Synthesis, characterization and antimicrobial activity of 4-amino-1-alkyl pyridinium salts

Medicinal Chemistry Research

Volumn 21, Issue 6, 2012, Pages 694-702

  Ilangovan, A ^a   Venkatesan, P ^a   Sundararaman, M ^a   Kumar, R Rajesh ^a  

^a BHARATHIDASAN UNIVERSITY   (India)

Author keywords

4 Amino 1 alkyl pyridinium salts; Antibacterial activity; Anticandidal activity; Germ tube inhibition; Haemolytic activity; Phospholipase inhibition

Indexed keywords

4 AMINO 1 BUTYLPYRIDINIUM; 4 AMINO 1 DECYLPYRIDINIUM; 4 AMINO 1 ETHYLPYRIDINIUM; 4 AMINO 1 HEPTYLPYRIDINIUM; 4 AMINO 1 HEXADECYLPYRIDINIUM; 4 AMINO 1 HEXYLPYRIDINIUM; 4 AMINO 1 OCTYLPYRIDINIUM; 4 AMINO 1 PENTYLPYRIDINIUM; 4 AMINO 1 PROPYLPYRIDINIUM; 4 AMINO 1 TETRADECYLPYRIDINIUM; PHOSPHOLIPASE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; CANDIDA ALBICANS; CANDIDA GLABRATA; DRUG SYNTHESIS; ENZYME INHIBITION; ERYTHROCYTE; ESCHERICHIA COLI; HEMOLYSIS; HUMAN; HUMAN CELL; NONHUMAN; STAPHYLOCOCCUS AUREUS;

EID: 84861902202     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-011-9578-4     Document Type: Article

References (28)

1. Bauer AW, Kirby WMM, Sherris JC, Turok M (1966) Antibiotic susceptibility testing by a standardized single disk method. Am J Clin Pathol 45:493-496
2. Christoph T, Thorsten M, Matthias K (2010) Synthesis of 3-Alkyl pyridinium alkaloids from the arctic sponge Haliclona viscose. Mar Drugs 8:483-497
3. Ellepola AN, Samaranayake LP (1998) The effect of limited exposure to antifungal agents on the germ tube formation of oral Candida albicans. J Oral Pathol Med 27:213-219 (Pubitemid 28278867)
4. Kadir T, Gumru B, Uygun-Can B (2007) Phospholipase activity of Candida albicans isolates from patients with denture stomatitis: the influence of chlorhexidine gluconate on phospholipase production. Arch Oral Biol 52:691-696 (Pubitemid 46691298)
5. Kas'yan LI, Tarabara IN, Pal'chikov VA, Krishchik OV, Isaev AK, Kasyan AO (2005) Acylation of aminopyridines and related compounds with Endic anhydride. Russ J Org Chem 41: 1530-1538 (Pubitemid 41831042)
6. Madaan P, Tyagi VK (2008) Synthesis and characterization of the antimicrobial 4-amino-decyl pyridinium bromide cationic surfactant. Surf Rev Lett 15:531-536
7. Maeda T, Okazaki K, Nagamune H, Manabe Y, Kourai H (1998) Bactericidal Action of 4,4′-(α,ω-Polymethylenedithio)bis-(1-alkyl pyridinium iodide)s. Biol Pharm Bull 21:1057-1061 (Pubitemid 28513982)
8. Maeda T, Manabe Y, Yamamoto M, Yoshida M, Okazaki K, Nagamune H, Hiroki K (1999) Synthesis and antimicrobial characteristics of novel biocides, 4,4′-(1,6-Hexamethylene dioxydicarbonyl) bis(1-alkyl pyridinium iodide)s. Chem Pharm Bull 47:1020-1023
9. Mark C, Donglai Y, Klaus K, Adelbert B (2001) Design, synthesis, and evaluation of 9-D-Ribityl-1, 3, 7-trihydro-2, 6, 8-purinetrione, a potent Inhibitor of riboflavin synthase and lumazine synthase. J Org Chem 66:8320-8327
10. Morgunova E, Saller S, Hasse I, Cushman M, Bacher A, Fischer M, Ladenstein R (2007) Synthase from Candida albicans as an antifungal target enzyme structural and biochemical basis for drug Design. J Biol Chem 282:17231-17241 (Pubitemid 47093204)
11. National Committee for Clinical Laboratory Standards (NCCLS) (1997) Approved standard M27-A. Reference methods for broth dilution antifungal susceptibility testing of yeasts, NCCLS, Wayne, PA
12. National Committee for Clinical Laboratory Standards (NCCLS) (2001) Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically; approved standard, 5th edn. NCCLS document M7-A5 (ISBN 1-56238-394-9), NCCLS, Wayne, PA
13. Ng CKL, Daniel O, Widmer F, Wright LC, Sorrell TC, Jolliffe KAJ (2006) Correlation of antifungal activity with fungal phospholipase inhibition using a series of bisquaternary ammonium salts. Med Chem 49:811-816 (Pubitemid 43157508)
14. Ng CKL, Singhal V, Widmer F, Wright LC, Sorrell TC, Jolliffe KA (2007) Synthesis, antifungal and haemolytic activity of a series of bis(pyridinium)alkanes. Bioorg Med Chem 15:3422-3429 (Pubitemid 46546637)
15. Obando D, Pantarat N, Handke R, Koda Y, Widmer F, Djordjevic JT, Ellis D, Sorrell TC, Jolliffe KA (2009) Synthesis, antifungal, haemolytic and cytotoxic activities of a series of bis(alkypyridinium) alkanes. Bioorg Med Chem 17:6329-6339
16. Okazaki K, Maeda T, Nagamune H, Manabe Y, Kourai H (1997) Synthesis and antimicrobial characteristics of 4, 4'-(α, ω-Polymethylenedithio) bis(1-alkyl pyridinium iodide)s. Chem Pharm Bull 45:1970-1974 (Pubitemid 28047307)
17. Parag M, Vinod KT (2008) Quaternary pyridinium salts: a review. J Oleo Sci 57:197-215
18. Pillay MK, Jeyaraman R, Nallu M, Venuvanalingam P, Ramalingam M (1997) Kinetic and theoretical studies on the reaction of phenacyl bromide with 4dmap in the presence of certain phenols. Indian J Chem 36A:414-417 (Pubitemid 127516996)
19. Runyoro KBD, Matee IM, Ngassapa DO, Joseph CC, Mbwambo ZH (2006) Screening of Tanzanian medicinal plants for anti-Candida activity. BMC Complement Altern Med 6:11
20. Samaranayake LP, Raeside JM, MacFarlane TW (1984) Factors affecting the phospholipase activity of Candida species in vitro. Sabouraudia 22:201-207 (Pubitemid 14075279)
21. Seethalakshmi T, Venkatesan P, Butcher RJ, Nallu M, Kaliannan P (2006a) 1-Allyl-4-aminopyridinium bromide. Acta Cryst E62:o4730-o4731 (Pubitemid 44571542)
22. Seethalakshmi T, Venkatesan P, Kaliannan P, Fronczek FR, Thamotharan S (2006b) 4-Amino -(1-ethoxycarbonylmethyl) pyridinium iodide. Acta Cryst E62:o2560-o2562
23. Sundar TV, Parthasarathi V, Sridhar B, Venkatesan P, Nallu M (2006) 2-Amino-1-(4-Nitrobenzyl) pyridinium bromide. Acta Cryst E62:o74-o76
24. Thorsteinsson T, Masson M, Kristinsson KG, Hjalmarsdottir MA, Hilmarsson H, Loftsson T (2003) Soft antimicrobial agents: synthesis and activity of labile environmentally friendly long chain quaternary ammonium compounds. J Med Chem 46: 4173-4181 (Pubitemid 37122459)
25. Vildan A, Sulunay P, Huseyin T, Ercin E (2009) Synthesis and antimicrobial activity of some pyridinium salts. Molecules 14:5203-5215
26. White TC, Marr KA, Bowden RA (1998) Clinical, cellular and molecular factors that contribute to antifungal drug resistance. Clin Microbiol Rev 11:382-402 (Pubitemid 28197359)
27. Zhao T, Sun G (2006) Synthesis and characterization of antimicrobial cationic surfactants: aminopyridinium salts. J Surfactants Deterg 9:325-330 (Pubitemid 46101915)
28. Zhao T, Sun G (2008) Hydrophobicity and antimicrobial activities of quaternary pyridinium salts. J Appl Microbiol 104:824-830 (Pubitemid 351257750)