ci400529h_si_001.pdf (1.05 MB)
Download file

ZINClick: A Database of 16 Million Novel, Patentable, and Readily Synthesizable 1,4-Disubstituted Triazoles

Download (1.05 MB)
journal contribution
posted on 24.02.2014, 00:00 by Alberto Massarotti, Angelo Brunco, Giovanni Sorba, Gian Cesare Tron
Since Professors Sharpless, Finn, and Kolb first introduced the concept of “click reactions” in 2001 as powerful tools in drug discovery, 1,4-disubstituted-1,2,3-triazoles have become important in medicinal chemistry due to the simultaneous discovery by Sharpless, Fokin, and Meldal of a perfect click 1,3-dipolar cycloaddition reaction between azides and alkynes catalyzed by copper salts. Because of their chemical features, these triazoles are proposed to be aggressive pharmacophores that participate in drug–receptor interactions while maintaining an excellent chemical and metabolic profile. Surprisingly, no virtual libraries of 1,4-disubstituted-1,2,3-triazoles have been generated for the systematic investigation of the click-chemical space. In this manuscript, a database of triazoles called ZINClick is generated from literature-reported alkynes and azides that can be synthesized within three steps from commercially available products. This combinatorial database contains over 16 million 1,4-disubstituted-1,2,3-triazoles that are easily synthesizable, new, and patentable! The structural diversity of ZINClick (http://www.symech.it/ZINClick) will be explored. ZINClick will also be compared to other available databases, and its application during the design of novel bioactive molecules containing triazole nuclei will be discussed.

History