2,7-二氯-8-甲基喹啉-3-羧醛 | 131923-69-8

• 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
• 中文名称: 2,7-二氯-8-甲基喹啉-3-羧醛
• 英文名称: 2,7-dichloro- 8-methyl-3-formylquinoline
• 英文别名: 2,7-Dichloro-8-methylquinoline-3-carbaldehyde
• CAS: 131923-69-8
• 化学式: C₁₁H₇Cl₂NO
• mdl: MFCD09702831
• 分子量: 240.089
• InChiKey: NNYWEFPNGJCTKY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  2,7-二氯-8-甲基喹啉-3-羧醛 在 草酰氯 、 碘 、 sodium 、 potassium carbonate 、 三乙胺 、 丙酮氰醇 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Herbicidal Activity of Triketone–Quinoline Hybrids as Novel 4-Hydroxyphenylpyruvate Dioxygenase Inhibitors

  摘要：

  4-Hydroxyphenylpyruvate dioxygenase (EC 1.13.11.27, HPPD) is one of the most important targets for herbicide discovery. In the search for new HPPD inhibitors with novel scaffolds, triketone-quinoline hybrids were designed and subsequently optimized on the basis of the structure -activity relationship (SAR) studies. Most of the synthesized compounds displayed potent inhibition of Arabidopsis thaliana HPPD (AtHPPD), and some of them exhibited broad-spectrum and promising herbicidal activity at the rate of 150 g ai/ha by postemergence application. Most promisingly, compound III-1, 3-hydroxy-2-(2-methoxy-7-(methylthio)quinoline-3-carbonyl)cyclohex-2-enone (K-i = 0.009 mu M, AtHPPD), had broader spectrum of weed control than mesotrione. Furthermore, compound III-1 was much safer to maize at the rate of 150 g ai/ha than mesotrione, demonstrating its great potential as herbicide for weed control in maize fields. Therefore, triketone-quinoline hybrids may serve as new lead structures for novel herbicide discovery.

  DOI：

  10.1021/acs.jafc.5b01530
• 作为产物：
  描述：

  3-氯-2-甲基苯胺 在 磷酸 、 三氯氧磷 作用下， 生成 2,7-二氯-8-甲基喹啉-3-羧醛
  参考文献：
  名称：

  喹啉基查耳酮作为潜在的抗疟疾药物的抗疟疾，细胞毒性和分子对接研究。

  摘要：

  筛选喹啉基查耳酮系列（A1-A14）的抗疟活性。根据体外抗疟疾研究，许多喹啉基查耳酮对CQ敏感和抗药性恶性疟原虫菌株具有潜在活性，而对Vero细胞系无毒性。活性最高的喹啉基查耳酮A4（IC50为0.031μM）制成稳定的A4-血红素络合物，结合能为-25 kcal / mol，并且在3.5Å时也显示出很强的π-π相互作用。因此，稳定的A4-血红素复合物形成表明这些喹啉基查耳酮充当血红素聚合反应的阻滞剂。喹啉基查耳酮与Pf-DHFR的对接结果表明，与喹啉部分相比，喹啉基查耳酮的卤化苯部分与Pf-DHFR有很强的相互作用。以低结合能（-11.04kcal /摩尔）形成强的A4-Pf-DHFR复合物。还研究了喹啉基查耳酮的ADMET性质。体内抗疟疾研究也证实了A4是一种有效的抗疟疾剂。

  DOI：

  10.1007/s10822-019-00210-2

文献信息

• High catalytic performance of CoCuFe2O4/ZIF-8(Zn) nanocatalyst for synthesis of new benzimidazole derivatives
  作者：Firouz Matloubi Moghaddam、Atefeh Jarahiyan、Mahdi Heidarian Haris、Parisa Yaqubnezhad Pazoki、Bagher Aghamiri

  DOI：10.1016/j.molstruc.2023.135496

  日期：2023.8

  microscopy (TEM) were used to characterize the catalyst structure. This catalytic system gave us a satisfactory answer and provided the corresponding products with excellent yields. In order to implement procedures to comply with green chemistry, water was used for the synthesis of both catalyst and benzimidazole (benzimidazole-quinoline, benzothiazole, and benzoxazole) derivatives. This publication is

  在此，我们报道了一种高效的催化体系，用于在绿色条件下通过芳基醛和邻苯二胺（2-氨基苯硫酚、2-氨基苯酚）之间的反应快速构建苯并咪唑、苯并咪唑-喹啉、苯并噻唑和苯并恶唑衍生物。借助十六烷基三甲基溴化铵 (CTAB) 结合 CoCuFe 2 O 4 和 ZIF-8(Zn)，通过简单易行的程序合成了磁性 CoCuFe 2 O 4 / ZIF - 8 ( Zn ) 。不同的技术，如傅里叶透射红外光谱 (FT-IR)、X射线衍射 (XRD)、场发射扫描电子显微镜 (FESEM) 和透射电子显微镜 (TEM) 用于表征催化剂结构。该催化体系给了我们一个满意的答案，并提供了具有优异产率的相应产品。为了实施符合绿色化学的程序，水用于合成催化剂和苯并咪唑（苯并咪唑-喹啉、苯并噻唑和苯并恶唑）衍生物。该出版物是第一个在室温下无需苛刻条件下快速合成苯并咪唑（苯并咪唑-喹啉、苯并噻唑和苯并恶唑）衍生物的简单方案。
• Synthesis, characterization, theoretical, anti-bacterial and molecular docking studies of quinoline based chalcones as a DNA gyrase inhibitor
  作者：Muhammad Imran Abdullah、Asif Mahmood、Murtaza Madni、Sara Masood、Muhammad Kashif

  DOI：10.1016/j.bioorg.2014.03.006

  日期：2014.6

  A series of fourteen (A(1)-A(14)) new qunioline based chalcones were synthesized by condensing 2,7-dichloro- 8-methyl-3-formyl quinoline with acetophenone and acetylthiophenes, and subsequently characterized by IR, NMR and Mass spectroscopy. All the compounds were screened for antibacterial activities and found potentially active antibacterial agents. Bioassay, theoretical and dockings studies with DNA gyrase (the enzyme required for super coiling of DNA of bacteria) results showed that the type and positions of the substituents seemed to be critical for their antibacterial activities. The bromo and chloro substituted chalcone displayed high anti-bacterial activity. The A(4) and A(6) showed high interaction with DNA gyrase, contributing high free binding energy (Delta G - 8.18 and - 8.88 kcal). (C) 2014 Elsevier Inc. All rights reserved.
• Synthesis and biological evaluation of new [1,3,4]thiadiazepino[7,6-b]quinolin-2-amines as potent anti-microbial agents
  作者：Hasnain Muhammad Raza、Nada-E-Ali Rizvi、Hamid Latif Siddiqui、Arshad Javaid、Mazhar Iqbal

  DOI：10.1007/s00044-012-0389-z

  日期：2013.8

  Four series of 56 new thiadiazepinoquinoline amines were synthesized and characterized by spectroscopic techniques (NMR, IR, and MS) and elemental analysis. All the compounds were screened for in vitro anti-microbial activity. Highest inhibitory activity (MIC of 0.03 mg/ml) was exerted by 2e against Bacillus subtilis and Streptococcus pyogenes, 2f against Escherichia coli and Streptococcus pyogenes, and 4k against only Bacillus subtilis. Only compounds 1g and 2g revealed potent anti-fungal activity (MIC 0.03 mg/ml) compared to the standard against Alternaria alternata. Most of the compounds exhibited better anti-bacterial activity than anti-fungal activity against the microorganisms employed in this study. These studies suggest that the thiadiazepinoquinoline scaffold may serve as a new promising template for further elaboration as anti-bacterial and anti-fungal drugs.
• Cziaky; Korodi; Frank, Pharmazie, 1990, vol. 45, # 9, p. 690 - 690
  作者：Cziaky、Korodi、Frank

  DOI：——

  日期：——
• Anti-HIV cytotoxicity enzyme inhibition and molecular docking studies of quinoline based chalcones as potential non-nucleoside reverse transcriptase inhibitors (NNRT)
  作者：Asima Hameed、Muhammad Imran Abdullah、Ejaz Ahmed、Ahsan Sharif、Ahmad Irfan、Sara Masood

  DOI：10.1016/j.bioorg.2016.02.008

  日期：2016.4

  A series of fourteen (A(1) - A(14)) qunioline based chalcones were screened for reverse transcriptase inhibitors (RT) and found potentially active against RT. Bioassay, theoretical and dockings studies with RT (the enzyme required for reverse transcription of viral RNA) results showed that the type and positions of the substituents seemed to be critical for their inhibition against RT. The bromo and chloro substituted chalcone displayed high degree of inhibition against RT. The A(4) andA(6) showed high interaction with RT, contributing high free binding energy (Delta G -9.30 and -9.13 kcal) and RT inhibition value (IC50 0.10 mu g/ml and 0.11 mu g/ml). (C) 2016 Elsevier Inc. All rights reserved.