Synthesis of Lactam Derivatives of Goniothalamin

Synthesis of Lactam Derivatives of Goniothalamin

Caixeta, V.; Vendramini-Costa, D. B.; Pilli, R. A.; de Carvalho, J. E.

Abstract:

(R)-Goniothalamin (1) is a natural product isolated from plants of the Goniothalamus gender. The natural enantiomer presents antiproliferative activity against the following tumor cell lines: cervical (HeLa), kidney (786-0) and adriamycin resistant ovary (NCI-ADR/RES). Posterior reports indicate that goniothalamin may act in the apoptotic process in cancer cells via different mechanisms. Based on the presence of lactam moieties in several biologically active natural product, we decide to search for compounds displaying enhanced cytotoxicity and selectivity. Therefore, we propose the synthesis of lactam derivatives (2a-f) based on the goniothalamin structure.

(R)-Goniothalamin (1) is a natural product isolated from plants of the Goniothalamus gender. The natural enantiomer presents antiproliferative activity against the following tumor cell lines: cervical (HeLa), kidney (786-0) and adriamycin resistant ovary (NCI-ADR/RES). Posterior reports indicate that goniothalamin may act in the apoptotic process in cancer cells via different mechanisms. Based on the presence of lactam moieties in several biologically active natural product, we decide to search for compounds displaying enhanced cytotoxicity and selectivity. Therefore, we propose the synthesis of lactam derivatives (2a-f) based on the goniothalamin structure.

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DOI: 10.5151/chempro-14bmos-R0374-1

Referências bibliográficas

• [1] 1 de Fátima, A. et. al. Bioorg. Med. Chem. 2006, 14, 622.
• [2] 2 a) de Fatima, A. et. al. Chem. Biol. Interact. 2008, 176, 143; b) Vendramini-Costa, D. B. et. al. Bioorg. Med. Chem. 2010, 18, 6742 ; c) Wach, J.-Y. et. al. Bioorg. Med. Chem. Lett. 2010, 20, 2843.

Como citar:

Caixeta, V.; Vendramini-Costa, D. B.; Pilli, R. A.; de Carvalho, J. E.; "Synthesis of Lactam Derivatives of Goniothalamin", p-374-374. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0374-1