RESUMEN
An access to different glycohybrids involving nucleophilic addition of N- and C-nucleophiles to the butenonyl glycosides followed by cyclization and subsequent reactions is reported. In the present communication, three different prototypes, ß-D-glucopyranosylmethyl pyrazolines, ß-D-glucopyranosylmethyl pyrimidines and ß-D-glucopyranosylmethyl biphenyls, were prepared in moderate to good yields.
Asunto(s)
Compuestos de Bifenilo/síntesis química , Glucósidos/química , Pirazoles/síntesis química , Pirimidinas/síntesis química , Compuestos de Bifenilo/química , Estructura Molecular , Pirazoles/química , Pirimidinas/químicaRESUMEN
A series of 1-phenyl-4-glycosyl-dihydropyridines (4-17 and 19-21) were prepared by the one pot multicomponent reaction of glcosyl aldehyde, beta-keto compounds and aniline or substituted aniline in the presence of TBAHS as catalyst. The compounds were screened in vitro and in vivo for their antileishmanial activities. Most of the compounds exhibited moderate to good activity against amastigotes and promastigotes of Leishmania donovani. The compounds 4, 11, 12, 13, and 17 exhibited potent in vivo activity with selectivity index (SI) values 7.43-18.93. Molecular docking studies with these compounds revealed L. donovani PTR1 as the possible target to show antileishmanial activities.
Asunto(s)
Antiprotozoarios/síntesis química , Antiprotozoarios/farmacología , Leishmania donovani/efectos de los fármacos , Modelos Moleculares , Piridinas/síntesis química , Piridinas/farmacología , Animales , Antiprotozoarios/metabolismo , Antiprotozoarios/toxicidad , Línea Celular , Leishmania donovani/enzimología , Leishmania donovani/crecimiento & desarrollo , Estadios del Ciclo de Vida , Ratones , Conformación Molecular , Oxidorreductasas/química , Oxidorreductasas/metabolismo , Piridinas/metabolismo , Piridinas/toxicidadRESUMEN
A highly atom economic one pot synthesis of tetrahydropyridines was achieved by L-proline/TFA catalysed multicomponent reaction of beta-keto-esters, aromatic aldehydes and anilines. The synthesized compounds were screened against Plasmodium falciparum in vitro and one of them showed antimalarial activity with MIC as low as 0.09 microg/mL.