2-chloro-3-[3-(4-methylphenyl)-4,5-dihydroisoxazol-5-yl]quinoline | 1316303-95-3

• 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: 2-chloro-3-[3-(4-methylphenyl)-4,5-dihydroisoxazol-5-yl]quinoline
• 英文别名: 5-(2-chloroquinolin-3-yl)-3-p-tolyl-4,5-dihydroisoxazoline；5-(2-Chloroquinolin-3-yl)-3-(4-methylphenyl)-4,5-dihydro-1,2-oxazole
• CAS: 1316303-95-3
• 化学式: C₁₉H₁₅ClN₂O
• 分子量: 322.794
• InChiKey: LFAVAZSHRYPKLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  34.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-(2-chloroquinolin-3-yl)-1-(p-tolyl)prop-2-en-1-one 在 盐酸羟胺 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以83%的产率得到2-chloro-3-[3-(4-methylphenyl)-4,5-dihydroisoxazol-5-yl]quinoline
  参考文献：
  名称：

  An efficient one-pot synthesis and photoinduced DNA cleavage studies of 2-chloro-3-(5-aryl-4,5-dihydroisoxazol-3-yl)quinolines

  摘要：

  4,5-Dihydroisoxazoles continue to attract considerable interest due to their wide spread biological activities. Here, we identify an efficient protocol for the preparation of 4,5-dihydroisoxazoles (2-isaxazolines) (4a-g) from quinolinyl chalcones. The nucleolytic activities of synthesized compounds were investigated by agarose gel electrophoresis. All these compounds were showed the remarkable DNA cleavage activity (concentration dependent) with pUC19 DNA at 365 nm UV light. The DNA cleavage activity was significantly enhanced by the presence of iminyl and carboxy radicals of DIQ. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.08.034

文献信息

• Benign methodology and improved synthesis of 5-(2-chloroquinolin-3-yl)-3-phenyl-4,5-dihydroisoxazoline using acetic acid aqueous solution under ultrasound irradiation
  作者：Vandana Tiwari、Ali Parvez、Jyotsna Meshram

  DOI：10.1016/j.ultsonch.2010.12.003

  日期：2011.9

  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.
• An efficient one-pot synthesis and photoinduced DNA cleavage studies of 2-chloro-3-(5-aryl-4,5-dihydroisoxazol-3-yl)quinolines
  作者：P.J. Bindu、K.M. Mahadevan、T.R. Ravikumar Naik

  DOI：10.1016/j.bmcl.2012.08.034

  日期：2012.10

  4,5-Dihydroisoxazoles continue to attract considerable interest due to their wide spread biological activities. Here, we identify an efficient protocol for the preparation of 4,5-dihydroisoxazoles (2-isaxazolines) (4a-g) from quinolinyl chalcones. The nucleolytic activities of synthesized compounds were investigated by agarose gel electrophoresis. All these compounds were showed the remarkable DNA cleavage activity (concentration dependent) with pUC19 DNA at 365 nm UV light. The DNA cleavage activity was significantly enhanced by the presence of iminyl and carboxy radicals of DIQ. (C) 2012 Elsevier Ltd. All rights reserved.