C-2 phenyl replacements to obtain potent quinoline-based Staphylococcus aureus NorA inhibitors

References

• WHO. Antimicrobial resistance. Bull World Health Organ 2014; 61:383–94.
   Google Scholar
• Ten threats to global health in 2019. Available from: https://www.who.int/emergencies/ten-threats-to-global-health-in-2019 [last accessed 7 Apr 2019].
   Google Scholar
• Opperman TJ, Nguyen ST. Recent advances toward a molecular mechanism of efflux pump inhibition. Front Microbiol 2015;6:1–16.
   PubMed Web of Science ®Google Scholar
• Piddock LJV. Understanding the basis of antibiotic resistance: a platform for drug discovery. Microbiology 2014;160:2366–73.
   PubMed Web of Science ®Google Scholar
• Wright GD. Antibiotic adjuvants: rescuing antibiotics from resistance. Trends Microbiol 2016;24:862–71.
   PubMed Web of Science ®Google Scholar
• Brown D. Antibiotic resistance breakers: can repurposed drugs fill the antibiotic discovery void? Nat Rev Drug Discov 2015;14:821–32.
   PubMed Web of Science ®Google Scholar
• Piddock LJV. Multidrug-resistance efflux pumps - not just for resistance. Nat Rev Microbiol 2006; 4:629–36.
   PubMed Web of Science ®Google Scholar
• Ricci V, Tzakas P, Buckley A, et al. Ciprofloxacin-resistant Salmonella enterica serovar typhimurium strains are difficult to select in the absence of AcrB and TolC. Antimicrob Agents Chemother 2006;50:38–42.
   PubMed Web of Science ®Google Scholar
• Zhang Q, Lambert G, Liao D, et al. Acceleration of emergence of bacterial antibiotic resistance in connected microenvironments. Science 2011;333:1764–7.
   PubMed Web of Science ®Google Scholar
• Schillaci D, Spanò V, Parrino B, et al. Pharmaceutical approaches to target antibiotic resistance mechanisms. J Med Chem 2017;60:8268–97.
   PubMed Web of Science ®Google Scholar
• Boucher HW, Talbot GH, Bradley JS, et al. Bad bugs, no drugs: no ESKAPE! an update from the Infectious Diseases Society of America. Clin Infect Dis 2009;48:1–12.
   PubMed Web of Science ®Google Scholar
• Schindler BD, Kaatz GW. Multidrug efflux pumps of Gram-positive bacteria. Drug Resist Updat 2016;27:1–13.
   PubMed Web of Science ®Google Scholar
• Singh S, Kalia NP, Joshi P, et al. Boeravinone B, a novel dual inhibitor of NorA bacterial efflux pump of Staphylococcus aureus and human P-glycoprotein, reduces the biofilm formation and intracellular invasion of bacteria. Front Microbiol 2017;8:1868.
   PubMed Web of Science ®Google Scholar
• Lepri S, Buonerba F, Goracci L, et al. Indole based weapons to fight antibiotic resistance: a structure-activity relationship study. J Med Chem 2016;59:867–91.
   PubMed Web of Science ®Google Scholar
• Schindler BD, Jacinto P, Kaatz GW. Inhibition of drug efflux pumps in Staphylococcus aureus: current status of potentiating existing antibiotics. Future Microbiol 2013;8:491–507.
   PubMed Web of Science ®Google Scholar
• Rath SK, Singh S, Kumar S, et al. Synthesis of amides from (E)-3-(1-chloro-3,4-dihydronaphthalen-2-yl)acrylic acid and substituted amino acid esters as NorA efflux pump inhibitors of Staphylococcus aureus. Bioorg Med Chem 2019;27:343–53.
   PubMed Web of Science ®Google Scholar
• Sabatini S, Gosetto F, Iraci N, et al. Re-evolution of the 2-phenylquinolines: ligand-based design, synthesis, and biological evaluation of a potent new class of Staphylococcus aureus NorA efflux pump inhibitors to combat antimicrobial resistance. J Med Chem 2013;56:4975–89.
   PubMed Web of Science ®Google Scholar
• Astolfi A, Felicetti T, Iraci N, et al. Pharmacophore-based repositioning of approved drugs as novel Staphylococcus aureus NorA efflux pump inhibitors. J Med Chem 2017;60:1598–604.
   PubMed Web of Science ®Google Scholar
• Felicetti T, Cannalire R, Pietrella D, et al. 2-Phenylquinoline S. aureus NorA efflux pump inhibitors: evaluation of the importance of methoxy group introduction. J Med Chem 2018;61:7827–48.
   PubMed Web of Science ®Google Scholar
• Felicetti T, Cannalire R, Nizi MG, et al. Studies on 2-phenylquinoline Staphylococcus aureus NorA efflux pump inhibitors: new insights on the C-6 position. Eur J Med Chem 2018;155:428–33.
   PubMed Web of Science ®Google Scholar
• Cannalire R, Machado D, Felicetti T, et al. Natural isoflavone biochanin A as a template for the design of new and potent 3-phenylquinolone efflux inhibitors against Mycobacterium avium. Eur J Med Chem 2017; 140:321–30.
   PubMed Web of Science ®Google Scholar
• Felicetti T, Machado D, Cannalire R, et al. Modifications on C6 and C7 positions of 3-phenylquinolone efflux pump inhibitors led to potent and safe antimycobacterial treatment adjuvants. ACS Infect Dis 2019; 5:982–1000.
   PubMed Web of Science ®Google Scholar
• Sabatini S, Gosetto F, Manfroni G, et al. Evolution from a natural flavones nucleus to obtain 2-(4-propoxyphenyl)quinoline derivatives as potent inhibitors of the S. aureus NorA efflux pump. J Med Chem 2011; 54:5722–36.
   PubMed Web of Science ®Google Scholar
• Jones CP, Anderson KW, Buchwald SL. Sequential Cu-catalyzed amidation-base-mediated camps cyclization: a two-step synthesis of 2-aryl-4-quinolones from o-halophenones. J Org Chem 2007; 72:7968–73.
   PubMed Web of Science ®Google Scholar
• Chanda T, Chowdhury S, Ramulu BJ, et al. Regioselective quadruple domino aldolization/aldol condensation/Michael/SNAr-cyclization: construction of hexacyclic indeno-fused C-nor-D-homo-steroid frameworks. Tetrahedron 2014; 70:2190–4.
   Web of Science ®Google Scholar
• Kumar S, Kumar D. Polystyrene-supported iodobenzene diacetate (PSIBD)-mediated synthesis of 1,2-diacylbenzenes from 2-hydroxyaryl aldehyde/ketone acylhydrazones. Synth Commun 2008; 38:3683–99.
   Web of Science ®Google Scholar
• Santhi J, Baire B. Carbonyl directed regioselective hydration of alkynes under Ag-catalysis. ChemistrySelect 2017; 2:4338–42.
   Web of Science ®Google Scholar
• CLSI. M07-A10: methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; Approved Standard – Tenth edition. Wayne (PA): Clinical and Laboratory Standards Institute; 2015.
   Google Scholar
• Isenberg HD. Clinical microbiology procedures handbook. Washington (DC): ASM; 1992.
   Google Scholar
• Kaatz GW, Seo SM, O'Brien L, et al. Evidence for the existence of a multidrug efflux transporter distinct from NorA in Staphylococcus aureus. Antimicrob Agents Chemother 2000; 44:1404–6.
   PubMed Web of Science ®Google Scholar
• Chongsiriwatana NP, Patch JA, Czyzewski AM, et al. Peptoids that mimic the structure, function, and mechanism of helical antimicrobial peptides. Proc Natl Acad Sci USA 2008; 105:2794–9.
   PubMed Web of Science ®Google Scholar
• Schrödinger Release 2016-2: Maestro, version 10.6. New York (NY): Schrödinger, LLC; 2016.
   Google Scholar
• Cruciani G, Carosati E, De Boeck B, et al. MetaSite: understanding metabolism in human cytochromes from the perspective of the chemist. J Med Chem 2005; 48:6970–9.
   PubMed Web of Science ®Google Scholar
• See SAR version 5.5-2017. Sankt Augustin (Germany): BioSolveIT GmbH. Available from: www.biosolveit.de.
   Google Scholar
• Bietz S, Urbaczek S, Schulz B, et al. Protoss: a holistic approach to predict tautomers and protonation states in protein-ligand complexes. J Cheminform 2014; 6:12.
   PubMed Web of Science ®Google Scholar
• Optibrium. Available from: http://www.optibrium.com/stardrop.
   Google Scholar
• Brouwer C, Jenko K, Zoghbi SS, et al. Development of N-methyl-(2-arylquinolin-4-yl)oxypropanamides as leads to PET radioligands for translocator protein (18 kDa). J Med Chem 2014; 57:6240–51.
   PubMed Web of Science ®Google Scholar
• Kaatz GW, Seo SM. Mechanisms of fluoroquinolone resistance in genetically related strains of Staphylococcus aureus. Antimicrob Agents Chemother 1997; 41:2733–7.
   PubMed Web of Science ®Google Scholar
• Rasko DA, Sperandio V. Anti-virulence strategies to combat bacteria-mediated disease. Nat Rev Drug Discov 2010; 9:117–28.
   PubMed Web of Science ®Google Scholar
• Odds FC. Editorial synergy, antagonism, and what the chequerboard puts between them. J Antimicrob Chemother 2003; 52:1.
   PubMed Web of Science ®Google Scholar
• Novo DJ, Perlmutter NG, Hunt RH, et al. Multiparameter flow cytometric analysis of antibiotic effects on membrane potential, membrane permeability, and bacterial counts of Staphylococcus aureus and Micrococcus luteus. Antimicrob Agents Chemother 2000; 44:827–834.
   PubMed Web of Science ®Google Scholar
• Segall MD, Barber C. Addressing toxicity risk when designing and selecting compounds in early drug discovery. Drug Discov Today 2014; 19:688–693.
   PubMed Web of Science ®Google Scholar