3-Hydroxy-7,8-dimethoxy-1-methyl-4-nitroisoquinoline | 113983-47-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 3-Hydroxy-7,8-dimethoxy-1-methyl-4-nitroisoquinoline
• 英文别名: 7,8-dimethoxy-1-methyl-4-nitro-2H-isoquinolin-3-one
• CAS: 113983-47-4
• 化学式: C₁₂H₁₂N₂O₅
• 分子量: 264.238
• InChiKey: GPHQPBRRDKOYFW-UHFFFAOYSA-N

物化性质

• 熔点：
  214-216 °C
• 沸点：
  560.4±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  93.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-7,8-dimethoxy-1-methyl-4-nitroisoquinoline 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 生成 4-Amino-7,8-dimethoxy-3-hydroxy-1-methylisoquinoline
  参考文献：
  名称：

  肾血管扩张药。4-取代基在异喹啉-3-醇心血管药物中的作用：异喹啉-3-醇的4-脲基衍生物具有选择性的肾血管舒张特性。

  摘要：

  描述了一系列在C-4带有多个氮取代基（氨基，酰基氨基，氨基甲酸酯和脲基）的异喹啉-3-醇衍生物的合成及心血管系统评价。这些化合物中的某些具有选择性的肾血管舒张特性，并且在用仪器麻醉的狗中静脉内给药时对动脉血压或心率的影响最小。该系列中最有效的肾血管舒张药是4-（烯丙基铝）-6,7-二甲氧基异喹啉-3-醇（38），以1.2 mg / kg的剂量静脉注射可使肾血流量最大增加97％，而无明显变化降压或变时作用。讨论了有关异喹啉醇核芳香环中4-取代基的性质和烷氧基取代模式的结构活性观察结果。

  DOI：

  10.1021/jm00125a011
• 作为产物：
  描述：

  3,4-二甲氧基苯乙腈 在 高氯酸 、 硝酸 作用下， 以 溶剂黄146 为溶剂， 反应 42.33h， 生成 3-Hydroxy-7,8-dimethoxy-1-methyl-4-nitroisoquinoline
  参考文献：
  名称：

  Isoquinolinol derivatives: potent, short-acting inotropic and vasodilating agents with potential utility for cardiac emergencies

  摘要：

  The synthesis and cardiovascular evaluation of a series of 4-nitroisoquinolin-3-ol derivatives are reported. These compounds are potent, short-acting cardiovascular agents with both positive inotropic and peripheral vasodilating effects when administered intravenously. Compounds with this profile could be of particular therapeutic benefit in cardiac emergencies such as severe late stage heart failure and myocardial infarction. Of particular interest is 7-ethoxy-6-methoxy-1-methyl-4-nitroisoquinolin-3-ol (6) which has potent, non beta-adrenergic parenteral inotropic properties similar to those of dopamine, and also has peripheral vasodilator activity, up to 10-fold greater than amrinone.

  DOI：

  10.1016/0223-5234(91)90023-g

文献信息

• KANOJIA, RAMESH M.;LEVER, O. WILLIAM;PRESS, JEFFERY B.;WILLIAMS, LOUELLA;+, J. MED. CHEM., 32,(1989) N, C. 990-997
  作者：KANOJIA, RAMESH M.、LEVER, O. WILLIAM、PRESS, JEFFERY B.、WILLIAMS, LOUELLA、+

  DOI：——

  日期：——
• Renal vasodilators. The role of the 4-substituent in isoquinolin-3-ol cardiovascular agents. 4-Ureido derivatives of isoquinolin-3-ol with selective renal vasodilator properties
  作者：Ramesh M. Kanojia、O. William Lever、Jeffery B. Press、Louella Williams、Harvey M. Werblood、Edward C. Giardino、Robert Falotico、Alfonso J. Tobia

  DOI：10.1021/jm00125a011

  日期：1989.5

  The synthesis and cardiovascular evaluation of a series of isoquinolin-3-ol derivatives bearing a variety of nitrogen substituents (amino, acylamino, carbamate, and ureido) at C-4 are described. Certain of these compounds have a selective renal vasodilating profile and have minimal effects on arterial blood pressure or heart rate when administered intravenously in the instrumented anesthetized dog

  描述了一系列在C-4带有多个氮取代基（氨基，酰基氨基，氨基甲酸酯和脲基）的异喹啉-3-醇衍生物的合成及心血管系统评价。这些化合物中的某些具有选择性的肾血管舒张特性，并且在用仪器麻醉的狗中静脉内给药时对动脉血压或心率的影响最小。该系列中最有效的肾血管舒张药是4-（烯丙基铝）-6,7-二甲氧基异喹啉-3-醇（38），以1.2 mg / kg的剂量静脉注射可使肾血流量最大增加97％，而无明显变化降压或变时作用。讨论了有关异喹啉醇核芳香环中4-取代基的性质和烷氧基取代模式的结构活性观察结果。
• Isoquinolinol derivatives: potent, short-acting inotropic and vasodilating agents with potential utility for cardiac emergencies
  作者：RM Kanojia、JB Press、OW Lever、L Williams、HM Werblood、R Falotico、JM Moore、AJ Tobia

  DOI：10.1016/0223-5234(91)90023-g

  日期：1991.3

  The synthesis and cardiovascular evaluation of a series of 4-nitroisoquinolin-3-ol derivatives are reported. These compounds are potent, short-acting cardiovascular agents with both positive inotropic and peripheral vasodilating effects when administered intravenously. Compounds with this profile could be of particular therapeutic benefit in cardiac emergencies such as severe late stage heart failure and myocardial infarction. Of particular interest is 7-ethoxy-6-methoxy-1-methyl-4-nitroisoquinolin-3-ol (6) which has potent, non beta-adrenergic parenteral inotropic properties similar to those of dopamine, and also has peripheral vasodilator activity, up to 10-fold greater than amrinone.