Synthesis, computational evaluation and pharmacological assessment of acetylsalicylic esters as anti-inflammatory agents
- Autori: Mancuso, Raffaella; Ferlazzo, Nadia; De Luca, Giorgio; Amuso, Roberta; Piccionello, Antonio Palumbo; Giofrè, Salvatore V.; Navarra, Michele*; Gabriele, Bartolo
- Anno di pubblicazione: 2019
- Tipologia: Articolo in rivista (Articolo in rivista)
- OA Link: http://hdl.handle.net/10447/351104
Abstract
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.