Click Chemistry Approach to Structurally Simplified Pancratistatin Analogs

Click Chemistry Approach to Structurally Simplified Pancratistatin Analogs

Sovera, V. de la; Bellomo, A.; Gonzalez., D.

Abstract:

The alkaloid pancratistatin isolated from the Polynesian plant Pancratium litoralle exhibits strong antitumor, antiviral, and antiparasitic activity. The mechanism of action has not been fully elucidated but it is known that the compound acts as a selective apoptosis inducer in tumor cells without affecting the normal tissue. There are several syntheses of pancratistatin but none of the available methods has been adapted to produce large quantities of material which cannot be obtained efficiently from the natural source either. In that sense, research has focused in the synthesis of simplified pancratistatin analogs. In this opportunity, we present our more recent results in the construction of a tricyclic analog of the Amarillidaceae alkaloids of the pancratistatin and narciclasine group by means of a strategy that involves biocatalysis and Huisgen cycloaddition.

The alkaloid pancratistatin isolated from the Polynesian plant Pancratium litoralle exhibits strong antitumor, antiviral, and antiparasitic activity. The mechanism of action has not been fully elucidated but it is known that the compound acts as a selective apoptosis inducer in tumor cells without affecting the normal tissue. There are several syntheses of pancratistatin but none of the available methods has been adapted to produce large quantities of material which cannot be obtained efficiently from the natural source either. In that sense, research has focused in the synthesis of simplified pancratistatin analogs. In this opportunity, we present our more recent results in the construction of a tricyclic analog of the Amarillidaceae alkaloids of the pancratistatin and narciclasine group by means of a strategy that involves biocatalysis and Huisgen cycloaddition.

Palavras-chave:

DOI: 10.5151/chempro-14bmos-R0064-1

Referências bibliográficas

• [1] 1 Kornienko A.; Evidente A., Chem. Rev. 2008, 108, 1982-2014.
• [2] 2 Rinner, U.; Hillebrenner, H. L.; Adams, D. R.; Hudlicky, T.; Pettit, G. R., Bioorganic And Medicinal Chemistry Letters 2004, 14, 2911- 2915.
• [3] 3 Bellomo, A.; Gonzalez, D., Tetrahedron: Asymmetry 2006, 17, 474-478.
• [4] 4 de la Sovera V.; Bellomo A.; Gonzalez D. Tetrahedron Lett. 2011, 52, 430-433.

Como citar:

Sovera, V. de la; Bellomo, A.; Gonzalez., D.; "Click Chemistry Approach to Structurally Simplified Pancratistatin Analogs", p-64-64. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0064-1