[(2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)(thiophen-2-yl)]methanone | 374926-21-3

• 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)(thiophen-2-yl)]methanone
• 英文别名: (2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)(2-thienyl)methanone；(2-Amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-thiophen-2-yl-methanone；(2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)-thiophen-2-ylmethanone
• CAS: 374926-21-3
• 化学式: C₁₂H₁₁NOS₂
• 分子量: 249.357
• InChiKey: FOPLAPZHPXBYSP-UHFFFAOYSA-N

物化性质

• 熔点：
  133-134 °C(Solv: ligroine (8032-32-4))
• 沸点：
  509.8±50.0 °C(Predicted)
• 密度：
  1.401±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  16
• 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

• 作为反应物：
  描述：

  三氟乙酰丙酮 、 [(2-amino-5,6-dihydro-4H-cyclopenta[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 20:1) afforded 19 mg (22%) 2,2,2-trifluoro-1-(2-methyl-4-thiophen-2-yl-6,7-dihydro-5H-cyclopenta[4,5]thieno [2,3-b]pyridin-3-yl)-ethanone as a colorless oil的产率得到2,2,2-trifluoro-1-(2-methyl-4-thiophen-2-yl-6,7-dihydro-5H-cyclopenta[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：

  本发明涉及式I化合物，其中R1、R2、R3、R4和R5如规范中所定义。本发明的化合物在GABAB受体上具有活性，并可用于治疗多种中枢神经系统疾病，包括焦虑、抑郁、癫痫、精神分裂症、认知障碍、痉挛和骨骼肌强直、脊髓损伤、多发性硬化症、肌萎缩性侧索硬化、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：

  US20060135552A1
• 作为产物：
  描述：

  2-噻吩基乙酰腈 、 环戊酮 在 吗啉 、 sulfur 作用下， 反应 21.0h， 以67%的产率得到[(2-amino-5,6-dihydro-4H-cyclopenta[b]thiophen-3-yl)(thiophen-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

• [EN] THIENO [2, 3-B] PYRIDINE DERIVATIVES AS VIRAL REPLICATION INHIBITORS<br/>[FR] DÉRIVÉS DE LA THIÉNO [2, 3-B] PYRIDINE EN TANT QU'INHIBITEURS DE RÉPLICATION VIRALE
  申请人：UNIV LEUVEN KATH

  公开号：WO2010130842A1

  公开（公告）日：2010-11-18

  The present invention relates to a series of compounds of formula (A) having antiviral activity, more specifically HIV (Human Immunodeficiency Virus) replication inhibiting properties. The invention also relates to methods for the preparation of such compounds, as well as to novel intermediates useful in one or more steps of such syntheses. The invention also relates to pharmaceutical compositions comprising an effective amount of such compounds as active ingredients. This invention further relates to the use of such compounds as medicines or in the manufacture of a medicament useful for the treatment of animals suffering from viral infections, in particular HIV infection. This invention further relates to methods for the treatment of viral infections in animals by the administration of a therapeutical amount of such compounds, optionally combined with one or more other drugs having anti-viral activity.

  本发明涉及一系列具有抗病毒活性的化合物(A)的公式，更具体地说是具有抑制HIV（人类免疫缺陷病毒）复制的特性。该发明还涉及制备这类化合物的方法，以及在这类合成的一个或多个步骤中有用的新中间体。该发明还涉及包含有效量这类化合物作为活性成分的药物组合物。本发明进一步涉及将这类化合物用作药物或用于制造用于治疗患有病毒感染的动物，尤其是HIV感染的药物。本发明还涉及通过给予这类化合物的治疗量，可选地与一个或多个具有抗病毒活性的其他药物结合，来治疗动物的病毒感染的方法。
• 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。
• THIENO [2, 3-B] PYRIDINE DERIVATIVES AS VIRAL REPLICATION INHIBITORS
  申请人：Bardiot Dorothée

  公开号：US20120059028A1

  公开（公告）日：2012-03-08

  The present invention relates to a series of compounds having antiviral activity, more specifically HIV (Human Immunodeficiency Virus) replication inhibiting properties. The invention also relates to methods for the preparation of such compounds, as well as to novel intermediates useful in one or more steps of such syntheses. The invention also relates to pharmaceutical compositions comprising an effective amount of such compounds as active ingredients. This invention further relates to the use of such compounds as medicines or in the manufacture of a medicament useful for the treatment of animals suffering from viral infections, in particular HIV infection. This invention further relates to methods for the treatment of viral infections in animals by the administration of a therapeutic amount of such compounds, optionally combined with one or more other drugs having anti-viral activity.

  本发明涉及一系列具有抗病毒活性的化合物，更具体地说是具有抑制人类免疫缺陷病毒（HIV）复制的特性。本发明还涉及制备这种化合物的方法，以及在这些合成步骤中有用的新型中间体。本发明还涉及含有这种化合物作为活性成分的有效剂量的制药组合物。此外，本发明还涉及将这种化合物用作药物或用于制造对治疗患有病毒感染，特别是HIV感染的动物有用的药物。此外，本发明还涉及通过给予治疗量的这种化合物的管理，可选地与一个或多个具有抗病毒活性的其他药物结合，用于治疗动物的病毒感染的方法。
• Microwave-Assisted Synthesis of 2-Aminothiophene Derivatives via Improved Gewald Reactions
  作者：Luolan Li、Bankang Ruan、Zhiyan Zhang、Lei Huang、Chao Xu

  DOI：10.3987/com-21-14513

  日期：——
• WO2006/63732
  申请人：——

  公开号：——

  公开（公告）日：——