6,6-dimethyl-3-methylthio-1-(1-(tert-butyloxycarbonyl)pyrrol-2-yl)-6,7-dihydro-2-benzothiophen-4(5H)-one | 207307-85-5

• 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-1-(1-(tert-butyloxycarbonyl)pyrrol-2-yl)-6,7-dihydro-2-benzothiophen-4(5H)-one
• 英文别名: 6,6-Dimethyl-3-methylthio-1-((1-tert-butyloxycarbonyl)pyrrol-2-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one；Tert-butyl 2-(6,6-dimethyl-3-methylsulfanyl-4-oxo-5,7-dihydro-2-benzothiophen-1-yl)pyrrole-1-carboxylate
• CAS: 207307-85-5
• 化学式: C₂₀H₂₅NO₃S₂
• 分子量: 391.555
• InChiKey: PASRWZIKSXJKTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6,6-dimethyl-3-methylthio-1-(1-(tert-butyloxycarbonyl)pyrrol-2-yl)-6,7-dihydro-2-benzothiophen-4(5H)-one 以 乙酸乙酯 、 三氟乙酸 为溶剂， 以59%的产率得到6,6-Dimethyl-3-methylthio-1-(pyrrol-2-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one
  参考文献：
  名称：

  Thienycyclohexanone derivatives as ligands of the GABAA &agr;5 receptor subtype

  摘要：

  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。

  公开号：

  US06262103B1
• 作为产物：
  描述：

  1-bromo-6,6-dimethyl-3-methanesulfonyl-6,7-dihydro-2-benzothiophen-4(5H)-one 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 溶剂黄146 为溶剂， 反应 72.0h， 生成 6,6-dimethyl-3-methylthio-1-(1-(tert-butyloxycarbonyl)pyrrol-2-yl)-6,7-dihydro-2-benzothiophen-4(5H)-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

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。
• 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
• US6262103B1
  申请人：——

  公开号：US6262103B1

  公开（公告）日：2001-07-17
• Identification of a Novel, Selective GABA_A α5 Receptor Inverse Agonist Which Enhances Cognition
  作者：Mark S. Chambers、John R. Atack、Howard B. Broughton、Neil Collinson、Susan Cook、Gerard R. Dawson、Sarah C. Hobbs、George Marshall、Karen A. Maubach、Goplan V. Pillai、Austin J. Reeve、Angus M. MacLeod

  DOI：10.1021/jm020582q

  日期：2003.5.1

  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.