(2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(5-bromothiophen-2-yl)-methanone

• 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-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(5-bromothiophen-2-yl)-methanone
• 英文别名: (2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(5-bromothio-phen-2-yl)-methanone；(2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(5-bromothiophen-2-yl)methanone
• 化学式: C₁₂H₁₀BrNOS₂
• 分子量: 328.253
• InChiKey: ZUTABZWFIQBEGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  99.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-溴-1-(5-溴噻吩)-2-乙酮 在 吗啉 、 sulfur 作用下， 以 乙醇 、 水 为溶剂， 反应 21.0h， 生成 (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-(5-bromothiophen-2-yl)-methanone
  参考文献：
  名称：

  Synthesis of 2-amino-3-heteroaroylthiophenes and evaluation of their activity as potential allosteric enhancers at the human A1 receptor

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2004.06.009

文献信息

• Allosteric adenosine receptor modulators
  申请人：——

  公开号：US20040077630A1

  公开（公告）日：2004-04-22

  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.

  本发明涉及式（IA）和（IB）的化合物：它们的制备、药物制剂以及它们在医学上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变构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
• [EN] ALLOSTERIC ADENOSINE RECEPTOR MODULATORS<br/>[FR] MODULATEURS ALLOSTERIQUES DES RECEPTEURS DE L'ADENOSINE
  申请人：KING PHARMACEUTICALS RES & DEV

  公开号：WO2002074056A2

  公开（公告）日：2002-09-26

  The present invention relates to compounds of formulas (IA) and (IB): 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.
• 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.