1-(3-hydroxypropyl)-3-[4-(6-methoxyquinolin-8-ylamino)pentyl]urea | 1185934-32-0

• 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: 1-(3-hydroxypropyl)-3-[4-(6-methoxyquinolin-8-ylamino)pentyl]urea
• 英文别名: 1-(3-Hydroxypropyl)-3-[4-[(6-methoxyquinolin-8-yl)amino]pentyl]urea
• CAS: 1185934-32-0
• 化学式: C₁₉H₂₈N₄O₃
• 分子量: 360.456
• InChiKey: REBRTQHYDOCHTF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  95.5
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (N-(4-((6-methoxyquinolin-8-yl)amino)pentyl)-1H-benzo[d][1,2,3]triazole-1-carboxamide) 、 3-氨基-1-丙醇 在 三乙胺 作用下， 以 乙醇 为溶剂， 反应 96.0h， 以70%的产率得到1-(3-hydroxypropyl)-3-[4-(6-methoxyquinolin-8-ylamino)pentyl]urea
  参考文献：
  名称：

  Urea and carbamate derivatives of primaquine: Synthesis, cytostatic and antioxidant activities

  摘要：

  The novel urea primaquine derivatives 3 were prepared by aminolysis of primaquine benzotriazolide 2 with several hydroxyamines and ethylendiamine, while carbamates 4 were synthesized from the same precursor 2 and alcohols. All compounds are fully chemically characterized and evaluated for their cytostatic and antioxidant activities. The most prominent antiproliferative activity was obtained by compounds 3c, 3d, 3g, and 5b (IC50 = 9-40 mu M). 1-(5-Hydroxypentyl)-3-[4-(6-methoxy-quinolin-8-ylamino)-pentyl]urea (3c) showed extreme selectivity toward SW 620 colon cancer cells (IC50 = 0.2 mu M) and a bit less toward lung cancer cells H 460. Hydroxyurea 3h showed the highest interaction with DPPH. Primaquine twin drug 3g showed very significant inhibition on LOX soybean (IC50 = 62 mu M). Almost all the tested derivatives highly inhibited lipid peroxidation, significantly stronger than primaquine phosphate. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.030

文献信息

• Urea and carbamate derivatives of primaquine: Synthesis, cytostatic and antioxidant activities
  作者：M. Šimunović、I. Perković、B. Zorc、K. Ester、M. Kralj、D. Hadjipavlou-Litina、E. Pontiki

  DOI：10.1016/j.bmc.2009.06.030

  日期：2009.8

  The novel urea primaquine derivatives 3 were prepared by aminolysis of primaquine benzotriazolide 2 with several hydroxyamines and ethylendiamine, while carbamates 4 were synthesized from the same precursor 2 and alcohols. All compounds are fully chemically characterized and evaluated for their cytostatic and antioxidant activities. The most prominent antiproliferative activity was obtained by compounds 3c, 3d, 3g, and 5b (IC50 = 9-40 mu M). 1-(5-Hydroxypentyl)-3-[4-(6-methoxy-quinolin-8-ylamino)-pentyl]urea (3c) showed extreme selectivity toward SW 620 colon cancer cells (IC50 = 0.2 mu M) and a bit less toward lung cancer cells H 460. Hydroxyurea 3h showed the highest interaction with DPPH. Primaquine twin drug 3g showed very significant inhibition on LOX soybean (IC50 = 62 mu M). Almost all the tested derivatives highly inhibited lipid peroxidation, significantly stronger than primaquine phosphate. (C) 2009 Elsevier Ltd. All rights reserved.