Synthesis, computational evaluation and pharmacological assessment of acetylsalicylic esters as anti-inflammatory agents
- 37 Downloads
A convenient approach to the synthesis of alkyl esters of aspirin (ASA-OR) has been developed. The synthesis of ASA-OR has been realized in two steps: (1) direct esterification of salicylic acid with alcohols in the presence of dicyclohexylcarbodiimide to give alkyl salicylates (SAL-OR); (2) acetylation of SAL-OR with acetyl chloride to yield ASA-OR. Molecular mechanics simulations, performed to calculate the kinetic radii of several ASA-OR, indicated that the pentyl and hexyl acetylsalicylates possess the best properties to cross cell membranes. The in vitro biological tests demonstrate their anti-inflammatory activity, superimposable to that of aspirin. The results of our study suggest that ASA-OR may be used as anti-inflammatory drugs for topical application.
KeywordsAcetylsalicylic acid Acetylsalicylic esters Anti-inflammatory activity Aspirin Computational study
Compliance with ethical standards
Conflict of interest
The authors declare that they have no conflict of interest.
- Romeo R, Giofrè SV, Carnovale C, Chiacchio MA, Campisi A, Mancuso R, Cirmi S, Navarra M (2014a) Synthesis and biological activity of triazole-appended N,O-nucleosides. Eur J Org Chem 25:5422–5447Google Scholar