6533b86dfe1ef96bd12ca0f4
RESEARCH PRODUCT
Synthesis, computational evaluation and pharmacological assessment of acetylsalicylic esters as anti-inflammatory agents
Salvatore V. GiofrèMichele NavarraBartolo GabrieleRoberta AmusoAntonio Palumbo PiccionelloGiorgio De LucaRaffaella MancusoNadia Ferlazzosubject
medicine.drug_classAcetylsalicylic ester01 natural sciencesAnti-inflammatoryAnti-inflammatory activitychemistry.chemical_compoundAcetyl chlorideAcetylsalicylic acidmedicineGeneral Pharmacology Toxicology and PharmaceuticsAlkylchemistry.chemical_classificationAspirinAspirin010405 organic chemistryAcetylsalicylic acid; Acetylsalicylic esters; Anti-inflammatory activity; Aspirin; Computational study; Pharmacology Toxicology and Pharmaceutics (all); Organic ChemistryOrganic ChemistryCombinatorial chemistry0104 chemical sciences010404 medicinal & biomolecular chemistryMembranechemistryAcetylationPharmacology Toxicology and Pharmaceutics (all)Yield (chemistry)Computational studySalicylic acidmedicine.drugdescription
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.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2019-01-03 |