Investigation of Biological Properties of New 1-(2,6-Dimetilmorfolin-4-ylmetil)-3-alkyl(aryl)-4-[3-ethoxy-(4-benzenesulfonyloxy)-benzylidenamino]- 4,5-dihydro-1H-1,2,4-triazol-5-ones

Abstract

In this study, six new 1-(2,6-dimethylmorpholin-4-yl-methyl)-3-alkyl(aryl)-4-[3-ethoxy-(4- benzenesulfonyloxy)-benzylideneamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones were obtained from the reactions of 3-alkyl(aryl)-4-[3-ethoxy-(4-benzenesulfonyloxy)-benzylideneamino]-4,5-dihydro-1H-1,2,4-triazol-5-ones with 2,6-dimethylmorpholine and formaldehyde. Characterization of new compounds obtained was carried out by IR, ¹H-NMR, ¹³C-NMR spectral data. Antibacterial properties of the synthesized novel compounds were evaluated by agar well method against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, Bacillus subtilis, Bacillus cereus and Klepsiella pneumoniae strains.

Keywords

• 1
• 2
• 4-triazol-5-one
• Schiff base
• Mannich base
• Synthesis
• Antimicrobial actvitiy

References

1. Ahmad, I., Mehmood, Z., Mohammed, F., (1998). Screening of Some Indian Medicinal Plants for Their Antimicrobial Properties, J. Ethnopharmacol. 62 (1998), 183–193. Gürsoy-Kol, Ö., Yüksek, H., İslamoğlu, F., In-vitro Antioxidant and Acidic Properties of Novel 4-(5-methyl-2-thienylmethyleneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives. Synthesis and Characterization, Revista de Chimie (Rev. Chim.) (Bucharest), 63(11); 1103-1111 (2012). Gürsoy-Kol, Ö., Yüksek, H., İslamoğlu, F., Synthesis and In-vitro Antioxidant Activities of Novel 4-(3-Methyl-2-thienylmethylene-amino)-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives with Their Acidic Properties, J. Chem. Soc. Pak., 35(4); 1179-1190 (2013). Ikizler, A. A., Ikizler, A., Yüksek, H., Serdar, M., “Antitumor Activities of Some 4,5-dihydro-1H-1,2,4-triazol-5-ones”, Modelling, Masurement & Control C, AMSE res, 57; 25-33 (1998). Ikizler, A.A., Uçar, F., Yuksek, H., Aytin, A., Yasa, I., Gezer, T., “Synthesis and Antifungal Activity of Some New Arylidenamino Compounds”, Acta Pol. Pharm., 54 (2); 135-140 (1997). Kardaş, F., (2006). Synthesis, Potentiometric Titrations and Antioxidant Properties of Some Novel 3-Substituted-4- (4-methylthiobenzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives, Master Thesis, Kafkas University, Institute of Science, Kars. Manap, S., (2009). Synthesis of some novel 3-alkyl (aryl) -4- (3,4-disubstituedbenzylideneamino)-4,5-dihydro-1H-1,2,4-triazol-5-one derivatives, Characterization of Their Structure, Investigation of Antioxidant and Acidity Properties, Master Thesis, Kafkas University, Institute of Science, Kars. Ocak, M., Yüksek, H., Kolaylı, S., Küçük, M., Ocak, Ü., Bahçeci, Ş., Alkan,M., Şahinbaş, E., Yıldırım, N., Antioxidant Properties of Some Schiff Bases Containing Triazole Ring, XVIII. International Chemistry Congress, Kars, 556 (2004). Özdemir, G. (2016), Synthesis of Some Novel 4- [3-ethoxy-4 (benzenesulfonyloxy) benzylideneamino] -4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives, Characterization of Their Structure and Investigation of Some Properties, Master Thesis, Kafkas University, Institute of Science, Kars. Perez, C., Pauli, M., Bazerque, P. (1990). An Antibiotic Assay by Agar Well Diffusion Method, Acta Biol. Med. Exp. 15, 113–115. Pinner, A., (1982). Die Imidoäther und Ihre Derivate, 1.Auflage, Oppenheim, Berlin. Üre, S., (2010). Synthesis of Some 1-methyl-3-alkyl (aryl) -4- (3,4-dimethoxybenzylideneamino) -4,5-dihydro-1H-1,2,4-triazol-5-one to Characterization Structures and Investigation Antioxidant Properties, Master Thesis, Kafkas University, Institute of Science, Kars. Yüksek, H., Alkan, M., Çakmak, I., Ocak, Z., Bahçeci, Ş., Calapoğlu, M., Elmastaş, M., Kolomuç, A., Aksu, H., (2008). Preparation, GIAO NMR Calculations and Acidic Properties ofSome Novel 4,5-dihydro-1H-1,2,4triazol-5-one Derivatives with Their Antioxidant Activities, Int. J. Mol. Sci. 9: 12-32. Yuksek, H., Alkan, M., Ocak, Z., Bahceci, S., Ocak, M., Ozdemir, M., (2004). Synthesis and Acidic Properties of Some New Potential Biologically Active 4-acylamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives” Indian J.Chem., 43 (7): 1527-153. Yüksek, H., Bahçeci, Ş., Alkan, M.,(2001). Bazı 4-(4-hidroksibenzilidenamino-4,5-dihidro-1H-1,2,4-triazol-5-on Bileşiklerinin ve Asetil Türevlerinin Sentezi” XV. National Chemistry Congress, İstanbul, OK-P13 (2001).