RESUMEN
A small library of compounds was prepared by a combination of toluene dioxygenase (TDO)-catalyzed enzymatic dihydroxylation and copper(I)-catalyzed Hüisgen cycloaddition. Some compounds were obtained by coupling an alkyne and a conduritol derivative, while more complex structures were obtained by a double Hüisgen reaction of a dialkyne and two molecules of the cyclitol. The compounds were fully characterized and subjected to preliminary biological screening.
Asunto(s)
Ciclitoles/síntesis química , Ciclitoles/farmacología , Bibliotecas de Moléculas Pequeñas/síntesis química , Bibliotecas de Moléculas Pequeñas/farmacología , Animales , Antifúngicos/síntesis química , Antifúngicos/química , Antifúngicos/farmacología , Proliferación Celular/efectos de los fármacos , Células Cultivadas , Ciclitoles/química , Reacción de Cicloadición , Inmunosupresores/síntesis química , Inmunosupresores/química , Inmunosupresores/farmacología , Masculino , Ratones , Ratones Endogámicos C57BL , Estructura Molecular , Bibliotecas de Moléculas Pequeñas/química , Triazoles/síntesis química , Triazoles/química , Triazoles/farmacologíaRESUMEN
The palladium catalyzed cross-coupling reaction of phenyltrifluoroborate with a chemoenzymatically derived bromoazidoconduritol, combined with 1,3-dipolar cycloaddition, with a variety of alkynes is described. Fourteen new compounds were synthesized in moderate to good yields. The click chemistry reaction can be effected by using sodium ascorbate and CuSO(4) · 5H(2)O as catalyst in toluene-H(2)O at room temperature.
Asunto(s)
Biocatálisis , Química Clic/métodos , Ciclitoles/química , Paladio/química , Ciclitoles/síntesis química , Dioxigenasas/metabolismo , Pseudomonas putida/enzimologíaRESUMEN
The first syntheses of two deoxythiocyanocyclitols (4-deoxy-4-thiocyano-L-chiro-inositol and deoxythiocyanoconduritol F) and two deoxysulfonylcyclitol acetals are reported by a chemoenzymatic enantioselective route. The compounds were prepared by a sequence of enzymatic and ruthenium-catalyzed dihydroxylations, and the results were studied regarding reaction conditions and co-catalyst for different derivatives. The new compounds were included in a minilibrary of deoxygenated cyclitols and evaluated for their capacity to influence the feeding behavior of Epilachna paenulata (Coleoptera: Coccinellidae), a common pest of the Curcubitaceae crops.