4-(5,7-Dibromoquinolin-8-yl)oxy-3-methylbutanal | 1416989-13-3

• 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-(5,7-Dibromoquinolin-8-yl)oxy-3-methylbutanal
• 英文别名: 4-(5,7-dibromoquinolin-8-yl)oxy-3-methylbutanal
• CAS: 1416989-13-3
• 化学式: C₁₄H₁₃Br₂NO₂
• 分子量: 387.071
• InChiKey: XGOIPDOFUQEQKJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5,7-Dibromoquinolin-8-yl)oxy-3-methylbutanal 、 二乙胺 在 溶剂黄146 、 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以95%的产率得到4-[(5,7-dibromo-8-quinolyl)oxy]-N,N-diethyl-3-methyl-butan-1-amine
  参考文献：
  名称：

  Synthesis and antiplasmodial evaluation of novel (4-aminobutyloxy)quinolines

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2012.10.094
• 作为产物：
  描述：

  5,7-二溴-8-羟基喹啉 在 acetylacetonatodicarbonylrhodium(l) 、 2-(diphenylphosphoryl)benzoic acid 、 氢气 、 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 生成 4-(5,7-Dibromoquinolin-8-yl)oxy-3-methylbutanal
  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

• 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.
• 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.