

  (R)-3‘-(3-Methylbenzo[b]thiophen-5-yl)spiro[1-azabicyclo[2,2,2]octane-3,5‘-oxazolidin]-2‘-one, a Novel and Potent α7 Nicotinic Acetylcholine Receptor Partial Agonist Displays Cognitive Enhancing Properties

  摘要：

  Recent studies have suggested that the alpha 7 nicotinic acetylcholine receptors play important roles in learning and memory. Herein, we describe our research of the structure-activity relationships (SAR) in a series of (S)-spiro[1-azabicyclo[2.2.2]octane-3,5'-oxazolidin]-2'-ones bearing various bicyclic moieties to discover novel alpha 7 receptor agonists. Through a number of SAR studies on the series, we have found out that inhibition of CYP 2D6 isozyme, which was a primary obstacle for the previously identified compound, was avoidable by the introduction of bicyclic moieties. Chemical optimization of the series led to the identification of a novel and potent alpha 7 nicotinic acetylcholine receptor partial agonist 23. This compound not only possessed high binding affinity (K-i) 3 nmol/L) toward the alpha 7 receptor but also showed agonistic activity even at a concentration of 0.1 mu mol/L. In addition, compound 23 improved cognition in several rat models, which might suggest the potential of the alpha 7 receptor partial agonist for the treatment of neurological disorders including cognitive dysfunction.

  DOI：

  10.1021/jm060249c