4-Ethyl-5-hexoxy-6-methoxy-8-nitroquinoline | 663953-19-3

• 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: 4-Ethyl-5-hexoxy-6-methoxy-8-nitroquinoline
• CAS: 663953-19-3
• 化学式: C₁₈H₂₄N₂O₄
• 分子量: 332.4
• InChiKey: WFMAFRMWEFSDLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  77.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-Ethyl-5-hexoxy-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 4-N-(4-ethyl-5-hexoxy-6-methoxyquinolin-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
• 作为产物：
  描述：

  1-氯-3-戊酮 、 3-hexyloxy-4-methoxy-6-nitroaniline 在 arsenic(V) oxide 、 磷酸 作用下， 反应 3.0h， 以75%的产率得到4-Ethyl-5-hexoxy-6-methoxy-8-nitroquinoline
  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

文献信息

• 8-Quinolinamines and Their pro prodrug conjugates as potent blood-Schizontocidal antimalarial agents
  作者：Suryanarayana Vangapandu、Sandeep Sachdeva、Meenakshi Jain、Savita Singh、Prati Pal Singh、Chaman Lal Kaul、Rahul Jain

  DOI：10.1016/j.bmc.2003.07.003

  日期：2003.10

  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.