A study of fluorinated β-nitrostyrenes as antimicrobial agents

Applied Sciences (Switzerland)

Volumn 2, Issue 1, 2012, Pages 114-128

  Lo, King ^a   Cornell, Hugh ^a   Nicoletti, Gina ^a   Jackson, Neale ^a   Hügel, Helmut ^a  

^a RMIT UNIVERSITY   (Australia)

Author keywords

Antimicrobial agents; Fluoro methyl nitrostyrenes; Henry reaction; Log P values; MIC; Partition coefficients

Indexed keywords

EID: 84872298371     PISSN: None     EISSN: 20763417     Source Type: Journal    
DOI: 10.3390/app2010114     Document Type: Article

References (27)

1. Payne, D.J.; Gwynn, M.N.; Holmes, D.J.; Pompliano, D.L. Drugs for bad bugs: Confronting the challenges of antibacterial discovery. Nat. Rev. Drug Discov. 2007, 6, 29-40
2. Schales, O.; Graefe, H.A. Arylnitroalkenes: A new group of antibacterial agents. J. Am. Chem. Soc. 1952, 74, 4486-4490
3. Denisenko, P.P.; Sapronov, N.S.; Tarasenko, A.A. Antimicrobial and radioprotective compounds. Patent No. 20040266844, issued on 30 December 2004
4. Milhazes, N.; Calheiros, R.; Marques, M.P.M.; Garrido, J.; Cordeiro, M.N.D.S.; Rodrigues, C.; Quinteira, S.; Novais, C.; Peixe, L.; Borges, F. β-Nitrostyrene derivatives as potential antibacterial agents: A structure-property-activity relationship study. Bioorg. Med. Chem. 2006, 14, 4078-4088
5. Bialy, L.; Waldmann, H. Inhibitors of protein tyrosine phosphatases: Next-generation drugs? Angew. Chem. Int. Ed. 2005, 44, 3814-3839
6. Heneberg, P. Use of protein tyrosine phosphatase inhibitors as promising targeted therapeutic drugs. Curr. Med. Chem. 2009, 16, 706-733
7. Zhang, S.; Zhang, Z.-Y. PTP1B as a drug target: Recent developments in PTP1B inhibitor discovery. Drug Discov. Today 2007, 12, 373-381
8. Park, J.; Pei, D. Trans-β-nitrostyrene derivatives as slow-binding inhibitors of protein tyrosine phosphatases. Biochemistry 2004, 43, 15014-15021
9. Jung, G.; Fouad, H.; Heusel, G. 2-Nitro-1-phenylethyl: A new protecting and chiroptical reporter group for cysteine peptides. Angew. Chem. Int. Ed. 1975, 14, 817-818
10. Hwu, J.R.; Wong, F.F.; Shiao, M.-J. Reduction of aromatic nitro compounds to aromatic amines by sodium trimethylsilanethiolate. J. Org. Chem. 1992, 57, 5254-5255
11. Berner, O.M.; Tedeschi, L.; Enders, D. Asymmetric Michael additions to nitroalkenes. Eur. J. Org. Chem. 2002, 67, 1877-1894
12. Baker, L.M.S.; Baker, P.R.S.; Golin-Bisello, F.; Schopfer, F.J.; Fink, M.; Woodcock, S.R.; Branchaud, B.P.; Radi, R.; Freeman, B.A. Nitro-fatty acid reaction with glutathione and cysteine: Kinetic analysis of thiol alkylation by a Michael addition reaction. J. Biol. Chem. 2007, 282, 31085-31093
13. Bernasconi, C.F.; Schuck, D.F. Kinetics of reversible thiolate ion addition to substituted beta-nitrostyrenes in water. Radicaloid transition state or principle of nonperfect synchronization? J. Org. Chem. 1992, 57, 2365-2373
14. Nicoletti, G.; Cornell, H.; Hügel, H.; White, K.S.; Nguyen, T.; Zalizniak, L. Synthesis and biological activity of nitropropenyl arenes. 2012, in preparation
15. Ojima, I. Fluorine in Medicinal Chemistry and Chemical Biology; Wiley-Blackwell: Chichester, UK, 2009
16. Smart, B.E. Fluorine substituent effects (on bioactivity). J. Fluorine Chem. 2001, 109, 3-11
17. Giménez, D.; Andreu, C.; del Olmo, M.; Varea, T.; Diaz, D.; Asensio, G. The introduction of fluorine atoms or trifluoromethyl groups in short cationic peptides enhances their antimicrobial activity. Bioorg. Med. Chem. 2006, 14, 6971-6978
18. Cherian, J.; Choi, I.; Nayyar, A.; Manjunatha, U.H.; Mukherjee, T.; Lee, Y.S.; Boshoff, H.I.; Singh, R.; Ha, Y.H.; Goodwin, M.; et al. Structure-activity relationships of antitubercular nitroimidazoles. 3. Exploration of the linker and lipohilic tail of ((S)-2-nitro-6,7-dihydro-5Himidazo[ 2,1-b][1,3]oxazin-6-yl)-(4-trifluoromethoxybenzyl)amine (6-amino PA-824). J. Med. Chem. 2011, 54, 5639-5659
19. Boonyawan, D.; Sarapirom, S.; Tunma, S.; Chaiwong, C.; Rachtanapun, P.; Auras, R. Characterization and antimicrobial properties of fluorine-rich carbon films deposited on poly(lactic acid). Surf. Coat. Technol. 2011, 205, S552-S557
20. Privett, B.J.; Youn, J.; Hong, SA.; Lee, J.; Han, J.; Shin, J.H.; Schoenfisch, M.H. Antibacterial fluorinated silica colloid superhydrophobic surfaces. Langmuir 2011, 27, 9597-9601
21. Gadakh, A.V.; Pandit, C.; Rindhe, S.S.; Karale, B.K. Synthesis and antimicrobial activity of novel fluorine containing 4-(substituted-2-hydroxybenzoyl)-H-pyrazoles and pyrazolyl benzo[d]oxazoles. Bioorg. Med. Chem. Lett. 2010, 20, 5572-5576
22. Luzzio, F.A. The Henry Reaction: Recent examples. Tetrahedron 2001, 57, 915-945
23. Werbel, L.M.; Cook, P.D.; Elslager, E.F.; Hung, J.H.; Johnson, J.L.; Kesten, S.J.; McNamara, D.J.; Ortwine, D.F.; Worth, D.F. Antimalarial drugs. 60. Synthesis, antimalarial activity, and quantitative structure-activity relationships of tebuquine and a series of related 5-[(7-chloro-4-quinolinyl)amino]-3-[(alkylamino)methyl][1,1'-biphenyl]-2-ols and N-oxides. J. Med. Chem. 1986, 29, 924-39
24. Cote, A.; Lindsay, V.N.G.; Charette, A.B. Application of the chiral bis(phosphine) monoxide ligand to catalytic enantioselective addition of dialkylzinc reagents to beta-nitroalkenes. Org. Lett. 2007, 9, 85-87
25. Bergner, I.; Opatz, T. Modular one-pot synthesis of tetrasubstituted pyrroles from alpha-(alkylideneamino)nitriles. J. Org. Chem. 2007, 72, 7083-7090
26. NCCLS. Reference Method for Broth Dilution Susceptibility Testing of Yeasts; Approved Standard 2nd ed.; National Committee for Clinical Laboratory Standards: Wayne, PA, USA, 2002; M27-A2; Volume 22:15
27. NCCLS. National Committee for Clinical Laboratory Standards. Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Document M7-A6. NCCLS, Wayne, PA, USA, 2003; Volume 22