(2-amino-6-hydroxy-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(4-chlorophenyl)methanone | 374926-23-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2-amino-6-hydroxy-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(4-chlorophenyl)methanone
• 英文别名: (2-Amino-6-hydroxy-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)-(4-chlorophenyl)methanone
• CAS: 374926-23-5
• 化学式: C₁₅H₁₄ClNO₂S
• 分子量: 307.801
• InChiKey: QEXDZOFLSIKWQR-UHFFFAOYSA-N

物化性质

• 熔点：
  176-177 °C
• 沸点：
  580.8±50.0 °C(predicted)
• 密度：
  1.431±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  91.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2-amino-6-hydroxy-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(4-chlorophenyl)methanone 、 甲基磺酰氯 以 二氯甲烷 、 三乙胺 为溶剂， 反应 2.0h， 以56%的产率得到[2-amino-6-[(methanesulfonyl)oxy]-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl]-(4-chlorophenyl)methanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Allosteric A1-Adenosine Receptor Modulators Structurally Related to (2-Amino-4,5,6,7-Tetrahydro-Benzo[B]Thiophen-3-YL)-(4-Chloro-Phenyl)-Methanone, a Potent Compound Useful to Reduce Neuropathic Pain

  摘要：

  New derivatives of (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(4-chlorophenyl)methanone (compound 1), an allosteric enhancer of agonist binding to the A(1)-adenosine receptor, have been synthesized and evaluated in an intact cell assay at different concentrations to determine which among them were potential allosteric enhancers of the action of adenosine to activate the human-A(1)adenosine receptor. None of the synthesized compounds appear to be more potent than 1 at a concentration of 10 mu M. Most of the compounds increase the cAMP content of CHO cells expressing the human A(1)-adenosine receptor, indicating an antagonist activity. Only two of the evaluated compounds (2 and 8) appeared to be allosteric enhancers at high concentration (10 mu M).

  DOI：

  10.1007/s00044-005-0129-8
• 作为产物：
  描述：

  4-羟基环己酮 、 对氯苯乙酰腈 在 吗啉 、 sulfur 作用下， 以 乙醇 为溶剂， 反应 21.0h， 以56%的产率得到(2-amino-6-hydroxy-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(4-chlorophenyl)methanone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Allosteric A1-Adenosine Receptor Modulators Structurally Related to (2-Amino-4,5,6,7-Tetrahydro-Benzo[B]Thiophen-3-YL)-(4-Chloro-Phenyl)-Methanone, a Potent Compound Useful to Reduce Neuropathic Pain

  摘要：

  New derivatives of (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-(4-chlorophenyl)methanone (compound 1), an allosteric enhancer of agonist binding to the A(1)-adenosine receptor, have been synthesized and evaluated in an intact cell assay at different concentrations to determine which among them were potential allosteric enhancers of the action of adenosine to activate the human-A(1)adenosine receptor. None of the synthesized compounds appear to be more potent than 1 at a concentration of 10 mu M. Most of the compounds increase the cAMP content of CHO cells expressing the human A(1)-adenosine receptor, indicating an antagonist activity. Only two of the evaluated compounds (2 and 8) appeared to be allosteric enhancers at high concentration (10 mu M).

  DOI：

  10.1007/s00044-005-0129-8

文献信息

• Allosteric adenosine receptor modulators
  申请人：——

  公开号：US20010047008A1

  公开（公告）日：2001-11-29

  The present invention relates to compounds of formulas (IA) and (IB): 1 the preparation thereof, pharmaceutical formulations thereof, and their use in medicine as allosteric adenosine receptor modulators for uses including protection against hypoxia and ischemia induced injury and treatment of adenosine-sensitive cardiac arrhythmias.

  本发明涉及以下化合物的公式（IA）和（IB）：其制备、药物配方以及在医学中作为变构腺苷受体调节剂的用途，包括保护免受缺氧和缺血引起的损伤以及治疗对腺苷敏感的心律失常。
• EP1401441A4
  申请人：——

  公开号：EP1401441A4

  公开（公告）日：2006-09-06
• ALLOSTERIC ADENOSINE RECEPTOR MODULATORS
  申请人：King Pharmaceuticals Research and Development Inc.

  公开号：EP1401441A2

  公开（公告）日：2004-03-31
• US6727258B2
  申请人：——

  公开号：US6727258B2

  公开（公告）日：2004-04-27
• US7112607B2
  申请人：——

  公开号：US7112607B2

  公开（公告）日：2006-09-26