RESUMO
A series of novel bisbenzofuran-imidazolium salts were designed and prepared. The in vitro antitumor activity of these derivatives was evaluated against a panel of human tumor cell lines (A549, HL-60, MCF-7, SMMC-7721 and SW480). Results demonstrated that 2-methyl-benzimidazole ring and substitution of the imidazolyl-3-position with a 4-methoxyphenacyl or 2-naphthylacyl substituent were important for promoting cytotoxic activity. Notably, compound 23 was found to be the most potent compound with IC50 values of 0.64-1.47 µM against five human tumor cell lines, and exhibited higher selectivity to MCF-7 and SW-480 cell lines with IC50 values 15.3-fold and 9.1-fold lower than DDP.
Assuntos
Antineoplásicos/farmacologia , Benzofuranos/farmacologia , Imidazóis/farmacologia , Antineoplásicos/síntese química , Benzofuranos/síntese química , Linhagem Celular Tumoral , Ensaios de Seleção de Medicamentos Antitumorais , Humanos , Imidazóis/síntese química , Estrutura Molecular , Relação Estrutura-AtividadeRESUMO
A simple and convenient synthesis of 3-salicyloylquinoline-4-carboxylic esters has been developed through an AlCl3-catalyzed reaction of easily available Baylis-Hillman adducts from chromones and isatin-derivatives. This reaction involves esterification, cyclization and ring opening in a one-step process, and provides an efficient approach for easy access to a series of valuable salicyloylquinoline derivatives with high yields. Moreover, this protocol offers several advantages, such as availability of starting materials, economic availability, operational simplicity and mild reaction conditions.