RT Journal Article
T1 Amide-controlled, one-pot synthesis of tri-substituted purines generates structural diversity and analogues with trypanocidal activity.
A1 Pineda de las Infantas y Villatoro, Maria J
A1 Unciti-Broceta, Juan D
A1 Contreras-Montoya, Rafael
A1 Garcia-Salcedo, Jose A
A1 Gallo Mezo, Miguel A
A1 Unciti-Broceta, Asier
A1 Diaz-Mochon, Juan J
K1 Técnicas de químicas  sintética
K1 Purinas
K1 Tripanocidas
K1 Trypanosoma brucei brucei
K1 Amidas
AB A novel one-pot synthesis of tri-substituted purines and the discovery of purine analogues with trypanocidal activity are reported. The reaction is initiated by a metal-free oxidative coupling of primary alkoxides and diaminopyrimidines with Schiff base formation and subsequent annulation in the presence of large N,N-dimethylamides (e.g. N,N-dimethylpropanamide or larger). This synthetic route is in competition with a reaction previously-reported by our group, allowing the generation of a combinatorial library of tri-substituted purines by the simple modification of the amide and the alkoxide employed. Among the variety of structures generated, two purine analogues displayed trypanocidal activity against the protozoan parasite Trypanosoma brucei with IC50 < 5 μM, being each of those compounds obtained through each of the synthetic pathways.
PB Nature Publishing Group
YR 2015
FD 2015-03-16
LK http://hdl.handle.net/10668/2376
UL http://hdl.handle.net/10668/2376
LA en
NO Pineda de las Infantas y Villatoro MJ, Unciti-Broceta JD, Contreras-Montoya R, Garcia-Salcedo JA, Gallo Mezo MA, Unciti-Broceta A, et al. Amide-controlled, one-pot synthesis of tri-substituted purines generates structural diversity and analogues with trypanocidal activity. Sci Rep. 2015; 5:9139
NO Journal Article; Research Support, Non-U.S. Gov't;
DS RISalud
RD Jun 1, 2025