Synthesis of 1H-1,2,3-triazoles and study of their antifungal and cytotoxicity activities

Medicinal Chemistry

Volumn 9, Issue 8, 2013, Pages 1085-1090

  Da Silva, Iara F ^a   Martins, Prisicila R C ^b   Da Silva, Emanuelly G ^b   Ferreira, Sabrina B ^c   Ferreira, Vitor F ^b   Da Costa, Karen Regina C ^a   De Vasconcellos, Marne C ^a   Lima, Emerson S ^a   Da Silva, Fernando De C ^b  

^a FEDERAL UNIVERSITY OF AMAZONAS   (Brazil)

^b FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

^c FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

1H 1,2,3 Triazoles; Antifungal activity; Aspergillus spp.; Candida spp.; Cytotoxicity; Microporum canis; Tricophyton rubrum

Indexed keywords

4 CARBOXALDEHYDE 1H 1,2,3 TRIAZOLE DERIVATIVE; ALKYNE; AZIDE; COPPER; DOXORUBICIN; ITRACONAZOLE; KETOCONAZOLE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ANTIFUNGAL AGENT;

ANIMAL CELL; ANTICOAGULATION; ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS NIGER; BIOCATALYSIS; CANDIDA ALBICANS; CANDIDA DUBLINIENSIS; CANDIDA KRUSEI; CANDIDA PARAPSILOSIS; CANDIDA TROPICALIS; CELL STRAIN 3T3; CONTROLLED STUDY; CYCLIZATION; DRUG CYTOTOXICITY; DRUG SYNTHESIS; IN VITRO STUDY; KLUYVEROMYCES MARXIANUS; MICROSPORUM CANIS; MINIMUM INHIBITORY CONCENTRATION; MOUSE; NONHUMAN; PRIORITY JOURNAL; RAT; TRICHOPHYTON RUBRUM; 3T3 CELL LINE; ANIMAL; CANDIDA; CHEMICAL STRUCTURE; CHEMISTRY; DOSE RESPONSE; DRUG EFFECTS; FIBROBLAST; MICROBIAL SENSITIVITY TEST; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TOXICITY; TRICHOPHYTON;

ANIMALS; ANTIFUNGAL AGENTS; ASPERGILLUS NIGER; CANDIDA; DOSE-RESPONSE RELATIONSHIP, DRUG; FIBROBLASTS; MICE; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; NIH 3T3 CELLS; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES; TRICHOPHYTON;

EID: 84890260749     PISSN: 15734064     EISSN: 18756638     Source Type: Journal    
DOI: 10.2174/1573406411309080010     Document Type: Article

References (30)

1. Perlin, D.S. Antifungal drug resistance: do molecular methods provide a way forward? Curr. Opin. Infect. Dis., 2009, 22, 568-73.
2. Cherif, A.; Sadfi-Zouaoui, N.; Eleuch, D.; Ben Osman Dhahri, A.; Boudabous, A. Pseudomonas isolates have in vitro antagonistic activity against the dermatophytes Trichophyton rubrum, Trichophyton mentagrophytes var interdigitale and Microsporum canis. J. Med. Mycol., 2009, 19, 178-84.
3. Segal, E. Candida, still number one-what do we know and where are we going from there? Mycoses, 2005, 48, 3-11.
4. Sobel, J.D.; Wiesenfeld, H.C.; Martens, M.; Danna, P.; Hooton, T.M.; Rompalo, A.; Sperling, M.; Livengood, C.; Horowitz, B.; Von Thron, J.; Edwards, L.; Panzer, H.; Chu, T. Maintenance fluconazole therapy foro recurrent vulvovaginal candidiasis. N. Engl. J. Med., 2004, 351, 876-83.
5. Heimark, L.; Shipkova, P.; Greene, J.; Munayyer, H.; Yarosh- Tomaine, T.; DiDomenico, B.; Hare, H.; Pramanik, B.N. Mechanism of azole antifungal activity as determined by liquid chromatographic/ mass spectrometric monitoring of ergosterol biosynthesis. J. Mass. Spectrom., 2002, 37, 265-9.
6. Pfaller, M.A.; Diekema, D.J.; Sheehan, D.J. Interpretative breakpoints for fluconazole and Candida revisited: a blueprint for the future of the antifungal susceptibility testing. Clin. Microbiol. Rev., 2006, 19, 435-47.
7. Spanakis, F.K.; Aperis, G.; Mylonakis, E. New agensts for the treatment of fungal infections: clinical efficacy for the treatment of fungal infections: clinical efficacy and gaps in coverage. Clin. Infect. Dis., 2006, 43, 1060-8.
8. Stevens, D.A.; Espiritu, M.; Parmar, R. Paradoxical effect of caspofungin: reduced activity against Candida albicans at high drug concentrations. Antimicrob. Agents Chemother., 2004, 48, 3407-11.
9. Trosken, E.R.; Adamska, M.; Arand, M.; Zarn, J.A.; Patten, C.; Volkel, W.; Lutz, W.K. Comparison of lanosterol-14-demethylase (CYP51) of human and Candida albicans for inhibition by different antifungal azoles. Toxicology, 2006, 228, 24-32.
10. da Silva, F.C.; de Souza, M.C.B.V.; Frugulhetti, I.C.P.P.; Castro, H.C.; Souza, S. L.O.; De Souza, T.M.L.; Rodrigues, D.Q.; Souza, A.M.T.; Abreu, P.A.; Passamani, F.; Rodrigues, C.R.; Ferreira, V. F. Synthesis, HIV-RT inhibitory activity and SAR of 1-benzyl-1H-1,2,3-triazole derivatives of carbohydrates. Eur. J. Med. Chem., 2009, 44, 373-83.
11. Boechat, N.; Ferreira, V.F.; Ferreira, S.B.; Ferreira, M.L.G.; da Silva, F.C.; Bastos, M.M.; Costa, M.S.; Lourenço, M.C.S.; Pinto, A.C.; Krettli, A.U.; Aguiar, A.C.; Teixeira, B.M.; da Silva, N.V.; Martins, P.R.C.; Bezerra, F.A.F.M.; Camilo, A.L.S.; da Silva, G.P.; Costa, C.C.P. Novel 1,2,3-triazole derivatives for use against Mycobacterium tuberculosis H37Rv (ATCC 27294) strains. J. Med. Chem., 2011, 54, 5988-99.
12. Jordão, A.K.; Ferreira, V.F.; Souza, T.M.L.; Faria, G.G.S.; Machado, V.; Abrantes, J.L.; Souza, M.C.B.V.; Cunha, A.C. Synthesis and anti-HSV-1 activity of new 1,2,3-triazole derivatives. Bioorg. Med. Chem., 2011, 19, 1860-5.
13. Kadaba, P.K. Triazolines. 1,2,3-Triazolines and triazoles, a new class of anticonvulsants. Drug design and structure-activity relationships. J. Med. Chem., 1988, 31(1), 196-203.
14. Rogawski, M.A. Diverse mechanisms of antiepileptic drugs in the development pipeline. Epilepsy Res., 2006, 69, 273-94.
15. Cunha, A.C.; Figueiredo, J.M.; Tributino, J.L.M.; Miranda, A.L.P.; Castro, H.C.; Zingali, R.B.; Fraga, C.A.M.; de Souza, M.C.B.V.; Ferreira, V.F.; Barreiro, E.J. Antiplatelet properties of novel N-substitutedphenyl-1,2,3- triazole-4-acylhydrazone derivatives. Bioorg. Med. Chem., 2003, 11, 2051-9.
16. Buckler, R.T.; Hartzler, H.E.; Kurchacova, E.; Nichols, G.; Phillips, B.M. Synthesis and antiinflammatory activity of some 1,2,3-and 1,2,4-triazolepropionic. J. Med Chem., 1978, 21, 1254-60.
17. Shafi, S.; Alam, M.M.; Mulakayala, N.; Mulakayala, C.; Vanja, G.; Kalle, A.M.; Pallu, R.; Alam, M.S. Synthesis of novel 2-mercapto benzothiazole and 1,2,3-triazole based bis-heterocycles: Their antiinflammatory and anti-nociceptive activities. Eur. J. Med. Chem., 2012, 49, 324-33.
18. Banday, A.H.; Shameem, S.A.; Ganai, B. Antimicrobial studies of unsymmetrical bis-1,2,3-triazoles. Org. Med. Chem. Lett., 2012, 2, 13-7.
19. Sumangala, V.; Poojary, B.; Chidananda, N.; Fernandes, J.; Kumari, N.S. Synthesis and antimicrobial activity of 1,2,3-triazoles containing quinoline moiety. Arch. Pharm. Res., 2010, 33, 1911-8.
20. Lima-Neto, R.G.; Cavalcante, N.N.M.; Srivastava, R.M.; Mendonça, F.J.B.; Wanderley, A.G.; Neves, R.P.; Dos Anjos, J.V. Synthesis of 1,2,3-triazole derivatives and in vitro antifungal evaluation on Candida Strains. Molecules, 2012, 17, 5882-92.
21. Micetich, R.G.; Maiti, S.N.; Spevak, P.; Hall, T.W.; Yamabe, S.; Ishida, N.; Tanaka, M.; Yamazaki, T.; Nakai, A.; Ogawa, K. Synthesis and beta-lactamase inhibitory properties of 2 beta-[(1,2,3-triazol-1-yl)methyl]-2 alpha-methylpenam-3 alpha-carboxylic acid 1,1-dioxide and related triazolyl derivatives. J. Med. Chem., 1987, 30, 1469-74.
22. Weide, T.; Saldanha, S.A.; Minond, D.; Spicer, T.P.; Fotsing, J.R.; Spaargaren, M.; Frère, J-M.; Bebrone, C.; Sharpless, K.B.; Hodder, P.S.; Fokin, V.V. NH-1,2,3-Triazole inhibitors of the VIM-2 Metallo-, -Lactamase. ACS Med. Chem. Lett., 2010, 1, 150-4.
23. Ferreira, S.B.; Sodero, A.C.R.; Cardoso, M.F.C.; Lima, E.S.; Kaiser, C.R.; Silva, F.P.; Ferreira, V.F. Synthesis, biological activity, and molecular modeling studies of 1,2,3-Triazole derivatives of carbohydrates as alfa-Glucosidases inhibitors. J. Med. Chem., 2010, 53, 2364-75.
24. Menegatti, R.; Cunha, A.C.; Ferreira, V.F.; Perreira, E.F.R.; El- Nabawi, A.; Eldefrawi, A.T.; Albuquerque, E.X.; Neves, G.; Rates, S.M.K.; Fraga, C.A.M.; Barreiro, E.J. Design, Synthesis and Pharmacological Profile of Novel Dopamine D2 Receptor Ligands. Bioorg. Med. Chem., 2003, 11, 4807-13.
25. NCCLS (National Committee for Clinical Laboratory Standards), currently Clinical and Laboratory Standards Institute (CLSI). Publication of M27-A2: reference method for broth dilution antifungal susceptibility testing of yeasts: approved standard-second edition. NCCLS, 2002, 22, 1-29.
26. Lu, H.W.; Sugahara, K.; Sagara, Y.; Masuoka, N.; Asaka, Y.; Manabe, M.; Kodama, H. Effect of three flavonoids, 5,7,3′,4′-tetrahydroxy-3- methoxy flavone, luteolin, and quercetin, on the stimulus-induced superoxide generation and tyrosyl phosphorylation of proteins in human neutrophil. Arch. Biochem. Biophys., 2001, 393,73-7.
27. Osoniyi, O.; Onajobi, F. Coagulant and anticoagulant activities in Jatropha curcas latex. J. Ethnopharmacol., 2003, 89, 101-5.
28. Stein, A.C.; Alvarez, S.; Avancini, C.; Zacchino, S.; Poser, G.V. Antifungal activity of some coumarins obtained from species of Pterocaulon (Asteraceae). Ethnopharmacology, 2006, 107, 95-8.
29. Perea, S.; Patterson, T.F. Antifungal resistance in pathogenis fungi. Antimicrob. Resist., 2002, 15, 1073-80.
30. Vandeputte, P.; Larcher, G.; Bergés, T.; Renier, G.; Chabaise, D.; Bouchara, J.P. Mechanisms of azole resistance in clinical isolate of Candida tropicalis. Antimicrob. Agents Chemother., 2005, 49, 4608-15.