The novel title macrocycles, based on methylene-bridged 1,5-naphthalene units, have been obtained by template effect in a thermodynamically controlled synthesis. In details, the prism[5]arene 1 or the prism[6]arene 3 was selectively taken away from the equilibrium mixture by using the complemen-tary ammonium-templating agent. When only the solvent 1,2-DCE was used, then the 1,4-confused derivative 2 was ob-tained. The prism[5]arene here described shows a deep π-electron rich aromatic cavity thanks to which exhibits a great affinity for the quaternary ammonium guests, originat-ing from favorable cation··· π and +NC−H··· π interactions. This recognition motif is the basis of the templated synthesis of the prism[n]arenes here reported.

β-lactam antibiotics are among the most important and widely used antimicrobials worldwide and are comprised of a large family of compounds, obtained by chemical modifications of the common scaffolds. Usually these modifications include the addition of active groups, but less frequently, molecules were synthesized in which either two β-lactam rings were joined to create a single bifunctional compound, or the azetidinone ring was joined to another antibiotic scaffold or another molecule with a different activity, in order to create a molecule bearing two different pharmacophoric functions. In this review, we report some examples of these derivatives, highlighting their biological properties and discussing how this strategy can lead to the development of innovative antibiotics that can represent either novel weapons against the rampant increase of antimicrobial resistance, or molecules with a broader spectrum of action.

When a 1,3-dipolar cycloaddition between nitrones and α,β-unsaturated aldehydes catalyzed by L-proline derivatives takes place inside the hexameric resorcin[4]arene capsule the products are obtained in higher yields and selectivity, with respect to the reaction in bulk solution. The 4-formyl regioisomers were obtained preferentially, with an excellent preference for the endo-diastereoisomers and with moderate to good enantioselectivities. An extended in silico study was conducted to rationalize the observed outcome and to investigate the equilibria between the reagents outside and inside the capsule.