3-(2-chloroquinolin-3-yl)-1-(2,4-dichlorophenyl)prop-2-en-1-one | 1304704-37-7

• 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: 3-(2-chloroquinolin-3-yl)-1-(2,4-dichlorophenyl)prop-2-en-1-one
• 英文别名: 3-(2-Chloro-3-quinolinyl)-1-(2,4-dichlorophenyl)-2-propen-1-one
• CAS: 1304704-37-7
• 化学式: C₁₈H₁₀Cl₃NO
• 分子量: 362.642
• InChiKey: ZJZRWEBCARRDTO-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-(2,4-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87%的产率得到5-(2-chloroquinolin-3-yl)-3-(2,4-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：

  N-乙酰苯胺 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 反应 24.0h， 生成 3-(2-chloroquinolin-3-yl)-1-(2,4-dichlorophenyl)prop-2-en-1-one
  参考文献：
  名称：

  带有吡唑啉和吡啶类似物的新型喹啉衍生物的合成和抑菌活性

  摘要：

  本研究符合某些含有（5-（2-氯喹啉-3-基）-3-（芳基）-4,5-二氢-1 H-吡唑-1-基）（吡啶-结合了不同的生物活性杂环（例如喹啉，吡唑啉和吡啶衍生物）的4-yl）methanenes（4a-o）部分。为了确定本文报道的化合物是基于IR，1 H NMR，13 C NMR和质谱数据，并筛选了相同的化合物对四种细菌（金黄色葡萄球菌，化脓性链球菌，大肠埃希氏菌，铜绿假单胞菌）和三种真菌（以氨苄青霉素和灰黄霉素为标准药物的白色念珠菌，黑曲霉，克拉维斯曲霉。使用MTT比色测定法（HeLa细胞系）进行细胞毒性研究。在筛选出的化合物中，4e，4f和4n表现出最强的抗菌活性，而化合物4d和4g表现出对真菌菌株最有活性。结果表明，化合物4o对所有微生物菌株均具有显着活性。从SAR研究的观点来看，观察到吸电子基团的存在显着增强了合成化合物的抗菌活性。另外，对HeLa细胞的MTT初步细胞毒性研究表明，有效的4e

  DOI：

  10.1007/s00044-016-1732-6

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.