Are 1,4-and 1,5-disubstituted 1,2,3-triazoles good pharmacophoric groups?

Alberto Massarotti, Silvio Aprile, Valentina Mercalli, Erika Del Grosso, Giorgio Grosa, Giovanni Sorba, Gian Cesare Tron

Risultato della ricerca: Contributo su rivistaArticolo in rivistapeer review

Abstract

Over the last decade, 1,2,3-triazoles have received increasing attention in medicinal chemistry thanks to the discovery of the highly useful and widely applicable 1,3-dipolar cycloaddition reaction between azides and alkynes (click chemistry) catalyzed by copper salts and ruthenium complexes. After a decade of medicinal chemistry research on 1,2,3-triazoles, we feel that the time is ripe to demonstrate the real ability of this heterocycle to participate in important and pivotal binding interactions with biological targets while maintaining a good pharmacokinetic profile. In this study, we retrieved and analyzed X-ray crystal structures of complexes between 1,2,3-triazoles and either proteins or DNA to understand the pharmacophoric role of the triazole. Furthermore, the metabolic stability, the capacity to inhibit cytochromes, and the contribution of 1,2,3-triazoles to the overall aqueous solubility of compounds containing them have been analyzed. This information should furnish fresh insight for medicinal chemists in the design of novel bioactive molecules that contain the triazole nucleus.

Lingua originaleInglese
pagine (da-a)2497-2508
Numero di pagine12
RivistaChemMedChem
Volume9
Numero di pubblicazione11
DOI
Stato di pubblicazionePubblicato - 1 nov 2014

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