4-甲基硫烷基-5,6,7,8-四氢-喹唑啉-2-基胺 | 28753-11-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 4-甲基硫烷基-5,6,7,8-四氢-喹唑啉-2-基胺
• 英文名称: 2-Amino-4-methylthio-5,6,7,8-tetrahydro-chinazolin
• 英文别名: 4-methylsulfanyl-5,6,7,8-tetrahydro-quinazolin-2-ylamine；4-Methylsulfanyl-5,6,7,8-tetrahydroquinazolin-2-amine
• CAS: 28753-11-9
• 化学式: C₉H₁₃N₃S
• 分子量: 195.288
• InChiKey: QOTLEYWCBLKNDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  77.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-bromo-1-phenylpropane-1,2-dione 、 4-甲基硫烷基-5,6,7,8-四氢-喹唑啉-2-基胺 生成 (5-Methylsulfanyl-6,7,8,9-tetrahydro-imidazo[1,2-a]quinazolin-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

• 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.