2,3,4-trimethyl-quinolin-8-ol

• 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: 2,3,4-trimethyl-quinolin-8-ol
• 英文别名: 2,3,4-Trimethyl-chinolin-8-ol；2,3,4-Trimethylquinolin-8-ol；2,3,4-trimethylquinolin-8-ol
• 化学式: C₁₂H₁₃NO
• 分子量: 187.241
• InChiKey: YOUTUQQOLBXVOP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  33.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2,3,4-trimethyl-quinolin-8-ol 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以88%的产率得到8-hydroxy-7-iodo-2,3,4-trimethylquinoline
  参考文献：
  名称：

  一种光化学-卤代喹啉联合治疗策略，用于治疗致病性细菌

  摘要：

  随着耐药细菌感染的持续增加，以及抗生素管道的当前令人沮丧的状况，与传统抗生素相比，通过独特机制起作用并与其他药物协同作用的新型抗菌药物的需求空前高涨。 。我们发现，没食子酸是一种植物来源的植物化学物质，可以显着增强几种卤代喹啉的抗细菌活性（对金黄色葡萄球菌的增强作用高达11 800倍）对病原菌，包括耐药性临床分离株。金黄色葡萄球菌证明对没食子酸-卤代喹啉组合具有最高的敏感性，包括一种卤代喹啉，其对生物耐甲氧西林金黄色葡萄球菌（MRSA）临床分离株的生物膜根除活性增强。在我们的研究中，我们还证明了这些卤代喹啉通过有趣的金属（II）阳离子依赖性机制起作用，并显示出有希望的哺乳动物细胞毒性。

  DOI：

  10.1002/cmdc.201500179
• 作为产物：
  描述：

  3-甲基-3-戊烯-2-酮 在 硫酸 、 氢溴酸 、 sodium iodide 作用下， 反应 42.0h， 生成 2,3,4-trimethyl-quinolin-8-ol
  参考文献：
  名称：

  Discovery of quinoline small molecules with potent dispersal activity against methicillin-resistant Staphylococcus aureus and Staphylococcus epidermidis biofilms using a scaffold hopping strategy

  摘要：

  Staphylococcus aureus and Staphylococcus epidermidis are recognized as the most frequent cause of biofilm-associated nosocomial and indwelling medical device infections. Biofilm-associated infections are known to be highly resistant to our current arsenal of clinically used antibiotics and antibacterial agents. To exacerbate this problem, no therapeutic option exists that targets biofilm-dependent machinery critical to Staphylococcal biofilm formation and maintenance. Here, we describe the discovery of a series of quinoline small molecules that demonstrate potent biofilm dispersal activity against methicillin-resistant S. aureus and S. epidermidis using a scaffold hopping strategy. This interesting class of quinolines also has select synthetic analogues that demonstrate potent antibacterial activity and biofilm inhibition against S. aureus and S. epidermidis. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.09.009

文献信息

• [EN] COMBINATION THERAPY FOR TREATING INFECTIONS DISEASES<br/>[FR] POLYTHÉRAPIE POUR LE TRAITEMENT DE MALADIES INFECTIEUSES
  申请人：UNIV FLORIDA

  公开号：WO2016154051A1

  公开（公告）日：2016-09-29

  The present invention provides compositions comprising a quinoline, a potentiating agent, and optionally a pharmaceutically acceptable carrier, for treating and/or preventing infectious diseases. The provided compositions may also include another therapeutic agent (e.g., antibiotic). The provided compositions may be useful in treating and/or preventing bacterial infections as well as inhibiting and eradicating biofilm formation.

  本发明提供了包含喹啉、增效剂和可选的药用载体的组合物，用于治疗和/或预防传染病。所提供的组合物也可以包括另一种治疗剂（例如抗生素）。所提供的组合物可能对治疗和/或预防细菌感染以及抑制和根除生物膜形成有用。
• Preparation of Some Substituted 8-Hydroxy- and 8-Methoxyquinolines
  作者：John P. Phillips、Rebecca Leash. Elbinger、Lynne L. Merritt

  DOI：10.1021/ja01180a031

  日期：1949.12
• Discovery of quinoline small molecules with potent dispersal activity against methicillin-resistant Staphylococcus aureus and Staphylococcus epidermidis biofilms using a scaffold hopping strategy
  作者：Yasmeen Abouelhassan、Aaron T. Garrison、Gena M. Burch、Wilson Wong、Verrill M. Norwood、Robert W. Huigens

  DOI：10.1016/j.bmcl.2014.09.009

  日期：2014.11

  Staphylococcus aureus and Staphylococcus epidermidis are recognized as the most frequent cause of biofilm-associated nosocomial and indwelling medical device infections. Biofilm-associated infections are known to be highly resistant to our current arsenal of clinically used antibiotics and antibacterial agents. To exacerbate this problem, no therapeutic option exists that targets biofilm-dependent machinery critical to Staphylococcal biofilm formation and maintenance. Here, we describe the discovery of a series of quinoline small molecules that demonstrate potent biofilm dispersal activity against methicillin-resistant S. aureus and S. epidermidis using a scaffold hopping strategy. This interesting class of quinolines also has select synthetic analogues that demonstrate potent antibacterial activity and biofilm inhibition against S. aureus and S. epidermidis. (C) 2014 Elsevier Ltd. All rights reserved.
• A Phytochemical-Halogenated Quinoline Combination Therapy Strategy for the Treatment of Pathogenic Bacteria
  作者：Yasmeen Abouelhassan、Aaron T. Garrison、Fang Bai、Verrill M. Norwood、Minh Thu Nguyen、Shouguang Jin、Robert W. Huigens

  DOI：10.1002/cmdc.201500179

  日期：2015.7

  potentiates the antibacterial activities of several halogenated quinolines (up to 11 800‐fold potentiation against Staphylococcus aureus) against pathogenic bacteria, including drug‐resistant clinical isolates. S. aureus demonstrated the highest sensitivity towards gallic acid–halogenated quinoline combinations, including one halogenated quinoline that demonstrated potentiation of biofilm eradication activity

  随着耐药细菌感染的持续增加，以及抗生素管道的当前令人沮丧的状况，与传统抗生素相比，通过独特机制起作用并与其他药物协同作用的新型抗菌药物的需求空前高涨。 。我们发现，没食子酸是一种植物来源的植物化学物质，可以显着增强几种卤代喹啉的抗细菌活性（对金黄色葡萄球菌的增强作用高达11 800倍）对病原菌，包括耐药性临床分离株。金黄色葡萄球菌证明对没食子酸-卤代喹啉组合具有最高的敏感性，包括一种卤代喹啉，其对生物耐甲氧西林金黄色葡萄球菌（MRSA）临床分离株的生物膜根除活性增强。在我们的研究中，我们还证明了这些卤代喹啉通过有趣的金属（II）阳离子依赖性机制起作用，并显示出有希望的哺乳动物细胞毒性。