Synthesis and antibacterial activity of some heterocyclic chalcone analogues alone and in combination with antibiotics

Molecules

Volumn 17, Issue 6, 2012, Pages 6684-6696

  Tran, Thanh Dao ^a   Nguyen, Thi Thao Nhu ^a   Do, Tuong Ha ^b   Huynh, Thi Ngoc Phuong ^a   Tran, Cat Dong ^a   Thai, Khac Minh ^a  

^a UNIVERSITY OF MEDICINE AND PHARMACY AT HO CHI MINH CITY   (Viet Nam)

^b TON DUC THANG UNIVERSITY   (Viet Nam)

Author keywords

Antibacterial; Antibiotics combination; Chalcone; Heterocyclic chalcone analogues; MRSA; Synergitic activity; Synthesis

Indexed keywords

ANTIINFECTIVE AGENT; CHALCONE; DRUG DERIVATIVE;

ARTICLE; CHEMISTRY; DRUG EFFECT; DRUG POTENTIATION; MICROBIOLOGICAL EXAMINATION; STAPHYLOCOCCUS AUREUS; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CHALCONE; DRUG SYNERGISM; MICROBIAL SENSITIVITY TESTS; STAPHYLOCOCCUS AUREUS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84863005743     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17066697     Document Type: Article

References (36)

1. Neu, H. C. The crisis in antibiotic resistance. Science 1992, 257, 1064-1073.
2. Michel, M.; Gutmann, L. Methicillin-resistant Staphyllococus aureus and vancomycin-resistan enterococci: therapeut realities and possibilities. Lancet 1997, 349, 1901-1906. (Pubitemid 27270132)
3. Normark, B. H.; Normark, S. Evolution and spread of antibiotic resistance. J. Intern. Med. 2002, 252, 91-106. (Pubitemid 34989270)
4. Shekarchi, M.; Pirali-Hamedani, M.; Navidpour, L.; Adib, N.; Shafiee, A. Synthesis, Antibacterial and Antifungal Activities of 3-Aryl-5-(pyridin-3-yl)-4, 5-dihydropyrazole-1-carbothioamide Derivatives. J. Iran. Chem. Soc. 2008, 5, 150-158.
5. Silverman, R. B. Organic Chemistry of Drug Design and Drug Action; Academic Press: San Diego, CA, USA, 1992.
6. Thompson, L. A.; Ellman, J. A. Synthesis and applications of small molecule libraries. Chem. Rev. 1996, 96, 555-600. (Pubitemid 126637733)
7. Alcaraz, L. E.; Blanco, S. E.; Puig, O. N.; Tomas, F.; Ferretti, F. H. Antibacterial activity of Flavonoids against methicillin-resistant Staphylococcus aureus strains. J. Theor. Biol. 2000, 205, 231-240. (Pubitemid 30662922)
8. Baviskar, B. A.; Baviskar, B.; Shiradkar, M. R.; Deokate, U. A.; Khadabadi, S. S. Antimicrobial activity of some novel. Benzimidazolyl chalcones. E-J. Chem. 2009, 6, 196-200.
9. Echeverria, C.; Santibañez, J. F.; Donoso-Tauda, O.; Escobar, C. A.; Ramirez-Tagle, R. Structural antitumoral activity relationships of synthetic chalcones. Int. J. Mol. Sci. 2009, 10, 221-231.
10. Modzelewska, A.; Pettit, C.; Achanta, G.; Davidson, N. E.; Huang, P.; Khan S. R. Anticancer activities of novel chalcone and bis-chalcone derivatives. Bioorg. Med. Chem. 2006, 14, 3491-3495.
11. Vogel, S.; Heilmann, J. Synthesis, cytotoxicity, and antioxidative activity of minor prenylated chalcones from Humulus lupulus. J. Nat. Prod. 2008, 71, 1237-1241.
12. Babasaheb, P. B.; Sachin, A. P.; Rajesh, N. G. Synthesis and biological evaluation of nitrogencontaining chalcones as possible anti-inflammatory and antioxidant agents. Bioorg. Med. Chem. Lett. 2010, 20, 730-733.
13. Vogel, S.; Barbic, M.; Jürgenliemk, G.; Heilmann, J. Synthesis, cytotoxicity, anti-oxidative and anti-inflammatory activity of chalcones and influence of A-ring modifications on the pharmacological effect. Eur. J. Med. Chem. 2010, 45, 2206-2213.
14. Tran, T.-D.; Park, H.; Kim, H. P.; Ecker, G. F.; Thai, K.-M. Inhibitory activity of prostaglandin E2 production by the synthetic 2'-hydroxychalcone analogues: Synthesis and SAR study. Bioorg. Med. Chem. Lett. 2009, 19, 1650-1653.
15. Beom-Tae, K.; Kwang-Joong, O.; Jae-Chul, C.; Ki-Jun, H. Synthesis of dihydroxylated chalcone derivatives with diverse substitution patterns and their radical scavenging ability toward DPPH free radicals. Bull. Korean Chem. Soc. 2008, 29, 1125-1130.
16. Doan, T. N.; Tran, T.-D. Synthesis, antioxidant and antimicrobial activities of a novel series of chalcones, pyrazolic chalcones, and allylic chalcones. Pharmacol. Pharm. 2011, 2, 282-288.
17. Sivakumar, P. M.; Prabhakar, P. K.; Doble, M. Synthesis, antioxidant evaluation, and quantitative structure-activity relationship studies of chalcones. Med. Chem. Res. 2011, 20, 482-492.
18. Vogel, S.; Ohmayer, S.; Brunner, G.; Heilmann, J. Natural and non-natural prenylated chalcones: synthesis, cytotoxicity and anti-oxidative activity. Bioorg. Med. Chem. 2008, 16, 4286-4293. (Pubitemid 351539046)
19. Munawar, M. A.; Azad, M.; Siddiqui, H. L. Synthesis and antimicrobial studies of some quinolinylpyrimidine derivatives. J. Chin. Soc. 2008, 55, 394-400.
20. Azad, M.; Munawar, M. A.; Siddiqui, H. L. Antimicrobial activity and synthesis of quinoline-base chalcones. J. Appl. Sci. 2007, 7, 2485-2489.
21. Kalirajan, R.; Sivakumar, S. U.; Jubie, S.; Gowramma, B.; Suresh, B. Synthesis and biological evaluation of some heterocyclic derivatives of chalcones. Int. J. ChemTech Res. 2009, 1, 27-34.
22. Talia, J. M.; Debattista, N. B.; Pappano, N. B. New antimicrobial combinations: Substituted chalcones-oxacillin against methicillin resistant Staphylococcus aureus. Braz. J Microbiol. 2011, 42, 470-475.
23. Eumkeb, G.; Siriwong, S.; Phitaktim, S.; Rojtinnakorn, N.; Sakdarat, S. Synergistic activity and mode of action of flavonoids isolated from smaller galangal and amoxicillin combinations against amoxicillin-resistant Escherichia coli. J. Appl. Microbiol. 2012, 112, 55-64.
24. Sato, Y.; Shibata, H.; Arakaki, N.; Higuti, T. 6, 7-dihydroxyflavone dramatically intensifies the susceptibility of methicillin-resistant or -sensitive Staphylococcus aureus to beta-lactams. Antimicrob. Agents Chemother. 2004, 48, 1357-1360. (Pubitemid 38405495)
25. Liu, M. H.; Otsuka, N.; Noyori, K.; Shiota, S.; Ogawa, W.; Kuroda, T.; Hatano, T.; Tsuchiya, T. Synergistic effect of kaempferol glycosides purified from Laurus nobilis and fluoroquinolones on methicillin-resistant Staphylococcus aureus. Biol. Pharm. Bull. 2009, 32, 489-492.
26. Tiwari, B.; Pratapwar, A. S.; Tapas, A. R.; Butle, S. R.; Vatkar, B. S. Synthesis and antimicrobial activity of some chalcone derivatives. Int. J. ChemTech Res. 2010, 2, 499-503.
27. Sivakumar, P. M.; Priya, S.; Doble, M. Synthesis, biological evaluation, mechanism of action and quantitative structure-activity relationship studies of chalcones as antibacterial agents. Chem. Biol. Drug Des. 2009, 73, 403-415.
28. Zheng, C. J.; Jiang, S. M.; Chen, Z. H.; Ye, B. J.; Piao, H. R. Synthesis and anti-bacterial activity of some heterocyclic chalcone derivatives bearing thiofuran, furan, and quinoline moieties. Arch. Pharm. Chem. Life Sci. 2011, 344, 689-695.
29. Lopez, S. N.; Castelli, M. V.; Zacchino, S. A.; Domnguez, J. N.; Lobo, G.; Charris-Charris, J.; Cortes, J. C. G.; Ribas, J. C.; Devia, C.; Rodrguez, A. M.; et al. In Vitro Antifungal evaluation and structure-activity relationships of a new series of chalcone derivatives and synthetic analogues, with inhibitory properties against polymers of the fungal cell wall. Bioorg. Med. Chem. 2001, 9, 1999-2013. (Pubitemid 32739188)
30. Funiss, B. S.; Hannford, A. J.; Smith, P. W. G.; Tatchell, A. R. Vogel's Textbook of Practical Organic Chemistry, 5th ed.; Prentice Hall: Upper Saddle River: NJ, USA, 2004; pp. 1032-1035.
31. National Committee for Clinical Laboratory Standards. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts. Approved Standard M27-A2, 3rd ed.; NCCLS: Wayne, PA, USA, 2002; Volume 22, No. 15, pp. 1-30.
32. Bauer, A. W.; Kirby, W. M. M.; Sherris, J. C.; Turck, M. Antibiotic Susceptibility Testing by a Standardized Single Disk Method. Am. J. Clin. Pathol. 1966, 36, 493-496.
33. Jorgensen, J. H.; Turnidge, J. D. Manual of Clinical Microbiology, 9th ed.; Murray, P. R., Baron, E. J., Jorgensen, J. H., Landry, M. L., Pfaller, M. A., Eds.; ASM Press: Washington, DC, USA, 2007; pp. 1152-1172.
34. National Committee for Clinical Laboratory Standards. Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically. Approved standard M7-A6, 6th ed.; NCCLS: Wayne, PA, USA, 2003.
35. National Committee for Clinical Laboratory Standards. Performance Standards for Antimicrobial Susceptibility Testing. Informational supplement M100-S13, 12th ed.; NCCLS: Wayne, PA, USA, 2003.
36. Bajaksouzian, S.; Visalli, M. A.; Jacobs, MR.; Appelbaum, PC. Activities of levofloxacin, ofloxacin, and ciprofloxacin, alone and in combination with amikacin, against acinetobacters as determined by checkerboard and time-kill studies. Antimicrob. Agents Chemother. 1997, 41, 1073-1076. (Pubitemid 27194188)