4-(5-Chloro-8-hydroxyquinolin-7-yl)-3-methylbutanal | 1416989-17-7

• 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: 4-(5-Chloro-8-hydroxyquinolin-7-yl)-3-methylbutanal
• 英文别名: 4-(5-chloro-8-hydroxyquinolin-7-yl)-3-methylbutanal
• CAS: 1416989-17-7
• 化学式: C₁₄H₁₄ClNO₂
• 分子量: 263.724
• InChiKey: WFLMGVWGGYOKPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  50.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(5-Chloro-8-hydroxyquinolin-7-yl)-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81%的产率得到5-chloro-7-(4-diethylamino-2-methylbutyl)quinolin-8-ol
  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-Chloro-8-(2-methylallyloxy)quinoline 在 (acetylacetonato)dicarbonylrhodium (l) 、 BINAPa 、 氢气 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 甲苯 为溶剂， 80.0 ℃ 、2.0 MPa 条件下， 反应 42.0h， 生成 4-(5-Chloro-8-hydroxyquinolin-7-yl)-3-methylbutanal
  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

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.