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Carbohydrate recognition of C3-symmetrical tripodal receptor-type 2,4,6-trisubstituted 1,3,5-triazine derivatives with antiviral activities

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Abstract

In our search for new bioactive compounds that interfere with the sugar recognition process, we have designed and synthesized C3- and Cs-symmetrical tripodal receptor-type molecules. Among the synthesized C3-symmetrical 2,4,6-trisubstituted 1,3,5-triazine (TAZ) derivatives, compounds A [2,4,6-tris(2-propoxy)-TAZ] and B [2,4,6-tris(3,4-dimethoxyphenyl)-TAZ] showed high levels of anti-HSV-1 activity. We carried out isothermal titration calorimetry on compound B·HCl in aqueous 25% 2-PrOH solution with some sugar derivatives including methyl α/β-d-galactopyranoside (MeO-α/β-Gal), methyl α/β-d-mannopyranoside (MeO-α/β-Man) and methyl α/β-d-glucopyranoside (MeO-α/β-Glc). The reactions of compound B·HCl with MeO-β-Gal and MeO-α-Man were exothermic, and the obtained thermodynamic profiles indicated that both reactions are spontaneous and that there is a considerably large enthalpic contribution (ΔH) in total Gibbs free energy change (ΔG), indicating favorable hydrogen bonding interactions. The reaction of compound B·HCl showed a thermodynamic signature different from that of the entropically driven reaction of compound A.

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Correspondence to Kunihiro Sumoto.

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Mibu, N., Ohata, T., Sano, M. et al. Carbohydrate recognition of C3-symmetrical tripodal receptor-type 2,4,6-trisubstituted 1,3,5-triazine derivatives with antiviral activities. J Therm Anal Calorim 135, 2807–2811 (2019). https://doi.org/10.1007/s10973-018-7573-4

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  • DOI: https://doi.org/10.1007/s10973-018-7573-4

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