A study on the thermal stability of carbamate and carbonate derivatives of N-(pyridin-2-yl)-2-aminoethanol

Abstract

Currently, research on controlled selective release of drugs for the treatment of diseases such as cancer is a point of interest. In this sense, thermolabile ligands are a nice choice for binding the drug to a carrier in order to release it when desired by using a suitable source of heat. The Nanoscience and Bioinorganic Chemistry group (nanoBIC) of the Department of Inorganic and Organic Chemistry is investigating a system made of magnetic nanoparticles containing a 2-aminopyridine derivative as a thermolabile ligand for controlled drug release by means of an external magnetic field. The present Degree Final Work has been carried out in the framework of a collaboration between the Synthetic Methodology Applied to Bioactive Compounds group (SMBioCom) of the same department and the research group above mentioned. In this project, the 2-aminopyridine derivative of methyl 4-[N-(2-hydroxyethyl)-N-(pyridin-2-yl)aminomethyl] benzoate has been studied as precursor of potentially thermolabile carbamates or carbonates. Thus, this derivative has been synthesized and used to prepare some carbamate/carbonate derivatives. The thermal decomposition of these derivatives by intramolecular cyclization with the concomitant release of the corresponding alcohol(carbonate) or amine (carbamate) has been studied by 1H-NMR