Enantiocontrolled Preparation of ϒ-Substituted Cyclohexenones: Synthesis and Kinase Activity Assays of Cyclopropyl-Fused Cyclohexane Nucleosides

Sergio Jurado, Beatriz Domínguez-Pérez, Ona Illa, Jan Balzarini, Félix Busqué*, Ramon Alibés

*Autor corresponent d’aquest treball

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1 Citació (Scopus)
2 Descàrregues (Pure)

Resum

The enantioselective preparation of the two isomers of 4-hydroxy-2-cyclohexanone derivatives 1a,b was achieved, starting from a common cyclohexenone, through asymmetric transfer hydrogenation (ATH) reactions using bifunctional ruthenium catalysts. From these versatile intermediates, a stereoselective route to a cytosine analogue built on a bicyclo [4.1.0]heptane scaffold is described. Nucleoside kinase activity assays with this cyclopropyl-fused cyclohexane nucleoside, together with other related nucleosides (2a–e), were performed, showing that thymine- and guanine- containing compounds have affinity for herpes simplex virus Type 1 (HSV-1) thymidine kinase (TK) but not for human cytosolic TK-1, thus pointing to their selectivity for herpetic TKs but not cellular TKs.

Idioma originalAnglès
Número d’article9704
Nombre de pàgines15
RevistaInternational journal of molecular sciences
Volum23
Número17
DOIs
Estat de la publicacióPublicada - de set. 2022

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