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BIBTEX RIS

One‐Step Synthesis of 3,4‐Diphenyl‐2‐pyrrolinones by Solvent‐Free and Bi 2 O 3 ‐Catalyzed Approaches and Cytotoxicity Screening Against Glioma Cells

2017; Wiley; Volume: 54; Issue: 6 Linguagem: Inglês

10.1002/jhet.2921

1943-5193

Sílvio Cunha, José Cláudio Serafim, Lourenço Luís Botelho de Santana, Fabiano Damasceno, José Tiago Menezes Correia, Airam Oliveira Santos, Mona N. Oliveira, Janaína da Silva Ribeiro, Jéssika Alves Oliveira Amparo, Sílvia Lima Costa,

Catalytic C–H Functionalization Methods

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 Bi 2 O 3 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‐2 H ‐pyrrol‐2‐one was the most cytotoxic and appears to be a new possibility as an antitumor scaffold to this aggressive brain tumor.