ethyl 2-(3-methyl-4-oxo-5,6-dihydro-4H-cyclopenta[b]thiophen-5-yl)-2-oxoacetate | 1623023-27-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-(3-methyl-4-oxo-5,6-dihydro-4H-cyclopenta[b]thiophen-5-yl)-2-oxoacetate
• CAS: 1623023-27-7
• 化学式: C₁₂H₁₂O₄S
• 分子量: 252.291
• InChiKey: ZTPUZSLSBVOTJR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.54
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  60.44
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-(3-methyl-4-oxo-5,6-dihydro-4H-cyclopenta[b]thiophen-5-yl)-2-oxoacetate 在 氯化亚砜 、 水 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 7-methyl-1-(2,4-dichlorophenyl)-N-menthyl-1,4-dihydrothieno[2',3'-4,5]cyclopenta[1,2c]pyrazole-3-carboxamide
  参考文献：
  名称：

  Tricyclic pyrazoles part 7. Discovery of potent and selective dihydrothienocyclopentapyrazole derived CB2 ligands

  摘要：

  A series of dihydrothienocyclopentapyrazole-based derivatives was synthesized and evaluated for the affinity at CBI and CB2 receptors. The major term, the 6-methyl-1-(1,4-dichloropheny1)-N-piperidiny1)-1,4-dihydrothieno[2',3'-4,5]cyclopenta[1,2-c]pyrazole-3-carboxamide (6a), displayed a high affinity and good selectivity for CB2 receptors (Ki values of 2.30 nM for CB2 receptor and 440 nM for CB1 receptors respectively). Subsequent analogue preparation resulted in the identification of compounds such as 6b, 6d, 6e, 6k, 6l, 6m, 6s and 6t that showed 1.3-485 fold selectivity for CB2 receptors with potencies in the 1.1-7.2 nM range. These compounds profiled as full agonists at CB2 receptor in an inhibition assay of P-ERK 1/2 up regulation in HL-60 cells. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.042
• 作为产物：
  描述：

  4-甲基噻吩-2-甲醛 在 哌啶 、 吡啶 、 乙醇 、 氢气 、 sodium 、 palladium(II) hydroxide 作用下， 以 乙醇 为溶剂， 20.0~115.0 ℃ 、103.42 kPa 条件下， 反应 24.0h， 生成 ethyl 2-(3-methyl-4-oxo-5,6-dihydro-4H-cyclopenta[b]thiophen-5-yl)-2-oxoacetate
  参考文献：
  名称：

  Tricyclic pyrazoles part 7. Discovery of potent and selective dihydrothienocyclopentapyrazole derived CB2 ligands

  摘要：

  A series of dihydrothienocyclopentapyrazole-based derivatives was synthesized and evaluated for the affinity at CBI and CB2 receptors. The major term, the 6-methyl-1-(1,4-dichloropheny1)-N-piperidiny1)-1,4-dihydrothieno[2',3'-4,5]cyclopenta[1,2-c]pyrazole-3-carboxamide (6a), displayed a high affinity and good selectivity for CB2 receptors (Ki values of 2.30 nM for CB2 receptor and 440 nM for CB1 receptors respectively). Subsequent analogue preparation resulted in the identification of compounds such as 6b, 6d, 6e, 6k, 6l, 6m, 6s and 6t that showed 1.3-485 fold selectivity for CB2 receptors with potencies in the 1.1-7.2 nM range. These compounds profiled as full agonists at CB2 receptor in an inhibition assay of P-ERK 1/2 up regulation in HL-60 cells. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.042