Abstract
Herein, an excellent method for the synthesis of twelve novel Schiff base derivatives containing indole and triazole assisted by microwave irradiation is reported. Compared with the conventional method, the yields increased from 59–84 % to 85–96 % and the reaction time was reduced from 24–30 h to 4–8 min. Moreover, all series of the newly synthesized Schiff bases were evaluated for their antibacterial activity. The values of minimum inhibitory concentration (MIC) and IC50 indicated that many target compounds possessed excellent antibacterial activity against Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa, and Bacillus subtilis.
Similar content being viewed by others
References
Akhaja, T. N., & Raval, J. P. (2011). 1,3-Dihydro-2H-indol-2-ones derivatives: Design, synthesis, in vitro antibacterial, antifungal and antitubercular study. European Journal of Medicinal Chemistry, 46, 5573–5579. DOI: 10.1016/j.ejmech.2011.09.023.
Akhaja, T. N., & Raval, J. P. (2012). Design, synthesis, in vitro evaluation of tetrahydropyrimidine-isatin hybrids as potential antibacterial, antifungal and anti-tubercular agents. Chinese Chemical Letters, 23, 446–449. DOI: 10.1016/j.cclet.2012.01.040.
Appukkuttan, P., Mehta, V. P., & Van der Eycken, E. V. (2009). Microwave-assisted cycloaddition reactions. Chemical Society Reviews, 39, 1467–1477. DOI: 10.1039/b815717k.
Bharti, S. K., Nath, G., Tilak, R., & Singh, S. K. (2010). Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring. European Journal of Medicinal Chemistry, 45, 651–660. DOI: 10.1016/j.ejmech.2009.11.008.
Burchak, O. N., Le Pihive, E., Maigre, L., Guinchard, X., Bouhours, P., Jolivalt, C., Schneider, D., Maurin, M., Giglione, C., Meinnel, T., Paris, J. M., & Denis, J. N. (2011). Synthesis and evaluation of 1-(1H-indol-3-yl)ethanamine derivatives as new antibacterial agents. Bioorganic & Medicinal Chemistry, 19, 3204–3215. DOI: 10.1016/j.bmc.2011.03.060.
da Silva, C. M., da Silva, D. L., Modolo, L. V., Alves, R. B., de Resende, M. A., Martins, C. V. B., & de Fátima, Â. (2011). Schiff bases: A short review of their antimicrobial activities. Journal of Advanced Research, 2, 1–8. DOI: 10.1016/j.jare.2010.05.004.
Eswaran, S., Adhikari, A. V., & Shetty, N. S. (2009). Synthesis and antimicrobial activities of novel quinoline derivatives carrying 1,2,4-triazole moiety. European Journal of Medicinal Chemistry, 44, 4637–4647. DOI: 10.1016/j.ejmech.2009.06. 031.
Farghaly, A. R. A. H. (2004). Synthesis, reactions and antimicrobial activity of some new indolyl-1,3,4-oxadiazole, triazole and pyrazole derivatives. Journal of the Chinese Chemical Society, 51, 147–156.
Giske, C. G., & Cornaglia, G. (2010). Supranational surveillance of antimicrobial resistance: The legacy of the last decade and proposals for the future. Drug Resistance Updates, 13, 93–98. DOI: 10.1016/j.drup.2010.08.002.
Ju, Y. H., & Varma, R. S. (2005). Microwave-assisted cyclocondensation of hydrazine derivatives with alkyl dihalides or ditosylates in aqueous media: syntheses of pyrazole, pyrazolidine and phthalazine derivatives. Tetrahedron Letters, 46, 6011–6014. DOI: 10.1016/j.tetlet.2005.07.018.
Khalil, N. S. A. M. (2010). Efficient synthesis of novel 1,2,4-triazole fused acyclic and 21–28 membered macrocyclic and/or lariat macrocyclic oxaazathia crown compounds with potential antimicrobial activity. European Journal of Medicinal Chemistry, 45, 5265–5277. DOI: 10.1016/j.ejmech.2010.08.046.
Nadal, M., Schuhmacher, M., & Domingo, J. L. (2011). Longterm environmental monitoring of persistent organic pollutants and metals in a chemical/petrochemical area: Human health risks. Environmental Pollution, 159, 1769–1777. DOI: 10.1016/j.envpol.2011.04.007.
National Committee for Clinical Laboratory Standards (2000). U.S. standard: Methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard, 5th ed. M7-A5. Villanova, PA, USA.
Negm, N. A., Aiad, I. A., & Tawfik, S. M. (2010). Screening for potential antimicrobial activities of some cationic uracil biocides against wide-spreading bacterial strains. Journal of Surfactants and Detergents, 13, 503–511. DOI: 10.1007/s11743-010-1229-0.
Pardeshi, S., & Bobade, V. D. (2011). Synthesis and biological evaluation of some novel triazol-3-ones as antimicrobial agents. Bioorganic & Medicinal Chemistry Letters, 21, 6559–6562. DOI: 10.1016/j.bmcl.2011.08.049.
Patil, B. S., Krishnamurthy, G., Naik, H. S. B., Latthe, P. R., & Ghate, M. (2010). Synthesis, characterization and antimicrobial studies of 2-(4-methoxy-phenyl)-5-methyl-4-(2-arylsulfanyl-ethyl)-2,4-dihydro-[1,2,4]triaz olo-3-ones and their corresponding sulfones. European Journal of Medicinal Chemistry, 45, 3329–3334. DOI: 10.1016/j.ejmech.2010.04.016.
Reddy, B. V. S., Rajeswari, N., Sarangapani, M., Reddy, G. R., Madan, C., Kumar, K. P., & Rao, M. S. (2011). Iodine-catalyzed conjugate addition of indoles onto en-1,4-dione: A novel synthesis of 3-(1-(1H-indol-3-yl)-2-oxo-2-phenylethyl)indolin-2-ones as antibacterial and antifungal agents. Bioorganic & Medicinal Chemistry Letters, 21, 6510–6514. DOI: 10.1016/j.bmcl.2011.08.075.
Shi, Y., Peng, Y. L., Zhao, Z. G., Li, G. H., & Li, H. R. (2011). Synthesis of new Schiff bases derived from dimers of 4-amino-3-(1-naphthyl)-5-thiomethyl-1,2,4-triazole using microwave irradiation. Journal of Chemical Research, 35, 15–17. DOI: 10.3184/174751911x12964930076647.
Singh, K., Kumar, Y., Puri, P., Kumar, M., & Sharma, C. (2012). Cobalt, nickel, copper and zinc complexes with 1,3-diphenyl-1H-pyrazole-4-carboxaldehyde Schiff bases: Antimicrobial, spectroscopic, thermal and fluorescence studies. European Journal of Medicinal Chemistry, 52, 313–321. DOI: 10.1016/j.ejmech.2012.02.053.
Zhang, H. J., Qin, X., Liu, K., Zhu, D. D., Wang, X. M., & Zhu, H. L. (2011). Synthesis, antibacterial activities and molecular docking studies of Schiff bases derived from N-(2/4-benzaldehyde-amino) phenyl-N-phenylthiourea. Bioorganic & Medicinal Chemistry, 19, 5708–5715. DOI: 10.1016/j.bmc.2011.06.077.
Zhao, Z. G., Liu, X. L., Liu, L. L., & Li, G. H. (2010). Microwave-assisted synthesis of new steroidal thiosemicarbazones derived from methyl 3-oxocholanate under solventfree conditions. Journal of Chemical Research, 34, 455–458. DOI: 10.3184/030823410x12798092457988.
Zoumpoulakis, P., Camoutsis, C., Pairas, G., Soković, M., Glamočlija, J., Potamitis, C., & Pitsas, A. (2012). Synthesis of novel sulfonamide-1,2,4-triazoles, 1,3,4-thiadiazoles and 1,3,4-oxadiazoles, as potential antibacterial and antifungal agents. Biological evaluation and conformational analysis studies. Bioorganic & Medicinal Chemistry, 20, 1569–1583. DOI: 10.1016/j.bmc.2011.12.031.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Peng, YL., Liu, XL., Wang, XH. et al. Microwave-assisted synthesis and antibacterial activity of derivatives of 3-[1-(4-fluorobenzyl)-1H-indol-3-yl]-5-(4-fluorobenzylthio)-4H-1,2,4-triazol-4-amine. Chem. Pap. 68, 401–408 (2014). https://doi.org/10.2478/s11696-013-0461-2
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.2478/s11696-013-0461-2