RESUMO
The first total synthesis of prasinic acid is being reported along with its biological evaluation. The ten step synthesis involved readily available and cheap starting materials and can easily be transposed to large scale manufacturing. The crucial steps of the synthesis included the formation of two different aromatic units (7 and 9) and their coupling reaction. The synthetic prasinic acid exhibited moderate antitumor activity (IC(50) 4.3-9.1 µM) in different lines of cancer cells.
Assuntos
Antineoplásicos/síntese química , Antineoplásicos/farmacologia , Benzoatos/síntese química , Benzoatos/farmacologia , Heptanos/síntese química , Heptanos/farmacologia , Antineoplásicos/química , Benzoatos/química , Linhagem Celular Tumoral , Proliferação de Células/efeitos dos fármacos , Ensaios de Seleção de Medicamentos Antitumorais , Heptanos/química , Humanos , Concentração Inibidora 50 , Estrutura MolecularRESUMO
A short and efficient synthesis of cyrmenin B(1), an antifungal metabolite of myxobacteria Cystobacter armeniaca and Archangium gephyra, is described. The crucial steps of the synthesis included the formation of the dehydroalanine moiety from the corresponding serine acetate and the formation of the beta-methoxyacrylate system via trimethylsilyldiazomethane methylation of the corresponding beta-hydroxy enamide.
