3-Bromo-7-chloro-1-(2-methylallyl)quinolin-4-one | 1564279-77-1

• 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: 3-Bromo-7-chloro-1-(2-methylallyl)quinolin-4-one
• 英文别名: 3-bromo-7-chloro-1-(2-methylprop-2-enyl)quinolin-4-one
• CAS: 1564279-77-1
• 化学式: C₁₃H₁₁BrClNO
• 分子量: 312.593
• InChiKey: MEHDRNCDLAQMLR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-氯吲哚 、 3-Bromo-7-chloro-1-(2-methylallyl)quinolin-4-one 在 铜 、 potassium carbonate 、 N,N-二甲基乙二胺 作用下， 以 甲苯 为溶剂， 反应 48.0h， 以71%的产率得到7-Chloro-3-(5-chloroindol-1-yl)-1-(2-methylallyl)quinolin-4-one
  参考文献：
  名称：

  Synthesis of halogenated 4-quinolones and evaluation of their antiplasmodial activity

  摘要：

  Treatment of 4-hydroxyquinolines with (2-methyl) allyl bromide in the presence of K2CO3 resulted in the formation of novel N-[(2-methyl) allyl]-4-quinolones through selective N-alkylation. Further reaction of N-(2-methylallyl)-4-quinolones with bromine or N-bromosuccinimide yielded the corresponding 3-bromo- 1-(2,3-dibromo-2-methylpropyl)-4-quinolones and 3-bromo-1-(2-methylallyl)-4-quinolones, respectively. Furthermore, a copper-catalyzed C-N coupling of the latter 3-bromo-4-quinolones with (5-chloro) indole afforded novel 3-[(5-chloro) indol-1-yl]-4-quinolone hybrids. Antifungal and antiplasmodial assays of all new 4-quinolones were performed and revealed no antifungal properties but moderate antiplasmodial activities. All 15 compounds displayed micromolar activities against a chloroquine- sensitive strain of Plasmodium falciparum, and the five most potent compounds also showed micromolar activities against a chloroquine-resistant strain of P. falciparum with IC50-values ranging between 4 and 70 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.067
• 作为产物：
  描述：

  7-chloro-1,4-dihydroquinolin-4-ol 在 N-溴代丁二酰亚胺(NBS) 、 potassium carbonate 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 48.0h， 生成 3-Bromo-7-chloro-1-(2-methylallyl)quinolin-4-one
  参考文献：
  名称：

  Synthesis of halogenated 4-quinolones and evaluation of their antiplasmodial activity

  摘要：

  Treatment of 4-hydroxyquinolines with (2-methyl) allyl bromide in the presence of K2CO3 resulted in the formation of novel N-[(2-methyl) allyl]-4-quinolones through selective N-alkylation. Further reaction of N-(2-methylallyl)-4-quinolones with bromine or N-bromosuccinimide yielded the corresponding 3-bromo- 1-(2,3-dibromo-2-methylpropyl)-4-quinolones and 3-bromo-1-(2-methylallyl)-4-quinolones, respectively. Furthermore, a copper-catalyzed C-N coupling of the latter 3-bromo-4-quinolones with (5-chloro) indole afforded novel 3-[(5-chloro) indol-1-yl]-4-quinolone hybrids. Antifungal and antiplasmodial assays of all new 4-quinolones were performed and revealed no antifungal properties but moderate antiplasmodial activities. All 15 compounds displayed micromolar activities against a chloroquine- sensitive strain of Plasmodium falciparum, and the five most potent compounds also showed micromolar activities against a chloroquine-resistant strain of P. falciparum with IC50-values ranging between 4 and 70 mu M. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.12.067

文献信息

• Synthesis of halogenated 4-quinolones and evaluation of their antiplasmodial activity
  作者：Stéphanie Vandekerckhove、Tom Desmet、Hai Giang Tran、Carmen de Kock、Peter J. Smith、Kelly Chibale、Matthias D’hooghe

  DOI：10.1016/j.bmcl.2013.12.067

  日期：2014.2

  Treatment of 4-hydroxyquinolines with (2-methyl) allyl bromide in the presence of K2CO3 resulted in the formation of novel N-[(2-methyl) allyl]-4-quinolones through selective N-alkylation. Further reaction of N-(2-methylallyl)-4-quinolones with bromine or N-bromosuccinimide yielded the corresponding 3-bromo- 1-(2,3-dibromo-2-methylpropyl)-4-quinolones and 3-bromo-1-(2-methylallyl)-4-quinolones, respectively. Furthermore, a copper-catalyzed C-N coupling of the latter 3-bromo-4-quinolones with (5-chloro) indole afforded novel 3-[(5-chloro) indol-1-yl]-4-quinolone hybrids. Antifungal and antiplasmodial assays of all new 4-quinolones were performed and revealed no antifungal properties but moderate antiplasmodial activities. All 15 compounds displayed micromolar activities against a chloroquine- sensitive strain of Plasmodium falciparum, and the five most potent compounds also showed micromolar activities against a chloroquine-resistant strain of P. falciparum with IC50-values ranging between 4 and 70 mu M. (C) 2013 Elsevier Ltd. All rights reserved.