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Abstract
Synthesis of xanthone derivatives had been conducted to obtain new antimalaria active compounds. The characterization of the synthesized xanthones was also conducted. Synthesis of xanthone was conducted from the raw material of hydroxybenzoic acid and phenol derivatives using Eaton's reagent via acylation-dehydration reaction by modified Grover, Shah and Shah (GSS) method. The synthesis of 2,3,4-trihydroxy-5-methyl xanthone was carried out using gallic acid, o-cresol and Eaton's reagent.The mixture was heated for 3 h at 80 °C to yield 2,3,4-trihydroxy-5-methyl xanthone in 43% yield as dark red viscous liquid. The results of IR, 1H-NMR and 13C-NMR analysis of sampleshowed that the compound2,3,4-trihydroxy-5-methyl xanthonehas successfully synthesized.
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References
- Fotie, J., Nkkengfack, A.E., Rukunga, G., Tolo, F., Peter, M.G., Heydenreich, M., and Fomum, Z.T., 2003. In vivo antimalarial activity of some oxygenated xanthones. Annals of Tropical Medicine and Parasitology, 97 (7), 683–688.
- Hay, A., E., He’lesbeux, J., J., Duval, O., LabaRed, M., Grellier, P. and Richomme, P., 2004, Antimalarial Xanthones from Calophyllum caledonicum and Garcinia vieillardii, J. Lif. Sci., 75, 3077-3085.
- Ignatuschenko, M.V., Winter, R.W., Bachinger, H.P., Hinrichs, D.J., and Riscoe, M.K., 1997.
- Ito, C., Itoigawa, M., Furukawa, H., Rao, K.S., Enjo, F., Bu, P., Takayasu, J., Tokuda, H., Nishino, H., 1998. Xanthones as inhibitors of Epstein-Barr virus activation. Cancer Lett. 132, 113–7.
- Likhitwitayawuid, K., Phadungcharoen, T., Krungkrai, J., 1998. Antimalarial xanthones from Garcinia cowa. Planta Med. 64, 70–2.
- Naidoo, J. M., 2009. Novel methodology for the synthesis of xanthones. Thesis, University of the Witwatersrand, Johannesburg.
- Portela, C., Afonso, C.M.M., Pinto, M.M.M., Lopes, D., Nogueira, F., do Rosário, V., 2007. Synthesis and antimalarial properties of new chloro-9H-xanthones with an aminoalkyl side chain. Chem. Biodivers. 4, 1508–19.
- Riscoe, M., Kelly, J., and Winter, R., 2005. Xanthones as Antimalarial Agents: Discovery, Mode of Action, and Optimization. Curr. Med. Chem. 12, 2539–2549.
- Saha, P., Mandal, S., Das, A., Das, P.C., and Das, S., 2004. Evaluation of the anticarcinogenic activity of Swertia chirata Buch.Ham, an Indian medicinal plant, on DMBA-induced mouse skin carcinogenesis model. Phytother. Res. 18, 373–8.
- Syamsudin, Soesanto, T., Wahyuono Subagus, and Mustofa, 2008. In vivo Antiplasmodial Activity and Acute Toxicity of the Fraction of the Garcinia parvifolia Miq. Stem Bark. J. Pharmacol. Toxicol. 3, 324–329.
- WHO, 1997, Roll Back Malaria, A Global Partnership, Geneva.
References
Fotie, J., Nkkengfack, A.E., Rukunga, G., Tolo, F., Peter, M.G., Heydenreich, M., and Fomum, Z.T., 2003. In vivo antimalarial activity of some oxygenated xanthones. Annals of Tropical Medicine and Parasitology, 97 (7), 683–688.
Hay, A., E., He’lesbeux, J., J., Duval, O., LabaRed, M., Grellier, P. and Richomme, P., 2004, Antimalarial Xanthones from Calophyllum caledonicum and Garcinia vieillardii, J. Lif. Sci., 75, 3077-3085.
Ignatuschenko, M.V., Winter, R.W., Bachinger, H.P., Hinrichs, D.J., and Riscoe, M.K., 1997.
Ito, C., Itoigawa, M., Furukawa, H., Rao, K.S., Enjo, F., Bu, P., Takayasu, J., Tokuda, H., Nishino, H., 1998. Xanthones as inhibitors of Epstein-Barr virus activation. Cancer Lett. 132, 113–7.
Likhitwitayawuid, K., Phadungcharoen, T., Krungkrai, J., 1998. Antimalarial xanthones from Garcinia cowa. Planta Med. 64, 70–2.
Naidoo, J. M., 2009. Novel methodology for the synthesis of xanthones. Thesis, University of the Witwatersrand, Johannesburg.
Portela, C., Afonso, C.M.M., Pinto, M.M.M., Lopes, D., Nogueira, F., do Rosário, V., 2007. Synthesis and antimalarial properties of new chloro-9H-xanthones with an aminoalkyl side chain. Chem. Biodivers. 4, 1508–19.
Riscoe, M., Kelly, J., and Winter, R., 2005. Xanthones as Antimalarial Agents: Discovery, Mode of Action, and Optimization. Curr. Med. Chem. 12, 2539–2549.
Saha, P., Mandal, S., Das, A., Das, P.C., and Das, S., 2004. Evaluation of the anticarcinogenic activity of Swertia chirata Buch.Ham, an Indian medicinal plant, on DMBA-induced mouse skin carcinogenesis model. Phytother. Res. 18, 373–8.
Syamsudin, Soesanto, T., Wahyuono Subagus, and Mustofa, 2008. In vivo Antiplasmodial Activity and Acute Toxicity of the Fraction of the Garcinia parvifolia Miq. Stem Bark. J. Pharmacol. Toxicol. 3, 324–329.
WHO, 1997, Roll Back Malaria, A Global Partnership, Geneva.