RESUMO
A facile, one-pot synthesis of thio and selenourea derivatives from amines using tetrathiomolybdate 1 and tetraselenotungstate 2 as sulfur and selenium transfer reagents, respectively, is reported. The compounds were tested for their activity as urease inhibitors and some of the compounds showed potent activity in the nanomolar range towards jack bean urease.
Assuntos
Molibdênio/química , Compostos Organosselênicos/síntese química , Compostos Organosselênicos/farmacologia , Tioureia/síntese química , Tioureia/farmacologia , Ureia/análogos & derivados , Urease/antagonistas & inibidores , Canavalia/enzimologia , Avaliação Pré-Clínica de Medicamentos , Inibidores Enzimáticos/síntese química , Inibidores Enzimáticos/química , Inibidores Enzimáticos/farmacologia , Modelos Moleculares , Estrutura Molecular , Compostos Organosselênicos/química , Tioureia/química , Ureia/síntese química , Ureia/química , Ureia/farmacologiaRESUMO
A facile and efficient methodology has been developed for the synthesis of dithymidine and di-uridine derived disulfides using benzyltriethylammonium tetrathiomolybdate as a sulfur transfer reagent. However, a similar reaction of thymidine derivative with tetraethylammonium tetraselenotungstate as a selenium transfer reagent resulted in the formation of an unexpected cyclic diselenide. The disulfide derivatives of nucleosides have been used as precursors in a tandem disulfide cleavage-Michael addition/ring opening reactions to construct aminoacid and carbocyclic derivatives of nucleosides.
Assuntos
Dissulfetos/química , Timidina/química , Uridina/química , Cristalografia por Raios X , Dissulfetos/síntese química , Modelos Moleculares , Estrutura Molecular , Molibdênio/química , Nucleosídeos/química , EstereoisomerismoRESUMO
Tetrathiomolybdate has been used as an efficient sulfur-transfer reagent in the synthesis of a number of thiolevomannosan derivatives having an axial-rich 1C4 conformation. An unprecedented synthesis of a novel thioorthoester and its synthetic utility in glycosylation has been demonstrated. This is a general and efficient method for the synthesis of conformationally locked thiosugars.