Synthetic Studies Towards Combrestatin Analogues via Heck- Matsuda Reaction

Synthetic Studies Towards Combrestatin Analogues via Heck- Matsuda Reaction

Biajoli, André F. P.; Azambuja, Francisco de; Correia, Carlos R. D.

Abstract:

Combrestatins (Figure 1) and its analogues are electron rich cis-stilbene compounds possessing remarkable anti-cancer activity. Several studies have demonstrated the tubulin inhibition mode of action of such substances, making those interesting molecules against all types of cancer. The Heck-Matsuda (HM) reactions employ arenediazonium salts as arylating agents and present several advantages when compared to traditional protocols (aryl halides or triflates): they are phosphine-free, do not require inert atmosphere, are more economical, and can be carried out at lower temperatures and shorter reaction times. In this work, the HM arylation is evaluated as the key step for the synthesis of combrestatin analogues.

Combrestatins (Figure 1) and its analogues are electron rich cis-stilbene compounds possessing remarkable anti-cancer activity. Several studies have demonstrated the tubulin inhibition mode of action of such substances, making those interesting molecules against all types of cancer. The Heck-Matsuda (HM) reactions employ arenediazonium salts as arylating agents and present several advantages when compared to traditional protocols (aryl halides or triflates): they are phosphine-free, do not require inert atmosphere, are more economical, and can be carried out at lower temperatures and shorter reaction times. In this work, the HM arylation is evaluated as the key step for the synthesis of combrestatin analogues.

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DOI: 10.5151/chempro-14bmos-R0043-1

Referências bibliográficas

• [1] 1 Medarde, M.; Maya, A. B. S.; Pérez-Melero, C. J. Enz. Inh. Med. Chem. 2004, 19, 521.
• [2] 2 Taylor, J. G.; Moro, A. V.; Correia, C. R. D. Eur. J. Org. Chem. 2011, 1403.

Como citar:

Biajoli, André F. P.; Azambuja, Francisco de; Correia, Carlos R. D.; "Synthetic Studies Towards Combrestatin Analogues via Heck- Matsuda Reaction", p-43-43. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0043-1