(2-amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)-thiophen-2-yl-methanone | 29462-24-6

• 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-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)-thiophen-2-yl-methanone
• 英文别名: (2-amino-4,5,6,7-tetrahydrobenzo[b]thiophen-3-yl)-thiophen-2-yl-methanone；(2-Amino-4,5,6,7-tetrahydro-1-benzothien-3-yl)(thien-2-yl)methanone；(2-amino-4,5,6,7-tetrahydro-1-benzothiophen-3-yl)-thiophen-2-ylmethanone
• CAS: 29462-24-6
• 化学式: C₁₃H₁₃NOS₂
• mdl: MFCD06373461
• 分子量: 263.384
• InChiKey: PLVGUPYLMPDNAR-UHFFFAOYSA-N

物化性质

• 熔点：
  117-118 °C(Solv: ligroine (8032-32-4))
• 沸点：
  515.0±50.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.307
• 拓扑面积：
  99.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酰丙酮 、 (2-amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)-thiophen-2-yl-methanone 在 硫酸 ethyl acetate heptane 作用下， 以 溶剂黄146 为溶剂， 反应 0.17h， 以Flash chromatography (heptane/ethyl acetate 9:1) afforded 46 mg (74%) 1-(2-methyl-4-thiophen-2-yl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone as a yellow oil的产率得到1-(2-methyl-4-thiophen-2-yl-5,6,7,8-tetrahydro-benzo[4,5]thieno[2,3-b]pyridin-3-yl)-ethanone
  参考文献：
  名称：

  Thieno-pyridine derivatives as allosteric enhancers of the GABAB receptors

  摘要：

  本发明涉及公式I的化合物，其中R1，R2，R3，R4和R5如规范中所定义。本发明的化合物对GABAB受体具有活性，并且可用于治疗各种中枢神经系统疾病，包括焦虑症、抑郁症、癫痫、精神分裂症、认知障碍、痉挛和骨骼肌肌肉僵硬、脊髓损伤、多发性硬化症、肌萎缩侧索硬化、脑瘫、神经病性疼痛和与可卡因和尼古丁有关的渴望、精神病、惊恐障碍、创伤后应激障碍和胃肠疾病。

  公开号：

  US07390903B2
• 作为产物：
  描述：

  2-噻吩基乙酰腈 、 环己酮 在 吗啉 、 sulfur 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以98%的产率得到(2-amino-4,5,6,7-tetrahydro-benzo[b]thiophen-3-yl)-thiophen-2-yl-methanone
  参考文献：
  名称：

  WO2006/63732

  摘要：

  公开号：

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。
• 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.
• SERINE PROTEASE INHIBITORS
  申请人：Tularik Limited

  公开号：EP1343561B1

  公开（公告）日：2007-02-28
• THIENO-PYRIDINE DERIVATIVES AS GABA-B ALLOSTERIC ENHANCERS
  申请人：F. Hoffmann-La Roche AG

  公开号：EP1828199B1

  公开（公告）日：2009-05-06
• US7390903B2
  申请人：——

  公开号：US7390903B2

  公开（公告）日：2008-06-24