N⁴-(4-Ethyl-5-heptyloxy-6-methoxy-quinolin-8-yl)-pentane-1,4-diamine | 672912-27-5

• 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: N⁴-(4-Ethyl-5-heptyloxy-6-methoxy-quinolin-8-yl)-pentane-1,4-diamine
• 英文别名: 4-N-(4-ethyl-5-heptoxy-6-methoxyquinolin-8-yl)pentane-1,4-diamine
• CAS: 672912-27-5
• 化学式: C₂₄H₃₉N₃O₂
• 分子量: 401.593
• InChiKey: QLZOSIAMKYXZHL-UHFFFAOYSA-N

物化性质

• 沸点：
  561.1±50.0 °C(Predicted)
• 密度：
  1.039±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  29.0
• 可旋转键数：
  14.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  69.4
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N⁴-(4-Ethyl-5-heptyloxy-6-methoxy-quinolin-8-yl)-pentane-1,4-diamine 在 palladium on activated charcoal 氢气 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 (2S)-N¹-[4-(4-ethyl-5-heptyloxy-6-methoxy-8-quinolylamino)pentyl]-2,5-diaminopentanamide trihydrochloride
  参考文献：
  名称：

  8-Quinolinamines conjugated with amino acids are exhibiting potent blood-schizontocidal antimalarial activities

  摘要：

  Alanine, lysine, ornithine and valine conjugated to primaquine and other 8-quinolinamine antinialarials were prepared for blood-schizontocidal antimalarial activity evaluation. The analogues were examined in vivo against Plasmodium berghei (drug-sensitive strain) and Plasinodium yoelii nigeriensis (highly virulent multi-drug-resistant strain) infected mice models. N-1-[4-(5Butoxy-4-ethyl-6-methoxy-8-quinolylamino)pentyl]-(2S)-2,6-diaminohexanamide (20) which showed curative activity at 5 mg/kg in the P. berghei test emerged as the most effective compound. N-1-[4-(4-Ethyl-5-hexoxy-6-methoxy-8-quinolylamino)pentyl]-(2S)-2,6-diaminohexanamide (22) exhibited curative activity at 50 mg/kg against P. yoelii nigeriensis in mice and emerged as the most potent analogue against multi-drug resistant strain. The results of this study represent development of highly potent 8-quinolinamines for antimalarial drug development. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.10.028
• 作为产物：
  描述：

  4-Ethyl-5-heptoxy-6-methoxy-8-nitroquinoline 在 Raney nickel (T₁ grade) 氢气 、 一水合肼 、 三乙胺 作用下， 以 乙醇 为溶剂， 120.0 ℃ 、310.26 kPa 条件下， 反应 32.75h， 生成 N⁴-(4-Ethyl-5-heptyloxy-6-methoxy-quinolin-8-yl)-pentane-1,4-diamine
  参考文献：
  名称：

  8-Quinolinamines and Their pro prodrug conjugates as potent blood-Schizontocidal antimalarial agents

  摘要：

  Synthesis and antimalarial activities of N-8-(4-amino-1-methylbutyl)-5-alkoxy-4-ethyl-6-methoxy-8-quinolinamines (5) and their pro prodrug analogues (6-7) prepared by covalently linking 5 to the redox-sensitive (8) and esterase-sensitive (9) linkers through the amide linkage are reported. The most effective 8-quinolinamines [5c (R = C5H11) and 5f (R = C8H17)] A have exhibited in vitro and in vivo biological efficacy superior to that of the standard drug chloroquine against both drug-sensitive and drug-resistant malaria strains. Analogues 6-7 were evaluated for in vivo blood-schizontocidal activity as potential pro prodrug models for the primary amino group containing 8-quinolinamines (5). The most effective pro prodrug analogue (6c) has displayed promising activities against drug-sensitive and drug-resistant strains of Plasmodia in vivo. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.07.003