N⁴-[2-tert-Butyl-4-ethyl-6-methoxy-5-(3-trifluoromethyl-phenoxy)-quinolin-8-yl]-pentane-1,4-diamine

• 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-[2-tert-Butyl-4-ethyl-6-methoxy-5-(3-trifluoromethyl-phenoxy)-quinolin-8-yl]-pentane-1,4-diamine
• 英文别名: N4-[2-tert-butyl-4-ethyl-6-methoxy-5-[3-(trifluoromethyl)phenoxy]-8-quinolyl]pentane-1,4-diamine；4-N-[2-tert-butyl-4-ethyl-6-methoxy-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]pentane-1,4-diamine
• 化学式: C₂₈H₃₆F₃N₃O₂
• 分子量: 503.608
• InChiKey: LQLJBWLYTPVWDK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  69.4
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  5,6-dimethoxy-4-ethyl-8-nitroquinoline 在 硫酸 、 镍 盐酸 、 氢氧化钾 、 ammonium persulfate 、 氢气 、 一水合肼 、 silver nitrate 、 三乙胺 、 三氯氧磷 、 三甲基乙酸 作用下， 70.0~150.0 ℃ 、310.26 kPa 条件下， 反应 49.0h， 生成 N⁴-[2-tert-Butyl-4-ethyl-6-methoxy-5-(3-trifluoromethyl-phenoxy)-quinolin-8-yl]-pentane-1,4-diamine
  参考文献：
  名称：

  Synthesis, antimalarial, antileishmanial, and antimicrobial activities of some 8-quinolinamine analogues

  摘要：

  In the present communication, newly synthesized 8-quinolinamines (25-27) related to previously reported 2-tert-butylprimaquine (2) were evaluated for their in vitro antimalarial activity against chloroquine sensitive and resistant Plasmodium falciparum strains, in vivo antimalarial activity against P. berghei infected mice, in vitro antileishmanial activity against Leishmania donovani, in vitro antimicrobial activity against various fungi and bacteria, and cytotoxicity in a panel of mammalian cell lines. No promising cytotoxicities were observed for compounds reported herein. Analogue 25 was found to exhibit curative antimalarial activity at a dose of 25 mg/kg/day x 4 in a P. berghei infected mice model, and produced suppressive activity at a lower dose of 10 mg/kg/ day x 4. In vitro antileishmanial activities (IC50 and IC90) comparable to standard drug pentamidine were exhibited by all synthesized 8-quinolinamines 25-27. At the same time, promising antibacterial and antifungal activities were also observed for synthesized compounds against a panel consisting of several bacteria and fungi. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.034

文献信息

• Synthesis, antimalarial, antileishmanial, and antimicrobial activities of some 8-quinolinamine analogues
  作者：Meenakshi Jain、Shabana I. Khan、Babu L. Tekwani、Melissa R. Jacob、Savita Singh、Prati Pal Singh、Rahul Jain

  DOI：10.1016/j.bmc.2005.04.034

  日期：2005.7

  In the present communication, newly synthesized 8-quinolinamines (25-27) related to previously reported 2-tert-butylprimaquine (2) were evaluated for their in vitro antimalarial activity against chloroquine sensitive and resistant Plasmodium falciparum strains, in vivo antimalarial activity against P. berghei infected mice, in vitro antileishmanial activity against Leishmania donovani, in vitro antimicrobial activity against various fungi and bacteria, and cytotoxicity in a panel of mammalian cell lines. No promising cytotoxicities were observed for compounds reported herein. Analogue 25 was found to exhibit curative antimalarial activity at a dose of 25 mg/kg/day x 4 in a P. berghei infected mice model, and produced suppressive activity at a lower dose of 10 mg/kg/ day x 4. In vitro antileishmanial activities (IC50 and IC90) comparable to standard drug pentamidine were exhibited by all synthesized 8-quinolinamines 25-27. At the same time, promising antibacterial and antifungal activities were also observed for synthesized compounds against a panel consisting of several bacteria and fungi. (c) 2005 Elsevier Ltd. All rights reserved.