Synthesis and antibacterial evaluation of a new series of N-Alkyl-2-alkynyl/(E)-alkenyl-4-(1H)-quinolones

Molecules

Volumn 17, Issue 7, 2012, Pages 8217-8240

  Wube, Abraham ^a   Guzman, Juan David ^b,c   Hüfner, Antje ^a   Hochfellner, Christina ^a   Blunder, Martina ^a   Bauer, Rudolf ^a   Gibbons, Simon ^c   Bhakta, Sanjib ^b   Bucar, Franz ^a  

^a UNIVERSITY OF GRAZ   (Austria)

^b UNIVERSITY OF LONDON   (United Kingdom)

^c UNIVERSITY OF LONDON   (United Kingdom)

Author keywords

Antimycobacterial; Cytotoxicity; MRSA; N alkyl 2 alkynyl (E) alkenyl 4(1H) quinolone

Indexed keywords

ANTIINFECTIVE AGENT; QUINOLONE DERIVATIVE;

ARTICLE; CELL DEATH; CELL LINE; CHEMISTRY; DRUG EFFECT; HUMAN; MICROBIOLOGICAL EXAMINATION; MYCOBACTERIUM SMEGMATIS; SYNTHESIS;

ANTI-BACTERIAL AGENTS; CELL DEATH; CELL LINE; HUMANS; MICROBIAL SENSITIVITY TESTS; MYCOBACTERIUM SMEGMATIS; QUINOLONES;

EID: 84864623309     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17078217     Document Type: Article

References (24)

1. Comroe, J.H. Pay Dirt: The Story of Streptomycin. Part I: From Waksman to Waksman. Am. Rev. Respir. Dis. 1978, 117, 773-781.
2. Guzman, J.D.; Gupta, A.; Bucar, F.; Gibbons, S.; Bhakta, S. Antimycobacterials from Natural Sources: Ancient times, Antibiotic era and Novel Scaffolds. Front. Biosci. 2012, 17, 1861-1881.
3. Ruiz, J. Mechanisms of Resistance to Quinolones: Target Alterations, Decreased Accumulation and DNA Gyrase Protection. J. Antimicrob. Chemother. 2003, 51, 1109-1117. (Pubitemid 36622067)
4. WHO. Available online: http://www.who.int/tb/challenges/en/ (accessed on 3 March 2012).
5. Saraf, L.J.; Wilson, S.E. Telavancin, a New Lipoglycopeptide Antimicrobial, in Complicated Skin and Soft Tissue Infections. Infect. Drug Resist. 2011, 4, 87-95.
6. Gordon, E.; Flouret, B.; Chantalat, L.; van Heijenoort, J.; Mengin-Lecreulx, D.; Diseberg, O. Crystal Structure of UDP-N-Acetylmuramoyl-L- Alanyl-D-Glutamate-Meso-Diaminopimelate Ligase from Escherichia coli. J. Biol. Chem. 2001, 276, 10999-11006. (Pubitemid 38089280)
7. Guzman, J.D.; Wube, A.; Evangelopoulos, D.; Gupta, A.; Hüfner, A.; Basavannacharya, C.; Raman, M.M.; Thomaschitz, C.; Bauer, R.; McHugh, T.D.; et al. Interaction of N-Methyl-2-Alkenyl-4-Quinolones with ATP-Dependent MurE Ligase of Mycobacterium tuberculosis: Antibacterial Activity, Molecular Docking and Inhibition Kinetics. J. Antimicrob. Chemother. 2011, 66, 1766-1772.
8. Adams, M.; Wube, A.A.; Bucar, F.; Bauer, R.; Kunert, O.; Haslinger, E. Quinolone Alkaloids from Euodia rutaecarpa: A Potent New Group of Antimycobacterial Compounds. Int. J. Antimicrob. Agents 2005, 26, 262-264. (Pubitemid 41219616)
9. Adams, M.; Bauer, R.; Bucar, F.; Wube, A.A. Pharmaceutical Preparation for Treating Mycobacterial Infections with 4-quinolones from Euodia rutaecarpa. WO 2006094327, 14 September 2006.
10. Wube, A.A.; Hüfner, A.; Thomaschitz, C.; Blunder, M.; Kollroser, M.; Bauer, R.; Bucar, F. Design, Synthesis and Antimycobacterial Activities of 1-methyl-2-alkenyl-4(1H)-Quinolones. Bioorg. Med. Chem. 2011, 19, 567-579.
11. Wube, A.A.; Bucar, F.; Hochfellner, C.; Blunder, M.; Bauer, R.; Hüfner, A. Synthesis of N-Substituted 2-[(1E)-alkenyl]-4-(1H)-Quinolone Derivatives as Antimycobacterial Agents Against Non-Tubercular Mycobacteria. Eur. J. Med. Chem. 2011, 46, 2091-2101.
12. Gillespie, S.H.; Kennedy, H. Fluoroquinolones: A New Treatment for Tuberculosis? Int. J. Tuberc. Lung Dis. 1998, 2, 265-271. (Pubitemid 28168302)
13. Zhou, L.; Chen, L.; Skouta, R.; Jiang, H.-F.; Li, C.-J. Palladium-Catalyzed 1,4-Addition of Terminal Alkynes to Unsaturated Carbonyl Compounds Promoted by Electron-Rich Ligand. Org. Biomolec. Chem. 2008, 6, 2969-2977.
14. Xing, Y.; O'Doherty, G.A. De Novo Asymmetric Synthesis of Cladospolide B-D: Structural Reassignment of Cladospolide D via the Synthesis of Its Enantiomer. Org. Lett. 2009, 11, 1107-1110.
15. Rai, D.; Johar, M.; Manning, T.; Agrawal, B.; Kunimoto, D.Y.; Kumar, R. Design and Studies of Novel 5-Substituted Alkynylpyrimidine Nucleosides as Potent Inhibitors of Mycobacteria. J. Med. Chem. 2005, 48, 7012-7017. (Pubitemid 41533123)
16. Kidwai, M.; Jain, R.; Bhardwaj, S. 1, 4-Addition of Terminal Alkynes to Conjugated Enones in Water Using Green Catalyst Bis[(L)Prolinato-N,O]Zn-an Environmentally Benign Protocol. Catal. Lett. 2011, 141, 183-190.
17. Zhang, D.; Ready, I.M. Iron-Catalyzed Carbometalation of Propargylic and Homopropargylic Alcohols. J. Am. Chem. Soc. 2006, 128, 15050-15051. (Pubitemid 44853494)
18. Trost, B.M.; Ball, Z.T.; Laemmerhold, K.M. An Alkyne Hydrosilylation- Oxidation Strategy for the Selective Installation of Oxygen Functionality. J. Am. Chem. Soc. 2005, 127, 10028-10038. (Pubitemid 40995445)
19. Banaszak, E.; Xu, L.-W.; Bardeau, J.-F.; Castanet, A.-S.; Mortie, J. First Syntheses of Model long-Chain Trichloro[U-(Trimethylsilyl)Alkynyl]Silanes Suitable for Self-assembled Monolayers on Silicon Surfaces. Tetrahedron 2009, 65, 3961-3966.
20. Novotný, J.; Pospěchová, K.; Hrabálek, A.; Čáp, R.; Vávrová, K. Synthesis of Fluorescent C24-Ceramide: Evidence for Acyl Chain Length Dependent Differences in Penetration of Exogenous NBD-Ceramides into Human Skin. Bioorg. Med. Chem. Lett. 2009, 19, 6975-6977.
21. Houghton, S.A.; Furst, L.; Boddy, C.N. Biomimetic Transannular Oxa-conjugated Addition Approach to the 2,6-Disubstituted Dihydropyran of Laulimalide Yields an Unprecedented Transannular Oxetane. J. Org. Chem. 2009, 74, 1454-1463.
22. Porter, N.A.; Chang, V.H.-T.; Magnin, D.R.; Wright, B.T. Free Radical Macrocyclization-Transannular Cyclization. J. Am. Chem. Soc. 1988, 110, 3554-3560.
23. Wube, A.A.; Bucar, F.; Gibbons, S.; Asres, K. Sesquiterpenes from Warburgia ugandensis and their Antimycobacterial Activity. Phytochemistry 2005, 66, 2309-2315. (Pubitemid 41405814)
24. Evangelopoulos, D.; Bhakta, S. Rapid Methods for Testing Inhibitors of Mycobacterial Growth. In Antibiotic Resistance Protocols; Methods in Molecular Biology Human Press: London, UK, 2010; p. 279.