Abstract
New methyl pyrazolo[5,1-c][1,2,4]benzotriazine-2-carboxylate derivatives have been synthesized under mild conditions in two steps (reductive cyclization followed by diazotation) from hydrazones obtained by condensation of dimethyl acetylenedicarboxylate and 2-nitrophenylhydrazine derivatives. The synthesized compounds exhibited moderate to good antimicrobial activity against five bacterial strains (Escherichia coli, Staphylococcus aureus, Staphylococcus epidermidis, Bacillus subtilis, and Pseudomonas aeruginosa) and two fungal strains (Saccharomyces cerevisiae and Candida albicans).
REFERENCES
Guerrini, G., Costanzo, A., Bruni, F., Selleri, S., Casilli, L., Giusti, L., Martini, C., Lucacchini, A., Malmberg Aiello, P., and Ipponi, A., Eur. J. Med. Chem., 1996, vol. 31, p. 259. https://doi.org/10.1016/0223-5234(96)80363-1
Ciciani, G., Coronnello, M., Guerrini, G., Selleri, S., Cantor, M., Failli, P., Mini, E., and Costanzo, A., Bioorg. Med. Chem., 2008, vol. 16, p. 9409. https://doi.org/10.1016/j.bmc.2008.09.055
Guerrini, G., Ciciani, G., Costanzo, A., Daniele, S., Martini, C., Ghelardini, C., Di Cesare Mannelli, L., and Ciattini, S., Bioorg. Med. Chem., 2013, vol. 21, p. 2186. https://doi.org/10.1016/j.bmc.2013.02.027
Costanzo, A., Guerrini, G., Ciciani, G., Bruni, F., Selleri, S., Costa, B., Martini, C., Lucacchini, A., Malmberg-Aiello, P., and Ipponi, A., J. Med. Chem., 1999, vol. 42, p. 2218. https://doi.org/10.1021/jm981126y
Costanzo, A., Guerrini, G., Ciciani, G., Bruni, F., Costagli, C., Selleri, S., Besnard, F., Costa, B., Martini, C., and Malmberg-Aiello, P., J. Med. Chem., 2002, vol. 45, p. 5710. https://doi.org/10.1021/jm020944u
Guerrini, G., Costanzo, A., Ciciani, G., Bruni, F., Selleri, S., Costagli, C., Besnard, F., Costa, B., Martini, C., De Siena, G., and Malmberg-Aiello, P., Bioorg. Med. Chem., 2006, vol. 14, p. 758. https://doi.org/10.1016/j.bmc.2005.08.058
Guerrini, G., Ciciani, G., Cambi, G., Bruni, F., Selleri, S., Besnard, F., Montali, M., Martini, C., Ghelardini, C., Galeotti, N., and Costanzo, A., Bioorg. Med. Chem., 2007, vol. 15, p. 2573. https://doi.org/10.1016/j.bmc.2007.01.053
Guerrini, G., Ciciani, G., Bruni, F., Selleri, S., Melani, F., Daniele, S., Martini, C., and Costanzo, A., Bioorg. Med. Chem., 2011, vol. 19, p. 3074. https://doi.org/10.1016/j.bmc.2011.04.009
Guerrini, G., Ciciani, G., Bruni, F., Selleri, S., Martini, C., Daniele, S., Ghelardini, C., Di Cesare Mannelli, L., and Costanzo, A., Bioorg. Med. Chem., 2011, vol. 19, p. 7441. https://doi.org/10.1016/j.bmc.2011.10.047
Costanzo, A., Guerrini, G., Bruni, F., and Selleri, S., J. Heterocycl. Chem., 1994, vol. 31, p. 1369. https://doi.org/10.1002/jhet.5570310612
Schwesinger, H., Dalski, A., Sicker, D., Wilde, H., and Mann, G., J. Prakt. Chem., 1992, vol. 334, p. 257. https://doi.org/10.1002/prac.19923340311
Shen, L.Q., Huang, S.Y., Diao, K.S., and Lei, H.F., J. Mol. Struct., 2012, vol. 1021, p. 167. https://doi.org/10.1016/j.molstruc.2012.03.036
Le Count, D.J. and Greer, A.T., Tetrahedron Lett., 1973, vol. 14, p. 2905. https://doi.org/10.1016/S0040-4039(01)96278-1
Sieler, J., Kempe, R., Hennig, L., and Becher, J., Z. Kristallogr., 1992, vol. 198, p. 313. https://doi.org/10.1524/zkri.1992.198.14.313
Abbott, P.A., Bonnert, R.V., Caffrey, M.V., Cage, P.A., Cooke, A.J., Donald, D.K., Furber, M., Hill, S., and Withnal, J., Tetrahedron, 2002, vol. 58, p. 3185. https://doi.org/10.1016/S0040-4020(02)00269-7
Bauer, A.W., Kirby, W.M.M., Sherris, J.C., and Turck, M., Am. J. Clin. Pathol., 1966, vol. 45, p. 493. https://doi.org/10.1093/ajcp/45.4_ts.493
ACKNOWLEDGMENTS
The authors are grateful to the Institute of Analytical Chemistry, University of Leipzig (Germany) for measuring the NMR and mass spectra. We also express our gratitude to Prof. H. Boutoumi for his human and scientific skills.
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Lettreuch, H., Khodja, M., Moulay, S. et al. Synthesis and Antimicrobial Activity of New Methyl Pyrazolo[5,1-c][1,2,4]benzotriazine-2-carboxylate Derivatives. Russ J Org Chem 59, 674–678 (2023). https://doi.org/10.1134/S1070428023040164
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DOI: https://doi.org/10.1134/S1070428023040164