42123-33-1Relevant articles and documents
Microwave-enhanced Friedl?nder synthesis for the rapid assembly of halogenated quinolines with antibacterial and biofilm eradication activities against drug resistant and tolerant bacteria
Garrison, Aaron T.,Abouelhassan, Yasmeen,Yang, Hongfen,Yousaf, Hussain H.,Nguyen, Tho J.,Huigens, Robert W.III.
supporting information, p. 720 - 724 (2017/04/27)
Herein, we disclose the development of a catalyst- and protecting-group-free microwave-enhanced Friedl?nder synthesis which permits the single-step, convergent assembly of diverse 8-hydroxyquinolines with greatly improved reaction yields over traditional oil bath heating (increased from 34% to 72%). This rapid synthesis permitted the discovery of novel biofilm-eradicating halogenated quinolines (MBECs = 1.0-23.5 μM) active against MRSA, MRSE, and VRE. These small molecules exhibit activity through mechanisms independent of membrane lysis, further demonstrating their potential as a clinically useful treatment option against persistent biofilm-associated infections.
A Phytochemical-Halogenated Quinoline Combination Therapy Strategy for the Treatment of Pathogenic Bacteria
Abouelhassan, Yasmeen,Garrison, Aaron T.,Bai, Fang,Norwood, Verrill M.,Nguyen, Minh Thu,Jin, Shouguang,Huigens, Robert W.
supporting information, p. 1157 - 1162 (2015/07/07)
With the continued rise of drug-resistant bacterial infections coupled with the current discouraging state of the antibiotic pipeline, the need for new antibacterial agents that operate through unique mechanisms compared with conventional antibiotics and work in synergy with other agents is at an all-time high. We have discovered that gallic acid, a plant-derived phytochemical, dramatically 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 against a methicillin-resistant S. aureus (MRSA) clinical isolate. During our studies, we also demonstrated that these halogenated quionlines operate through an interesting metal(II) cation-dependent mechanism and display promising mammalian cytotoxicity.
A facile synthesis of 2-methylquinolines via Pd-catalyzed aza-Wacker oxidative cyclization
Zhang, Zuhui,Tan, Jiajing,Wang, Zhiyong
, p. 173 - 175 (2008/09/18)
(Chemical Equation Presented) A novel Pd-catalyzed Wacker-type oxidative cyclization under air is described. By using this cyclization, a series of 2-methylquinolines are readily prepared with good yields under mild conditions.