Compounds Combining a Macrocyclic Building Block and Flexible Side‐Arms as Carbohydrate Receptors: Syntheses and Structure‐Binding Activity Relationship Studies

Abstract A series of new representatives of compounds combining a macrocyclic building block and flexible side‐arms were prepared and their ability to act as carbohydrate receptors evaluated. The target compounds were obtained by multi‐step syntheses, which included the preparation of numerous precursors as well as the isolation of a large number of by‐products. The structure‐binding activity relationship studies comprise, in particular, the variation of the side‐arms in order to demonstrate the importance of the presence of a hydrogen bond donor in these units for the effective complexation of carbohydrates. Based on the findings of our previous studies, the variation of the bridge units is limited to benzene‐ and pyrrole‐based moieties, whereby the use of the last‐mentioned bridge type was expected to produce more effective systems. This assumption was confirmed by 1 H NMR titrations and isothermal titration calorimetry.