In vitro antibacterial and antifungal activity of salicylanilide pyrazine-2-carboxylates

Medicinal Chemistry

Volumn 8, Issue 4, 2012, Pages 732-741

  Krátký, Martin ^a   Vinšová, Jarmila ^a   Buchta, Vladimír ^a,b  

^a Charles University in Prague Faculty of Pharmacy   (Czech Republic)

^b CHARLES UNIVERSITY   (Czech Republic)

Author keywords

Antibacterial activity; Antifungal activity; In vitro activity; Pyrazine 2 carboxylic acid ester; Salicylanilide; Salicylanilide ester

Indexed keywords

2 (4 BROMOPHENYLCARBAMOYL) 4 CHLOROPHENYL PYRAZINE 2 CARBOXYLATE; 5 CHLORO 2( 3 CHLOROPHENYLCARBAMOYL)PHENYL PYRAZINE 2 CARBOXYLATE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; CARBOXYLIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL THERAPY; ARTICLE; BACTERIAL STRAIN; CONTROLLED STUDY; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; IN VITRO STUDY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL;

ANTI-BACTERIAL AGENTS; ANTIFUNGAL AGENTS; FUNGI; GRAM-NEGATIVE BACTERIA; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; PYRAZINES; SALICYLANILIDES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84863745983     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/157340612801216346     Document Type: Article

References (39)

1. Gould, I. M. Antibiotic resistance: the perfect storm. Int. J. Antimicrob. Agents, 2009, 34, S2-S5.
2. Mielke, M. Prevention and control of nosocomial infections and resistance to antibiotics in Europe - Primum non-nocere: Elements of successful prevention and control of healthcare-associated infections. Int. J. Med. Microbiol., 2010, 300, 346-350.
3. Rehm, S. J.; Tice, A. Staphylococcus aureus: Methicillin-Susceptible S. aureus to Methicillin-Resistant S. aureus and Vancomycin-Resistant S. aureus. Clin. Infect. Dis., 2010, 51, S176-S182.
4. Welte, T.; Pletz, M. W. Antimicrobial treatment of nosocomial meticillin-resistant Staphylococcus aureus (MRSA) pneumonia: current and future options. Int. J. Antimicrob. Agents, 2010, 36, 391-400.
5. Morschhäuser, J. Regulation of multidrug resistance in pathogenic fungi. Fungal Genet. Biol., 2010, 47, 94-106.
6. Dahlgren, M. K.; Kauppi, A. M.; Olsson, I. M.; Linusson, A.; Elofsson, M. Design, synthesis, and multivariate quantitative structureactivity relationship of salicylanilides - potent inhibitors of type III secretion in Yersinia. J. Med. Chem., 2007, 50, 6177-6188.
7. De La Fuente, R.; Sonawane, N. D.; Arumainayagam, D.; Verkman, A. S. Small molecules with antimicrobial activity against E. coli and P. aeruginosa identified by high-throughput screening. Br. J. Pharmacol., 2006, 149, 551-559.
8. Hilliard, J. J.; Goldschmidt, R. M.; Licata, L.; Baum, E. Z.; Bush, K. Multiple mechanisms of action for inhibitors of histidine protein kinases from bacterial two-component systems. Antimicrob. Agents Chemother., 1999, 43, 1693-1699.
9. Hlasta, D. J.; Demers, J. P.; Foleno, B. D.; Fraga-Spano, S. A.; Guan, J.; Hilliard, J. J.; Macielag, M. J.; Ohemeng, K. A.; Sheppard, C. M.; Sui, Z. H.; Webb, G. C.; Weidner-Wells, M. A.; Werblood, H.; Barrett, J. F. Novel inhibitors of bacterial two-component systems with Gram positive antibacterial activity: Pharmacophore identification based on the screening hit closantel. Bioorg. Med. Chem. Lett., 1998, 8, 1923-1928.
10. Ienacu, I. M. C.; Lupea, A. X.; Hadaruga, D.; Hadaruga, N.; Popescu, I. M. The antimicrobial activity and quantitative structure - biological activity relationships evaluation of some novel 2-hydroxybenzamide derivatives. Rev. Chim., 2008, 59, 247-250.
11. Macielag, M. J.; Demers, J. P.; Fraga-Spano, S. A.; Hlasta, D. J.; Johnson, S. G.; Kanojia, R. M.; Russel, R. K.; Sui, Z. H.; Weidner-Wells, M. A.; Werblood, H.; Foleno, B. D.; Goldschmidt, R. M.; Loeloff, M. J.; Webb, G. C.; Barrett, J. F. Substituted salicylanilides as inhibitors of two-component regulatory systems in bacteria. J. Med. Chem., 1998, 41, 2939-2945.
12. Vinšová, J.; Imramovský, A. Salicylanilidy - stále aktuální skupina s potenciální antibakteriální aktivitou [written in Czech language]. Cesk. Slov. Farm., 2004, 53, 294-299.
13. Waisser, K.; Macháček, M.; Dostál, H.; Gregor, J.; Kubicová, L.; Klimešová, V.; Kuneš, J.; Palát, K.; Hladůvková, J.; Kaustová, J.; Mollmann, U. Relationships between the Chemical Structure of Substances and their Antimycobacterial Activity Against Atypical Strains. Part 18. 3-Phenyl-2H-1, 3-benzoxazine-2, 4 (3H)-diones and Isosteric 3-Phenylquinazoline-2, 4-(1H, 3H)-diones. Collect. Czech Chem. Commun., 1999, 24, 1902-1924.
14. Krátký, M.; Višnová, J. Salicylanilide ester prodrugs as potential antimicrobial agents - a review. Curr. Pharm. Des., 2011, 17, 3494-3505.
15. Zhang, Y.; Mitchison, D. The curious characteristics of pyrazinamide: a review. Int. J. Tuberc. Lung. Dis., 2003, 7, 6-21.
16. Lambert, P. A. Bacterial resistance to antibiotics: Modified target sites. Adv. Drug Deliv. Rev., 2005, 57, 1471-1485.
17. Speirs, R. J.; Welch, J. T.; Cynamon, M. H. Activity of n-propyl pyrazinoate against pyrazinamide-resistant Mycobacterium tuberculosis: investigations into mechanism of action of and mechanism of resistance to pyrazinamide. Antimicrob. Agents Chemother., 1995, 39, 1269-1271.
18. Jampilek, J.; Dolezal, M.; Buchta, V. Antimicrobial evaluation of some arylsulfanylpyrazinecarboxylic acid derivatives. Med. Chem., 2007, 3, 277-280.
19. Simoes, M. F.; Valente, E.; Rodríguez Gómez, M. J.; Anes, E.; Constantino, L. Lipophilic pyrazinoic acid amide and ester prodrugs. Stability, activation and activity against M. tuberculosis. Eur. J. Pharm. Sci., 2009, 37, 257-263.
20. Kung, P. P.; Casper, M. D.; Cook, K. L.; Wilson-Lingardo, L.; Risen, L. M.; Vickers, T. A.; Ranken, R.; Blyn, L. B.; Wyatt, J. R.; Dan Cook, P.; Ecker, D. J. Structure-activity relationships of novel 2-substituted quinazoline antibacterial agents. J. Med. Chem., 1999, 42, 4705-4713.
21. Guiles, J.; Jarvis, T.; Strong, S.; Sun, X. Antibacterial heterocyclic ureas. PCT Int. Appl. WO 2008011191, January 24, 2008.
22. Xia, Y.; Alley, M. R. K.; Zhou, Y.; Hernandez, V. S.; Plattner, J. J.; Ding, C. Z.; Cao, K.; Zhang, Y.-K.; Akama, T.; Sligar, J.; Benowitz, A.; Jia, G.; Ou, L.; Saraswat, N.; Ramachandran, S.; Diaper, C.; Zhang, Y.; Banda, G. R.; Nieman, J.; Keramane, M.; Mohammad, R.; Subedi, R.; Liang, H.; Singh, R. Boron-containing small molecules. PCT Int. Appl. WO 2009140309, November 19, 2009.
23. Jab, D.; Rossi, R.; Della Bruna, C.; Perrone, E.; Alpegiani, M.; Andreini, B. P.; Visentin, G.; Zarini, F.; Franceschi, G. Activity of new penems against defined MRSA strains. Bioorg. Med. Chem. Lett., 1993, 3, 2165-2170.
24. Henninger, T. C.; Macielag, M. J.; Marinelli, B. A.; Zhu, B. 3-Descladinosyl-6-O-carbamoyl and 6-O-carbonoyl macrolide antibacterial agents. PCT Int. Appl. WO 2003102010, December 11, 2003.
25. Kato, H.; Kado, N.; Yoshida, T.; Nishino, H.; Nishimoto, A. Erythromycin derivatives. PCT Int. Appl. WO 9929709, June 17, 1999.
26. Michaelis, A. F.; Maulding, H. V.; Sayada, C.; Zha, C. Targeted therapeutics and uses thereof. PCT Int. Appl. WO 2003045319, May 25, 2003.
27. Betts, M. J.; Swain, M. L. Substituted phenyloxazolidinones and their use as antibiotics. PCT Int. Appl. WO 99028317, Jun. 10, 1999.
28. Gravestock, M. B.; Hales, N. J.; Carcanague, D. R. Hydroxymethyl substituted dihydroisoxazole derivatives useful as antibiotic agents. PCT Int. Appl. WO 2004078753, September 22, 2004.
29. Dolezal, M.; Jampílek, J.; Osicka, Z.; Kuneš, J.; Buchta, V.; Víchová, P. Substituted 5-aroylpyrazine-2-carboxylic acid derivatives: synthesis and biological activity. Farmaco, 2003, 58, 1105-1111.
30. Krátký, M.; Vinšová, J.; Buchta, V.; Horvati, K.; Bösze, S.; Stolaříková, J. New amino acid esters of salicylanilides active against MDR-TB and other microbes. Eur. J. Med. Chem., 2010, 45, 6106-6113.
31. Imramovský, A.; Vinšová, J.; Férriz, J. M.; Buchta, V.; Jampílek, J. Salicylanilide esters of N-protected amino acids as novel antimicrobial agents. Bioorg. Med. Chem. Lett., 2009, 19, 348-351.
32. Vinsova, J.; Imramovsky, A.; Buchta, V.; Ceckova, M.; Dolezal, M.; Staud, F.; Jampilek, J.; Kaustova, J. Salicylanilide acetates: Synthesis and antibacterial evaluation. Molecules, 2007, 12, 1-12.
33. Clinical and Laboratory Standards Institute (CLSI): Methods for Dilution Antimicrobial Susceptibility Test for Bacteria That Growth Aerobically; Approved Standard - Seventh Edition. http://www.clsi.org/source/orders/free/m11a7.pdf (Accessed March 7, 2011).
34. Clinical and Laboratory Standards Institute (CLSI): Reference Method for Broth Dilution Antifungal Susceptibility Testing of Filamentous Fungi; Approved Standard - Second Edition. http://www.clsi.org/source/orders/free/M38-a2.pdf (Accessed March 7, 2011).
35. Clinical and Laboratory Standards Institute (CLSI): Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts; Approved Standard - Third Edition. http://www.clsi.org/source/orders/free/M27-A3.pdf (Accessed March 7, 2011).
36. Gelmetti, C. Local antibiotics in dermatology. Dermatol. Ther., 2008, 21, 187-195.
37. Hamada, Y.; Takeuchi, I.; Ito, Y.; Matsui, S.; Ito, T. On the antimicrobial activity and syntheses of salicylanilide derivatives. Yakugaku Zasshi, 1981, 101, 633-641.
38. Yoon, M. Y.; Lee, K. M.; Jeong, S. H.; Kim, J.; Yoon, S. S. Heterogeneous virulence potential and high antibiotic resistance of Pseudomonas aeruginosa Strains Isolated from Korean Pneumonia Patients. J. Microbiol., 2010, 48, 518-525.
39. Ozawa, I.; Takeuchi, I.; Yamamoto, K.; Hamada, Y.; Ito, T.; Kuwahara, M.; Takagaki, T. Synthesis and antimicrobial activity of salicylanilide derivatives. 2. Chem. Pharm. Bull., 1984, 2, 305-312.