Abstract
Efficient syntheses of a series of novel bisquinolines have been accomplished from 8-hydroxy quinolines under phase transfer catalyzed conditions using tetrabutylamoniumbromide as phase transfer catalyst. In vitro antibacterial and antifungal study of the synthesized analogues revealed six of them to show significant antibacterial and four to show significant antifungal activity. Among them 3c and 6c show most significant antibacterial activities with minimum inhibitory concentration value 32 μg/mL against four bacterial strains. Ultra structural studies of the microbes treated with 6c demonstrated deformation of cell wall and cell agglomeration. The bisquinolines exhibiting bacteriostatic or fungistatic activity may be developed as newer antimicrobial agents.
Similar content being viewed by others
References
Barchechath SD, Tawatao RI, Corr M, Carson DA, Cottam HB (2005) Quinolinium salt as a potent inhibitor of lymphocyte apoptosis. Bioorg Med Chem Lett 15:1785–1788
Barrow GI, Feltham RKA (1993) Cowan and steel’s manual for the identification of medical bacteria. Cambridge University Press, Cambridge
Brana MF, Cacho M, Gradillas A, Pascual-Teresa B, Ramos A (2001) Intercalators as anticancer drugs. Curr Pharm Des 7:1745–1780
Chattopadhyay D, Arunachalam G, Mandal AB, Sur KT, Mandal SC, Bhattacharya SK (2002) Antimicrobial and anti-inflammatory activity of folklore: Mallotus peltatus leaf extract. J Ethnopharmacol 82:229–237
Chikhalia KH, Patel MJ, Vashi DB (2008) Design, synthesis and evaluation of novel quinolyl chalcones as antibacterial agents. ARKIVOC xiii: 189–197
Dillard RD, Pavey DE, Benslay DN (1973) Synthesis and anti-inflammatory activity of some 2,2-dimethyl-1,2-dihydroquinolines. J Med Chem 16(3):251–253
Dominguez JN, Charris JE, Lobo G, Dominguez N, Gamboa de, Moreno MM, Riggione F, Sanchez E, Olson J, Rosenthal PJ (2001) Synthesis of quinolinyl chalcones and evaluation of their antimalarial activity. Eur J Med Chem 36:555–560
Gholap AR, Toti KS, Shirazi F, Kumari R, Bhat MK, Deshpande MV, Srinivasan KV (2007) Synthesis and evaluation of antifungal properties of a series of the novel 2-amino-5-oxo 4-phenyl-5,6,7,8-tetrahydroquinoline-3-carbonitrile and its analogues. Bioorg Med Chem 15:6705–6715
Ghosh J, Swarup V, Saxena A, Das S, Hazra A, Paira P, Banerjee S, Mondal NB, Basu A (2008) Therapeutic effect of a novel anilidoquinoline derivative, 2-(2-methyl-quinoline-4ylamino)-N-(2-chlorophenyl)-acetamide, in Japanese encephalitis: correlation with in vitro neuroprotection. Int J Antimicrob Agents 32:349–354
Girault S, Grellier P, Berecibar A, Maes L, Lemiére P, Mouray E, Davioud-Charvet E, Sergheraert C (2001) Antiplasmodial activity and cytotoxicity of bis-, tris-, and tetraquinolines with linear or cyclic amino linkers. J Med Chem 44:1658–1665
Gokhale VM, Kulkarni VM (2000) Understanding the antifungal activity of terbinafine analogues using quantitative structure–activity relationship (qsar) models. Bioorg Med Chem 8:2487–2499
Hayat MA (1981) Principles and techniques of electron microscopy, vol 1. Edward Arlond, London
Hayat F, Moseley E, Salahuddin A, Van Zyl RL, Azam A (2011) Antiprotozoal activity of chloroquinoline based chalcones. Eur J Med Chem 46:1897–1905
Holla BS, Mahalinga M, Karthikeyan MS, Akberalib PM, Shettyc NS (2006) Synthesis of some novel pyrazolo [3,4-d] pyrimidine derivatives as potential antimicrobial agents. Bioorg Med Chem 14:2040–2047
Kuo SC, Lee HZ, Juang JP, Lin YT, Wu TS, Chang JJ, Lednicer D, Paull KD, Lin CM (1993) Synthesis and cytotoxicity of 1,6,7,8-substituted 2-(4′-substituted phenyl)-4 quinolones and related compounds: identification as antimitotic agents interacting with tubulin. J Med Chem 36:1146–1156
Mahato SB, Mandal NB, Chattopadhyay S, Nandi G, Luger P, Weber M (1994) Synthesis of indolylquinolines under Friedel-Crafts reaction conditions. Tetrahedron 50:10803–10812
Martinez R, Chacon-Garcia L (2005) The search of DNA-intercalators as antitumoral drugs: what it worked and what did not work. Curr Med Chem 12:127–151
Maruoka K (2008) Practical aspects of recent asymmetric phase-transfer catalysis. Org Process Res Dev 12:679–697
McFarland J (1907) An instrument for estimating the number of bacteria in suspensions used for calculating the opsonic index and for vaccines. J Am Med Assoc 14:1176–1178
Mistry B, Jauhari S (2010) Synthesis and characterization of some quinoline based azeti-dinones and thiazolidinones as antimicrobial agents. Arch Appl Sci Res 2:332–343
Musiol R, Jampilek J, Buchta V, Silva L, Niedbala H, Podeszwa B, Palka A, Majerz-Maniecka K, Oleksyn B, Polanski J (2006) Antifungal properties of new series of quinoline derivatives. Bioorg Med Chem 14:3592–3598
Musiol R, Serda M, Hensel-Bielowka S, Polanski J (2010) Quinoline-based antifungals. Curr Med Chem 17:1960–1973
National Committee for Clinical Laboratory Standards (NCCLS) (1993) approved standard M7-A3, 3rd edn. NCCLS, Villanova
Paira P, Paira R, Hazra A, Naskar S, Sahu KB, Saha P, Mondal S, Maity A, Banerjee S, Mondal NB (2009) Facile synthesis of 6,6,8,6,6-ring fused pentacyclic heterocycles: annelation of quinolines to quinoxalines under PTC condition. Tetrahedron Lett 50:4619–4623
Paira R, Maity A, Naskar S, Mondal S, Paira P, Hazra A, Sahu KB, Saha P, Banerjee S, Mondal NB (2010) Naphtho- and benzo[g]quinoxalino-fused oxazocinoquinolinones and their diaryl and alkynyl analogues from quinolin-8-ols: a library of novel polynuclear heteroaromatics. Synthesis 20:3520–3535
Palit P, Paira P, Hazra A, Banerjee S, Das Gupta A, Ghoshdastidar S, Mondal NB (2009) Phase transfer catalyzed synthesis of bis-quinolines: antileishmanial activity in experimental visceral leishmaniasis and in vitro antibacterial evaluation. Euro J Med Chem 44:845–853
Raynes K, Foley M, Tilley L, Deady LW (1996) Novel bisquinoline antimalarials: synthesis, antimalarial activity, and inhibition of haem polymerisation. Biochem Pharmacol 52:551–559
Rhim JW, Hong SI, Ha CS (2009) Tensile, water vapor barrier and antimicrobial properties of PLA/nanoclay composite films. Food Sci Technol 42:612–617
Russell AD, Hugo WB (1994) Antimicrobial activity and action of silver. Prog Med Chem 31:351–358
Wang XY, Du YM, Yang JH, Wang XH, Shi XW, Hu Y (2006) Preparation, characterization and antimicrobial activity of chitosan/layered silicate nanocomposites. Polymer 47:6738–6744
Acknowledgments
The authors express their gratitude to the Director, IICB for laboratory facilities, the Council of Scientific and Industrial Research (CSIR) for providing the funding and fellowships to K. B. S., A. M., S. M., R. P., P. S., S. N. and A. H. We are indebted to Dr. B. Achari, Emeritus Scientist, CSIR, for his valuable suggestions.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
44_2012_11_MOESM1_ESM.docx
Supplementary data: 1H and 13C NMR spectra of all compounds associated with this article can be found in the online version (DOCX 1303 kb)
Rights and permissions
About this article
Cite this article
Sahu, K.B., Ghosh, S., Banerjee, M. et al. Synthesis and in vitro study of antibacterial, antifungal activities of some novel bisquinolines. Med Chem Res 22, 94–104 (2013). https://doi.org/10.1007/s00044-012-0011-4
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00044-012-0011-4