2-(2,6-Difluoro-phenylamino)-9,10-dimethoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one | 91210-08-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶并嘧啶类
• 英文名称: 2-(2,6-Difluoro-phenylamino)-9,10-dimethoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one
• 英文别名: 2-(2,6-Difluoroanilino)-9,10-dimethoxy-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one
• CAS: 91210-08-1
• 化学式: C₂₀H₁₇F₂N₃O₃
• 分子量: 385.37
• InChiKey: SDHGSIOZOAHNDO-UHFFFAOYSA-N

物化性质

• 沸点：
  523.3±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  63.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(2,6-Difluoro-phenylamino)-9,10-dimethoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 以33%的产率得到4-(2,6-Difluoroanilino)-6-(4,5-dimethoxy-2-vinylphenyl)-2(1H)-pyrimidinone
  参考文献：
  名称：

  A novel base-catalyzed carbon-nitrogen bond fission in some heterocycles

  摘要：

  DOI：

  10.1021/jo00304a025
• 作为产物：
  描述：

  1-carbamidomethylene-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 在 sodium ethanolate 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 2-(2,6-Difluoro-phenylamino)-9,10-dimethoxy-6,7-dihydro-pyrimido[6,1-a]isoquinolin-4-one
  参考文献：
  名称：

  Trequinsin, a potent new antihypertensive vasodilator in the series of 2-(arylimino)-3-alkyl-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido[6,1-a]isoquinolin-4-ones

  摘要：

  Series of 3-substituted-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido [6,1-a]isoquinoline-2,4-diones and 2-substituted-9,10-dimethoxy-6,7-dihydro-4H-pyrimido [6,1-a]isoquinolin-4-ones were synthesized and tested for blood pressure lowering properties in anesthetized normotensive cats and conscious spontaneously hypertensive rats. Several compounds in the 2-(arylamino)-9,10-dimethoxy-6,7-dihydro-4H-pyrimido [6,1-a]isoquinolin-4-one series display a high order of activity. The most active compounds are the alkyl derivatives of the 2-mesitylamino/2-mesitylimino tautomeric forms. The 2-(mesitylimino)-3-methyl analogue trequinsin is a potent antihypertensive agent and displays a hemodynamic profile characteristic of an arteriolar dilator. It is also a potent inhibitor of both cAMP phosphodiesterase and platelet aggregation.

  DOI：

  10.1021/jm00377a016

文献信息

• LAL, BANSI;GIDWANI, RAMESH M.;DE, SOUZA NOEL J., J. ORG. CHEM., 55,(1990) N7, C. 5117-5124
  作者：LAL, BANSI、GIDWANI, RAMESH M.、DE, SOUZA NOEL J.

  DOI：——

  日期：——
• Trequinsin, a potent new antihypertensive vasodilator in the series of 2-(arylimino)-3-alkyl-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido[6,1-a]isoquinolin-4-ones
  作者：Bansi Lal、Alihussein Nomanbhai Dohadwalla、Nandkumar Keshav Dadkar、Adolf D'Sa、Noel John De Souza

  DOI：10.1021/jm00377a016

  日期：1984.11

  Series of 3-substituted-9,10-dimethoxy-3,4,6,7-tetrahydro-2H-pyrimido [6,1-a]isoquinoline-2,4-diones and 2-substituted-9,10-dimethoxy-6,7-dihydro-4H-pyrimido [6,1-a]isoquinolin-4-ones were synthesized and tested for blood pressure lowering properties in anesthetized normotensive cats and conscious spontaneously hypertensive rats. Several compounds in the 2-(arylamino)-9,10-dimethoxy-6,7-dihydro-4H-pyrimido [6,1-a]isoquinolin-4-one series display a high order of activity. The most active compounds are the alkyl derivatives of the 2-mesitylamino/2-mesitylimino tautomeric forms. The 2-(mesitylimino)-3-methyl analogue trequinsin is a potent antihypertensive agent and displays a hemodynamic profile characteristic of an arteriolar dilator. It is also a potent inhibitor of both cAMP phosphodiesterase and platelet aggregation.
• A novel base-catalyzed carbon-nitrogen bond fission in some heterocycles
  作者：Bansi Lal、Ramesh M. Gidwani、Noel J. De Souza

  DOI：10.1021/jo00304a025

  日期：1990.8