Carbohydrate recognition of C 3 -symmetrical tripodal receptor-type 2,4,6-trisubstituted 1,3,5-triazine derivatives with antiviral activities
Journal of Thermal Analysis and Calorimetry(2018)
Abstract
In our search for new bioactive compounds that interfere with the sugar recognition process, we have designed and synthesized C 3 - and Cs -symmetrical tripodal receptor-type molecules. Among the synthesized C 3 -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 (Δ H ) in total Gibbs free energy change (Δ G ), 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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Key words
Carbohydrate recognition,1,3,5-Triazine,C3 Symmetry,Tripodal receptor,Isothermal titration calorimetry
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