Synthesis and antifungal activity of new C-2 pyridyl and pyridinylvinyl substituted quinolines

KOUZNETSOV, VLADIMIR; MELÉNDEZ GÓMEZ, CARLOS; DERITA, MARCOS; SVETAZ, LAURA; DEL OLMO, ESTHER; ZACCHINO, SUSANA

BIOORGANIC & MEDICINAL CHEMISTRY.

PERGAMON-ELSEVIER SCIENCE LTD

Lugar: Amsterdam; Año: 2012

0968-0896

New 2-pyridinyl quinolines 6-12 and 2-pyridinilvinyl quinolines 13-17 were prepared using a straightforward synthesis based on the BiCl3-catalyzed multicomponent imino Diels-Alder (imino DA) reaction or a novel tandem imino DA/catalytic tetrahydroquinoline ring oxidation/Perkin condensation sequential process. All members of the series showed activities against dermatophytes and some of them possessed a broader spectrum of action. 2- (Pyridin-4-yl)quinoline 9 and 2-(2-pyridin-4-yl)vinyl)quinoline 16 showed the best MIC80 and MIC50 against the clinically important fungi C. albicans and non-albicans Candida species. In turn, 6-ethyl-2-(pyridin-2-yl)quinoline 6 showed the best properties against standardized as well as clinical strains of C. neoformans. 2009 Elsevier Ltd. All rights reserved.