2-(4-((5-(4-chlorophenoxy)-6-methoxy-4-methylquinolin-8-yl)amino)pentyl)isoindoline-1,3-dione | 158430-91-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(4-((5-(4-chlorophenoxy)-6-methoxy-4-methylquinolin-8-yl)amino)pentyl)isoindoline-1,3-dione
• CAS: 158430-91-2
• 化学式: C₃₀H₂₈ClN₃O₄
• 分子量: 530.023
• InChiKey: HITKNRHROYGZPV-UHFFFAOYSA-N

物化性质

• 沸点：
  701.2±60.0 °C(predicted)
• 密度：
  1.311±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.87
• 重原子数：
  38.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  80.76
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-(4-((5-(4-chlorophenoxy)-6-methoxy-4-methylquinolin-8-yl)amino)pentyl)isoindoline-1,3-dione 在 一水合肼 作用下， 以 乙醇 为溶剂， 生成 N4-(5-(4-chlorophenoxy)-6-methoxy-4-methylquinolin-8-yl)pentane-1,4-diamine succinate
  参考文献：
  名称：

  Inhibition of human monoamine oxidase A and B by 5-phenoxy 8-aminoquinoline analogs

  摘要：

  8-Aminoquinolines (8-AQs) are important class of anti-infective therapeutics. 5-Phenoxy 8-aminoquinoline analogs have shown improved metabolic stability compared to primaquine. In view or predictive role of monoamine oxidases (MAO) in metabolism of 8-aminoquinolines the 5-phenoxy analogs were evaluated in vitro for the inhibition of recombinant human MAO-A and MAO-B. The analogs were several folds more potent inhibitors of MAO-A and MAO-B compared to primaquine, the parent drug, with selectivity for MAO-B. 5-(4-Trifluoromethylphenoxy)-4-methylprimaquine (6) Inhibited MAO-B with IC50 value of 150 nM (626-fold more potent than primaquine). These results will have important implications in optimizing metabolic stability of 8-AQs to improve therapeutic value and also indicate scope for development of 8-AQs as selective MAO inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.108
• 作为产物：
  描述：

  5-(4-chlorophenoxy)-4-methoxy-2-nitroaniline hydrochloride 在 sodium tetrahydroborate 、 磷酸 、 palladium on activated charcoal 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 生成 2-(4-((5-(4-chlorophenoxy)-6-methoxy-4-methylquinolin-8-yl)amino)pentyl)isoindoline-1,3-dione
  参考文献：
  名称：

  Inhibition of human monoamine oxidase A and B by 5-phenoxy 8-aminoquinoline analogs

  摘要：

  8-Aminoquinolines (8-AQs) are important class of anti-infective therapeutics. 5-Phenoxy 8-aminoquinoline analogs have shown improved metabolic stability compared to primaquine. In view or predictive role of monoamine oxidases (MAO) in metabolism of 8-aminoquinolines the 5-phenoxy analogs were evaluated in vitro for the inhibition of recombinant human MAO-A and MAO-B. The analogs were several folds more potent inhibitors of MAO-A and MAO-B compared to primaquine, the parent drug, with selectivity for MAO-B. 5-(4-Trifluoromethylphenoxy)-4-methylprimaquine (6) Inhibited MAO-B with IC50 value of 150 nM (626-fold more potent than primaquine). These results will have important implications in optimizing metabolic stability of 8-AQs to improve therapeutic value and also indicate scope for development of 8-AQs as selective MAO inhibitors. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.108