Synthesis of Triazole Derivatives of Levoglucosenone As Promising Anticancer Agents: Effective Exploration of the Chemical Space through retro -aza-Michael//aza-Michael Isomerizations

TSAI, YI-HSUAN; BORINI ETICHETTI, CARLA M.; DI BENEDETTO, CAROLINA; GIRARDINI, JAVIER E.; MARTINS, FELIPE TERRA; SPANEVELLO, ROLANDO A.; SUÁREZ, ALEJANDRA G.; SAROTTI, ARIEL M.

JOURNAL OF ORGANIC CHEMISTRY

AMER CHEMICAL SOC

Lugar: Washington; Año: 2018 vol. 83 p. 3516 - 3528

0022-3263

The design and synthesis of biomass-derived triazoles and the in vitro evaluation as potential anticancer agents are described. The discovery of base-catalyzed retro-aza-Michael//aza-Michael isomerizations allowed the exploration of the chemical space by affording novel types of triazoles, difficult to obtain otherwise. Following this strategy, 2,4-disubstituted 1,2,3-triazoles could be efficiently obtained from the corresponding 1,4-disubstituted analogues.