(E)-1-(4-chlorophenyl)-3-(2-chloroquinolin-3-yl)prop-2-en-1-one

• 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: (E)-1-(4-chlorophenyl)-3-(2-chloroquinolin-3-yl)prop-2-en-1-one
• 英文别名: 1-(4-chlorophenyl)-3-(2-chloroquinolin-3-yl)prop-2-en-1-one；(E)-3-(2-chloroquinolin-3-yl)-1-(4-chlorophenyl)prop-2-en-1-one；(E)-1-(4-chlorophenyl)-3-(2-chloro-3-quinolyl)-2-propen-1-one
• 化学式: C₁₈H₁₁Cl₂NO
• 分子量: 328.197
• InChiKey: CNCILJVOBAUBPS-JXMROGBWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (E)-1-(4-chlorophenyl)-3-(2-chloroquinolin-3-yl)prop-2-en-1-one 、 尿素 在 neutral alumina 作用下， 以 乙醇 为溶剂， 反应 0.05h， 以77%的产率得到6-(4-chlorophenyl)-4-(2-chloro-3-quinolyl)-1,2,3,4-tetrahydro-2-pyrimidinone
  参考文献：
  名称：

  Hemasri, Heterocyclic Communications, 2009, vol. 15, # 6, p. 423 - 427

  摘要：

  DOI：
• 作为产物：
  描述：

  N-乙酰苯胺 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 41.0h， 生成 (E)-1-(4-chlorophenyl)-3-(2-chloroquinolin-3-yl)prop-2-en-1-one
  参考文献：
  名称：

  Antiprotozoal activity of chloroquinoline based chalcones

  摘要：

  A new series of chloroquinoline based chalcones were synthesized and evaluated for in vitro antiamoebic and antimalarial activities. The results showed that out of fifteen compounds, four were found to be more active against the Entamoeba histolytica; while one compound was moderatively active compared to the standard drug metronidazole (IC50 = 1.46 mu M). In contrast, in vitro antimalarial activity against the chloroquine-sensitive (3D7) strain of P. falciparum indicated relatively low activity when compared to controls such as chloroquine and quinine (IC50 = 0.0065 mu M and 0.14 mu M, respectively). The toxicological studies of these compounds on human breast cancer MCF-7 cell line showed that all the compounds were non-toxic at the concentration range of 1.56-50 mu M. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.02.004

文献信息

• Synthesis, DNA binding, docking and photocleavage studies of quinolinyl chalcones
  作者：P. J. Bindu、K. M. Mahadevan、T. R. Ravikumar Naik、B. G. Harish

  DOI：10.1039/c4md00185k

  日期：——

  A series of simple quinoline–chalcone conjugates have been synthesized and evaluated for their nucleolytic activity. The compounds 3c and 3d exhibited promising DNA binding and DNA photocleavage studies.

  一系列简单的喹啉-香豆素共轭物已被合成并评估其核酸酶活性。化合物3c和3d表现出有希望的DNA结合和DNA光解研究。
• Synthesis and Anti-Bacterial Activity of Some Heterocyclic Chalcone Derivatives Bearing Thiofuran, Furan, and Quinoline Moieties
  作者：Chang-Ji Zheng、Sheng-Ming Jiang、Zhen-Hua Chen、Bai-Jun Ye、Hu-Ri Piao

  DOI：10.1002/ardp.201100005

  日期：2011.10

  36 Novel heterocyclic chalcone derivatives were synthesized and tested for their anti‐bacterial activity. Some compounds presented good anti‐microbial activities against Gram‐positive bacteria (including the multidrug‐resistant clinical isolates). This class of compounds presented high potency against Streptococcus mutans, among which the derivatives F2 with an MIC of 2 µg/mL was as active as the standard

  合成了 36 种新型杂环查耳酮衍生物并测试了它们的抗菌活性。一些化合物对革兰氏阳性菌（包括耐多药临床分离株）具有良好的抗菌活性。这类化合物对变形链球菌表现出高效能，其中MIC为2 µg/mL的衍生物F2与标准药物（诺氟沙星）活性相同，但活性低于苯唑西林。所有化合物在 64 µg/mL 时均不抑制革兰氏阴性菌（大肠杆菌 CCARM 1924 或大肠杆菌 CCARM 1356）的生长。
• <i>p</i>-TsOH Catalysed a Facile One-Pot Synthesis of Some New Substituted [1,2,4]Triazolo[3,4-<i>b</i>][1,3,4] thiadiazepines under Microwave Irradiation in Solvent-Free Conditions
  作者：M. Raghavendra、Halehatty S. Bhojya Naik、Tangali R. R Ravikumar Naik、Bailure S. Sherigara

  DOI：10.1080/10426500701323408

  日期：2007.6.14

  A series of triazolothiadiazepines were synthesized by the reaction of 4-substituted-5-aryl-1,2,4-triazoles and chalcones using p-TsOH as catalyst under solvent-free microwave irradiation conditions. Structure of all the prepared compounds were elucidated by elemental, IR, 1H NMR and mass spectral data.

  以p-TsOH为催化剂，在无溶剂微波辐照条件下，通过4-取代-5-芳基-1,2,4-三唑与查耳酮反应合成了一系列三唑噻二氮卓类药物。所有制备的化合物的结构都通过元素、IR、1H NMR和质谱数据阐明。
• 1,5-Bis(4-chlorophenyl)-3-(2-chloroquinolin-3-yl)pentane-1,5-dione: sheets of<i>R</i>₄⁴(26) rings built from C—H...N and C—H...O hydrogen bonds
  作者：Braulio Insuasty、Harlen Torres、Justo Cobo、John N. Low、Christopher Glidewell

  DOI：10.1107/s0108270105039193

  日期：2006.1.15

  Molecules of the title compound, C26H18Cl3NO2, are linked into sheets of R-4(4)(26) rings by a combination of C-H (...) N and C-H (...) O hydrogen bonds.
• Antiprotozoal activity of chloroquinoline based chalcones
  作者：Faisal Hayat、Emma Moseley、Attar Salahuddin、Robyn L. Van Zyl、Amir Azam

  DOI：10.1016/j.ejmech.2011.02.004

  日期：2011.5

  A new series of chloroquinoline based chalcones were synthesized and evaluated for in vitro antiamoebic and antimalarial activities. The results showed that out of fifteen compounds, four were found to be more active against the Entamoeba histolytica; while one compound was moderatively active compared to the standard drug metronidazole (IC50 = 1.46 mu M). In contrast, in vitro antimalarial activity against the chloroquine-sensitive (3D7) strain of P. falciparum indicated relatively low activity when compared to controls such as chloroquine and quinine (IC50 = 0.0065 mu M and 0.14 mu M, respectively). The toxicological studies of these compounds on human breast cancer MCF-7 cell line showed that all the compounds were non-toxic at the concentration range of 1.56-50 mu M. (C) 2011 Elsevier Masson SAS. All rights reserved.