Abstract
A series of quaternary ammonium derivatives of triazolyl pyranochromen-2-ones have been synthesized and characterized; their antibacterial potential were investigated against two gram negative (Pseudomonas aeruginosa and Escherichia coli) and two gram positive bacterial strains (Bacillus cereus and Staphylococcus aureus). In order to develop structure-activity relationship (SAR), the effect of varying the substituent (R) at the C-10 position of pyranochromen-2-one as well as the length of the spacer (n) between the triazolyl pyranochromen-2-ones and quaternary ammonium group, on the antibacterial activity of compounds has been evaluated. Some of the screened compounds exhibited antibacterial potential against the studied strains in the microgram range.
Similar content being viewed by others
References
McDonnell G and Russell A D 1999 Antiseptics and Disinfectants: Activity, Action, and Resistance Clin. Microbiol. Rev. 12 147
Demberelnyamba D, Kim K, Choi S, Park S Y, Lee H, Kimb C J and Yoo I D 2004 Synthesis and antimicrobial properties of imidazolium and pyrrolidinonium salts Bioorg. Med. Chem. 12 853
Kourai H, Yabuhara T, Shirai A, Maeda T and Nagamune H 2006 Syntheses and antimicrobial activities of a series of new bis-quaternary ammonium compounds Eur. J. Med. Chem. 41 437
Thorsteinsson T, Masson M, Kristinsson K G, Hjalmarsdottir M A, Hilmarsson H and Loftsson T 2003 Soft antimicrobial agents: synthesis and activity of labile environmentally friendly long chain quaternary ammonium compounds J. Med. Chem. 46 4173
Gilbert P and Al-Taae A 1985 Antimicrobial activity of some alkyl-trimethyl ammonium bromides Lett. Appl. Microbiol. 1 101
Bradbury B J and Pucci M J 2008 Recent advances in bacterial topoisomerase inhibitors Curr. Opin. Pharmacol. 8 574
Patrick L, Ferroud D, Klich M, Dupuis-Hamelin C, Mauvais P, Lassaigne P, Bonnefoy A and Musicki B 1999 Synthesis and in vitro evaluation of novel highly potent coumarin inhibitors of gyrase B Bioorg. Med. Chem. Lett. 9 2079
Gupta S, Singh S, Kathuria A, Kumar M, Sharma S, Kumar R, Parmar V S, Singh B, Gupta A, Eycken E V D, Sharma G L and Sharma S K 2012 Ammonium derivatives of chromenones and quinolinones as lead antimicrobial agents J. Chem. Sci. 124 437
Singh S, Gupta S, Singh B, Sharma S K, Gupta V K and Sharma G L 2012 Proteomic characterization of Aspergillus fumigatus treated with an antifungal coumarin for identification of novel target molecules of key pathways J. Proteome Res. 11 3259
Singh S, Dabur R, Gatne M M, Singh B, Gupta S, Pawar S, Sharma S K and Sharma G L 2014 In vivo efficacy of a synthetic coumarin derivative in a murine model of Aspergillosis PLoS One 9 103039
Prasad S, Kumar S, Kumar B, Singh A K, Gautam H K and Sharma S K 2015 Quaternary ammonium and amido derivatives of pyranochromenones and chromenones: Synthesis and antimicrobial activity evaluation Med. Chem. Res. 24 2297
Damu G L V, Cui S F, Peng X M, Wen Q M, Cai G X and Zhou C H 2014 Synthesis and bioactive evaluation of a novel series of coumarinazoles Bioorg. Med. Chem. Lett. 24 3605
Shi Y and Zhou C H 2011 Synthesis and evaluation of a class of new coumarin triazole derivatives as potential antimicrobial agents Bioorg. Med. Chem. Lett. 21 956
Ronad P M, Noolvi M N, Sapkal S, Dharbhamulla S and Maddi V S 2010 Synthesis and antimicrobial activity of 7-(2-substituted phenylthiazolidinyl)-benzopyran-2-one derivatives Eur. J. Med. Chem. 45 85
Raghu M, Nagaraj A and Reddy C S 2009 Synthesis and in vitro study of novel bis-[3-(2-arylmethylidenimino- 1,3-thiazol-4-yl)-4-hydroxy-2H-chromen-2-one-6-yl] methane and bis-[3-(2-arylidenhydrazo-1,3-thiazol-4-yl)-4-hydroxy-2H-chromen-2-one-6-yl]methane as potential antimicrobial agents J. Heterocycl. Chem. 46 261
Zhou C and Wang Y 2012 Recent researches in triazole compounds as medicinal drugs Curr. Med. Chem. 19 239
Ahluwalia V K, Arora K K and Jolly R S 1982 Acid-catalysed condensation of isoprene with phenols. Formation of 2,2-dimethylchromans J. Chem. Soc. Perkin Trans. 1 335
Pechmann H V and Duisberg C 1883 Uber die verbindungen der phenole mit acetessigather Chem. Ber. 16 2119
Waykole P and Usgaonkar R N 1982 Novel compounds from 4-formyl-6,7-dihydroxanthyletins: Synthesis of furobenzopyrandicarboxylic acids, 2- oxohexahydrofurofurobenzopyrans and 1-dihydroxanthyletinylmethyl-2-oxohexahydropyranobenzofuropyrrole Indian J. Chem. Sect B 8 707
Pathak R, Kumar R and Gautam H K 2013 Cross-species induction and enhancement of antimicrobial properties in response to gamma irradiation in Exiguobacterium sp. HKG 126 Indian J. Microbiol. 53 130
Yadav S, Mahato M, Pathak R, Jha D, Kumar B, Deka S R, Gautam H K and Sharma A K 2014 Multifunctional self-assembled cationic peptide nanostructures efficiently carry plasmid DNA in vitro and exhibit antimicrobial activity with minimal toxicity J. Mater. Chem. B 2 4848
Ciornei C D, Sigurdardottir T, Schmidtchen A and Bodelsson M 2005 Antimicrobial and chemoattractant activity, lipopolysaccharide neutralization, cytotoxicity and inhibition by serum of analogs of Human cathelicidin LL-37 Antimicrob. Agents Chemother. 49 2845
Dobrovolskaia M A, Clogston J D, Neun B W, Hall J B, Patri A K and McNeil S E 2008 Method for analysis of nanopaticle hemolytic properties in vitro Nano Lett. 8 2180
Himo F, Lovell T, Hilgarf R, Rostovtsev V V, Noodleman L, Sharpless K B and Fokin V V 2005 Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates J. Am. Chem. Soc. 127 210
Acknowledgements
We gratefully acknowledge the financial assistance from the University of Delhi for the DU-DST PURSE Grant and Council of Scientific and Industrial Research (CSIR) task force project (BSC0302). The author PY is thankful to Council of Scientific and Industrial Research (CSIR, New Delhi) for the award of Junior/Senior Research Fellowships.
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
YADAV, P., KUMAR, B., GAUTAM, H.K. et al. Synthesis and antibacterial activity screening of quaternary ammonium derivatives of triazolyl pyranochromenones. J Chem Sci 129, 211–222 (2017). https://doi.org/10.1007/s12039-016-1214-x
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12039-016-1214-x