Synthesis and in vitro study of antibacterial, antifungal activities of some novel bisquinolines

Medicinal Chemistry Research

Volumn 22, Issue 1, 2013, Pages 94-104

  Sahu, Krishnendu B ^a   Ghosh, Soma ^b   Banerjee, Maitreyee ^a   Maity, Arindam ^a   Mondal, Shyamal ^a   Paira, Rupankar ^a   Saha, Pritam ^a   Naskar, Subhendu ^a   Hazra, Abhijit ^a   Banerjee, Sukdeb ^a   Samanta, Amalesh ^b   Mondal, Nirup B ^a  

^a INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

^b JADAVPUR UNIVERSITY   (India)

Author keywords

Bacteriostatic; Bisquinolines; Fungistatic; Phase transfer catalysis

Indexed keywords

1,2 BIS (5 CHLORO 8 QUINOLYLOXYMETHYL)BENZENE; 1,3 BIS (5 CHLORO 8 QUINOLYLOXYMETHYL)BENZENE; 1,3 BIS (8 QUINOLYLOXYMETHYL)BENZENE; 1,4 BIS (2 METHYL 8 QUINOLYLOXYMETHYL)BENZENE; 1,4 BIS (5 CHLORO 8 QUINOLYLOXYMETHYL)BENZENE; 1,4 BIS (8 QUINOLYL)OXYMETHYL)BENZENE; 2,3 BIS (2 METHYL 8 QUINOLYLOXYMETHYL)NAPTHALINE; 2,3 BIS (2 METHYL 8 QUINOLYLOXYMETHYL)QUINOXALINE; 2,3 BIS (5 CHLORO 8 QUINOLYLOXYMETHYL)NAPTHALINE; 2,3 BIS (5 CHLORO 8 QUINOLYLOXYMETHYL)QUINOXALINE; 2,3 BIS (8 QUINOLYLOXYMETHYL)NAPTHALINE; 2,3 BIS (8 QUINOLYLOXYMETHYL)QUINOXALINE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CELL WALL; DRUG SYNTHESIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; SCANNING ELECTRON MICROSCOPY;

EID: 84872007031     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-012-0011-4     Document Type: Article

References (30)

1. 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
2. Barrow GI, Feltham RKA (1993) Cowan and steel's manual for the identification of medical bacteria. Cambridge University Press, Cambridge
3. Brana MF, Cacho M, Gradillas A, Pascual-Teresa B, Ramos A (2001) Intercalators as anticancer drugs. Curr Pharm Des 7:1745-1780
4. 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
5. Chikhalia KH, Patel MJ, Vashi DB (2008) Design, synthesis and evaluation of novel quinolyl chalcones as antibacterial agents. ARKIVOC xiii: 189-197
6. 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
7. 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
8. 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
9. 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
10. 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
11. 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
12. Hayat MA (1981) Principles and techniques of electron microscopy, vol 1. Edward Arlond, London
13. 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
14. 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
15. 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
16. 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
17. 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
18. Maruoka K (2008) Practical aspects of recent asymmetric phase-transfer catalysis. Org Process Res Dev 12:679-697
19. 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
20. 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
21. 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
22. Musiol R, Serda M, Hensel-Bielowka S, Polanski J (2010) Quinoline-based antifungals. Curr Med Chem 17:1960-1973
23. National Committee for Clinical Laboratory Standards (NCCLS) (1993) approved standard M7-A3, 3rd edn. NCCLS, Villanova
24. 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
25. 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
26. 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
27. 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
28. 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
29. Russell AD, Hugo WB (1994) Antimicrobial activity and action of silver. Prog Med Chem 31:351-358
30. 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