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J Org Chem. 2018 Apr 6;83(7):3516-3528. doi: 10.1021/acs.joc.7b03141. Epub 2018 Mar 8.

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

Author information

1
Instituto de Química Rosario (IQUIR, CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas , Universidad Nacional de Rosario , Suipacha 531 , Rosario 2000 , Argentina.
2
Instituto de Biología Molecular y Celular de Rosario (IBR, CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas , Universidad Nacional de Rosario , Ocampo y Esmeralda , Rosario 2000 , Argentina.
3
Instituto de Química , Universidade Federal de Goiás , Campus Samambaia , Goiânia , GO CP 131, 74001-970 , Brazil.

Abstract

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.

PMID:
29481076
DOI:
10.1021/acs.joc.7b03141

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