(2E)-1-(2’-naphthyl)-3-(2-chloro-6-methoxyquinolin-3-yl)-2-propen-1-one | 1253278-38-4

• 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: (2E)-1-(2’-naphthyl)-3-(2-chloro-6-methoxyquinolin-3-yl)-2-propen-1-one
• 英文别名: (2E)-1-(2'-naphthyl)-3-(2-chloro-6-methoxyquinolin-3-yl)-2-propen-1-one；(2E)-1-(2-naphthyl)-3-(2-chloro-5-methoxyquinolin-3-yl)-2-propen-1-one；(2E)-3-(2-chloro-6-methoxyquinolin-3-yl)-1-(2-naphthyl)prop-2-en-1-one；(E)-3-(2-chloro-6-methoxy-3-quinolyl)-1-(2-naphthyl)prop-2-en-1-one；(E)-3-(2-chloro-6-methoxyquinolin-3-yl)-1-naphthalen-2-ylprop-2-en-1-one
• CAS: 1253278-38-4
• 化学式: C₂₃H₁₆ClNO₂
• 分子量: 373.839
• InChiKey: PBVTXLKJBDMAIM-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  39.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4'-甲氧基乙酰苯胺 在 sodium hydroxide 、 三氯氧磷 作用下， 以 乙醇 、 水 为溶剂， 生成 (2E)-1-(2’-naphthyl)-3-(2-chloro-6-methoxyquinolin-3-yl)-2-propen-1-one
  参考文献：
  名称：

  Anti-HIV-1 screening of (2E)-3-(2-chloro-6-methyl/methoxyquinolin-3-yl)-1-(aryl)prop-2-en-1-ones

  摘要：

  Biological studies of two series of 38 quinolinyl chalcones (4a-s and 5a-s) were investigated for their in vitro anti-HIV-1 and cytotoxic activities. Out of 38 compounds, seventeen compounds were observed as good anti-HIV-1 agents with EC50 values less than 20 mu M. Compounds 4a, 4l, 4o, 5e, 5h, 5l, 5o, and 5r displayed potent anti-HIV-1 activity with EC50 values less than 5 mu M. Among these, compound 5h emerged as the best anti-HIV-1 agent (EC50 = 1.1 mu M). Compounds 4d, 4n, 4q, 4r, 4s, 5n, and 5r showed no toxicity in human lymphocytes. Bioassay results show that the type(s) and position(s) of the substituents seem to be critical for their cytotoxic and anti-HIV-1 activities. These results could be useful in the invention of new anti-HIV agents through structural modification.

  DOI：

  10.1007/s00044-013-0652-y

文献信息

• Antimicrobial and Antileishmanial Studies of Novel (2E)-3-(2-Chloro-6-methyl/methoxyquinolin-3-yl)-1-(Aryl)prop-2-en-1-ones
  作者：Syed Umar Farooq Rizvi、Hamid Latif Siddiqui、Masood Parvez、Matloob Ahmad、Waseeq Ahmad Siddiqui、Muhammad Masoom Yasinzai

  DOI：10.1248/cpb.58.301

  日期：——

  Thirty eight heterocyclic chalcones were synthesized by condensing formylquinolines with diverse methyl arylketones. The target compounds were characterized by spectroscopic techniques (NMR, IR, MS) and elemental analysis. The X-ray crystallographic study of (2E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-en-1-one (1p) was also performed for the structure confirmation. The title compounds were screened for anti-microbial and antileishmanial activities. The compounds 1c—e, 1g, 1j—m, 1p, 1r—s, 2g, 2j—p, and 2r—s were found potentially active antileishmanial agents, while 1f—i, 1l, 1o—p, 2f—i, 2l, and 2o—p showed remarkable antibacterial activity. Only compounds 1g and 2g—h exhibited significant antifungal activity.

  通过将甲酰基喹啉与不同的甲基芳基酮缩合，合成了 38 种杂环查耳酮。目标化合物通过光谱技术（核磁共振、红外光谱、质谱）和元素分析进行了表征。为了确认结构，还对 (2E)-3-(2-chloro-6-methylquinolin-3-yl)-1-(2,3-dihydro-1,4-benzodioxin-6-yl)prop-2-en-1-one (1p) 进行了 X 射线晶体学研究。对标题化合物进行了抗微生物和抗利什曼病活性筛选。结果发现，化合物 1c-e、1g、1j-m、1p、1r-s、2g、2j-p 和 2r-s 具有潜在的抗利什曼病活性，而 1f-i、1l、1o-p、2f-i、2l 和 2o-p 具有显著的抗菌活性。只有化合物 1g 和 2g-h 具有明显的抗真菌活性。
• Antibacterial activity of chalcones, hydrazones and oxadiazoles against methicillin-resistant Staphylococcus aureus
  作者：Thaís Moreira Osório、Franco Delle Monache、Louise Domeneghini Chiaradia、Alessandra Mascarello、Taisa Regina Stumpf、Carlos Roberto Zanetti、Douglas Bardini Silveira、Célia Regina Monte Barardi、Elza de Fatima Albino Smânia、Aline Viancelli、Lucas Ariel Totaro Garcia、Rosendo Augusto Yunes、Ricardo José Nunes、Artur Smânia

  DOI：10.1016/j.bmcl.2011.11.059

  日期：2012.1

  The increase in antibiotic resistance due to multiple factors has encouraged the search for new compounds which are active against multidrug-resistant pathogens. In this context, chalcones, dihydrochalcones, hydrazones and oxadiazoles were tested against Staphylococcus aureus ATCC 25923 and methicillin-resistant S. aureus (MRSA) isolates, which were obtained from clinical laboratories and were characterized as MRSA using traditional and molecular methods. Among 65 tested compounds, two chalcones, one dihydrochalcone and two hydrazones were active against MRSA. Based on the minimal inhibitory concentration and cytotoxicity, hydrazones provided a better selectivity index than chalcones. Active hydrazones are promising antibiotic-like substances and they should be the subject of further microbiological studies. (C) 2011 Elsevier Ltd. All rights reserved.
• Anti-HIV-1 screening of (2E)-3-(2-chloro-6-methyl/methoxyquinolin-3-yl)-1-(aryl)prop-2-en-1-ones
  作者：Syed Umar Farooq Rizvi、Matloob Ahmad、Mujahid Hussain Bukhari、Catherine Montero、Payel Chatterjee、Mervi Detorio、Raymond F. Schinazi

  DOI：10.1007/s00044-013-0652-y

  日期：2014.1

  Biological studies of two series of 38 quinolinyl chalcones (4a-s and 5a-s) were investigated for their in vitro anti-HIV-1 and cytotoxic activities. Out of 38 compounds, seventeen compounds were observed as good anti-HIV-1 agents with EC50 values less than 20 mu M. Compounds 4a, 4l, 4o, 5e, 5h, 5l, 5o, and 5r displayed potent anti-HIV-1 activity with EC50 values less than 5 mu M. Among these, compound 5h emerged as the best anti-HIV-1 agent (EC50 = 1.1 mu M). Compounds 4d, 4n, 4q, 4r, 4s, 5n, and 5r showed no toxicity in human lymphocytes. Bioassay results show that the type(s) and position(s) of the substituents seem to be critical for their cytotoxic and anti-HIV-1 activities. These results could be useful in the invention of new anti-HIV agents through structural modification.