2-Amino-3-(2-pyridylcarbonyl)-4,5,6,7-tetrahydro-1-benzthiophen | 38125-54-1

• 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-Amino-3-(2-pyridylcarbonyl)-4,5,6,7-tetrahydro-1-benzthiophen
• 英文别名: (2-Amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-pyridin-2-yl-methanone；(2-Amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)-pyridin-2-ylmethanone
• CAS: 38125-54-1
• 化学式: C₁₄H₁₄N₂OS
• 分子量: 258.344
• InChiKey: MEBLKHKWJCEWOR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  吗啉 、 3-氧代-3-(2-吡啶基)丙腈 在 硫化氢 作用下， 以 环己酮 为溶剂， 以58%的产率得到2-Amino-3-(2-pyridylcarbonyl)-4,5,6,7-tetrahydro-1-benzthiophen
  参考文献：
  名称：

  Allosteric adenosine receptor modulators

  摘要：

  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。

  公开号：

  US20010047008A1

文献信息

• Synthesis of 2-amino-3-heteroaroylthiophenes and evaluation of their activity as potential allosteric enhancers at the human A1 receptor
  作者：Pier Giovanni Baraldi、Maria Giovanna Pavani、John C. Shryock、Allan R. Moorman、Valeria Iannotta、Pier Andrea Borea、Romeo Romagnoli

  DOI：10.1016/j.ejmech.2004.06.009

  日期：2004.10

  2-Amino-3-benzoylthiophenes are allosteric enhancers of agonist binding to the adenosine A, receptor. New compounds bearing an heteroaroyl instead of the benzoyl moiety at the 3-position of the thiophene were synthesized. The phenyl ring was replaced with heterocycles that possess heteroatoms able to form hydrogen bonds (2-furanyl, 2-benzofuranyl, 2-pyridinyl in compounds 2-13) or with a thienyl moiety as isoster of the phenyl ring (2-thienyl, 3-thienyl and 5-halo-2-thienyl in compounds 14-29). The effect of several alkyl substituents at positions 4 and 5 of the thiophene ring to increase enhancer activity was determined. The ability of the new molecules to reduce the cAMP content in CHO cells expressing the human adenosine A, receptor was evaluated. Compounds 2-13 with hydrogen bond-forming heteroatoms did not show significant activity as allosteric enhancers. On the other hand, compounds 15-16 and 19-20 with an unsubstituted thienyl moiety as replacement for the phenyl ring were nearly as efficacious as PD 81,723, the prototypical A, allosteric enhancer. Alkyl substituents at positions 4 and 5 of the thiophene ring were tolerated while a substituted piperidine ring was not tolerated. We conclude that hydrogen bonds could not be formed in the domain of the receptor that accommodates the phenyl ring of 2-amino-3-benzoylthiophene derivatives, indicating that this domain is hydrophobic. (C) 2004 Elsevier SAS. All rights reserved.
• 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