Simple and efficient synthesis of novel porphyrinphosphoramidates

Simple and efficient synthesis of novel porphyrinphosphoramidates

Pedrosa, Leandro F.; Souza, Marcos C.; Ferreira, Vitor F.; Cavaleiro, José A. S.

Abstract:

Medicinal formulations which include the use of porphyrin derivatives as photosensitisers are already being considered in several countries for the photodynamic therapy (PDT) of malignant tumors and also for the treatment of age-related macular degeneration. Organophosphorus compounds also have a prominent place in medicine, being used as anticancer drugs, antivirals, antifungals, inhibitors of bone resorption among other applications. Porphyrin phosphonates, in particular, display interesting binding properties, where the P=O group plays a significant role as a strong hydrogen bond acceptor. Phosphoramidates possess a great biological activity and have been used in several prodrug strategies. Therefore, the synthesis of porphyrins containing phosphoramidate moieties may lead to new compounds with interesting biological properties or with adequate properties to be used as photosensitisers in photodynamic therapy.

Medicinal formulations which include the use of porphyrin derivatives as photosensitisers are already being considered in several countries for the photodynamic therapy (PDT) of malignant tumors and also for the treatment of age-related macular degeneration. Organophosphorus compounds also have a prominent place in medicine, being used as anticancer drugs, antivirals, antifungals, inhibitors of bone resorption among other applications. Porphyrin phosphonates, in particular, display interesting binding properties, where the P=O group plays a significant role as a strong hydrogen bond acceptor. Phosphoramidates possess a great biological activity and have been used in several prodrug strategies. Therefore, the synthesis of porphyrins containing phosphoramidate moieties may lead to new compounds with interesting biological properties or with adequate properties to be used as photosensitisers in photodynamic therapy.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0213-1

Referências bibliográficas

• [1] 1 Cavaleiro, J. A. S.; et al., in Handbook of Porphyrin Science, 2010, Vol 2. Ch. 9, pp. 194-294.
• [2] 2 Bhosale, S. V.; et al., Eur. J. Org. Chem. 2009,24, 4128.
• [3] 3 Pedrosa, L. F.; et al., Aust. J. Chem. 2011, in press.
• [4] 4 De Paula, R.; et al., J. Heterocycl. Chem. 2008, 45, 453.
• [5] 5 Souza, M. C.; et al., Phosphorus, Sulfur, and Silicon 2006, 181, 1885.

Como citar:

Pedrosa, Leandro F.; Souza, Marcos C.; Ferreira, Vitor F.; Cavaleiro, José A. S.; "Simple and efficient synthesis of novel porphyrinphosphoramidates", p-213-213. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0213-1