RESUMO
A sequential single-flask multicomponent reactions is highly effective for the synthesis of 1,2-dihydroisoquinolines through amidealkylation from intermediate N-acylisoquinolinium salts under mild conditions. N-Acylisoquinolinium ions and trichloromethyl-1-(1H-indol-3-yl)isoquinoline-2(1H)-carboxylate have demonstrated their reactivity toward aromatic and aliphatic π-nucleophiles. One of the 1,2-dihydroisoquinoline derivatives was found to be a potent inhibitor for transcription factor NF-κB by blocking IκBα degradation, p65 nuclear translocation, and NF-κB DNA binding in TNF-α-induced NIH 3T3 cells.
Assuntos
Isoquinolinas/síntese química , Isoquinolinas/farmacologia , NF-kappa B/antagonistas & inibidores , Animais , Células Cultivadas , Humanos , Isoquinolinas/química , Camundongos , Estrutura Molecular , NF-kappa B/metabolismo , Células NIH 3T3 , Relação Estrutura-Atividade , Fator de Necrose Tumoral alfa/antagonistas & inibidores , Fator de Necrose Tumoral alfa/metabolismoRESUMO
An efficient C-C bond formation reaction assisted by a fluoride ion has been identified for N,N'-diphenyl-1,4-phenylenediimine with the compounds having an active methylene group. The reaction follows the typical Michael addition fashion and proceeds to completion within 1 h at 70 degrees C in acetonitrile in the presence of tetrabutylammonium fluoride (TBAF), while the same reaction failed to proceed in the absence of a fluoride anion. The new finding reported herein also offers an unprecedented method for a direct functionalization of polyaniline backbone with versatile functional alkyl groups.