N-acetyl-primaquine | 77229-67-5

• 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: N-acetyl-primaquine
• 英文别名: N-acetylprimaquine；N-acetylprimaquin；N-[4-[(6-methoxyquinolin-8-yl)amino]pentyl]acetamide
• CAS: 77229-67-5
• 化学式: C₁₇H₂₃N₃O₂
• 分子量: 301.389
• InChiKey: YVURERLGLAYCCQ-UHFFFAOYSA-N

物化性质

• 沸点：
  560.2±50.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  63.2
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 储存条件：
  室温

反应信息

• 作为反应物：
  描述：

  氯仿 、 N-acetyl-primaquine 反应 5.5h， 生成 N-(4-{5-[8-[(Z)-4-Acetylamino-1-methyl-butylimino]-6-methoxy-8H-quinolin-(5E)-ylidenemethyl]-6-methoxy-quinolin-8-ylamino}-pentyl)-acetamide; hydrochloride
  参考文献：
  名称：

  Gessner, Wieslaw P.; Venugopalan Bindumadhavan; Brossi, Arnold, Canadian Journal of Chemistry, 1986, vol. 64, p. 2196 - 2198

  摘要：

  DOI：
• 作为产物：
  描述：

  磷酸伯氨喹 、 乙酸酐 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到N-acetyl-primaquine
  参考文献：
  名称：

  Anti-tumoral activity of imidazoquines, a new class of antimalarials derived from primaquine

  摘要：

  The growth inhibitory activity of imidazoquines, antimalarial imidazolidin-4-ones derived from primaquine, on human cancer cell lines HT-29, Caco-2, and MCF-7 has been evaluated. Primaquine, N-dipeptidyl-primaquine derivatives, and other quinolines have been included in the study for comparison purposes. Primaquine and some of its derivatives were significantly active against the MCF-7 human breast cancer cell line, so these compounds might represent useful leads targeted at the development of novel specific agents against breast cancer. Conversely, all compounds were generally inactive against HT-29, with only one of the imidazoquines having IC50 below 50 mu M. Activities against the Caco-2 cell line were modest and did not follow any defined trend. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.081