6-ethyl-7-methoxy-5-methylimidazo<1,2-a>pyrimidine-2-thiocarboxamide | 118506-76-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并[1，2-a]嘧啶
• 英文名称: 6-ethyl-7-methoxy-5-methylimidazo<1,2-a>pyrimidine-2-thiocarboxamide
• 英文别名: 6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidine-2-thiocarboxamide；6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidine-2-carbothioamide
• CAS: 118506-76-6
• 化学式: C₁₁H₁₄N₄OS
• 分子量: 250.324
• InChiKey: QLKMUXCKDQFCQT-UHFFFAOYSA-N

物化性质

• 熔点：
  248-259 °C
• 密度：
  1.37±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  97.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-溴-1,1,1-三氟丙酮 、 6-ethyl-7-methoxy-5-methylimidazo<1,2-a>pyrimidine-2-thiocarboxamide 在 三乙胺 、 三氟乙酸酐 作用下， 生成 2-(4-Trifluoromethyl-2-thiazolyl)-6-ethyl-7-methoxy-5-methylimidazo[1,2-a]pyrimidine
  参考文献：
  名称：

  2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-a]pyrimidines as agonists and inverse agonists at benzodiazepine receptors

  摘要：

  Oxadiazoles, like the benzoyl group in a series of imidazo[1,2-alpha]pyrimidines, have been found to be metabolically stable alternatives to ester groups in benzodiazepine-receptor ligands. This change has lead to a number of compounds which bind to the receptors and which exhibit potent agonist activity in a food-motivated conflict test thought to predict anxiolytic properties. Compounds 4, 5, and 13 were equipotent with chlordiazepoxide but showed little or no myorelaxant effects. Replacing the oxadiazole group by thiazole gave compounds such as 23 which binds to the benzodiazepine receptor but exhibits the intrinsic activity of a partial inverse agonist in vivo.

  DOI：

  10.1021/jm00111a021
• 作为产物：
  描述：

  5-ethyl-4-methoxy-6-methyl-2-pyrimidinamine 在 劳森试剂 、 氨 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 34.0h， 生成 6-ethyl-7-methoxy-5-methylimidazo<1,2-a>pyrimidine-2-thiocarboxamide
  参考文献：
  名称：

  2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-a]pyrimidines as agonists and inverse agonists at benzodiazepine receptors

  摘要：

  Oxadiazoles, like the benzoyl group in a series of imidazo[1,2-alpha]pyrimidines, have been found to be metabolically stable alternatives to ester groups in benzodiazepine-receptor ligands. This change has lead to a number of compounds which bind to the receptors and which exhibit potent agonist activity in a food-motivated conflict test thought to predict anxiolytic properties. Compounds 4, 5, and 13 were equipotent with chlordiazepoxide but showed little or no myorelaxant effects. Replacing the oxadiazole group by thiazole gave compounds such as 23 which binds to the benzodiazepine receptor but exhibits the intrinsic activity of a partial inverse agonist in vivo.

  DOI：

  10.1021/jm00111a021

文献信息

• 2-thiazolyl-imidazo[1,2,-a]pyrimidines
  申请人：Roussel Uclaf

  公开号：US04925846A1

  公开（公告）日：1990-05-15

  A compound selected from the group consisting of a compound of the formula ##STR1## wherein R.sub.1 is thiazol-2-yl optionally substituted by 1 or 2 alkyl of 1 to 3 carbon atoms optionally substituted by one or more fluorine or --COOAlk, Alk is alkyl of 1 to 3 carbon atoms, R.sub.2 and R.sub.3 are individually selected from the group consisting of hydrogen, alkyl of 1 to 3 carbon atoms and alkenyl of 2 to 5 carbon atoms or R.sub.2 and R.sub.3 together form alkylene of 3 to 5 carbon atoms, X is oxygen or sulfur and R.sub.4 is alkyl of 1 to 3 carbon atoms and their non-toxic, pharmaceutically acceptable acid addition salts having minor tranquillizing activity and useful for the treatment of obesity and cognitive impairment.

  从以下化合物中选取一种化合物：其中R.sub.1为噻唑-2-基，可选择地被1或2个1至3个碳原子的烷基取代，或者选择地被一个或多个氟或--COOAlk取代，Alk为1至3个碳原子的烷基，R.sub.2和R.sub.3分别选自氢、1至3个碳原子的烷基和2至5个碳原子的烯基，或者R.sub.2和R.sub.3一起形成3至5个碳原子的烷基，X为氧或硫，R.sub.4为1至3个碳原子的烷基及其无毒、药学上可接受的酸盐，具有轻微镇静作用，适用于肥胖和认知障碍的治疗。
• DEACON, ROBERT MICHAEL JOHN;GARDNER, COLIN ROBERT;GILLESPIE, ROGER JOHN;T+
  作者：DEACON, ROBERT MICHAEL JOHN、GARDNER, COLIN ROBERT、GILLESPIE, ROGER JOHN、T+

  DOI：——

  日期：——
• TULLY, W. ROGER;GARDNER, COLIN R.;GILLESPIE, ROGER J.;WESTWOOD, ROBERT, J. MED. CHEM., 34,(1991) N, C. 2060-2067
  作者：TULLY, W. ROGER、GARDNER, COLIN R.、GILLESPIE, ROGER J.、WESTWOOD, ROBERT

  DOI：——

  日期：——
• US4925846A
  申请人：——

  公开号：US4925846A

  公开（公告）日：1990-05-15
• 2-(Oxadiazolyl)- and 2-(thiazolyl)imidazo[1,2-a]pyrimidines as agonists and inverse agonists at benzodiazepine receptors
  作者：W. Roger Tully、Colin R. Gardner、Roger J. Gillespie、Robert Westwood

  DOI：10.1021/jm00111a021

  日期：1991.7

  Oxadiazoles, like the benzoyl group in a series of imidazo[1,2-alpha]pyrimidines, have been found to be metabolically stable alternatives to ester groups in benzodiazepine-receptor ligands. This change has lead to a number of compounds which bind to the receptors and which exhibit potent agonist activity in a food-motivated conflict test thought to predict anxiolytic properties. Compounds 4, 5, and 13 were equipotent with chlordiazepoxide but showed little or no myorelaxant effects. Replacing the oxadiazole group by thiazole gave compounds such as 23 which binds to the benzodiazepine receptor but exhibits the intrinsic activity of a partial inverse agonist in vivo.