3-(2-chloroquinolin-3-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-one | 1254973-44-8

• 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: 3-(2-chloroquinolin-3-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-one
• CAS: 1254973-44-8
• 化学式: C₁₈H₁₀Cl₃NO
• 分子量: 362.642
• InChiKey: FNTLNOBOAZXBFX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.09
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  29.96
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  3-(2-chloroquinolin-3-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-one 在 盐酸羟胺 、 sodium acetate 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 2.0h， 以89%的产率得到5-(2-chloroquinolin-3-yl)-3-(3,4-dichlorophenyl)-4,5-dihydroisoxazoline
  参考文献：
  名称：

  Benign methodology and improved synthesis of 5-(2-chloroquinolin-3-yl)-3-phenyl-4,5-dihydroisoxazoline using acetic acid aqueous solution under ultrasound irradiation

  摘要：

  In the present paper, we have executed the synthesis of substituted 5-(2-chloroquinolin-3-yl)-3-pheny-14,5-dihydroisoxazolines via the reactions of substituted 3-(2-chloroquinolin-3-yl)-1-phenylprop-2-en-1-ones with hydroxylamine hydrochloride and sodium acetate in aqueous acetic acid solution in 72-90% yields at room temperature under ultrasound irradiation. This method provides several advantages such as operational simplicity, higher yield, safety and environment friendly protocol. The resulting substituted isoxazolines were characterized on the basis of H-1 NMR, C-13 NMR, IR, elemental analysis, and mass spectral data. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2010.12.003
• 作为产物：
  描述：

  2-氯-3-喹啉甲醛 、 3,4-二氯苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以73%的产率得到3-(2-chloroquinolin-3-yl)-1-(3,4-dichlorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  Benign methodology and improved synthesis of 5-(2-chloroquinolin-3-yl)-3-phenyl-4,5-dihydroisoxazoline using acetic acid aqueous solution under ultrasound irradiation

  摘要：

  In the present paper, we have executed the synthesis of substituted 5-(2-chloroquinolin-3-yl)-3-pheny-14,5-dihydroisoxazolines via the reactions of substituted 3-(2-chloroquinolin-3-yl)-1-phenylprop-2-en-1-ones with hydroxylamine hydrochloride and sodium acetate in aqueous acetic acid solution in 72-90% yields at room temperature under ultrasound irradiation. This method provides several advantages such as operational simplicity, higher yield, safety and environment friendly protocol. The resulting substituted isoxazolines were characterized on the basis of H-1 NMR, C-13 NMR, IR, elemental analysis, and mass spectral data. (C) 2010 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ultsonch.2010.12.003

文献信息

• Novel oxazine skeletons as potential antiplasmodial active ingredients: Synthesis, <i>in vitro</i> and <i>in vivo</i> biology of some oxazine entities produced via cyclization of novel chalcone intermediates
  作者：Vandana Tiwari、Jyotsna Meshram、Parvez Ali、Javed Sheikh、Umanath Tripathi

  DOI：10.3109/14756366.2010.539566

  日期：2011.8.1

  A novel series of 6-(2-chloroquinolin-3-yl)-4-substituted-phenyl-6H-1,3-oxazin-2-amines were synthesized and evaluated for in vitro antimalarial efficacy against chloroquine sensitive (MRC-02) as well as chloroquine resistant (RKL9) strains of Plasmodium falciparum. The activity tested was at nanomolar concentration. beta-Hematin formation inhibition activity (BHIA(50)) of oxazines were determined and correlated with antimalarial activity. A reasonably good correlation (r = 0.49 and 0.51, respectively) was observed between antimalarial activity (IC50) and BHIA(50). This suggests that antimalarial mode of action of these compounds seems to be similar to that of chloroquine and involves the inhibition of hemozoin formation. Some of the compounds were showing better antimalarial activity than chloroquine against resistant strain of P. falciparum and were also found to be active in the in vivo experiment.