Design, Synthesis, and Biological Evaluation of Novel Pyrimido[4,5-b]indole Derivatives Against Gram-Negative Multidrug-Resistant Pathogens

Journal of Medicinal Chemistry
2021.0

Abstract

Due to the poor permeability across Gram-negative bacterial membranes and the troublesome bacterial efflux mechanism, only a few GyrB/ParE inhibitors with potent activity against Gram-negative pathogens have been reported. Among them, pyrimido[4,5-<i>b</i>]indole derivatives represented by GP-1 demonstrated excellent broad-spectrum antibacterial activity against both Gram-positive and Gram-negative bacteria but were limited by hERG inhibition and poor pharmacokinetics profile. To improve their drug-like properties, we designed a series of novel pyrimido[4,5-<i>b</i>]indole derivatives based on the tricyclic scaffold of GP-1 and the C-7 moiety of acorafloxacin. These efforts have culminated in the discovery of a promising compound <b>18r</b> with reduced hERG liability and an improved PK profile. Compound <b>18r</b> exhibited superior broad-spectrum <i>in vitro</i> antibacterial activity compared to GP-1, including a variety of clinical multidrug G<sup>-</sup> pathogens, especially <i>Acinetobacter baumannii</i>, and the <i>in vivo</i> efficacy was also demonstrated in a neutropenic mouse thigh model of infection with multidrug-resistant <i>A. baumannii</i>.

Knowledge Graph

Similar Paper

Design, Synthesis, and Biological Evaluation of Novel Pyrimido[4,5-b]indole Derivatives Against Gram-Negative Multidrug-Resistant Pathogens
Journal of Medicinal Chemistry 2021.0
Discovery of dual GyrB/ParE inhibitors active against Gram-negative bacteria
European Journal of Medicinal Chemistry 2018.0
New Broad-Spectrum Antibiotics Containing a Pyrrolobenzodiazepine Ring with Activity against Multidrug-Resistant Gram-Negative Bacteria
Journal of Medicinal Chemistry 2020.0
Design, synthesis and biological evaluation of novel indole-piperazine derivatives as antibacterial agents
Bioorganic &amp; Medicinal Chemistry Letters 2023.0
Design, synthesis and structure–activity relationship studies of novel indazole analogues as DNA gyrase inhibitors with Gram-positive antibacterial activity
Bioorganic &amp; Medicinal Chemistry Letters 2004.0
Discovery of Indazole Derivatives as a Novel Class of Bacterial Gyrase B Inhibitors
ACS Medicinal Chemistry Letters 2015.0
Discovery and Optimization of Indolyl-Containing 4-Hydroxy-2-Pyridone Type II DNA Topoisomerase Inhibitors Active against Multidrug Resistant Gram-negative Bacteria
Journal of Medicinal Chemistry 2018.0
Design, synthesis and antibacterial properties of pyrimido[4,5-b]indol-8-amine inhibitors of DNA gyrase
Bioorganic &amp; Medicinal Chemistry Letters 2018.0
Design, Synthesis, and Biological Evaluation of Novel 7-[(3aS,7aS)-3a-Aminohexahydropyrano[3,4-c]pyrrol-2(3H)-yl]-8-methoxyquinolines with Potent Antibacterial Activity against Respiratory Pathogens
Journal of Medicinal Chemistry 2018.0
Synthesis and structure-activity relationship of novel bisindole amidines active against MDR Gram-positive and Gram-negative bacteria
European Journal of Medicinal Chemistry 2018.0