Triazolyl Glycoconjugates in Medicinal Chemistry

Cu–Al mixed oxide-catalysed multi-component synthesis of gluco- and allofuranose-linked 1,2,3-triazole derivatives

“…The IR spectra of compounds 7a-e and 8a-e showed the characteristic absorption assigned to the N=N stretching for triazole compounds that appear nearly around 1490 cm − 1 and three or four intense absorption bands Furthermore, the identity of the carbohydrate-triazole conjugates presented in this work was supported by high-resolution mass spectrometry (HRMS) which confirmed the expected mass for all compounds in accordance with their molecular formula. The analysis of the NMR spectroscopic data ( 1 H, 13 C, homonuclear correlation spectroscopy (COSY), heteronuclear single quantum correlation (HSQC) and heteronuclear multiple bond correlation (HMBC) experiments) reveals the diagnostic singlet in the resonance of the 1 H NMR due to triazolyl protons in the region of 7.50 ppm and around 122.0 ppm in 13 C NMR due to C-5 of the triazole ring, which confirms the formation of glycoconjugates. Representative 1 H NMR spectra of diastereomeric compounds 7c and 8c are shown in figure 4.…”

“…Gratifyingly, in nearly all cases, very good yields of triazoles 7a-e and 8a-e were obtained and halogen substituents at the substrates were well tolerated. Both diastereomeric series of carbohydrate-triazole conjugates were fully characterized by FT-IR, HRMS, 1 H-and 13 C-NMR spectroscopy. The IR spectra of compounds 7a-e and 8a-e showed the characteristic absorption assigned to the N=N stretching for triazole compounds that appear nearly around 1490 cm − 1 and three or four intense absorption bands Furthermore, the identity of the carbohydrate-triazole conjugates presented in this work was supported by high-resolution mass spectrometry (HRMS) which confirmed the expected mass for all compounds in accordance with their molecular formula.…”

“…Besides, the double of doublet at 3.97 ppm (J = 8.7, 5.5 Hz) assigned to H-5 in 7c is slightly downshifted to 4.06 ppm (J = 8.7, 3.4 Hz) in the case of allofuranose derivative 8c. The regioselectivity of the cycloaddition reaction was elucidated by using 1 H- 13 C long-range NMR experiments (HMBC). The selective formation of 1,4-disubstituted 1,2,3-triazoles was confirmed by a long-range correlation between the methylene protons H-19 and H-25 with the carbon-bearing H-21 in the triazole ring, since in 1,5-regioisomer the correlation between the benzyl protons and the carbon bearing the proton in the triazole ring would not be present (figure 5).…”

“…In addition to its inherent biological properties [10], 1,2,3-triazole moiety is a fascinating connecting unit which could link pharmacophores providing hybrid molecules with an increased biological profile [11]. In this context, triazolylglycoconjugates, molecules possessing a triazole moiety linked to a carbohydrate backbone, have emerged as valuable pharmacophores in the field of medicinal chemistry (figure 1) [12][13][14].…”

An overview of carbohydrate-based carbonic anhydrase inhibitors

“…In the last decade, the click reaction was widely reported as medicinal chemistry synthetic strategy 37 , due to its high yields and easy purification step. Moreover, a lot of literature reported the click chemistry reaction as a powerful tool to synthesise glycoconjugated hit compounds [38][39][40] . In fact, the 1,2,3-triazole is a non-classical peptide bond bioisostere and may interact with the biological targets 41 .…”