Exploring isoxazoles and pyrrolidinones decorated with the 4,6‐dimethoxy‐1,3,5‐triazine unit as human farnesyltransferase inhibitors - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Archiv der Pharmazie / Chemistry in Life Sciences Année : 2019

Exploring isoxazoles and pyrrolidinones decorated with the 4,6‐dimethoxy‐1,3,5‐triazine unit as human farnesyltransferase inhibitors

Résumé

Unprecedented triazinyl‐isoxazoles were afforded via an effective cycloaddition reaction between nitrile oxides and the scarcely described 2‐ethynyl‐4,6‐dimethoxy‐1,3,5‐triazine as dipolarophile. The biological evaluation of the newly synthesized compounds showed that the inhibition of human farnesyltransferase by zinc complexation could be improved with triazine‐isoxazole moieties. The replacement of the isoxazole unit by a pyrrolidin‐2‐one was detrimental to the inhibitory activity while the pyrrolidin‐2‐thione derivatives conserved the biological potential. The potential of selected compounds to disrupt protein farnesylation in Chinese hamster ovary (CHO) cells transfected with pEGFP‐CAAX was also evaluated.

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Chimie
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Dates et versions

hal-02873628 , version 1 (18-06-2020)

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Liliana Lucescu, Alina Ghinet, Sergiu Shova, Romain Magnez, Xavier Thuru, et al.. Exploring isoxazoles and pyrrolidinones decorated with the 4,6‐dimethoxy‐1,3,5‐triazine unit as human farnesyltransferase inhibitors. Archiv der Pharmazie / Chemistry in Life Sciences, 2019, 352 (5), pp.1800227. ⟨10.1002/ardp.201800227⟩. ⟨hal-02873628⟩
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