2-{4-[2-tert-butyl-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)-8-quinolylamino]pentyl}-1,3-isoindolinedione | 861232-23-7

• 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: 2-{4-[2-tert-butyl-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)-8-quinolylamino]pentyl}-1,3-isoindolinedione
• CAS: 861232-23-7
• 化学式: C₃₅H₃₆F₃N₃O₄
• 分子量: 619.684
• InChiKey: KOUMZKCWYSGQCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.54
• 重原子数：
  45.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  80.76
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  2-{4-[2-tert-butyl-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)-8-quinolylamino]pentyl}-1,3-isoindolinedione 在 一水合肼 作用下， 反应 8.0h， 以90%的产率得到N⁴-[2-tert-Butyl-6-methoxy-4-methyl-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
• 作为产物：
  描述：

  2-tert-butyl-6-methoxy-4-methyl-8-nitro-5-(3-trifluoromethylphenoxy)quinoline 在 镍 氢气 、 三乙胺 作用下， 120.0 ℃ 、310.26 kPa 条件下， 反应 24.75h， 生成 2-{4-[2-tert-butyl-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)-8-quinolylamino]pentyl}-1,3-isoindolinedione
  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