3-Methyl-5,6-dihydro-cyclopentathiophen-4-on | 5833-99-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Methyl-5,6-dihydro-cyclopentathiophen-4-on
• 英文别名: 3-methyl-5,6-dihydro-4H-cyclopenta[b]thiophen-4-one；3-methyl-5,6-dihydrocyclopenta[b]thiophen-4-one
• CAS: 5833-99-8
• 化学式: C₈H₈OS
• 分子量: 152.217
• InChiKey: IFOPNNYCDHAGKN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-Methyl-5,6-dihydro-cyclopentathiophen-4-on 在 氯化亚砜 、 乙醇 、 水 、 sodium 、 溶剂黄146 、 sodium hydroxide 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 25.0h， 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：

  3-(4-methylthiophen-2-yl)propanoic acid 在 polyphosphoric acid 作用下， 反应 1.0h， 以32%的产率得到3-Methyl-5,6-dihydro-cyclopentathiophen-4-on
  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

文献信息

• Imidazol-Derivate
  申请人：CIBA-GEIGY AG

  公开号：EP0347378A1

  公开（公告）日：1989-12-20

  Imidazol-Derivate der Formel I sowie stereochemisch isomere Formen davon und deren Salze, haben nützliche herbizide Eigenschaften. Die Substituenten R1, L und X haben die hierin definierten Bedeutung.

  式 I 的咪唑衍生物及其立体异构体形式和盐类具有有用的除草特性。 及其立体异构体和盐类具有有用的除草特性。取代基 R1、L 和 X 具有本文所定义的含义。
• US4992090A
  申请人：——

  公开号：US4992090A

  公开（公告）日：1991-02-12
• Tricyclic pyrazoles part 7. Discovery of potent and selective dihydrothienocyclopentapyrazole derived CB2 ligands
  作者：Giansalvo Pinna、Maria Michela Curzu、Antonio Dore、Paolo Lazzari、Stefania Ruiu、Amedeo Pau、Gabriele Murineddu、Gérard A. Pinna

  DOI：10.1016/j.ejmech.2014.08.042

  日期：2014.10

  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.