SYNTHESIS AND ANTIOXIDANT ACTIVITY OF A NEW 4-AMINOCOUMARIN DERIVATIVE
Abstract
Synthesis, spectral characterization, and evaluation of in vitro antioxidant activity of a new coumarin derivative, 4-((1,3,4-thiadiazol-2-yl)amino)-3-nitro-2H-chromene-2-one, are described. The synthesis of the new product was performed in three reaction steps, with a good overall yield (78%). The structure was corroborated by detailed spectral analysis, including the 1D and 2D NMR experiments (1H- and 13C NMR; 1H-1H COSY, NOESY, HSQC, and HMBC). The in vitro antioxidant activity was evaluated using the DPPH test. The synthesized compound possesses a good free-radical scavenging activity, IC50=596.7±0.3 μg/ml, and can serve as a model for the synthesis of similar compounds with promising antioxidant effects.
References
Aiyelabola, T., Akinkunmi, E., Obuotor, E., Olawuni, I., Isabirye, D., & Jordaan, J. 2017. Synthesis Characterization and Biological Activities of Coordination Compounds of 4-Hydroxy-3-nitro-2 H -chromen-2-one and Its Aminoethanoic Acid and Pyrrolidine-2-carboxylic Acid Mixed Ligand Complexes. Bioinorganic Chemistry and Applications, pp. 1-9. doi:10.1155/2017/6426747
Al-Amiery, A.A., Kadhum, A.A.H., & Mohamad, A.B. 2012. Antifungal Activities of New Coumarins. Molecules, 17(5), pp. 5713-5723. doi:10.3390/molecules17055713
Anand, P., Singh, B., & Singh, N. 2012. A review on coumarins as acetylcholinesterase inhibitors for Alzheimer’s disease. Bioorganic and Medicinal Chemistry, 20(3), pp. 1175-1180. doi:10.1016/j.bmc.2011.12.042
Ayati, A., Oghabi, B. T., Moghimi, S., Esmaeili, R., Majidzadeh-A, K., Safavi, M., Firoozpour, L., Emami, S., & Foroumadi, A. 2018. Synthesis and biological evaluation of new coumarins bearing 2,4-diaminothiazole-5-carbonyl moiety. European Journal of Medicinal Chemistry, 155, pp. 483-491. doi:10.1016/j.ejmech.2018.06.015
Bansal, Y., Sethi, P., & Bansal, G. 2013. Coumarin: a potential nucleus for anti-inflammatory molecules. Medicinal Chemistry Research, 22(7), pp. 3049-3060. doi:10.1007/s00044-012-0321-6
Braca, A., De Tommasi, N., Bari, L. D., Pizza, C., Politi, M., & Morelli, I. 2001. Antioxidant Principles from Bauhinia t arapotensis. Journal of Natural Products, 64(7), pp. 892-895. doi:10.1021/np0100845
Danis, O., Yuce-Dursun, B., Gunduz, C., Ogan, A., Sener, G., Bulut, M., & Yarat, A. 2011. Synthesis of 3-amino-4-hydroxy coumarin and dihydroxy-phenyl coumarins as novel anticoagulants. Arzneimittelforschung, 60(10), pp. 617-620. doi:10.1055/s-0031-1296335
Dekić, B., Dekić, V., Radulović, N., Vukićević, R., & Palić, R. 2010. Synthesis of new antimicrobial 4-aminosubstituted 3-nitrocoumarins. Chemical Papers, 64(3). doi:10.2478/s11696-010-0004-z
Dekić, B., Radulović, N., Ristić, M., & Dekić, V. 2016. The synthesis and NMR spectral assignments of 3-nitro-4-((6- nitrobenzothiazol-2-yl)amino)-2H-chromen-2-one. The University Thought - Publication in Natural Sciences, 6(1), pp. 32-38. doi:10.5937/univtho6-10634
Dekić, V., Radulović, N., Vukićević, R., Dekić, B., Skropeta, D., & Palić, R. 2010. Complete assignment of the 1H and 13C NMR spectra of antimicrobial 4-arylamino- 3-nitrocoumarin derivatives. Magnetic Resonance in Chemistry, 48(11), pp. 896-902. doi:10.1002/mrc.2681
Fylaktakidou, K., Hadjipavlou-Litina, D., Litinas, K., & Nicolaides, D. 2004. Natural and Synthetic Coumarin Derivatives with Anti-Inflammatory / Antioxidant Activities. Current Pharmaceutical Design, 10(30), pp. 3813-3833. doi:10.2174/1381612043382710
Finn, G. J., Kenealy, E., Creaven, B. S., & Egan, D. A. 2002. In vitro cytotoxic potential and mechanism of action of selected coumarins, using human renal cell lines. Cancer Letters, 183(1), pp. 61-68. doi:10.1016/s0304-3835(02)00102-7
Hadjipavlou-Litina, D., Kontogiorgis, C., Pontiki, E., Dakanali, M., Akoumianaki, A., & Katerinopoulos, H. E. 2007. Anti-inflammatory and antioxidant activity of coumarins designed as potential fluorescent zinc sensors. Journal of Enzyme Inhibition and Medicinal Chemistry, 22(3), pp. 287-292. doi:10.1080/14756360601073914
Kaljaj, V., Trkovnik, M., & Stefanović-Kaljaj, L. 1987. Synthesis of new heterocyclocoumarins starting with 3-cyano-4-chlorocoumarin. Journal of the Serbian Chemical Society, 52(4), pp. 183-185.
Kostova, I., Raleva, S., Genova, P., & Argirova, R. 2006. Structure-Activity Relationships of Synthetic Coumarins as HIV-1 Inhibitors. Bioinorganic Chemistry and Applications, pp. 1-9. doi:10.1155/bca/2006/68274
Kotaiah, Y., Nagaraju, K., Harikrishna, N., Venkata, R. C., Yamini, L., & Vijjulatha, M. 2014. Synthesis, docking and evaluation of antioxidant and antimicrobial activities of novel 1,2,4-triazolo[3,4-b][1,3,4]thiadiazol-6-yl)selenopheno[2,3-d] pyrimidines. European Journal of Medicinal Chemistry, 75, pp. 195-202. doi:10.1016/j.ejmech.2014.01.006
Manojkumar, P., Ravi, T., & Subbuchettiar, G. 2009. Synthesis of coumarin heterocyclic derivatives with antioxidant activity and in vitro cytotoxic activity against tumour cells. Acta Pharmaceutica, 59(2), pp. 159-170. doi:10.2478/v10007-009-0018-7
Naik, N. S., Shastri, L. A., Joshi, S. D., Dixit, S. R., Chougala, B. M., Samundeeswari, S., Holiyachi, M., Shaikh, F., Madar, J., Kulkarni, R., & Sunagar, V. 2017. 3,4-Dihydropyrimidinone-coumarin analogues as a new class of selective agent against S. aureus: Synthesis, biological evaluation and molecular modelling study. Bioorganic and Medicinal Chemistry, 25(4), pp. 1413-1422. doi:10.1016/j.bmc.2017.01.001
Nofal, Z., El-Zahar, M., & Abd, E. S. 2000. Novel Coumarin Derivatives with Expected Biological Activity. Molecules, 5(12), pp. 99-113. doi:10.3390/50200099
Parfënov, É. A., & Smirnov, L. S. 1991. Heterocyclic bioantioxidants. 2. Interaction of 3-nitro-4-substituted coumarins with mercaptans. Chemistry of Heterocyclic Compounds, 27(11), pp. 1190-1192. doi:10.1007/bf00471742
Pasqualotto, A. C., Thiele, K. O., & Goldani, L. Z. 2010. Novel triazole antifungal drugs: focus on isavuconazole, ravuconazole and albaconazole. Current Opinion in Investigational Drugs, 11, pp. 165-174.
Piazzi, L., Cavalli, A., Colizzi, F., Belluti, F., Bartolini, M., Mancinni, F., Recanatini, M., Andrisana, V., & Rampa, A. 2008. Multi-target-directed coumarin derivatives: hAChE and BACE1 inhibitors as potential anti-Alzheimer compounds. Bioorganic and Medicinal Chemistry Letters, 18(1), pp. 423-426. doi:10.1016/j.bmcl.2007.09.100
Radulović, N., Stojanović-Radić, Z., Stojanović, P., Stojanović, N., Dekić, V., & Dekić, B. 2015. A small library of 4-(alkylamino)-3-nitrocoumarin derivatives with potent antimicrobial activity against gastrointestinal pathogens. Journal of the Serbian Chemical Society, 80(3), pp. 315-327. doi:10.2298/jsc140619085r
Savel'ev, V. L., Artamonova, O. S., Troitskaya, V. S., Vinokurov, V. G., & Zagorevskii, V. A. 1973. Investigations of pyrans and related compounds. Khimiya Geterotsiklicheskikh Soedinenii, 9(7), pp. 816-820. doi:10.1007/bf00471556
Stefanachi, A., Leonetti, F., Pisani, L., Catto, M., & Carotti, A. 2018. Coumarin: A Natural, Privileged and Versatile Scaffold for Bioactive Compounds. Molecules, 23(2), p. 250. doi:10.3390/molecules23020250
Su, C., Mouscadet, J., Chiang, C., Tsai, H., & Hsu, L. 2006. HIV-1 Integrase Inhibition of Biscoumarin Analogues. Chemical and pharmaceutical bulletin, 54(5), pp. 682-686. doi:10.1248/cpb.54.682
Vaso, K., Behrami, A., & Krasniqi, I. 2010. Antibacterial Activity of Compounds Synthesized From 4-Chloro-3-nitro-2H-[1]-benzopyran-2-one. Asian Journal of Chemistry, 22(9), pp. 7313-7317.
Venugopala, K. N., Rashmi, V., & Odhav, B. 2013. Review on Natural Coumarin Lead Compounds for Their Pharmacological Activity. BioMed Research International, pp. 1-14. doi:10.1155/2013/963248
Yeh, J. Y., Coumar, M. S., Horng, J. T., Shiao, H. Y., Kuo, F. M., Lee, H. L., Chen, I. C., Chang, C. W., Tang, W. F., Tseng, S. N., Chen, C. J., Shih, S. R., Hsu, J. T., Liao, C. C., Chao, Y. S., & Hsieh, H. P. 2010. Anti-Influenza Drug Discovery: Structure−Activity Relationship and Mechanistic Insight into Novel Angelicin Derivatives. Journal of Medicinal Chemistry, 53(4), pp. 1519-1533. doi:10.1021/jm901570x
Yu, D., Suzuki, M., Xie, L., Morris-Natschke, S. L., & Lee, K. 2003. Recent progress in the development of coumarin derivatives as potent anti-HIV agents. Medicinal Research Reviews, 23(3), pp. 322-345. doi:10.1002/med.10034
Zaki, R. M., Elossaily, Y. A., & Kamal, E. A. M. 2012. Synthesis and antimicrobial activity of novel benzo[f]coumarin compounds. Russian Journal of Bioorganic Chemistry, 38(6), pp. 639-646. doi:10.1134/s1068162012040152
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.