(7-Ethyl-5-methoxy-4-methyl-imidazo[1,2-a]quinolin-2-yl)-phenyl-methanone | 92412-78-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (7-Ethyl-5-methoxy-4-methyl-imidazo[1,2-a]quinolin-2-yl)-phenyl-methanone
• 英文别名: (7-Ethyl-5-methoxy-4-methylimidazo[1,2-a]quinolin-2-yl)-phenylmethanone
• CAS: 92412-78-7
• 化学式: C₂₂H₂₀N₂O₂
• 分子量: 344.413
• InChiKey: ILXNCHCEFFAJEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-bromo-1-phenylpropane-1,2-dione 、 2-amino-6-ethyl-4-methoxy-3-methylquinoline 生成 (7-Ethyl-5-methoxy-4-methyl-imidazo[1,2-a]quinolin-2-yl)-phenyl-methanone
  参考文献：
  名称：

  (Imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones and related compounds as potential nonsedative anxiolytics

  摘要：

  Several series of heterocyclic carboxylic esters were found to be active in the benzodiazepine receptor binding assay, a typical example being ethyl 7-ethyl-5-methoxyimidazo[1,2-a]quinoline-2-carboxylate (4b) with an IC50 of 150 nM. The corresponding phenylmethanone 5d was more potent with an IC50 of 14 nM and was orally active in animal models thought to predict anxiolytic effects. The synthesis of a large number of compounds resulted in the optimization of this activity in a series of (imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones of which compounds 7e, 8b, 8h, 8j, and 8k were equipotent with chlordiazepoxide while exhibiting reduced anticonvulsant activity, little or no muscle relaxation, and negligible sedative effects.

  DOI：

  10.1021/jm00401a025

文献信息

• Nouvelles imidazo/1,2-a/ quinoléines et leurs sels, leur préparation, leur application à titre de médicaments et les compositions les renfermant
  申请人：ROUSSEL-UCLAF

  公开号：EP0107988A2

  公开（公告）日：1984-05-09

  L'invention concerne des imidazo/1,2-a/quinoléines et leurs sels, de formule: où R, est hydrogène, chlore ou brome, R2 est benzoyle, R3 est hydrogène ou alcoyle, R4 est alcoxy, hydroxy, acyloxy ou alcoyle, R5 est alcoyle, R6 est alcoyle, R7 est alcoyle, R8 est hydrogène ou alcoyle et est phényle, R1 et R3 ne pouvant être hydrogène lorsque R2 est benzoyle et R4 alcoxy; leur préparation, leur application comme médicaments, notamment anxiolytiques et les compositions les renfermant.

  本发明涉及式中的咪唑/1,2-a/喹啉及其盐类： 其中 R 是氢、氯或溴，R2 是苯甲酰基、 R3是氢或烷基，R4是烷氧基、羟基、酰氧基或烷基，R5是烷基，R6是烷基，R7是烷基，R8是氢或烷基和苯基，当R2是苯甲酰基和R4是烷氧基时，R1和R3不可能是氢。
• CLEMENTS-JEWERY, STEPHEN;DANSWAN, GEOFFREY;GARDNER, COLIN R.;MATHARU, SAR+, J. MED. CHEM., 31,(1988) N 6, 1220-1226
  作者：CLEMENTS-JEWERY, STEPHEN、DANSWAN, GEOFFREY、GARDNER, COLIN R.、MATHARU, SAR+

  DOI：——

  日期：——
• (Imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones and related compounds as potential nonsedative anxiolytics
  作者：Stephen Clements-Jewery、Geoffrey Danswan、Colin R. Gardner、Saroop S. Matharu、Robert Murdoch、W. Roger Tully、Robert Westwood

  DOI：10.1021/jm00401a025

  日期：1988.6

  Several series of heterocyclic carboxylic esters were found to be active in the benzodiazepine receptor binding assay, a typical example being ethyl 7-ethyl-5-methoxyimidazo[1,2-a]quinoline-2-carboxylate (4b) with an IC50 of 150 nM. The corresponding phenylmethanone 5d was more potent with an IC50 of 14 nM and was orally active in animal models thought to predict anxiolytic effects. The synthesis of a large number of compounds resulted in the optimization of this activity in a series of (imidazo[1,2-a]pyrimidin-2-yl)phenylmethanones of which compounds 7e, 8b, 8h, 8j, and 8k were equipotent with chlordiazepoxide while exhibiting reduced anticonvulsant activity, little or no muscle relaxation, and negligible sedative effects.