2-氯-4-(4-甲氧基苄氧基)喹啉 | 733053-60-6

• 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-氯-4-(4-甲氧基苄氧基)喹啉
• 英文名称: 2-chloro-4-(4-methoxybenzyloxy)quinoline
• 英文别名: 2-chloro-4-[(4-methoxyphenyl)methoxy]quinoline
• CAS: 733053-60-6
• 化学式: C₁₇H₁₄ClNO₂
• 分子量: 299.757
• InChiKey: QLOPBGDYUDAJKP-UHFFFAOYSA-N

物化性质

• 沸点：
  431.6±35.0 °C(Predicted)
• 密度：
  1.262±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氯-4-(4-甲氧基苄氧基)喹啉 在 sodium methylate 、 potassium carbonate 、 溶剂黄146 作用下， 以 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 2-[3-(3,4-Dichlorobenzylamino)prop-1-ylamino]-1H-quinolin-4-one
  参考文献：
  名称：

  Design and synthesis of quinolinones as methionyl-tRNA synthetase inhibitors

  摘要：

  Five new structural analogues of substituted-1H-quinolinones (19, 20, 23, 24, and 26) have been synthesized and evaluated for Staphylococcus aureus methionyl-tRNA synthetase enzyme inhibitory activity. These compounds were also tested against pathogens of six S. aureus, two Enterococcus faecalis, and one Enterococcus faecium. Among all the synthesized quinolinones, compound 20 displayed significant inhibitory activities in the strains of E. faecalis and E faecium. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.062
• 作为产物：
  描述：

  2,4-二氯喹啉 、 4-甲氧基苄醇 以 四氢呋喃 、 正己烷 为溶剂， 以39%的产率得到2-氯-4-(4-甲氧基苄氧基)喹啉
  参考文献：
  名称：

  Quinolones used as MRS inhibitors and bactericides

  摘要：

  化合物的化学式（I）是细菌酶S aureus甲硫氨酰tRNA合成酶的抑制剂，并可用于治疗细菌感染。

  公开号：

  US06320051B1

文献信息

• Synthesis and Antibacterial Activity of New Diaryldiamines
  作者：Farhana Samrin、Akash Sharma、Inshad Ali Khan、Sadhna Puri

  DOI：10.1002/jhet.1040

  日期：2012.11

  Several new quinolines and quinazolines (4, 10, 13) have been synthesized from cheap and readily available chemicals through a series of simple chemical transformations. Most of the synthesized compounds have been evaluated for antibacterial activity against Gram positive and Gram negative strains. Some of the synthesized compounds displayed interesting activity but not very promising for further development

  几种新的喹啉和喹唑啉（4，10，13）已经从廉价易得的化学品通过一系列简单的化学转化的合成。已经评估了大多数合成化合物对革兰氏阳性和革兰氏阴性菌株的抗菌活性。一些合成的化合物显示出令人感兴趣的活性，但是对于进一步的开发不是很有希望。
• [EN] QUINOLONES USED AS MRS INHIBITORS AND BACTERICIDES<br/>[FR] QUINOLONES UTILISEES COMME INHIBITEURS DE MRS ET BACTERICIDES
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO1999055677A1

  公开（公告）日：1999-11-04

  (EN) Compounds of formula (I) are inhibitors of the bacterial enzyme $i(S aureus) methionyl tRNA synthetase and are of use in treating bacterial infections.(FR) L'invention concerne des composés de formule (I), qui sont des inhibiteurs de l'enzyme bactérienne méthionyl-ARNt synthétase de $i(S aureus) utilisés dans le traitement des infections bactériennes.

  化合物的公式（I）是细菌酶 $i(S aureus) 甲硫氨酰-tRNA 合成酶的抑制剂，并可用于治疗细菌感染。
• 2-[2-Substituted-3-(3,4-dichlorobenzylamino)propylamino]-1H-quinolin-4-ones as Staphylococcus aureus methionyl-tRNA synthetase inhibitors
  作者：Farhanullah、Taehee Kang、Eun-Jung Yoon、Eun-Chil Choi、Sunghoon Kim、Jeewoo Lee

  DOI：10.1016/j.ejmech.2008.02.021

  日期：2009.1

  New analogues of 2-[2-substituted-3-(3,4-dichlorobenzylamino)propylamino]quinolin-4-ones, 26a, 26b, 31a-e, 34, 35, 38 and 40, have been synthesized and evaluated against Staphylococcus aureus methionyl-tRNA synthetase. All of the synthesized compounds were less active than the reference compound 2. The compounds were also screened against various strains of S. aureus and Enterococci for their antibacterial activities. Among the compounds, 26b, 31c and 31e displayed significant inhibitory properties against various strains of Enterococci compared to compound 2. (C) 2008 Elsevier Masson SAS. All rights reserved.
• Optimisation of aryl substitution leading to potent methionyl tRNA synthetase inhibitors with excellent gram-Positive antibacterial activity
  作者：Richard L Jarvest、John M Berge、Murray J Brown、Pamela Brown、John S Elder、Andrew K Forrest、C.S.V Houge-Frydrych、Peter J O'Hanlon、David J McNair、Stephen Rittenhouse、Robert J Sheppard

  DOI：10.1016/s0960-894x(02)01027-2

  日期：2003.2

  Optimisation of the left-hand-side aryl moiety of a file compound screening hit against Staphylococcus aureus methionyl tRNA synthetase led to the identification of a series of potent nanomolar inhibitors. The best compounds showed excellent antibacterial activity against staphylococcal and enterococcal pathogens. including strains resistant to clinical antibiotics. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Definition of the heterocyclic pharmacophore of bacterial methionyl tRNA synthetase inhibitors: potent antibacterially active non-quinolone analogues
  作者：Richard L Jarvest、Sula A Armstrong、John M Berge、Pamela Brown、John S Elder、Murray J Brown、Royston C.B Copley、Andrew K Forrest、Dieter W Hamprecht、Peter J O'Hanlon、Darren J Mitchell、Stephen Rittenhouse、David R Witty

  DOI：10.1016/j.bmcl.2004.05.070

  日期：2004.8

  Potent inhibitors of bacterial methionyl tRNA synthetase (MRS) have previously been reported. Through SAR of the quinolone moiety, the right hand side pharmacophore for MRS inhibition has now been defined as an NH-C-NH functionality in the context of a bicyclic heteroaromatic system. Potent antibacterial fused-pyrimidone and fused-imidazole analogues have been obtained and enantioselective activity demonstrated. Compound 46 demonstrated very good antibacterial activity against panels of antibiotic-resistant staphylococci and enterococci. (C) 2004 Elsevier Ltd. All rights reserved.