One-Step Synthesis of 3,4-Diphenyl-2-pyrrolinones by Solvent-Free and Bi2 O3 -Catalyzed Approaches and Cytotoxicity Screening Against Glioma Cells

Autor: José Tiago Menezes Correia, Mona das Neves Oliveira, Fabiano Damasceno, Airam Oliveira Santos, Silvia Lima Costa, Janaína Ribeiro, Lourenço Luis Botelho de Santana, José Claudio Serafim, Jessika Amparo, Silvio Cunha
Rok vydání: 2017
Předmět:
Zdroj: Journal of Heterocyclic Chemistry. 54:3700-3710
ISSN: 0022-152X
DOI: 10.1002/jhet.2921
Popis: Multifunctionalized 2-pyrrolinones were synthesized from the formal aza-[3 + 2] cycloaddition reaction of acyclic enaminones and diphenylcyclopropenone. For primary enaminones, solventless reaction under microwave heating was developed. On the other hand, catalysis by Bi2O3 under conventional heating was the more suitable strategy when secondary enaminones were employed. These conditions allowed the synthesis of a set of 2-pyrrolinones with two vicinal phenyl substituents, which were evaluated for cytotoxicity against U251 and C6 glioblastoma cells. In general, all tested 2-pyrrolinones with two vicinal phenyl rings were more active than those without this structural moiety, and 1-butyl-5-methyl-5-(2-oxopropyl)-3,4-diphenyl-1,5-dihydro-2H-pyrrol-2-one was the most cytotoxic and appears to be a new possibility as an antitumor scaffold to this aggressive brain tumor.
Databáze: OpenAIRE
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