Research Article
Synthesis and Antioxidant Activities of Some Novel 1-(Morpholine-4-il-methyl)-3-alkyl(aryl)-4-(3-methoxy-4-isobutyryloxy)benzylideneamino-4,5-dihydro-1H-1,2,4-triazol-5-ones
Abstract
In this study, 3-alkyl(aryl)-4-(3-methoxy-4-isobutyryloxy)benzylideneamino-4,5-dihydro-1H-1,2,4-triazol-5-ones
(1) were treated with morpholine in the presence of formaldehyde according to
the Mannich reaction to synthesize five novel
1-(morpholine-4-yl-methyl)-3-alkyl(aryl)-4-(3-methoxy-4-isobutyryloxy)benzylideneamino-4,5-dihydro-1H-1,2,4-triazol-5-ones (2). In addition, the antioxidant properties of compounds 2 were analyzed and evaluated using three antioxidant assays,
including reducing power, free radical scavenging and metal chelating activity.
For the measurement of the reductive ability, Fe3+-Fe2+
transformation was investigated in the presence of compound using by the method
of Oyaizu (1986). The hydrogen atoms or
electrons donation ability of the synthesized compound was measured by DPPH. using the method of Blois (1958). The chelating effect of ferrous ions by the
compound was determined according to the method of Dinis, Madeira & Almeida (1994). BHT, BHA, EDTA and α-tocopherol
were used as reference antioxidant compounds.
Keywords
References
- Ali, K. A., Ragab, E. A., Farghaly, T. A., & Abdalla, M. M. (2011). Synthesis of new functionalized 3-substituted [1,2,4]triazolo [4,3-a]pyrimidine derivatives: potential antihypertensive agents. Acta Poloniae Pharmaceutica, 68(2), 237–47. Retrieved from http://www.ncbi.nlm.nih.gov/pubmed/21485297 Baumann, J., Wurn, G., & Bruchlausen, V. (1979). Prostaglandin synthetase inhibiting O2 – radical scavenging properties of some flavonoids and related phenolic compounds. Naunyn-Schmiedebergs Archives of Pharmacology, 308, R27. Blois, M. (1958). Antioxidant determinations by the use of a stable free radical. Nature, 181(4617), 1199–1200. http://doi.org/10.1038/1811199a0 Calis I, Hosny, M., Khalifa T & Nishibe, S. (1993). Phytochemistry, 33, 1453. Chen, X., Shi, Y. M., Huang, C., Xia, S., Yang, L. J., & Yang, X. D. (2016). Novel dibenzo[b,d]furan–1H-1,2,4-triazole derivatives: Synthesis and antitumor activity. Anti-Cancer Agents in Medicinal Chemistry, 16(3), 377–386. http://doi.org/10.2174/1871520615666150817115913 Chidananda, N., Poojary, B., Sumangala, V., Kumari, N. S., Shetty, P., & Arulmoli, T. (2012). Facile synthesis, characterization and pharmacological activities of 3,6-disubstituted 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 5,6-dihydro-3,6-disubstituted-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles. European Journal of Medicinal Chemistry, 51, 124–136. http://doi.org/10.1016/j.ejmech.2012.02.030 Dinis, T. C. P., Madeira, V. M. C., & Almeida, L. M. (1994). Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as proxyl radical scavengers. Archives of Biochemistry and Biophysics, 315(1), 161–169. http://doi.org/10.1006/abbi.1994.1485 Duh, P. D., Tu Y Y & Yen, G. C. ( 1999). Food Sci Technol-Leb, 32, 269. El-Serwy, W. S., Mohamed, N. A., Abbas, E. M., & Abdel-Rahman, R. F. (2013). Synthesis and anti-inflammatory properties of novel 1,2,4-triazole derivatives. Research on Chemical Intermediates, 39(6), 2543–2554. http://doi.org/10.1007/s11164-012-0781-9 Finefrock, A. E., Bush, A. I., & Doraiswamy, P. M. (2003). Current status of metals as therapeutic targets in Alzheimer’s disease. Journal of the American Geriatrics Society. 51(8), 1143–1148. http://doi.org/10.1046/j.1532-5415.2003.51368.x Gordon M H, (1990). Food Antioxidants (Elsevier, London). McClements, D., & Decker, E. (2000). Lipid oxidation in oil-in-water emulsions: Impact of molecular environment on chemical reactions in heterogeneous food systems. Journal of Food Science, 65(8), 1270–1282. http://doi.org/10.1111/j.1365-2621.2000.tb10596.x Meir, S., Kanner, J., Akiri, B., & Philosoph-Hadas, S. (1995). Determination and involvement of aqueous reducing compounds in oxidative defense systems of various senescing leaves. Journal of Agricultural and Food Chemistry, 43(7), 1813–1819. http://doi.org/10.1021/jf00055a012 Oyaizu, M. (1986). Studies on products of browning reaction. Antioxidative activities of products of browning reaction prepared from glucosamine. The Japanese Journal of Nutrition and Dietetics, 44(17), 307–315. http://doi.org/10.5264/eiyogakuzashi.44.307 Soares, J. R., Dinis, T. C. P., Cunha, A. P., & Almeida, L. M. (1997). Antioxidant activities of some extracts of Thymus zygis. Free Radical Research, 26(5), 469–478. http://doi.org/10.3109/10715769709084484 Uzgören-Baran, A., Tel, B. C., Sargöl, D., Öztürk, E. I., Kazkayas, I., Okay, G., Ertan, M., Tozkoparan, B. (2012). Thiazolo[3,2-b]-1,2,4-triazole-5(6H)-one substituted with ibuprofen: Novel non-steroidal anti-inflammatory agents with favorable gastrointestinal tolerance. European Journal of Medicinal Chemistry, 57, 398–406. http://doi.org/10.1016/j.ejmech.2012.07.009 Yamaguchi, F., Ariga, T., Yoshimura, Y., & Nakazawa, H. (2000). Antioxidative and anti-glycation activity of garcinol from Garcinia indica fruit rind. Journal of Agricultural and Food Chemistry, 48(2), 180–185. http://doi.org/10.1021/jf990845y Yildirim, A., Mavi, A., & Kara, A. A. (2001). Determination of antioxidant and antimicrobial activities of Rumex crispus L. extracts. Journal of Agricultural and Food Chemistry, 49(8), 4083–4089. http://doi.org/10.1021/jf0103572 Strlic, M., Radovic, T., Kolar, J., & Pihlar, B. (2002). J Agr Food Chem, 50, 6313. Yamaguchi, F., Ariga, T., Yoshimura, Y., & Nakazawa, H. (2000). J Agr Food Chem, 48, 180. Zhang, F., Wen, Q., Wang, S. F., Shahla Karim, B., Yang, Y. S., Liu, J. J., Zhang, W. M., Zhu, H. L. (2014). Design, synthesis and antibacterial activities of 5-(pyrazin-2-yl)-4H-1,2,4-triazole-3-thiol derivatives containing Schiff base formation as FabH inhibitory. Bioorganic & Medicinal Chemistry Letters, 24(1), 90–95. http://doi.org/10.1016/J.BMCL.2013.11.079
Abstract
References
- Ali, K. A., Ragab, E. A., Farghaly, T. A., & Abdalla, M. M. (2011). Synthesis of new functionalized 3-substituted [1,2,4]triazolo [4,3-a]pyrimidine derivatives: potential antihypertensive agents. Acta Poloniae Pharmaceutica, 68(2), 237–47. Retrieved from http://www.ncbi.nlm.nih.gov/pubmed/21485297 Baumann, J., Wurn, G., & Bruchlausen, V. (1979). Prostaglandin synthetase inhibiting O2 – radical scavenging properties of some flavonoids and related phenolic compounds. Naunyn-Schmiedebergs Archives of Pharmacology, 308, R27. Blois, M. (1958). Antioxidant determinations by the use of a stable free radical. Nature, 181(4617), 1199–1200. http://doi.org/10.1038/1811199a0 Calis I, Hosny, M., Khalifa T & Nishibe, S. (1993). Phytochemistry, 33, 1453. Chen, X., Shi, Y. M., Huang, C., Xia, S., Yang, L. J., & Yang, X. D. (2016). Novel dibenzo[b,d]furan–1H-1,2,4-triazole derivatives: Synthesis and antitumor activity. Anti-Cancer Agents in Medicinal Chemistry, 16(3), 377–386. http://doi.org/10.2174/1871520615666150817115913 Chidananda, N., Poojary, B., Sumangala, V., Kumari, N. S., Shetty, P., & Arulmoli, T. (2012). Facile synthesis, characterization and pharmacological activities of 3,6-disubstituted 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles and 5,6-dihydro-3,6-disubstituted-1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles. European Journal of Medicinal Chemistry, 51, 124–136. http://doi.org/10.1016/j.ejmech.2012.02.030 Dinis, T. C. P., Madeira, V. M. C., & Almeida, L. M. (1994). Action of phenolic derivatives (acetaminophen, salicylate, and 5-aminosalicylate) as inhibitors of membrane lipid peroxidation and as proxyl radical scavengers. Archives of Biochemistry and Biophysics, 315(1), 161–169. http://doi.org/10.1006/abbi.1994.1485 Duh, P. D., Tu Y Y & Yen, G. C. ( 1999). Food Sci Technol-Leb, 32, 269. El-Serwy, W. S., Mohamed, N. A., Abbas, E. M., & Abdel-Rahman, R. F. (2013). Synthesis and anti-inflammatory properties of novel 1,2,4-triazole derivatives. Research on Chemical Intermediates, 39(6), 2543–2554. http://doi.org/10.1007/s11164-012-0781-9 Finefrock, A. E., Bush, A. I., & Doraiswamy, P. M. (2003). Current status of metals as therapeutic targets in Alzheimer’s disease. Journal of the American Geriatrics Society. 51(8), 1143–1148. http://doi.org/10.1046/j.1532-5415.2003.51368.x Gordon M H, (1990). Food Antioxidants (Elsevier, London). McClements, D., & Decker, E. (2000). Lipid oxidation in oil-in-water emulsions: Impact of molecular environment on chemical reactions in heterogeneous food systems. Journal of Food Science, 65(8), 1270–1282. http://doi.org/10.1111/j.1365-2621.2000.tb10596.x Meir, S., Kanner, J., Akiri, B., & Philosoph-Hadas, S. (1995). Determination and involvement of aqueous reducing compounds in oxidative defense systems of various senescing leaves. Journal of Agricultural and Food Chemistry, 43(7), 1813–1819. http://doi.org/10.1021/jf00055a012 Oyaizu, M. (1986). Studies on products of browning reaction. Antioxidative activities of products of browning reaction prepared from glucosamine. The Japanese Journal of Nutrition and Dietetics, 44(17), 307–315. http://doi.org/10.5264/eiyogakuzashi.44.307 Soares, J. R., Dinis, T. C. P., Cunha, A. P., & Almeida, L. M. (1997). Antioxidant activities of some extracts of Thymus zygis. Free Radical Research, 26(5), 469–478. http://doi.org/10.3109/10715769709084484 Uzgören-Baran, A., Tel, B. C., Sargöl, D., Öztürk, E. I., Kazkayas, I., Okay, G., Ertan, M., Tozkoparan, B. (2012). Thiazolo[3,2-b]-1,2,4-triazole-5(6H)-one substituted with ibuprofen: Novel non-steroidal anti-inflammatory agents with favorable gastrointestinal tolerance. European Journal of Medicinal Chemistry, 57, 398–406. http://doi.org/10.1016/j.ejmech.2012.07.009 Yamaguchi, F., Ariga, T., Yoshimura, Y., & Nakazawa, H. (2000). Antioxidative and anti-glycation activity of garcinol from Garcinia indica fruit rind. Journal of Agricultural and Food Chemistry, 48(2), 180–185. http://doi.org/10.1021/jf990845y Yildirim, A., Mavi, A., & Kara, A. A. (2001). Determination of antioxidant and antimicrobial activities of Rumex crispus L. extracts. Journal of Agricultural and Food Chemistry, 49(8), 4083–4089. http://doi.org/10.1021/jf0103572 Strlic, M., Radovic, T., Kolar, J., & Pihlar, B. (2002). J Agr Food Chem, 50, 6313. Yamaguchi, F., Ariga, T., Yoshimura, Y., & Nakazawa, H. (2000). J Agr Food Chem, 48, 180. Zhang, F., Wen, Q., Wang, S. F., Shahla Karim, B., Yang, Y. S., Liu, J. J., Zhang, W. M., Zhu, H. L. (2014). Design, synthesis and antibacterial activities of 5-(pyrazin-2-yl)-4H-1,2,4-triazole-3-thiol derivatives containing Schiff base formation as FabH inhibitory. Bioorganic & Medicinal Chemistry Letters, 24(1), 90–95. http://doi.org/10.1016/J.BMCL.2013.11.079
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| Primary Language | English |
|---|---|
| Subjects | Engineering |
| Journal Section | Articles |
| Authors | |
| Publication Date | August 19, 2018 |
| Published in Issue | Year 2018 Issue: 2 |
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