Synthesis and citotoxicity activity of new aza-analogues of angucyclinones from (-)-shikimic acid

Synthesis and citotoxicity activity of new aza-analogues of angucyclinones from (-)-shikimic acid

Cuellar, M; Quiñones, N; Villena, J; Salas, C.

Abstract:

The synthesis of heterocyclic quinones is an attractive research area in organic synthesis due to the well-known biological activities of these compounds isolated from several natural sources. There are several natural products which contain a tetrahydrobenzo[a]anthraquinone skeleton. Most of these are named as angucyclines, which are wellknown for their broad range of biological properties including antifungal, antiviral, antibiotic, antitumor, platelet aggregation and enzyme inhibitory behavior, a representative example is provided by (+)-ochromycinone (1). These compounds, which are secreted by Actinomycetes are, after the tetracyclines and anthracyclines, the third class of natural antibiotics featuring a carbotetracyclic skeleton. On the other hand, (-)-shikimic acid (2), is a natural products has been used as a versatile chiral building block for the synthesis of many targets including therapeutic drugs, due that this compounds has three stereocenter with a specific configuration.

The synthesis of heterocyclic quinones is an attractive research area in organic synthesis due to the well-known biological activities of these compounds isolated from several natural sources. There are several natural products which contain a tetrahydrobenzo[a]anthraquinone skeleton. Most of these are named as angucyclines, which are wellknown for their broad range of biological properties including antifungal, antiviral, antibiotic, antitumor, platelet aggregation and enzyme inhibitory behavior, a representative example is provided by (+)-ochromycinone (1). These compounds, which are secreted by Actinomycetes are, after the tetracyclines and anthracyclines, the third class of natural antibiotics featuring a carbotetracyclic skeleton. On the other hand, (-)-shikimic acid (2), is a natural products has been used as a versatile chiral building block for the synthesis of many targets including therapeutic drugs, due that this compounds has three stereocenter with a specific configuration.

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DOI: 10.5151/chempro-15bmos-BMOS2013_201382005353

Referências bibliográficas

• [1] 1 Kharel, M. K.; Pahari, P.; Shepherd, M. D.; Tibrewal, N.; Nybo, S. E.; Shaaban, K. A.; Rohr, J. Nat Prod Rep 2012, 29, 264.
• [2] 2 Carreno, M. C.; Urbano, A. Synlett 2005, 1.
• [3] 3 Guo, Z. K.; Liu, S. B.; Jiao, R. H.; Wang, T.; Tan, R. X.; Ge, H. M. Bioorg Med Chem Lett 2012, 22, 7490.
• [4] 4 Estevez, A. M.; Estevez, R. J. Mini Rev Med Chem 2012, 12, 1443.
• [5] 5 Sanchez-Abella, L.; Fernandez, S.; Verstuyf, A.; Verlinden, L.; Ferrero, M.; Gotor, V. Bioorg Med Chem 2007, 15, 4193.

Como citar:

Cuellar, M; Quiñones, N; Villena, J; Salas, C.; "Synthesis and citotoxicity activity of new aza-analogues of angucyclinones from (-)-shikimic acid", p-52-52. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201382005353