N-cyclopentylquinoxaline-2-carboxamide | 311346-87-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: N-cyclopentylquinoxaline-2-carboxamide
• CAS: 311346-87-9
• 化学式: C₁₄H₁₅N₃O
• mdl: MFCD05029681
• 分子量: 241.293
• InChiKey: WZLJUOKACAQFQD-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：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.357
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-喹喔啉羧酸 、 环戊胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以63%的产率得到N-cyclopentylquinoxaline-2-carboxamide
  参考文献：
  名称：

  Design, synthesis and structure–activity relationship of novel quinoxalin-2-carboxamides as 5-HT3 receptor antagonists for the management of depression

  摘要：

  A novel series of quinoxalin-2-carboxamides were designed based on the ligand-based approach, employing a three-point pharmacophore model; it consists of an aromatic residue and a linking carbonyl group and a basic nitrogen. The target new chemical entities were synthesized from the key intermediate, quinoxalin-2-carboxylic acid, by coupling it with various amines in the presence of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC center dot HCl) and 1-hydroxybenzotriazole (HOBt). The obtained compounds' structures were confirmed by spectral data. The target new chemical entities were evaluated for their 5-HT3 receptor antagonisms in longitudinal muscle myenteric plexus preparation from guinea pig ileum against 5-HT3 agonist, 2-methyl-5-HT, which was expressed in the form of pA(2) value. All the synthesized compounds showed antagonism towards 5-HT3 receptor; based on this result, a structure-activity relationship was derived, which reveals that the aromatic residue in 5-HT3 receptor antagonists may have hydrophobic interaction with 5-HT3 receptor. Regardless of their antagonistic potentials, all the synthesized molecules were screened for their anti-depressant potentials by using forced swim test in mice model; interestingly none of the tested compounds affect the locomotion of mice in the tested dose levels. Compounds with significant pA(2) values exhibited good anti-depressant-like activity as compared to the vehicle-treated group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.128

文献信息

• Metabotropic glutamate receptor antagonists and their use for treating central nervous system diseases
  申请人：NPS PHARMACEUTICALS, INC.

  公开号：EP1595871A2

  公开（公告）日：2005-11-16

  The present invention provides compounds, and pharmaceutical compositions containing those compounds, that are active at metabotropic glutamate receptors. The compounds are useful for treating neurological diseases and disorders. Methods of preparing the compounds also are disclosed.

  本发明提供了在代谢型谷氨酸受体上具有活性的化合物和含有这些化合物的药物组合物。这些化合物可用于治疗神经系统疾病和失调。本发明还公开了制备这些化合物的方法。
• 代謝型グルタミン酸受容体アンタゴニストおよび中枢神経系の疾病を治療するためのその使用
  申请人：——

  公开号：JP2003500480A

  公开（公告）日：2003-01-07

  \n (57)【要約】\n本発明は、代謝型グルタミン酸受容体において活性である化合物、および該化合物を含む医薬組成物を提供する。これらの化合物は神経学的疾病および障害を治療するのに有効である。これらの化合物を製造する方法も開示する。\n \n

  \(57) [Abstract] The invention provides compounds that are active at metabolic glutamate receptors and pharmaceutical compositions containing the compounds.这些化合物可有效治疗神经系统疾病和失调。本发明还公开了生产这些化合物的方法。\n \n
• METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS AND THEIR USE FOR TREATING CENTRAL NERVOUS SYSTEM DISEASES
  申请人：NPS PHARMACEUTICALS, INC.

  公开号：EP1196397A1

  公开（公告）日：2002-04-17
• [EN] METABOTROPIC GLUTAMATE RECEPTOR ANTAGONISTS AND THEIR USE FOR TREATING CENTRAL NERVOUS SYSTEM DISEASES<br/>[FR] ANTAGONISTES DU RECEPTEUR DE GLUTAMATE METABOTROPIQUE ET LEUR UTILISATION POUR LE TRAITEMENT DE MALADIES DU SYSTEME NERVEUX CENTRAL
  申请人：NPS PHARMA INC

  公开号：WO2000073283A1

  公开（公告）日：2000-12-07

  The present invention provides compounds, and pharmaceutical compositions containing those compounds, that are active at metabotropic glutamate receptors. The compounds are useful for treating neurological diseases and disorders. Methods of preparing the compounds also are disclosed.