6,6-dimethyl-3-methylthio-4-oxo-4,5,6,7-tetrahydro-2-benzothiophene-1-carbothioamide | 207307-82-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 6,6-dimethyl-3-methylthio-4-oxo-4,5,6,7-tetrahydro-2-benzothiophene-1-carbothioamide
• 英文别名: 6,6-dimethyl-3-methylthio-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one-1-thiocarboxamide；6,6-dimethyl-3-methylthio-4-oxo-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carbothioamide；6,6-Dimethyl-3-(methylthio)-4-oxo-4,5,6,7-tetrahydro-2-benzothiophene-1-carbothioamide；6,6-dimethyl-3-methylsulfanyl-4-oxo-5,7-dihydro-2-benzothiophene-1-carbothioamide
• CAS: 207307-82-2
• 化学式: C₁₂H₁₅NOS₃
• mdl: MFCD20268826
• 分子量: 285.455
• InChiKey: DKNIPBXKJCPVSN-UHFFFAOYSA-N

物化性质

• 熔点：
  238-240 °C
• 沸点：
  462.2±55.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  129
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6,6-dimethyl-3-methylthio-4-oxo-4,5,6,7-tetrahydro-2-benzothiophene-1-carbothioamide 以 乙醇 、 水 为溶剂， 反应 41.0h， 生成 6,6-Dimethyl-3-methylthio-1-(1-methyl-1,2,4-triazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one
  参考文献：
  名称：

  Identification of a Novel, Selective GABA_A α5 Receptor Inverse Agonist Which Enhances Cognition

  摘要：

  In pursuit of a GABA(A) alpha5-subtype-selective inverse agonist to enhance cognition, a series of 6,7-dihydro-2-benzothiophen-4(5H)-ones has been identified as a novel class of GABAA receptor ligands. These thiophenes have higher binding affinity for the GABA(A) alpha(5) receptor subtype compared to the GABA(A) alpha(1), alpha(2), and alpha(3) subtypes, and several analogues exhibit high GABA(A) (alpha(5) receptor inverse agonism. 6,6-Dimethyl-3-(2-hydroxyethyl)thio-1-(thiazol-2-yl)-6,7-dihydro2-benzothiophen-4(5H)-one (43) has been identified as a full inverse agonist at the GABA(A) alpha5 receptor and is functionally selective over the other major GABA(A) receptor subtypes. 43 readily penetrates into the CNS to give selective occupancy of GABA(A) alpha5 receptors. In addition, 43 enhances cognitive performance in rats in the delayed 'matching-to-place' Morris water maze test-a hippocampal-dependent memory task-without the convulsant or proconvulsant activity associated with nonselective, GABA(A) receptor inverse agonists.

  DOI：

  10.1021/jm020582q
• 作为产物：
  描述：

  6,6-二甲基-3-甲硫基-4-氧代-4，5，6，7-四氢苯并噻酚缩腈 在 吡啶 、 硫化氢 、 三乙胺 作用下， 以68%的产率得到6,6-dimethyl-3-methylthio-4-oxo-4,5,6,7-tetrahydro-2-benzothiophene-1-carbothioamide
  参考文献：
  名称：

  Identification of a Novel, Selective GABA_A α5 Receptor Inverse Agonist Which Enhances Cognition

  摘要：

  In pursuit of a GABA(A) alpha5-subtype-selective inverse agonist to enhance cognition, a series of 6,7-dihydro-2-benzothiophen-4(5H)-ones has been identified as a novel class of GABAA receptor ligands. These thiophenes have higher binding affinity for the GABA(A) alpha(5) receptor subtype compared to the GABA(A) alpha(1), alpha(2), and alpha(3) subtypes, and several analogues exhibit high GABA(A) (alpha(5) receptor inverse agonism. 6,6-Dimethyl-3-(2-hydroxyethyl)thio-1-(thiazol-2-yl)-6,7-dihydro2-benzothiophen-4(5H)-one (43) has been identified as a full inverse agonist at the GABA(A) alpha5 receptor and is functionally selective over the other major GABA(A) receptor subtypes. 43 readily penetrates into the CNS to give selective occupancy of GABA(A) alpha5 receptors. In addition, 43 enhances cognitive performance in rats in the delayed 'matching-to-place' Morris water maze test-a hippocampal-dependent memory task-without the convulsant or proconvulsant activity associated with nonselective, GABA(A) receptor inverse agonists.

  DOI：

  10.1021/jm020582q

文献信息

• Thienycyclohexanone derivatives as ligands of the GABAA &agr;5 receptor subtype
  申请人：Merck Sharp & Dohme Limited

  公开号：US06262103B1

  公开（公告）日：2001-07-17

  A pharamceutical composition comprises a compound of formula (I) or a pharmaceutically acceptable salt thereof, wherein A is C1-6alkyl, C2-6alkenyl, C2-6-alkynyl, C3-6-cycloalkyl, arylC1-6alkyl, aryl, S(O)pR1.

  一种药物组合物包括式(I)的化合物或其药用可接受的盐，其中A为C1-6烷基，C2-6烯基，C2-6炔基，C3-6环烷基，芳基C1-6烷基，芳基，S(O)pR1。
• [EN] CONDENSED THIOPHENE DERIVATIVES AND THEIR USE AS CYCLIC GLP-1 AGONISTS<br/>[FR] DERIVES THIOPHENE CONDENSES ET UTILISATION EN TANT QU'AGONISTES DE GLP-1 CYCLIQUES
  申请人：NOVO NORDISK AS

  公开号：WO2006003096A1

  公开（公告）日：2006-01-12

  The invention provides compounds of formula (I) for use as GLP-1 receptor agonists.

  该发明提供了用作GLP-1受体激动剂的化合物的公式(I)。
• Condensed Thiophene Derivatives and Their Use as Cyclic Glp-1 Agonists
  申请人：Knudsen Sanne Moller

  公开号：US20080275066A1

  公开（公告）日：2008-11-06

  The invention provides compounds of formula (I) for use as GLP-1 receptor agonists.

  该发明提供了I式化合物，用作GLP-1受体激动剂。
• 6,7-Dihydro-2-benzothiophen-4(5<i>H</i>)-ones:  A Novel Class of GABA-A α5 Receptor Inverse Agonists
  作者：Mark S. Chambers、John R. Atack、Frances A. Bromidge、Howard B. Broughton、Susan Cook、Gerard R. Dawson、Sarah C. Hobbs、Karen A. Maubach、Austin J. Reeve、Guy R. Seabrook、Keith Wafford、Angus M. MacLeod

  DOI：10.1021/jm010471b

  日期：2002.3.1

  Nonselective inverse agonists at the benzodiazepine binding site on the GABA-A chloride ion channel enhance cognitive performance in animals but cannot be used in the treatment of cognitive disorders because of anxiogenic and convulsant side effects. We have identified a novel series of GABA-A alpha5 receptor ligands during our search for alpha5 receptor inverse agonists as potential cognition enhancers. In particular, 6,6-dimethyl-3-(2-hydroxyethyl)thio-1-(thiazol-2-yl)-6,7-dihydro- 2-benzothiophen-4(5H-)-one (26) has been identified as a functionally selective GABA-A alpha5 inverse agonist.
• THIENYLCYCLOHEXANONE DERIVATIVES AS LIGANDS OF THE GABA A alpha5 RECEPTOR SUBTYPE
  申请人：MERCK SHARP & DOHME LTD.

  公开号：EP0937072B1

  公开（公告）日：2002-01-09