BENZOKROMON VE BAZI BENZOKUMARİNLERİN ANTİOKSİDANT VE ANTİMİKROBİYAL AKTİVİTELERİ

Year 2008, Volume: 9 Issue: 2, - , 05.08.2016

Hakan Kolancılar Erkan Mozioğlu

Abstract

ANTIMICROBIAL ACTIVITIES OF SOME BENZOCOUMARINES AND BENZOCHROMONE

Abstract

Two benzocoumarins (1, 2) and a benzochromone (3) were obtained from the reaction of 2,7 dihydroxynaphthalene and ethyl acetoacetate in the presence of sulphuric acid (95-80 %) as a catalyst. These products were screened in order to assay their antimicrobial activies against standard bacterial strains such as E. coli ATCC 29995, S. S. aureus ATCC 6538P, Mycobacterum smegmatis and the yeast C. albicans ATCC 10239. Neither 1 nor 3 exhibited the antimicrobial activies against standard bacterial strains. The only 2 showed activity against S. S. aureus ATCC 6538P. Also, the antioxidant capacities of the compounds were investigated by using the CUPRAC method.

Keywords

2, 7-Dihydroxynapthalene, ethyl acetoacetate, benzocoumarin, benzochromone, antimicrobial activity, the CUPRAC method

References

• [1] Güneş M, Gören AC. Total synthesis of (±)-4'-demethylmacrophyllol, a naturally occurring compound. Nat. Prod. Res. 21: 362-365, 2007.
• [2] Laufer MC, Hausmann H. Hölderich WF. Synthesis of 7-hydroxycoumarins by Pechmann reaction using Nafion resin/silica nanocomposites as catalysts. J. Catal. 21: 315-320, 2003.
• [3] Campos-Toimil M, Orallo F, Santana L, Uriarte E. Synthesis and Vasorelaxant Activity of New Coumarin and Furocoumarin Derivatives. Bioorg. Med. Chem. Lett. 12: 783–786, 2002.
• [4] Mitra AK, Misra SK, Patra A. New Synthesis of 3-Alkyl Coumarins. Synth. Commun. 10: 915-919, 1980.
• [5] Hesse S, Kirsch G. A rapid access to coumarin derivatives (using Vilsmeier-Haack and Suzuki cross-coupling reactions). Tetrahedron Lett. 43: 1213–1215, 2002.
• [6] Sardari S, Mori Y, Horita K, Micetich RG, Nishibe S, Daneshtalab M. Synthesis and Antifungal Activity of Coumarins and Angular Furanocoumarins. Bioorg. Med. Chem. 7: 1933-1940, 1999.
• [7] Tripathi RP, Tripathi R, Bhaduri AP, Singh SN, Chatterjee RK, Murthy PK. Antifilarial activity of some 2H-1- benzopyran-2-ones (coumarins). Acta Tropica, 76: 101–106, 2000.
• [8] Alexander VM, Bhat RP, Samant SD. Bismuth(III) nitrate pentahydrate-a mild and inexpensive reagent for synthesis of coumarins under mild conditions, Tetrahedron Lett. 46: 6957–6959, 2005.
• [9] Huang W, Liu MZ, Li T, Tan Y, Yang GF. Design, syntheses, and antitumor activity of novel chromone and aurone derivatives. Bioorg. Med. Chem. 15: 5191–5197, 2007.
• [10] Nawrot-Modranka J, Nawrot E, Graczyk J. In vivo antitumor, in vitro antibacterial activity and alkylating properties of phosphorohydrazine derivatives of coumarin and chromone. Eur. J. Med. Chem. 41: 1301-1309, 2006.
• [11] Yu D, Brossi A, Kilgore N, Wild C, Allaway G, Lee KH. Anti-HIV Agents. Part 55: 3' R,4' R-Di-(O)-(-)- camphanoyl-2',2'-dimethyldihydropyrano[2,3-f]chromone(DCP), a Novel Anti-HIV Agent. Bioorg. Med. Chem. Lett. 13: 1575-1576, 2003.
• [12] Walenzyk T, Carola C, Buchholz H, König B. Chromone derivatives which bind to human hair. Tetrahedron. 61: 7366–7377, 2005.
• [13] Lee KS, Seo SH, Lee YH, Kim HD, Son MH, Chung BY, Lee JY, Jin C, Lee YS. Synthesis and biological evaluation of chromone carboxamides as calpain inhibitors. Bioorg. Med. Chem. Lett. 15: 2857–2860, 2005.
• [14] Karapire C, Kolancılar H, Oyman Ü, İçli S. Fluorescence emission and photooxidation studies with 5,6- and 6,7-benzocoumarins and a 5,6-benzochromone under direct and concentrated sun light. J. Photochem. Photobiol. A: Chem. 153: 173–184, 2002.
• [15] Li TS, Zhang ZH, Yang F, Fu CG. Montmorillonite Clay Catalysis. Part 7. An Environmentally Friendly Procedure for the Synthesis of Coumarins via Pechmann Condensation of Phenols with Ethyl Acetoacetate. J. Chem. Research (S), 38–39, 1998.
• [16] Palaniappan S, Shekhar RC. Synthesis of 7-hydroxy-4-methyl coumarin using polyaniline supported acid catalyst. J. Mol. Catal. A: Chem. 209: 117-124, 2004.
• [17] Kolancılar H. Trakya Uni. J. Scien. Research, 3(1): 7-10, 2002.
• [18] Apak R, Güçlü K, Özyürek M, Karademir SE. Novel total antioxidant capacity index for the dietary polyphenols and Vitamins C and E using their cupric ion reducing capability in the presence of neocuproine. J. Agri. Food Chem. 52: 7970-7981, 2004.
• [19] Apak R, Güçlü K, Özyürek M, Karademir, Çelik S.E. Mechanism of antioxidant capacity assays and the CUPRAC (cupric ion reducing antioxidant capacity) assay. Microchimica Acta 160(4): 413-419, 2008.
• [20] Gören AC, Topçu G, Bilsel G, Bilsel M, Wilkinson JM, Cavanagh HMA. Analysis of Essential Oil of Satureja thymbra by Hydrodistillation, Thermal Desorber and Head Space Techniques and Its Antibacterial Activity. Nat. Prod. Res. 18(2): 189-195, 2004.
• [21] National Committee for Clinical Laboratory Standards. Methods for dilution antimicrobial susceptibility test for bacteria that grow aerobically. Approved Standard M7-A2 NCCCLSi Villanova, PA, 1990.
• [22] Kavanagh F. Analytical Microbiology, S. 125, Academic pres, New York, 1963.