1,2,3-Triazoles are important structural motifs in diverse research fields, ranging from medicinal chemistry and agriculture to materials science.1
These heterocycles have proved very valuable as isostere of the amide group in bioactive molecules on account of their remarkable metabolic stability.2 While 1,2,3-triazoles are not present in naturally occurring compounds, the “amide-triazole bioequivalence” was exploited for development of, among others, HIV-1 protease inhibitor 13 and a potential anticancer agent 24 (Figure 1). Moreover, the 1,2,3-triazole unit is already present in three commercialized drugs (e.g., Tazobactam 3 in Fig. 1).5 The fragment 1,2,3-triazole is also intensively used in peptidomimetics.6
Technological applications of 1,2,3-triazoles include photostabilizing agents for polymers, whitening agents for thermoplastic resins (e.g., compound 4 in Figure 1) and corrosion inhibitors.7 Noteworthy, the recent advent of click-chemistry has resulted in novel 1,2,3-triazole-based materials such as linear polymers,8 dendrimers,9 and ionic liquids.10
Life Chemicals offers diversely functionalized 1,2,3-triazoles with several representative triazole structures shown below. The complete set of the functionalized 1,2,3-triazoles can be obtained upon request at firstname.lastname@example.org.
- (a) Rachwal, S.; Katritzky, A.R. in Comprehensive Heterocyclic Chemistry, 3rd edition, eds. A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, and R. J.K. Taylor; Pergamon, Oxford, 2008. Vol. 5, p. 1. (b) Bozorov, K.; Zhao, J.; Aisa, H. A. Bioorg. Med. Chem. 2019, 27, 3511-3531.
- Holub, J.M.; Kirshenbaum, K.; Chem. Soc. Rev. 2010, 39, 1325.
- Brik, A.; Muldoon, J.; Lin, Y.-C.; Elder, J.H.; Goodsell, D.S.; Olson, A.J.; Fokin, V.V.; Sharpless, K.B.; Wong, C.-H. ChemBioChem 2003, 4,1246.
- Soltis, M.J.; Yeh, H.J.; Cole, K.A.; Whittaker, N.; Wersto, R.P.; Kohn, E.C. Drug Metab. Dispos. 1996, 24, 799.
- According to www.drugbank.ca as of April 2019 there are 3 marketed and 18 experimental drugs containing the 1,2,3-triazole fragment.
- Colasson, B.; Save, M.; Milko, P.; Roithová, J.; Schröder, D.; Reinaud, O. Org. Lett. 2007, 9, 4987.
- Fan, W.-Q.; Katritzky, A.R. in Comprehensive Heterocyclic Chemistry, 2nd edition, eds. R. Katritzky, C. W. Rees, and E.F.V. Scriven Pergamon, Oxford, 1996. Vol. 4, p. 1.
- Schwartz, E.; Breitenkamp, K.; Fokin, V.V. Macromolecules 2011, 44, 4735.
- McNerny, D.Q.; Mullen, D.G.; Majoros, I.J.; Holl, M.M.B.; Baker Jr, J.R. in Click Chemistry for Biotechnology and Materials Science, ed.J. Lahann, John Wiley & Sons, 2009, p. 177.
- Yacob, Z.; Liebscher, J. Top. Heterocycl. Chem. 2015, 40, 167-210.