N-[(4-chlorophenyl)methyl]-3-methyl-4-(5-quinolyloxy)butan-1-amine | 1416988-95-8

• 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-[(4-chlorophenyl)methyl]-3-methyl-4-(5-quinolyloxy)butan-1-amine
• 英文别名: N-[(4-chlorophenyl)methyl]-3-methyl-4-quinolin-5-yloxybutan-1-amine
• CAS: 1416988-95-8
• 化学式: C₂₁H₂₃ClN₂O
• 分子量: 354.879
• InChiKey: CLUIYPQONMQFOB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  34.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  5-羟基喹啉 在 acetylacetonatodicarbonylrhodium(l) 、 sodium tetrahydroborate 、 2-(diphenylphosphoryl)benzoic acid 、 氢气 、 magnesium sulfate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 、 甲苯 为溶剂， 生成 N-[(4-chlorophenyl)methyl]-3-methyl-4-(5-quinolyloxy)butan-1-amine
  参考文献：
  名称：

  Evaluation of (4-aminobutyloxy)quinolines as a novel class of antifungal agents

  摘要：

  Antifungal assessment of eighteen 5-, 6- and 8-(4-aminobutyloxy)quinolines revealed a significant susceptibility of the tested fungi and yeast strains (Candida albicans, Rhodotorula bogoriensis, Aspergillus flavus and Fusarium solani) toward different halo-substituted 8-(4-aminobutyloxy)quinolines. The six most potent compounds displayed antifungal activities similar to those of established antifungal agents such as Amphotericin B, Fluconazole and Itraconazole, and one representative also showed a promising broad-spectrum antifungal profile. The introduction of an aminoalkoxy side chain at the 8-position of a halo-substituted quinoline core might thus provide a new class of lead structures in the search for novel antifungal agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.06.014

文献信息

• Evaluation of (4-aminobutyloxy)quinolines as a novel class of antifungal agents
  作者：Stéphanie Vandekerckhove、Hai Giang Tran、Tom Desmet、Matthias D’hooghe

  DOI：10.1016/j.bmcl.2013.06.014

  日期：2013.8

  Antifungal assessment of eighteen 5-, 6- and 8-(4-aminobutyloxy)quinolines revealed a significant susceptibility of the tested fungi and yeast strains (Candida albicans, Rhodotorula bogoriensis, Aspergillus flavus and Fusarium solani) toward different halo-substituted 8-(4-aminobutyloxy)quinolines. The six most potent compounds displayed antifungal activities similar to those of established antifungal agents such as Amphotericin B, Fluconazole and Itraconazole, and one representative also showed a promising broad-spectrum antifungal profile. The introduction of an aminoalkoxy side chain at the 8-position of a halo-substituted quinoline core might thus provide a new class of lead structures in the search for novel antifungal agents. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and antiplasmodial evaluation of novel (4-aminobutyloxy)quinolines
  作者：Stéphanie Vandekerckhove、Christian Müller、Dieter Vogt、Carmen Lategan、Peter J. Smith、Kelly Chibale、Norbert De Kimpe、Matthias D’hooghe

  DOI：10.1016/j.bmcl.2012.10.094

  日期：2013.1

  A variety of 5-, 6- and 8-(4-aminobutyloxy) quinolines as novel oxygen analogues of known 4- and 8-(4-aminobutylamino)quinoline antimalarial drugs was generated from hydroxyquinolines through a three-step approach with a rhodium-catalyzed hydroformylation as the key step. Antiplasmodial assays of these new quinolines revealed micromolar potency for all representatives against a chloroquine-sensitive strain of Plasmodium falciparum, and three compounds showed submicromolar activity against a chloroquine-resistant strain of P. falciparum with IC50-values ranging between 150 and 680 nM. (C) 2012 Elsevier Ltd. All rights reserved.