Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
권호 표지

Synthesis of 7-Hydroxy-4-Oxo-4H-Chromene- and 7-Hydroxychroman-2-Carboxylic Acid N-Alkyl Amides and Their Antioxidant Activities

  • Published : 2006.09.01
Download PDF
⟨ Previous Next ⟩

Abstract

A series of 7-hydroxy-4-oxo-4H-chromene- (3a - h) and 7-hydroxychroman-2-carboxylic acid N-alkyl amides (4a - g) were synthesized and their antioxidant activities were evaluated. While compounds 3a - h were less active, compounds 4a - g exhibited more potent inhibition of lipid peroxidation initiated by $Fe^{2+}$ and ascorbic acid in rat brain homogenates. Among them, 7-hydroxychroman-2-carboxylic acid N-alkylamides (4e - g) bearing nonyl, decyl, and undecyl side chain exhibited 3 times more potent inhibition than trolox (1).

Keywords

References

  1. Andersen, J. K., Oxidative stress in neurodegeneration. Nat. Rev. Neurosci., 5, S18-S25 (2004)
  2. Barnham, K. J., Masters, C. L., and Bush, A., Neurodegenerative diseases and oxidative stress. Nat. Rev. Drug Discovery, 3, 205-214 (2004) https://doi.org/10.1038/nrd1330
  3. Braughler, J. M., Duncan, L. A., and Chase, R. L., The involvement of iron in lipid Peroxidation. J. Bio. Chem. 261, 10282-10289 (1986)
  4. Cash, A., Smith, M., and Perry, G., Oxidative Stress Mechanisms and Potential Therapeutic Modalities in Alzheimer Disease. Med. Chem. Rev., 1, 19-23 (2004)
  5. Chabrier, P.-E., Auguet, M., Spinnewyn, B., Auvin, S., Cornet, S., Demerle-Pallardy, C., Guilmard-Favre, C., Marin, J.-G., Pignol, B., Gillard-Roubert, V., Roussillot-Charnet, C., Schulz, J., Viossat, I., Bigg, D., and Moncada, S., BN 80933, a dual inhibitor of neuronal nitric oxide synthase and lipid peroxidation: A promising neuroprotective strategy. Proc. Natl. Acad. Sci. U.S.A. 96, 10824-10829 (1999)
  6. Cho, J. and Lee, H., Wogonin inhibits excitotoxic and oxidative neuronal damage in primary cultured rat cortical cells. Eur. J. Pharm., 485, 105-110 (2004) https://doi.org/10.1016/j.ejphar.2003.11.064
  7. Crombie, L., Jones, R. C. R., and Palmer, C. J., Synthesis of mammeins and surangin A. Tet. Letters, 26, 2929-2932 (1985) https://doi.org/10.1016/S0040-4039(00)98874-9
  8. Forman, H. J. and Torres, M., Redox signaling in macrophages. Mol. Aspects Med., 22, 189-216 (2001) https://doi.org/10.1016/S0098-2997(01)00010-3
  9. Forrest, V. J., Kang, Y. H., McClain, D. E., Robinson D. H., and Ramakrishnan, N., Oxidative stress-induced apoptosis prevented by trolox. Free Rad. Biol. Med., 16, 675-684 (1994) https://doi.org/10.1016/0891-5849(94)90182-1
  10. Gilgun-Sherki, Y., Melamed, E., and Offen, D., Oxidative stress induced-neurodegenerative diseases: the need for antioxidants that penetrate the blood brain barrier. Neuropharmacol., 40, 959-975 (2001) https://doi.org/10.1016/S0028-3908(01)00019-3
  11. Gilgun-Sherki, Y., Rosenbaum, Z., Meland, E., and Offen D., Antioxidant Therapy in Acute Central Nervous System Injury: current state. Pharmacol. Rev., 54, 271-284 (2002) https://doi.org/10.1124/pr.54.2.271
  12. Griendling, K. K. and FitzGerald, G. A., Oxidative stress and cardiovascular injury. Circulation, 108, 2034-2040 (2003) https://doi.org/10.1161/01.CIR.0000093661.90582.c4
  13. Hall, E. D., Braughler, J. M., Yonkers, P. A., Smith, S. L., Linseman, K. L., Means, E. D., Scherch, H. M., Von Voigtlaender, P. F., Lahti, R. A., and Jacobsen, E. J., 78517F: a potent inhibitor of lipid peroxidation with activity in brain injury and ischemia. J. Pharm. Exp. Ther. 258, 688-694 (1991)
  14. Halliwell, B. and Gutteridge, J. M. C., Oxygen is poisonous an introduction to oxygen toxicity and free radicals, In Halliwell, B. and Gutteridge, J. M. C. (Eds.). Free radicals in biology and medicine. 2nd ed. Oxford Clarendon, Oxford University, pp. 1-20 (1989)
  15. Kohen, R. and Nyska, A., Oxidation of biological systems: Oxidative stress phenomena, Antioxidants, Redox reactions, and methods of their quantification. Toxicol. Pathol., 30, 620- 650 (2002) https://doi.org/10.1080/01926230290166724
  16. Koufaki, M., Detsi, A., Theodorou, E., Kiziridi, C., Calogeropoulou, T., Vassilopoulos, A., Kourounakis, A. P., Rekka, E., Kourounakis, P. N., Gaitanaki, C., and Papazafiri, P., Synthesis of chroman analogues of lipoic acid and evaluation of their activity against reperfusion arrhythmias. Bioorg. Med. Chem., 12, 4835-4841 (2004) https://doi.org/10.1016/j.bmc.2004.07.012
  17. Lee, H., Lee, K., Jung, J.-K., Cho, J., and Theodorakis, E. A., Synthesis and evaluation of 6-hydroxy-7-methoxy-4- chromanone- and chroman- 2-carboxamides as antioxidants. Bioorg. Med. Chem. Lett., 15, 2745-2748 (2005) https://doi.org/10.1016/j.bmcl.2005.03.118
  18. Maxwell, S. R. J., Prospects for the use of antioxidant therapies. Drugs, 49, 345-361 (1995) https://doi.org/10.2165/00003495-199549030-00003
  19. Mishima, K., Tanaka, T., Pu, F., Egashira, N., Iwasaki, K., Hidaka, R., Matsunaga, K., Takata, J., Karube, Y., and Fujiwara, M., Vitamin E isoforms alpha-tocotrienol and gamma-tocopherol prevent cerebral infarction in mice. Neurosci Lett., 337, 56-60 (2003) https://doi.org/10.1016/S0304-3940(02)01293-4
  20. Naderi, G. H., Asgary, A., Ani, S., Sarraf-Zadegan, M., Safari, N., and Reza, M., Effect of some volatile oils on the affinity of intact and oxidized low-density lipoproteins for adrenal cell surface receptors. Mol. Cell. Biochem., 267, 59-66 (2004) https://doi.org/10.1023/B:MCBI.0000049365.60694.81
  21. Priyadarsini, K., Indira, M., Dilip, K., Naik, G. H., Kumar, M. S., Unnikrishnan, M. K., Satav, J. G., and Mohan, H., Role of phenolic o-h and methylene hydrogen on the free radical reactions and antioxidant activity of curcumin. Free Rad. Bio. Med., 35, 475-484 (2003) https://doi.org/10.1016/S0891-5849(03)00325-3
  22. Rajan, P., Vedernikova, I., Cos, P., Berghe, V. D., Augustynsa K., and Haemersa, A., Synthesis and evaluation of caffeic acid amides as antioxidants. Bioorg. Med. Chem. Lett., 11, 215-217 (2001) https://doi.org/10.1016/S0960-894X(00)00630-2
  23. Rego, A. C., Santos, M. S., and Oliveira, C. R., Influence of the antioxidants vitamin E and idebenone on retinal cell injury mediated by chemical ischemia, hypoglycemia, or oxidative stress. Free Radic. Biol. Med., 26, 1405-1417 (1999) https://doi.org/10.1016/S0891-5849(98)00337-2
  24. Roberfroid, M. and Colderon, P. B., Definitions, properties and reactions of radicals. In Roberfroid, M. and Colderon, P. B. (Eds.) Free radicals and oxidation phenomena in biological systems. New York, University of Catholique de Louvain Brussels, pp. 11-32 (1995)
  25. Sagach, V. F., Scrosati, M., Fielding, J., Rossoni, G., Galli, C., and Visioli, F., The water-soluble vitamin E analogue Trolox protects against ischaemia/reperfusion damage in vitro and ex vivo: a comparison with vitamin E. Pharmacol. Res., 45, 435-439 (2002) https://doi.org/10.1006/phrs.2002.0993
  26. Suzuki, Y. J., Forman, H. J., and Sevanian, A., Oxidants as stimulators of signal transduction. Free Rad. Biol. Med., 22, 269-285 (1997) https://doi.org/10.1016/S0891-5849(96)00275-4
  27. Tsuchiya, M., Scita, G., Freisleben, H. J., Kagan, V. E., and Packer, L., Antioxidant radical-scavenging activity of carotenoids and retinoids compared to ${\alpha}$-tocopherol. Method Enzymol., 213, 460-472 (1992) https://doi.org/10.1016/0076-6879(92)13148-Q
  28. van der Worp, H. B., Bar, P. R., Kappelle, L. J., and de Wildt, D. J., Dietary vitamin E levels affect outcome of permanent focal cerebral ischemia in rats. Stroke, 29, 1002-1006 (1998) https://doi.org/10.1161/01.STR.29.5.1002
  29. Vairagupta, O., Toasaksiri, S., Boonyarat, C., Wongkrajang, Y., Peungvicha, P., Watanabe, H., and Boonchoong, P., Chroman amide and nicotinyl amide derivatives: inhibition of lipid peroxidation and protection against head trauma. Free Rad. Res., 32, 145-155 (2000) https://doi.org/10.1080/10715760000300151
  30. Wu, T.-W., Hashimoto, N., Wu, J., Carey, D., Li, R.-K., Mickle, D. A. G., and Weisel, R. D., The cytoprotective effect of trolox demonstrated with three types of human cells. Biochem. Cell Biol., 68, 1189-1194 (1990) https://doi.org/10.1139/o90-176