Abstract
Series of imino and amino derivatives of 4-hydroxy coumarins were synthesized via conventional and microwave promoted procedure and evaluated for antioxidant potential through different in vitro models such as (DPPH) free radical scavenging activity, linoleic acid emulsion model system, reducing power assay and phosphomolybdenum method. All prepared compounds possess good antioxidant activity and among them p-nitro-phenyl derivative 6c with IC50 at 25.9 μM possesses radical scavenging activity which is comparable to standard BHT, while the best reducing power was observed in a case of benzyl amino compound 8c (RP50 255.6 μM). Also, observed data indicated that compounds may serve as inhibitors of lipid peroxidation process.
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Barnham, K. J., Masters, C. L., and Bush, A, Neurodegenerative diseases and oxidative stress. Nat. Rev. Drug Disc., 3, 205–214 (2004).
Beillerot, A., Rodríguez Domínguez, J. C., Kirsch, G., and Bagrel, D., Synthesis and protective effects of coumarin derivatives against oxidative stress induced by doxorubicin. Bioorg. Med. Chem. Lett., 18, 1102–1105 (2008).
Dröge, W., Free Radicals in the Physiological Control of Cell Function. Physiol. Rev., 82, 47–95 (2002).
Egan, D., O’Kennedy, E., Moran, E., Cox, D., Prosser, E., and Thornes, R. D., The Pharmacology, Metabolism, Analysis, and Applications of Coumarin and Coumarin-Related Compounds. Drug Metab. Rev., 22, 503–529 (1990).
Ferrari, A. M., Sgobba, M., Gamberini, M. C., and Rastelli, G., Relationship between quantum-chemical descriptors of proton dissociation and experimental acidity constants of various hydroxylated coumarins. Identification of the biologically active species for xanthine oxidase inhibition. Eur. J. Med. Chem., 42, 1028–1031 (2007).
Festa, F., Aglitti, T., Duranti, G., Ricordi, R., Perticone, P., and Cozzi, R., Strong antioxidant activity of ellagic acid in mammalian cells in vitro revealed by comet assay. Anticancer Res., 21, 3903–3908 (2001).
Filomeni, G., Rotilio, G., and Ciriolo, Disulfide relays and phosphorylative cascades: partners in redox-mediated signaling pathways. M. R, Cell Death Differ., 12, 1555–1563 (2005).
Gilgun-Sherki, Y., Melamed, E., and Offen, D., Oxidative stress induced-neurodegenerative diseases: the need for antioxidants that penetrate the blood brain barrier. Neuropharm., 40, 959–975 (2001).
Gilgun-Sherki, Y., Rosenbaum, Z., Meland, E., and Offen, D., Antioxidant therapy in acute central nervous system injury: current state. Pharm. Rev., 54, 271–284 (2002).
Halliwell, B., How to Characterize a Biological Antioxidant. Free Rad. Res., 9, 1–32 (1990).
Hirsh, J., Dalen, J. E., Anderson, D. R., Poller, L., Bussey, H., Ansell, J., and Deykin, D., Oral Anticoagulants: Mechanism of Action, Clinical Effectiveness, and Optimal Therapeutic Range. Chest, 119, 8S–21S (2001).
Hoult, J. R. S. and Paya, M., Pharmacological and biochemical actions of simple coumarins: Natural products with therapeutic potential. Gen. Pharmacol. The Vasc. Syst., 27, 713–722 (1996).
Juliano, L., Colavita, A. R., Leo, R., Pratico, D., and Violi, F., Oxigen free radicals and platelet activation. Free Radic. Biol. Med., 22, 999–1006 (1997).
Jurd, L., Corse, J., King, A. D., Bayne, H., and Mihara, K., Antimicrobial properties of 6,7-dihydroxy-, 7,8-dihydroxy, 6-hydroxy- and 8-hydroxycoumarins. Phytochemistry, 10, 2971–2974 (1971).
Kostova, I., Synthetic and natural coumarins as cytotoxic agents. Curr. Med. Chem. Anticancer Agents, 5, 29–46 (2005).
Lassegue, B. and Griendling, K. K., Reactive oxygen species in hypertension: an update. Am. J. Hypertens., 17, 852–860 (2004).
Masude, T., Isibe, D., Jitoe, A., and Naramati, N., Antioxidant curcuminoids from rhizomes of Curcuma zanthorrhiza. Phytochemistry, 33, 3645–3647 (1992).
McIntosh, L. J., Trush, M. A., and Troncoso, J. C., Increased susceptibility of Alzheimer’s disease temporal cortex to oxygen free radical-mediated processes. Free Radic. Biol. Med., 23, 183–190 (1997).
Oyaizu, M., Antioxidative activities of browning reaction prepared from glucosamine. Jpn. J. Nutr., 44, 307–315 (1986).
Prieto, P., Pineda, M., and Aguilar, M., Spectrophotometric quantitation of antioxidant capacity through the formation of a phosphomolybdenum complex: Specific application to the determination of vitamin E. Anal. Biochem., 269, 337–341 (1999).
Schonberg, A. and Latif, N., Furochromones and coumarins. XI. The molluscicidal activity of bergapten, isopimpinillin and xanthotoxin. J. Am. Chem. Soc., 76, 6208 (1954).
Sharma, S. D., Rajor, H. K., Chopra, S., and Sharma, R. K., Studies on structure activity relationship of some dihydroxy-4-methylcoumarin antioxidants based on their interaction with Fe(III) and ADP. Biometals, 18, 143–154 (2005).
Takao, T., Watanabe, N., Yagi, I., and Sakata, K., A simple screening method for antioxidants and isolation of several antioxidants produced by marine bacteria from fish and shellfish. Biosci. Biotechnol. Biochem., 58, 1780–1783 (1994).
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Vukovic, N., Sukdolak, S., Solujic, S. et al. An efficient synthesis and antioxidant properties of novel imino and amino derivatives of 4-hydroxy coumarins. Arch. Pharm. Res. 33, 5–15 (2010). https://doi.org/10.1007/s12272-010-2220-z
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DOI: https://doi.org/10.1007/s12272-010-2220-z