Access to Highly Functional and Polymerizable Carbonate-Drug Conjugates.

Abstract

We here report the synthesis of two types of six-membered cyclic carbonate monomers equipped with various drug molecules through ester linkages. The target compounds can be isolated in good yields and feature diagnostic IR and 13C NMR spectroscopic fingerprints in line with their proposed connectivities. As a potential application, we investigated their ring-opening polymerization (ROP), showing that the nature of the cyclic carbonate is crucial towards macromolecular carbonate formation. The functionalized polycarbonates have molecular weights of up to 10 kg/mol, controllable functionality and a variable drug-to-carbonate ratio. This work demonstrates the adaptive synthesis of new types of functionalized six-membered cyclic carbonates with potential as precursors to polycarbonate-drug type macromolecules.