In the presented studies, the interactions between ezetimibe (EZE) and selected cyclodextrins were investigated. α-Cyclodextrin (αCD), β-cyclodextrin (βCD) and its modified derivatives, hydroxypropyl-β-cyclodextrin (HPβCD) and sulfobutylether-β-cyclodextrin (SBEβCD), were selected for the research. Measurements were carried out using calorimetric and spectroscopic methods. Additionally, the Hirshfeld surface and biochemical analysis were achieved. As a result of the study, the inclusion complexes with 1:1 stoichiometry were obtained. The most stable are the complexes of β-cyclodextrin and its derivatives. The comparison of βCD with its derivatives shows that the modifications have an affect on the formation of more durable and stable complexes.

The present study examines a series of flavanone and chalcone derivatives substituted with electron‐withdrawing groups (Cl or Br) and electron‐donating groups (OH, CH3 and OCH3), namely, 7‐methoxy‐2‐phenyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐one, C16H14O3, 2‐(4‐methoxyphenyl)‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐one, C16H14O3, 2‐(4‐methoxyphenyl)‐6‐methyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐one, C17H16O3, 2‐(4‐chlorophenyl)‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐one, C15H11ClO2, 8‐bromo‐6‐methyl‐2‐phenyl‐3,4‐dihydro‐2H‐1‐benzopyran‐4‐one, C16H13BrO2, (2E)‐1‐(2‐hydroxyphenyl)‐3‐(4‐methoxyphenyl)prop‐2‐en‐1‐one, C16H14O3, and (2E)‐1‐(2‐hydroxyphenyl)‐3‐(4‐hydroxyphenyl)prop‐2‐en‐1‐one, C15H12O3. It compares the two groups of derivatives with regard to their intermolecular interactions in the crystal lattice and lattice energy calculations, together with energy framework visualization and global reactivity descriptors (chemical hardness, chemical potential and electrophilicity index). It also discusses the relationships between different noncovalent interactions derived from Hirshfeld surface analysis, crystal lattice energy and global reactivity descriptors of the compounds.

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