1-(2-Chloro-ethyl)-3-cyclopent-1-enyl-1,3-dihydro-benzoimidazol-2-one | 202859-76-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 1-(2-Chloro-ethyl)-3-cyclopent-1-enyl-1,3-dihydro-benzoimidazol-2-one
• 英文别名: 1-(2-Chloroethyl)-3-(cyclopenten-1-yl)benzimidazol-2-one
• CAS: 202859-76-5
• 化学式: C₁₄H₁₅ClN₂O
• 分子量: 262.739
• InChiKey: XVRGOPUQOAFAEB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  1-(2-Chloro-ethyl)-3-cyclopent-1-enyl-1,3-dihydro-benzoimidazol-2-one 、 N-(3,4-dichlorophenyl)-N-(piperidin-4-yl)propionamide 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 1-{2-[4-(N-Propionyl-(3,4-dichlorophenyl)amino)piperidino]ethyl}-3-(1-cyclopentenyl)-2(3H)-benzimidazolone
  参考文献：
  名称：

  Pharmacological profile of a novel series of NK1 antagonists. In vitro and in vivo potency of benzimidazolone derivatives

  摘要：

  By low throughput examination of our chemical library, compound 7 was selected as a lead NK, antagonist with a K-i of 7.1 nM. Modifications of its structure led to the finding that the in vitro potency could be markedly enhanced by disubstituting the anilino phenyl ring as in compounds 13 or 22. Human binding data correlated rather well with results obtained with in vitro animal mice; compound 13 was the most active with ED50 of 0.001 and 0.3 mg/kg after iv and po administration respectively. Furthermore, antagonist 71 was found to be a potent inhibitor of SP-induced bronchoconstriction in guinea-pigs with an ED50 between 0.1 and 0.03 mg/kg iv. Furthermore, upon oral administration, 71 was observed to be active in a model of SP-induced bronchial hypersensitivity in mice, with an ID50 of around 3 mg/kg.

  DOI：

  10.1016/s0223-5234(97)82771-7
• 作为产物：
  描述：

  1-溴-2-氯乙烷 、 1-(1-环戊烯-1-基)-1H-苯并咪唑-2-醇 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1-(2-Chloro-ethyl)-3-cyclopent-1-enyl-1,3-dihydro-benzoimidazol-2-one
  参考文献：
  名称：

  Pharmacological profile of a novel series of NK1 antagonists. In vitro and in vivo potency of benzimidazolone derivatives

  摘要：

  By low throughput examination of our chemical library, compound 7 was selected as a lead NK, antagonist with a K-i of 7.1 nM. Modifications of its structure led to the finding that the in vitro potency could be markedly enhanced by disubstituting the anilino phenyl ring as in compounds 13 or 22. Human binding data correlated rather well with results obtained with in vitro animal mice; compound 13 was the most active with ED50 of 0.001 and 0.3 mg/kg after iv and po administration respectively. Furthermore, antagonist 71 was found to be a potent inhibitor of SP-induced bronchoconstriction in guinea-pigs with an ED50 between 0.1 and 0.03 mg/kg iv. Furthermore, upon oral administration, 71 was observed to be active in a model of SP-induced bronchial hypersensitivity in mice, with an ID50 of around 3 mg/kg.

  DOI：

  10.1016/s0223-5234(97)82771-7

文献信息

• N-ARYL-N-PIPERIDIN-4-YLMETHYL-AMIDE DERIVATIVES AND THIER USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS
  申请人：Peters Dan

  公开号：US20100298380A1

  公开（公告）日：2010-11-25

  This invention relates to novel N-aryl-N-piperidin-4-ylmethyl amide derivatives useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy, and to pharmaceutical compositions comprising the compounds of the invention.

  本发明涉及一种新颖的N-芳基-N-哌啶-4-基甲酰胺衍生物，其可用作单胺神经递质再摄取抑制剂。在其他方面，本发明涉及使用这些化合物进行治疗的方法，以及包含本发明化合物的制药组合物。
• N-ARYL-N-PIPERIDIN-4-YLMETHYL-AMIDE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS
  申请人：NeuroSearch AS

  公开号：EP2183240A2

  公开（公告）日：2010-05-12
• [EN] N-ARYL-N-PIPERIDIN-4-YLMETHYL-AMIDE DERIVATIVES AND THEIR USE AS MONOAMINE NEUROTRANSMITTER RE-UPTAKE INHIBITORS<br/>[FR] DÉRIVÉS N-ARYL-N-PIPÉRIDIN-4-YLMÉTHYL-AMIDE ET LEUR UTILISATION EN TANT QU'INHIBITEURS DE RECAPTAGE DE NEUROTRANSMETTEURS MONOAMINES
  申请人：NEUROSEARCH AS

  公开号：WO2009016215A2

  公开（公告）日：2009-02-05

  This invention relates to novel N-aryl-N-piperidin-4-ylmethyl amide derivatives useful as monoamine neurotransmitter re-uptake inhibitors. In other aspects the invention relates to the use of these compounds in a method for therapy, and to pharmaceutical compositions comprising the compounds of the invention.
• Pharmacological profile of a novel series of NK1 antagonists. In vitro and in vivo potency of benzimidazolone derivatives
  作者：G Rémond、B Portevin、J Bonnet、E Canet、D Regoli、G De Nanteuil

  DOI：10.1016/s0223-5234(97)82771-7

  日期：1997.11

  By low throughput examination of our chemical library, compound 7 was selected as a lead NK, antagonist with a K-i of 7.1 nM. Modifications of its structure led to the finding that the in vitro potency could be markedly enhanced by disubstituting the anilino phenyl ring as in compounds 13 or 22. Human binding data correlated rather well with results obtained with in vitro animal mice; compound 13 was the most active with ED50 of 0.001 and 0.3 mg/kg after iv and po administration respectively. Furthermore, antagonist 71 was found to be a potent inhibitor of SP-induced bronchoconstriction in guinea-pigs with an ED50 between 0.1 and 0.03 mg/kg iv. Furthermore, upon oral administration, 71 was observed to be active in a model of SP-induced bronchial hypersensitivity in mice, with an ID50 of around 3 mg/kg.