Abstract
7-Trifluoromethyl-4-hydroxy quinoline-3-carboxylic acid ethyl ester was prepared from 3-amino benzotrifluoride and EMME. The hydroxyquinoline was reacted with amino acids to furnish amino acid funtionalised quinolines (5, 6, 7). The compounds were alkylated by ethyl iodide followed by hydrolysis afforded the title compounds in good yields. They were screened for their antibacterial activity for in vitro against Gram +ve and Gram −ve bacterial strains and found 11e and 11b as promising compounds.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Bridges AJ, Domagala JM (1988) 8-trifluoromethyl quinolones as antibacterial agents. US Patent 4,780,468, 25 Oct 1988
Chu DTW, Prabhavathi BF, Akiyo KC, Pihuleae E, Nordeen CW, Maleczka RE, Pernet AG (1985) Synthesis and structure–activity relationships of novel arylfluoroquinolone antibacterial agents. J Med Chem 28:1558–1564
Filler R et al (eds) (1993) Organofluorine compounds in medicinal chemistry and biomedical applications. Elsevier, Amsterdam, pp 165
Hooper DC, Wolfson JS (1993) Quinolone antimicrobial agents, 2nd edn. American Society for Microbiology, Washington, DC, pp 3–51
Koga H, Itoh A, Murayama S, Suzue S, Irikura T (1980) Structure–activity relationships of antibacterial 6, 7- and 7, 8-disubstituted 1-alkyl-1,4-dihydro-4-oxoquinoline-3-carboxylic acids. J Med Chem 23:1358–1363
Lopez SE, Rebollo O, Salazar J, Charris JE, Yanez C (2003) Synthesis of 2-trifluoromethyl-1 (substituted aryl)-4(1H)-quinolones using trifluoroacetamidoyl chlorides. J Fluor Chem 120:71–75
Matsumoto J, Miyamoto T, Minamida A, Nishimura Y, Egawa H, Nishimura H (1984) 1,4-dihydro-4-oxopyridine carboxylic acids as antibacterial agents. Synthesis and structure activity relationships of 1,6,7-trisubstituted 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids including enoxacin, a new antibacterial agent. J Med Chem 27:292–301
Radl S, Bouzard D (1992) Recent advances in the synthesis of antibacterial quinolones. Heterocycles 34:2143
Sanchez JP, Bridges AJ, Bucsh R, Domagala JM, Gogliotti RD, Hagen SE, Heifetz CL, Joannides ET, Sesnie JC (1992) New 8-(trifluoromethyl)-substituted quinolones. The benefits of the 8-fluoro group with reduced phototoxic risk. J Med Chem 35:361–367
Uray G, Niederreiter K (2003) Luminescent 4-trifluoromethyl 1-2-quinolones with longwave UV absorption and use thereof. US Patent 6,635,759, 21 Oct 2003
Venkat Reddy G, Ravikanth S, Maitraie D, Narsaiah B, Shanthan Rao P, Harakishore K, Murthy USN, Ravi B, Ashok kumar B, Parthasarathy T (2009) Design, synthesis, structure–activity relationship and antibacterial activity series of novel imidazo fused quinolones carboxamides. Eur J Med Chem 44:1570–1578
Violetta C, Cristina P, Stefano M, Teresa P, Enrica F, Arianna C, Oriana T, Barbara G, Manlio P, Arnaldo F, Giorgio P (2000) 6-Aminoquinolones as new potential anti-HIV agents. J Med Chem 43:3799–3802
Wise R, Andrews JM, Edwards LJ (1983) In vitro activity of Bay 09867, a quinoline derivative, compared with these of other antimicrobial agents. Antimicrob Agents Chemother 23:559–564
Acknowledgments
The authors are thankful to Dr. J.S.Yadav, Director, IICT, Hyderabad for his constant encouragement and support.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Venkat Lingaiah, B.P., Yakaiah, T., Ravi Kumar, A. et al. Synthesis of novel optically pure α-amino acid functionalised-7-trifluoromethyl substituted quinolone derivatives and their antibacterial activity. Med Chem Res 22, 186–194 (2013). https://doi.org/10.1007/s00044-012-0020-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-012-0020-3