Synthesis, computational evaluation and pharmacological assessment of acetylsalicylic esters as anti-inflammatory agents

Antonio Palumbo Piccionello, Salvatore V. Giofrè, Nadia Ferlazzo, Michele Navarra, Roberta Amuso, Bartolo Gabriele, Raffaella Mancuso, Giorgio De Luca

Risultato della ricerca: Articlepeer review

1 Citazioni (Scopus)

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.
Lingua originaleEnglish
pagine (da-a)292-299
Numero di pagine8
RivistaMedicinal Chemistry Research
Volume28
Stato di pubblicazionePublished - 2019

All Science Journal Classification (ASJC) codes

  • Pharmacology, Toxicology and Pharmaceutics(all)
  • Organic Chemistry

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