Design and synthesis of anti-MRSA benzimidazolylbenzenesulfonamides. QSAR studies for prediction of antibacterial activity

Molecules

Volumn 16, Issue 1, 2011, Pages 175-189

  González Chávez, Marco Martín ^a,b   Méndez, Francisco ^c   Martínez, Roberto ^d   Pérez González, Cuaúhtemoc ^e   Martínez Gutiérrez, Fidel ^b  

^a UNIVERSIDAD AUTÓNOMA METROPOLITANA   (Mexico)

^b UNIVERSIDAD AUTÓNOMA DE SAN LUIS POTOSÍ   (Mexico)

^c DEPARTAMENTO DE QUÍMICA   (Mexico)

^d UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

^e DEPARTAMENTO DE SISTEMAS BIOLÓGICOS   (Mexico)

Author keywords

Antibacterial activity; Benzimidazole; MRSA; Sulphonamide

Indexed keywords

EID: 79251480096     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules16010175     Document Type: Article

References (22)

1. Jones, M. E.; Blosser-Middleton, R. S.; Thornsberry, C.; Karlowsky, J. A.; Sahm, D. F. The activity of levofloxacin and other antimicrobials against clinical isolates of Streptococcus pneumoniae collected worldwide during 1999-2002. Diagn. Microbiol. Infect. Dis. 2003, 47, 579-586.
2. Fouda, S. I.; Kadry, A. A.; Shibl, A. M. Beta-lactam and macrolide resistance and serotype distribution among Streptococcus pneumoniae isolates from Saudi Arabia. J. Chemother. 2004, 16, 517-523.
3. Jenkins, S. G.; Farrell, D. J.; Patel, M.; Lavin, B. S. Trends in anti-bacterial resistance among Streptococcus pneumonia isolated in the USA, 2000-2003: PROTEK US years 1-3. J. Infect. 2005, 51, 355-363.
4. Krcméry, V.; Sefton, A. Vancomycin resistance in Gram-positive bacteria other than Enterococcus spp. Int. J. Antimicrob. Agents 2000, 14, 99-105.
5. Cuellar-Rodríguez, J.; Galindo-Fraga, A.; Guevara, V.; Pérez-Jiménez, C.; Espinosa-Aguilar, L.; Rolón, A. L.; Hernández-Cruz, A.; López-Jácome, E.; Bobadilla-del-Valle, M.; Martínez Gamboa, A.; Ponce-de-León, A.; Sifuentes-Osorio, J. Vancomycin-resistant enterococci, México City. Emerg. Infect. Dis. 2007, 13, 798-799.
6. Kaye, K. S.; Engemann, J. J.; Fraimow, H. S.; Abrutyn, E. Pathogens resistant to antimicrobial agents:epidemiology, molecular mechanisms, and clinical management. Infect. Dis. Clin. North. Am. 2004, 18, 467-511.
7. Tenover, F. C. Mechanisms of antimicrobial resistance in bacteria. Amer. J. Med. 2006, 119, S3-S10.
8. Murthy, A.; De Angelis, G.; Pittet, D.; Schrenzel, J.; Uckay, I.; Harbarth, S. Cost-effectiveness of universal MRSA screening on admission to surgery. Clin. Microbiol Infect. 2010, 16, 1747-1753.
9. Weidner-Well, M. A.; Ohemeng, K. A.; Nguyen, V. N.; Fraga-Spano, S.; Macielag, M. J.; Werblood, H. M.; Foleno, B. D.; Webb, G. C., Barret, J. F.; Hlasta, D. J. Amidino Benzimidazole inhibitors of bacterial two-component systems. Bioorg. Med. Chem. Lett. 2001, 11, 1545-1548.
10. Bürli, R. W.; McMinn, D.; Kaizerman, J. A.; Hu, W.; Ge, Y.; Pack, Q.; Jiang, V.; Gross, M.; Garcia, M.; Tanaka, R.; Moser, H. E. DNA binding ligands targeting drug-resistant Gram-positive bacteria. Part 1: internal benzimidazole derivatives. Bioorg. Med. Chem. Lett. 2004, 14, 1253-1257. (Pubitemid 38229867)
11. Hu, L.; Kully, ML.; Boykin, D. W.; Abood, N. Optimization of the central linker of dicationic bisbenzimidazole anti-MRSA and anti-VRE agents. Bioorg. Med. Chem. Lett. 2009, 19, 3374-3377.
12. Zimmerman, S.; Innocenti, A.; Casini, A.; Ferry, J. G.; Scozzafava, A.; Supuran, C. T. Carbonic anhydrase inhibitors. Inhibition of the prokaryotic beta and gamma-class enzymes from Archaea with sulfonamides. Bioorg. Med. Chem. Lett. 2004, 14, 6001-6006.
13. Isik, K.; Özdemir-Kocak, F. Antimicrobial activity screening of some sulfonamides on some Nocardia species and isolates. Microbiol Res. 2009, 164, 49-58.
14. Hauel, N. H.; Nar, H.; Priepke, H.; Ries, U.; Stassen, J.-M.; Wienen, W. Structure-based design of novel potent nonpeptide thrombin inhibitors. J. Med. Chem. 2002, 45, 1757-1766.
15. McCauley, J. A.; Theberge, C. R.; Romano, J. J.; Billings, SB.; Anderson, K. D.; Claremon, D. A.; Freidinger, R. M.; Bednar, R. A.; Mosser, S. D.; Gaul, S. L.; Connolly, T. M.; Condra, C. L.; Xia, M.; Cunningham, M. E.; Bednar, B.; Stump, G. L.; Lynch, J. J.; Macaulay, A.; Wafford, K. A.; Koblan, K. S.; Liverton, N. J. NR2B-Selective N-methyl-D-aspartate antagonists: synthesis and evaluation of 5-substituted benzimidazoles. J. Med. Chem. 2004, 47, 2089-2096.
16. Schuster, D.; Maurer, E. M.; Laggner, C.; Nashev, L. G.; Wilckens, T.; Langer, T.; Odermatt. A. The discovery of new 11 β-Hydroxysteroid dehydrogenase type 1 inhibitors by common feature pharmacophore modelling and virtual screening. J. Med. Chem. 2006, 49, 3454-3466.
17. Middleton, T.; Lim, H. B.; Montgomery, D.; Rockway, T.; Tang, H.; Cheng, X.; Lu, L.; Mo, H.; Kohlbrenner, W. E.; Molla, A.; Kati, W. M. Inhibition of human immunodeficiency virus type I integrase by naphthamidines and 2-aminobenzimidazoles. Antivir. Res. 2004, 64, 35-45.
18. National Committee for Clinical Laboratory Standards. Methods for Dilution Antimicrobial Susceptibility Test for Bacteria that Grow Aerobically; Approved Standard M7-A4, 4th ed.; National Committee for Clinical Laboratory Standards: Villanova, PA, USA, 1997.
19. Frisch, M. J.; Trucks, GW.; Schlegel, H. B.; Scuseria, GE.; Robb, M. A.; Cheeseman, JR.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M.; Farkas, CO.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C; Adamo, C; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, S. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Baboul, A. G; Stefanov, B. B.; Liu, G; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. GAUSSIAN 03 (Revision A.9) ; Gaussian, Inc.: Pittsburgh, PA, USA, 2003.
20. Ören, İ.; Temiz; Ö.; Yalçin, İ.; Šener, E.; Altanlar N. Synthesis and antimicrobial activity of some novel 2, 5-and/or 6-substituted benzoxazole and benzimidzole derivatives. Eur. J. Pharm. Sci. 1998, 7, 153-160.
21. Moro, W. B.; Yang, Z.; Kane, T. A.; Zhou, Q.; Harville, S.; Brouillette, C. G.; Brouillette, W. J. SAR studie for a new class of antibacterial NAD biosynthesis inhibitors. J. Comb. Chem. 2009, 11, 617-625.
22. Romero, M. L.; Méndez, F. Is the hydrogen atomic charge representative of the acidity of parasubstituted phenols? J. Phys. Chem. A. 2003, 107, 4526-4530.