Synthesis and antitubercular evaluation of new 1,2,3-triazole derivatives of carbohydrates
DOI:
https://doi.org/10.13171/mjc.1.6.2012.02.05.15Abstract
We reported in this work the preparation of novel 1,4-disubstituted-1,2,3-triazoles derivatives from D-glucose and D-fructose and their in vitro antibacterial activity against Mycobacterium tuberculosis were evaluated. The chemical synthesis was performed based on the 1,3-dipolar cycloaddition reaction, and antimicrobial activity was determined based on Resazurin Microtiter Assay against Mycobacterium. None of the triazole glycoconjugates tested showed activity against these microorganisms.References
- Da Silva, F.C.; De Souza, M.C.B.V.; Frugulhetti, I.I.P.; Castro, H.C.; Souza, S.L.O.; De Souza, T.M.L.; Rodrigues, D.Q.; Souza, A.M.T.; Abreu, A.P.; Passamani, F.; Rodrigues, C.R.; Ferreira, V.F. Eur. J. Med. Chem., 2009, 44, 373.
- Genin, M.J.; Allwine, D.A.; Anderson, D.J.; Barbachyn, M.R.; Emmert, D.E.; Garmon, S.A.; Graber, D.R.; Grega, K.C.; Hester, J.B.; Hutchinson, D.K.; Morris, J.; Reischer, R.J.; Ford, C.W.; Zurenko, G.E.; Hamel, J.C.; Schaadt, R.D.; Stapert, D.; Yagi, B.H. J. Med. Chem., 2000, 43, 953.
- Buckle, D.R.; Rockell, C.J.M.; Smith, H.; Spicer, B.A. J. Med. Chem., 1986, 29, 2262.
- Carvalho, I.; Andrade, P.; Campo, V.L.; Guedes, P.M.M.; Costa, R.S.; Silva, J.S.; Schenkman, S.; Dedola, S.; Hill, L.; Rejzek, M.; Nepogodiev, S.A.; Field, R.A. Bioorg. Med. Chem., 2010, 18, 2412.
- Ferreira, S.B.; Sodero, A.C.R.; Cardoso, M.F.C.; Lima, E.S.; Kaiser, C.R.; Junior, F.P.S.; Ferreira, V.F. J. Med. Chem., 2010, 53, 2364.
- Ferreira, M.L.; De Souza, M.V.N.; Wardell, S.M.S.V.; Wardell, J.L.; Vasconcelos, T.R.A.; Ferreira, V.F.; Lourenço, M.C. Journal of Carbohydrate Chemistry, 2010, 29, 265.
- Ferreira, M.L.; Vasconcelos, T.R.A.; De Carvalho, E.M.; Lourenço, M.C.S.; Wardell, S.M.S.V.; Wardell, J.L.; Ferreira, V.F.; De Souza, M.V.N. Carbohydrate Research, 2009, 344, 2042.
- Hager, C.; Miethchen, R.; Reinke, H. Journal of Fluorine Chemistry, 2000, 104, 135.
- Reddy, L.V.R.; Reddy, P.V.; Mishra, N.N.; Shukla, P.K.; Yadav, G.; Srivastava, R.; Shaw, A.K. Carbohydrate Research, 2010, 345, 1515.
- Neu, H.C.; Science, 1992, 257, 1064.
- Travis, J.; Science, 1994, 264, 360.
- Karthikeyan, K.; Sivakumar, P.M.; Doble, M.; Perumal, P.T. Eur. J. Med. Chem., 2010, 45, 3446.
- Orme, I. Antimicrobial Agents and Chemotherapy, 2001, 45, 1943.
- Roy, B.; Mukhopadhyay, B. Tetrahedron Letters, 2007, 48, 3783.
- Beksan, E.; Schieberle, P.; Robert, F.; Blank, I.; Fay, L.B.; Cerny, H.S.; Hofmann, T. J. Agric. Food Chem. 2003, 51, 5428.
- Sato, H.; Shizuma, M. Journal of Oleo Science, 2008, 57, 503.
- Parkhouse, S.M.; Garnett, M.C.; Chan, W.C.; Bioorg. Med. Chem. 2008, 16, 6641.
- Boyer, C.; Liu, J.; Bulmus, V.; Davis, T.P.; Kowollik, C.B.; Stenzel, M.H. Macromolecules 2008, 41, 5641.
- Shen, J.; Woodward, R.; Kedenburg, J.P.; Liu, X.; Chen, M.; Fang, L.; Sun, D.; Wang, P.G. J. Med. Chem. 2008, 51, 7417.
- Devulapalle, K.S.; De Segura, A.G.; Ferrer, M.; Alcalde, M.; Mooser, G.; Plou, F.J. Carbohydrate Research, 2004, 339, 1029.
- Barradas, J.S.; Errea, M.I.; D’Accorso, N.B.; Sepúlveda, C.S.; Damonte, E.B. Carbohydrate Research, 2008, 343, 2468.
- Lu, W.; Sun, X.; Zhu, C.; Xu, J.; Lin, G. Tetrahedron, 2010, 66, 750.
- Fernandez, A.M.; Muçoz, M.O.; Jaramillo, J.L.; Mateo, F.H.; Gonzalez, F.S. Adv. Synth. Catal. 2010, 352, 3306.
- Performance standards for antimicrobial susceptibility testing. Clinical and laboratory Standards Institute. Table: M100 - S19; M02-A10; West Valley Road, Suite 1400 Wayne, PA 19087-1898 USA, 2009.
- Alviano, W.S.; Alviano, D.S.; Diniz, C.G.; Antoniolli, A.R.; Alviano, C.S.; Farias, L.M.; Carvalho, M.A.; Souza, M.M.; Bolognese, A.M. Arch. Oral Biol., 2008, 53, 545.
Downloads
Published
Issue
Section
License
Authors who publish with this journal agree to the following terms:- Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal
- Authors are able to enter into separate, additional contractual arrangements for the non-exclusive distribution of the journal's published version of the work (e.g., post it to an institutional repository or publish it in a book), with an acknowledgement of its initial publication in this journal
- Authors are permitted and encouraged to post their work online (e.g., in institutional repositories or on their website) prior to and during the submission process, as it can lead to productive exchanges, as well as earlier and greater citation of published work (See The Effect of Open Access).