Abstract
A new series of phthalazine-based 1,2,3-triazole derivatives (5a–h, 6a–f and 7a–d) were synthesized from the corresponding 2-(4-methyl/chloro benzyloxy) benzoic acid by multi-step reactions. Synthesized compounds were characterized by spectral studies and C, H, N analysis. The final compounds were screened for their antimicrobial, antifungal and antioxidant activity. Among them compounds 5c, 5g, 5h, 6b and 6e showed good antibacterial activity as compared to the standard drug streptomycin,whereas compounds 5g and 6d showed good antifungal activity comparable to the standard drug Fluconazole. Compounds 5a, 5f and 7c showed significant antioxidant property when compared with the standard butylated hydroxytoluene.
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References
Ashok D, Mohan GD, Srinivas G, Vikas KA (2014) Microwave-assisted synthesis of novel 1,2,3-triazole derivatives and their antimicrobial activity. Med Chem Res 23:3005–3301
Aurelien M, Vincent R, Jan Balzarini, Robert S, Graciela A, Luigi AA (2011) Synthesis of new C5-(1-substituted-1,2,3-triazol-4 or 5-yl)-2′-deoxyuridines and their antiviral evaluation. Eur J Med Chem 46:778–786
Beth AA, Milwood M, David WW, Christine JM (2000) Comparative evaluation of PASCO and National Committee for Clinical Laboratory Standards M27—a broth microdilution methods for antifungal drug susceptibility testing of yeasts. J Clin Microbiol 38:2254–2260
Brand-Williams W, Cuvelier ME, Berset C (1995) Use of a free radical method to evaluate antioxidant activity. LWT-Food Sci. Technol 28:25–30
Chung-Kyu Ryu, Rae-Eun Park, Mi-Young Ma, Ji-Hee Nho (2007) Synthesis and antifungal activity of 6-arylamino-phthalazine-5,8-diones and 6,7-bis(arylthio)-phthalazine-5,8-diones. Bioorg Med Chem Letters 17:2577–2580
Desai AC, Desai CM (1980) Studies on the synthesis of heterocyclic compounds. Part II synthesis of 1-hydroxy and 1-aryl-3-substistuted-4-keto-3,4-hydroxy-4-aryl and 1,4-dihydroxy phthalazines. J Ind Chem Soc 57(7):757–758
Hichem E, Riadh S, Guy GC, Lionel Q, Daniel S, Christian G (2013) Synthesis and in vitro evaluation of potential anticancer activity of mono- and bis-1,2,3-triazole derivatives of bis-alkynes. Eur J Med Chem 60:360–364
Ibrahim HS, Eldehna WM, Abdel-Aziz HA, Elaasser MM, Abdel-Aziz MM (2014) Improvement of antibacterial activity of some sulfa drugs through linkage to certain phthalazin-1(2H)-one scaffolds. Eur J Med Chem 85:480–486
Joshi HD, Upadhyay PS, Baxi AJ (2000) Studies on 4-thiazolidinones–Synthesis and pharmacological activity of 1,4-bis[2′methy/ethy/phenyl-2′-substituted styryl-5′-H/methyl/carboxymethyl-4-thiazolidinon-3′-ylamino] phthalazines. Ind J Chem 39B:967–970
Khalil AM, Berghot MA, Gouda MA (2009) Synthesis and antibacterial activity of some new heterocycles incorporating phthalazine. Eur J Med Chem 44:4448–4454
Leandro R, Andrew M, Olivier P, Auxiliadora CK, Helen Stoeckli-Evans, Kurt Hostettmann (1995) Antibacterial phloroglucinols and flavonoids from Hypericum brasiliense. Phytochem 40:1447–1452
MacLowry JD, Jaqua MJ, Selepak ST (1970) Detailed methodology and implementation of a semiautomated serial dilution microtechnique for antimicrobial susceptibility testing. Appl Microbiol 20:46–53
Maher AE, Ahmed YE, Mamdouh AT, Ibrahim EE (2012) Synthesis and antimicrobial activity of some condensed [4-(2,4,6-trimethylphenyl)-1(2h)-oxo-phthalazin-2-yl]acetic acid hydrazide. Chin J Chem 30:616–626
Portillo A, Vila R, Freixa B, Adzet T, Can-igueral S (2001) Antifungal activity of paraguayan plants used in traditional medicines. J Ethnopharmacol 76:93–98
Rama PT, Amit KY, Arya Ajay, Surendra SB, Vinita C, Sudhir KS (2010) Application of Huisgen (3+2) cycloaddition reaction: synthesis of 1-(2,3-dihydrobenzofuran-2-yl-methyl [1,2,3]-triazoles and their antitubercular evaluations. Eur J Med Chem 45:142–148
Sridhara AM, Venugopala RKR, Keshavayya J, Goud PSK, Somashekar BC, Bose P, Peethambar SK, Gaddam SK (2010) Synthesis and antimicrobial activity of 2-substituted [4-(1,3,4-oxadiazol-2-yl methyl)]phthalazin-1(2H)-one derivatives. Eur J Med Chem 45:4983–4989
Thomas KD, Adhikari AV, Shetty NS (2010) Design, synthesis and antimicrobial activities of some new quinoline derivatives carrying 1,2,3-triazole moiety. Eur J Med Chem 45:3803–381
Ulloora S, Shabaraya R, Adhikari AV (2013) Facile synthesis of new imidazo[1,2-a]pyridines carrying 1,2,3-triazoles via click chemistry and their antiepileptic studies. Bioorg Med Chem Lett 23:3368–3372
Vsevolod VR, Luke GG, Valery VF, Sharpless KB (2002) A stepwise huisgen cycloaddition process: copper(i)-catalyzed regioselective “ligation” of azides and terminal alkynes. Angew Chem 41:2596–2599
Zhao XU, Lu BW, Lu JR, Xin CW, Li JF, Liu Y (2012) Design, synthesis and antimicrobial activities of 1,2,3-triazole derivatives. Chin Chem Lett 23:933–935
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The authors are grateful to the Management, SEQUENT SCIENTIFIC LTD, New Mangalore, India, for their invaluable support and allocation of resources for this work. The authors are also thankful to the Chairman, Department of Chemistry, Mangalore University. SPC thanks to MIT, Manipal for recording spectra.
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Shyma, P.C., Kalluraya, B., Peethambar, S.K. et al. Regioselective one pot synthesis of 1,2,3-triazole derivatives bearing phthalazine moiety and their pharmacological activity. Med Chem Res 25, 2680–2690 (2016). https://doi.org/10.1007/s00044-016-1629-4
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DOI: https://doi.org/10.1007/s00044-016-1629-4