1-Methoxy-5-nitroisoquinoline | 72678-03-6

• 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: 1-Methoxy-5-nitroisoquinoline
• CAS: 72678-03-6
• 化学式: C₁₀H₈N₂O₃
• 分子量: 204.185
• InChiKey: CAXSRYRPMLQNHD-UHFFFAOYSA-N

物化性质

• 沸点：
  352.8±27.0 °C(Predicted)
• 密度：
  1.337±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-Methoxy-5-nitroisoquinoline 在 palladium on activated charcoal 、 copper(l) iodide 、 铜 N-乙基吗啉 、 sodium hydroxide 、 sodium tetrahydroborate 、 氢气 、 三乙胺 作用下， 以 甲醇 、 异丙醇 为溶剂， 反应 4.0h， 生成 4-methoxypyrido[4,3-a]phenazine-11-carboxylic acid
  参考文献：
  名称：

  Structure−Activity Relationships for Pyrido-, Imidazo-, Pyrazolo-, Pyrazino-, and Pyrrolophenazinecarboxamides as Topoisomerase-Targeted Anticancer Agents

  摘要：

  Heterocyclic phenazinecarboxamides were prepared by condensation of aminoheterocycles and 2-halo-3-nitrobenzoic acids, followed by reductive ring closure and amidation. They showed similar inhibition of paired cell lines that underexpressed topo II or overexpressed P-glycoprotein, indicating a non topo II mechanism of cytotoxicity and indifference to P-glycoprotein mediated multidrug resistance. Compounds with a fused five-membered heterocyclic ring were generally less potent than the pyrido[4,3-alpha]phenazines. A 4-methoxypyrido[4,3-alpha]phenazine (IC(50)s 2.5-26 nM) gave modest (ca. 5 day) growth delays in H69/P xenografts with oral dosing.

  DOI：

  10.1021/jm010330+
• 作为产物：
  描述：

  1-氯异喹啉 在 硫酸 、 硝酸 、 potassium nitrate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 1-Methoxy-5-nitroisoquinoline
  参考文献：
  名称：

  Structure−Activity Relationships for Pyrido-, Imidazo-, Pyrazolo-, Pyrazino-, and Pyrrolophenazinecarboxamides as Topoisomerase-Targeted Anticancer Agents

  摘要：

  Heterocyclic phenazinecarboxamides were prepared by condensation of aminoheterocycles and 2-halo-3-nitrobenzoic acids, followed by reductive ring closure and amidation. They showed similar inhibition of paired cell lines that underexpressed topo II or overexpressed P-glycoprotein, indicating a non topo II mechanism of cytotoxicity and indifference to P-glycoprotein mediated multidrug resistance. Compounds with a fused five-membered heterocyclic ring were generally less potent than the pyrido[4,3-alpha]phenazines. A 4-methoxypyrido[4,3-alpha]phenazine (IC(50)s 2.5-26 nM) gave modest (ca. 5 day) growth delays in H69/P xenografts with oral dosing.

  DOI：

  10.1021/jm010330+

文献信息

• Substituted dihydroisoquinolinones and related compounds as potentiators
  申请人：Warner-Lambert Company

  公开号：US05177075A1

  公开（公告）日：1993-01-05

  The invention is selected, novel, and known analogs of isoquinolinones of the formula ##STR1## and pharmaceutically acceptable salts thereof; novel pharmaceutical compositions; and a method for enhancing the lethal effects for tumor cells to treatment having DNA damaging activity such as ionizing radiation or with chemotherapeutic agents.

  这项发明涉及选择的、新颖的、以及已知的异喹啉酮类化合物及其药学上可接受的盐；新颖的药物组合物；以及一种增强对肿瘤细胞的致命效应的方法，该方法包括对具有DNA损伤活性的治疗方法进行增强，例如电离辐射或化疗药物。
• Wozniak, Marian; Baranski, Andrzej; Nowak, Krystyna, Liebigs Annalen der Chemie, 1990, # 7, p. 653 - 657
  作者：Wozniak, Marian、Baranski, Andrzej、Nowak, Krystyna、Poradowska, Henryka

  DOI：——

  日期：——
• WOZNIAK, MARIAN;BARANSKI, ANDRZEJ;NOWAK, KRYSTYNA;PORADOWSKA, HENRYKA, LIEBIGS ANN. CHEM.,(1990) N, C. 653-657
  作者：WOZNIAK, MARIAN、BARANSKI, ANDRZEJ、NOWAK, KRYSTYNA、PORADOWSKA, HENRYKA

  DOI：——

  日期：——
• Substituted dihydroisoquinolinones and related compounds as potentiators of the lethal effects of radiation and certain chemotherapeutic agents; selected compounds, analogs and process
  申请人：WARNER-LAMBERT COMPANY

  公开号：EP0355750B1

  公开（公告）日：1995-01-25
• US5177075A
  申请人：——

  公开号：US5177075A

  公开（公告）日：1993-01-05