9,10-dimethoxy-2-phenoxy-6,7-dihydro-4H-pyrimido<6,1-a>isoquinolin-4-one | 91209-81-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 9,10-dimethoxy-2-phenoxy-6,7-dihydro-4H-pyrimido<6,1-a>isoquinolin-4-one
• 英文别名: 9,10-dimethoxy-2-phenoxy-6,7-dihydro-4H-pyrimido[6,1-a]isoquinolin-4-one；9,10-dimethoxy-2-phenoxy-6,7-dihydropyrimido[6,1-a]isoquinolin-4-one
• CAS: 91209-81-3
• 化学式: C₂₀H₁₈N₂O₄
• 分子量: 350.374
• InChiKey: OSXAHCXDVWLSKR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-carbamidomethylene-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 在 sodium ethanolate 、 sodium hydride 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 9,10-dimethoxy-2-phenoxy-6,7-dihydro-4H-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

• Derivatives of pyrimido[6,1-a]isoquinolin-4-one
  申请人：——

  公开号：US20030119813A1

  公开（公告）日：2003-06-26

  The invention provides compounds or salts thereof of the general formula (I): 1 wherein each of R 1 and R 2 independently represents a C 1-6 alkyl or C 2-7 acyl group; X represents OCH 2 or a group CR 3 R 4 ; wherein each of R 3 or R 4 independently represents a hydrogen atom or a C 1-3 alkyl group; R 5 represents a hydrogen atom or a C 1-3 alkyl, C 2-3 alkenyl or C 2-3 alkynyl group; R 6 represents a hydrogen atom or a C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, amino, C 1-6 alkylamino, di(C 1-6 ) alkylamino or C 2-7 acylamino group; each of R 7 and R 8 independently represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 2-7 acyl, C 1-6 alkylthio, C 1-6 alkoxy, C 3-6 cycloalkyl; and R 9 represents a hydrogen or halogen atom or a hydroxy, trifluoromethyl, C 1-6 alkyl, C 2-6 alkenyl, C 2-6 alkynyl, C 2-7 acyl, C 1-6 alkylthio, C 1-6 alkoxy or C 3-6 cycloalkyl group. The compounds or salts thereof are useful for treatment of respiratory disorders such as asthma. Compounds of the invention have a longer duration of action than the known compound trequinsin (9,10-dimethoxy-3 methyl-2-mesitylimino-2,3,6,7-tetrahydro-4H-pyrimido[6,1-a]isoquinolin-4-one).

  该发明提供了通式(I)的化合物或其盐： 其中R1和R2分别代表C1-6烷基或C2-7酰基基团；X代表OCH2或CR3R4基团；其中R3或R4分别代表氢原子或C1-3烷基基团；R5代表氢原子或C1-3烷基、C2-3烯基或C2-3炔基团；R6代表氢原子或C1-6烷基、C2-6烯基、C2-6炔基、氨基、C1-6烷基氨基、双(C1-6)烷基氨基或C2-7酰氨基团；R7和R8分别代表氢或卤原子或羟基、三氟甲基、C1-6烷基、C2-6烯基、C2-6炔基、C2-7酰基、C1-6烷基硫基、C1-6烷氧基、C3-6环烷基；R9代表氢或卤原子或羟基、三氟甲基、C1-6烷基、C2-6烯基、C2-6炔基、C2-7酰基、C1-6烷基硫基、C1-6烷氧基或C3-6环烷基。该化合物或其盐可用于治疗哮喘等呼吸系统疾病。该发明的化合物比已知的三氮杂环化合物trequinsin（9,10-二甲氧基-3-甲基-2-间甲苯基亚基-2,3,6,7-四氢-4H-嘧啶并［6,1-a］异喹啉-4-酮）具有更长的作用持续时间。
• LAL, BANSI;DOHADWALLA, ALIHUSSEIN, NOMANBHAI;DADKAR, NANDKUMAR, KESHAV;DS+, J. MED. CHEM., 1984, 27, N 11, 1470-1480
  作者：LAL, BANSI、DOHADWALLA, ALIHUSSEIN, NOMANBHAI、DADKAR, NANDKUMAR, KESHAV、DS+

  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.