Synthesis of 4-Aryl-5-arylidene-3-bromofuran-2(5H)-one Rubrolides Analogues

Synthesis of 4-Aryl-5-arylidene-3-bromofuran-2(5H)-one Rubrolides Analogues

Barcelos, R. C.; Barbosa, L. C. A.; Maltha, C. R. A.; Demuner, A. J.; Donà, A.; Forlani, G.

Abstract:

The γ-alkylidenebutenolides comprise a class of natural products presenting a variety of biological activities. Within this class of substances, there are the rubrolides (1a-d), lactones isolated from marine ascidians, which are recognized as a source of natural bioactive compounds. Rubrolides are known for their antibiotic, cytotoxic and anti-inflammatory activities. Among the numerous phytotoxic products of microbial origin is cyanobacterin, a natural lactone isolated from the blue-green alga Scytonema hofmanni. Because of the high structural similarity between rubrolides and cyanobacterin, rubrolides 14a-k were synthetized and their ability to interfere with the photosynthetic electron transport chain in isolated spinach chloroplasts and in intact Chlorella cells were investigated.

The γ-alkylidenebutenolides comprise a class of natural products presenting a variety of biological activities. Within this class of substances, there are the rubrolides (1a-d), lactones isolated from marine ascidians, which are recognized as a source of natural bioactive compounds. Rubrolides are known for their antibiotic, cytotoxic and anti-inflammatory activities. Among the numerous phytotoxic products of microbial origin is cyanobacterin, a natural lactone isolated from the blue-green alga Scytonema hofmanni. Because of the high structural similarity between rubrolides and cyanobacterin, rubrolides 14a-k were synthetized and their ability to interfere with the photosynthetic electron transport chain in isolated spinach chloroplasts and in intact Chlorella cells were investigated.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0343-1

Referências bibliográficas

• [1] 1 Pearce, A. N.; Chia, E. W.; Berridge, M. V.; Maas, E. W.; Page, M. J.; Webb, V. L.; Harper, J. L.; Copp, B. R. J. Natural Products. 2007, 70, 111.
• [2] 2Teixeira, R. R.; Barbosa, L. C.; Forlani, G.; Piló-Veloso, D.; Carneiro, J. W. M. J. Agric. Food Chem. 2008, 56, 2321.

Como citar:

Barcelos, R. C.; Barbosa, L. C. A.; Maltha, C. R. A.; Demuner, A. J.; Donà, A.; Forlani, G.; "Synthesis of 4-Aryl-5-arylidene-3-bromofuran-2(5H)-one Rubrolides Analogues", p-343-343. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0343-1