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Derivados Xantónicos Prenilados: Optimização De Métodos De Obtenção, Caracterização Estrutural E Avaliação De Bioactividades

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Derivados Xantónicos Prenilados: Optimização De Métodos De Obtenção, Caracterização Estrutural E Avaliação De Bioactividades Raquel Alexandra Pinto Castanheiro Derivados Xantónicos Prenilados: Optimização de Métodos de Obtenção, Caracterização Estrutural e Avaliação de Bioactividades Faculdade de Farmácia da Universidade do Porto Abril 2009 Raquel Alexandra Pinto Castanheiro Derivados Xantónicos Prenilados: Optimização de Métodos de Obtenção, Caracterização Estrutural e Avaliação de Bioactividades Tese apresentada para admissão a provas de Doutoramento em Química Orgânica à Faculdade de Farmácia da Universidade do Porto Trabalho realizado sob orientação da Professora Doutora Madalena Maria de Magalhães Pinto Abril 2009 O trabalho da presente Tese foi realizado no Serviço de Química Orgânica da Faculdade de Farmácia da Universidade do Porto e no Centro de Estudos de Química Orgânica, Fitoquímica e Farmacologia da Universidade do Porto (Unidade I&D 226/2003) / CEQUIMED-UP (Unidade I&D 4040/2007) e com o apoio financeiro da FCT (SFRH/BD/13167/2003; I&D 226/2003, FEDER, POCI/ POCTI). Autora: Raquel Alexandra Pinto Castanheiro [email protected] Tese de Doutoramento em Química Orgânica Título: Derivados Xantónicos Prenilados: Optimização de Métodos de Obtenção, Caracterização Estrutural e Avaliação de Bioactividades Ano de Publicação: 2009 Orientadora: Professora Doutora Madalena Maria de Magalhães Pinto [email protected] DE ACORDO COM A LEGISLAÇÃO EM VIGOR, NÃO É PERMITIDA A REPRODUÇÃO DE QUALQUER PARTE DESTA TESE. Faculdade de Farmácia da Universidade do Porto, 15 de Abril de 2009 Os resultados apresentados nesta tese fazem parte das seguintes publicações, resumos e comunicações científicas: Publicações Científicas – Capítulos de Livro Pinto, M.; Castanheiro, R. ; Natural Prenylated Xanthones: Chemistry and Biological Activities. Em Natural Products: Chemistry, Biochemistry and Pharmacology . Ed. Brahmachari, G., Narosa Publishing House PVT. LTD., Nova Deli, Índia, ISBN: 978-81- 7319-886-1, 2009, Cap. 17, pp.520-676. – Artigos publicados em revistas de circulação internacional com arbitragem científica Artigos submetidos: 5. Pinto, M. M. M. & Castanheiro, R. A. P. Synthesis of Prenylated Xanthones: An Overview. Curr. Org. Chem. 2009 . 4. Gales, L.; Castanheiro, R. A. P. ; Pinto, M. M. M.; Damas, A. M. 1-Hydroxy-3-(3-methylbut- 2-enyloxy)xanthone. Acta Cryst. E. 2009 . 3. Castanheiro, R. A. P. ; Pinto, M. M. M.; Silva, A. M. S., Campos, N. A. N.; Nascimento, M. S. J. Antitumor Xanthone Derivatives: Prenylation as a Key Approach to Improve Activity. Chem. & Biodiv. 2009 . Artigos publicados: 2. Castanheiro, R. A. P. ; Pinto, M. M. M.; Cravo, S. M. M.; Pinto, D. C. G. A.; Silva, A. M. S.; Kijjoa, A. Improved Methodologies for Synthesis of Prenylated Xanthones by Microwave Irradiation and Combination of Heterogeneous Catalysis (K10 clay) with Microwave Irradiation. Tetrahedron 2009, 65 , 3848-3857. 1. Castanheiro, R. A. P. , Pinto, M. M. M., Silva, A. M. S., Cravo, S. M. M., Gales, L., Damas, A. M., Nazareth, N., Nascimento, M. S. J., Eaton, G. Dihydroxyxanthones Prenylated Derivatives: Synthesis, Structure Elucidation and Growth Inhibitory Activity on Human Tumor Cell Lines with Improvement of Selectivity for MCF-7; Bioorg. Med. Chem. 2007 , 15 , 6080- 6088. Resumos em actas de encontros publicados em revistas com arbitragem científica 8. Castanheiro, R. , Pinto, M., Silva, A., Campos, N., Nascimento, M.S.J., “Prenylated Derivatives of 1-Hydroxyxanthone: Synthesis and Antitumor Activity”, Rev. Port. Farm. , 2008 , LII (nº3) Suplemento : “1º Encontro Nacional de Química Terapêutica”, P-104, 152. 7. Cravo, S., Castanheiro, R. , Vrbata, P., Pinto, M., Silva, A., Campos, N., Nascimento, M.S.J., “Microwave-Assisted Synthesis of Hydroxyxanthones”, Rev. Port. Farm. , 2008 , LII (nº2) Suplemento : “1º Encontro Nacional de Química Terapêutica”, P-103, 151. 6. Castanheiro, R. , Pinto, M., Cravo, S., Nazareth, N., Nascimento, M. S. J., “Cyclic Xanthonic Derivatives: A Key Approach to Optimize Antitumor Activity”, Drugs Fut., 2008 , 33 (Suppl. A): “XX th International Symposium on Medicinal Chemistry”, P-197, 123. 5. Cravo, S., Castanheiro, R. , Pinto, M., Nazareth, N., Nascimento, M. S. J., “Optimization of Synthetic Methodologies of Biological Active Prenylated Xanthones”, Drugs Fut. , 2008 , 33 (Suppl. A) : “XXth International Symposium on Medicinal Chemistry”, P-220, 133. 4. Pinto, M., Sousa, M. E., Castanheiro, R. , Saraiva, L., Pereira, G., Gonçalves, J., “Inhibition of α, βI, δ, η and ζ Protein Kinase C Isoforms by Xanthones: Improvements Towards Selectivity”, Drugs Fut. , 2006 , 31 (Suppl. A): “XIX th International Symposium on Medicinal Chemistry”, P-232, 154. 3. Pinto, M., Castanheiro, R. , Cravo, S., Pinto, D., Silva, A., “Xanthone derivatives: prenylation and cyclization under microwaves and heterogeneous catalysis”, J. Mex. Chem. Soc., 2006 , 50 (special issue 1): “16 th International Conference on Organic Synthesis”, P-133, 165. 2. Castanheiro, R. , Pinto, M., Silva, A., Cravo, S., Pedro, M., Wilairat, R., Nazareth, N., Nascimento, M. S. J., “Prenylated Xanthonic Derivatives: Synthesis, Structure Elucidation and Inhibition of Growth of Human Tumor Cell Lines”, Sci. Pharm. , 2005 , 73(2) , Suppl.1: Abstracts of the Contributions of the Joint Meeting on Medicinal Chemistry, P-161, S219. 1. Castanheiro, R. , Pinto, M., Silva, A., Cravo, S., “Prenylated Xanthones: Synthesis and Structure Elucidation”, Rev. Port. Farm. , 2005 , LII (nº2) Suplemento : 2nd Congress of the Portuguese Society of Pharmaceutical Sciences and 6th Congress of the Portuguese- Spanish Chapter of the Controlled Release Society (Trends and Challenges in Pharmaceutics), P-19, 84-85. Comunicações em actas de encontros científicos Comunicações Orais: 21. Castanheiro, R.* , Cravo, S., Pinto, M., Silva, A., Nazareth, N., Nascimento, M.S.J., “Prenylation of 1,3-Dihydroxy-2-Methylxanthone: Improvements on the Growth Inhibitory Activity Against MCF-7 Cell Line”, comunicação oral apresentada no “41 st IUPAC World Chemistry Congress”, Turim, Itália, 5-11 Agosto, 2007 (O9). Comunicações em Painel: 20. Castanheiro, R.*, Pinto, M., Silva, A., Campos, N., Nascimento, M.S.J., “Prenylated Derivatives of 1-Hydroxyxanthone: Synthesis and Antitumor Activity”, comunicação em painel apresentada no “1º Encontro Nacional de Química Terapêutica”, Porto, Portugal, 13- 15 Novembro, 2008 (P-104). 19. Cravo, S.*, Castanheiro, R. , Vrbata, P., Pinto, M., Silva, A., Campos, N., Nascimento, M.S.J.,“ Microwave-Assisted Synthesis of Hydroxyxanthones”, comunicação em painel apresentada no “1º Encontro Nacional de Química Terapêutica”, Porto, Portugal, 13-15 Novembro, 2008 (P-103). 18. Castanheiro, R.*, Cravo, S., Pinto, M., Nazareth, N., Nascimento, M.S.J., “Cyclic Xanthonic Derivatives: A Key Approach to Optimize Antitumor Activity”, comunicação em painel apresentada no “XX th International Symposium on Medicinal Chemistry – EFMC-ISMC 2008”, Viena, Áustria, 31 Agosto a 4 Setembro, 2008 (P197). 17. Cravo, S.*, Castanheiro, R. , Pinto, M., Nazareth, N., Nascimento, M.S.J.,“Optimization of Synthetic Methodologies of Biological Active Prenylated Xanthones”, comunicação em painel apresentada no “XX th International Symposium on Medicinal Chemistry – EFMC- ISMC 2008”, Viena, Áustria, 31 Agosto a 4 Setembro, 2008 (P220). 16. Vrbata, P.*, Pinto, M., Castanheiro, R. , Cravo, S., “Synthesis of Xanthone Derivatives by Microwave-Assisted Methods”, comunicação em painel apresentada no “IJUP 2008: First Meeting of Young Researchers of University of Porto”, Porto, Portugal, 20-22 Fevereiro, 2008 (P-138). 15. Pinto, M.*, Castanheiro, R. , Cravo, S., Cidade, H., Neves, M., “Prenylation on Xanthonic and Flavonic Scaffolds: A Key Approach for Antitumor Activity”, comunicação em painel apresentada no “1st International Conference on Drug Design and Discovery”, Dubai, UAE, 4-7 Fevereiro, 2008 (Ref-125). 14. Cravo, S.*, Castanheiro, R. , Pinto, M., Pinto, D., Silva, A.,“Dihydropyran Xanthone Derivatives: Optimization of Synthetic Methodologies”, comunicação em painel apresentada no “41 st IUPAC World Chemistry Congress”, Turim, Itália, 5-11 Agosto, 2007 (P35). 13. Castanheiro, R.*, Cravo, S., Pinto, M., Azevedo, C. G., Afonso, C. M. M., Reis, S. H., “Microwave Assisted Synthesis of Xanthones: 1-Hydroxanthone, 1-Methoxyxanthone and one Dihydropyranoxanthone”, comunicação em painel apresentada no “7 th National Meeting of Organic Chemistry”, Lisboa, Portugal, 16-18 Julho, 2007 (PC24). 12. Fernandes, I.*, Castanheiro, R. , Pinto, M., Nascimento, M. S. J., “Assaying in vitro the Estrogenic/Antiestrogenic Activities of Two New Synthetic Prenylated Xanthones on Human Breast Cancer Cell lines”, comunicação em painel apresentada no “XV th National Congress of Biochemistry”, Aveiro, Portugal, 8-10 Dezembro, 2006 (P-38). 11. Pinto, M.*, Sousa, M. E., Castanheiro, R. , Saraiva, L., Pereira, G., Gonçalves, J., “Inhibition of α, βI, δ, η and ζ Protein Kinase C Isoforms by Xanthones: Improvements towards Selectivity” comunicação em painel apresentada no “XIX th International Symposium on Medicinal Chemistry (ISMC 2006)”, Istambul, Turquia, 29 de Agosto a 2 de Setembro de 2006 (P-232). 10. Castanheiro, R.*, Cravo, S., Pinto, M., Silva, A., Pedro, M., Nazareth, N., Nascimento, M. S. J., “Molecular Modification of Prenylated Xanthones: Heterogeneous Catalysis” comunicação em painel apresentada no “1 st European Chemistry Congress”, Budapeste, Hungria, 27-31 Agosto de 2006 (N-PO-29). 9. Cravo, S.*, Castanheiro, R. , Pinto, M., Pinto, D., Silva, A., Pedro, M., Nazareth, N., Nascimento, M. S. J., “Optimization of the Synthesis of Prenylated Xanthones by
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