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: Article

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

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Aspirin
Esters
Anti-Inflammatory Agents
Pharmacology
Dicyclohexylcarbodiimide
Acetylation
Molecular mechanics
Salicylic Acid
Salicylates
Esterification
Cell membranes
Mechanics
Alcohols
Cell Membrane
Kinetics
Pharmaceutical Preparations
In Vitro Techniques
acetyl chloride

All Science Journal Classification (ASJC) codes

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

Cita questo

Synthesis, computational evaluation and pharmacological assessment of acetylsalicylic esters as anti-inflammatory agents. / Palumbo Piccionello, Antonio; Giofrè, Salvatore V.; Ferlazzo, Nadia; Navarra, Michele; Amuso, Roberta; Gabriele, Bartolo; Mancuso, Raffaella; De Luca, Giorgio.

In: Medicinal Chemistry Research, Vol. 28, 2019, pag. 292-299.

Risultato della ricerca: Article

Palumbo Piccionello, A, Giofrè, SV, Ferlazzo, N, Navarra, M, Amuso, R, Gabriele, B, Mancuso, R & De Luca, G 2019, 'Synthesis, computational evaluation and pharmacological assessment of acetylsalicylic esters as anti-inflammatory agents', Medicinal Chemistry Research, vol. 28, pagg. 292-299.
Palumbo Piccionello, Antonio ; Giofrè, Salvatore V. ; Ferlazzo, Nadia ; Navarra, Michele ; Amuso, Roberta ; Gabriele, Bartolo ; Mancuso, Raffaella ; De Luca, Giorgio. / Synthesis, computational evaluation and pharmacological assessment of acetylsalicylic esters as anti-inflammatory agents. In: Medicinal Chemistry Research. 2019 ; Vol. 28. pagg. 292-299.
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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.",
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AU - Palumbo Piccionello, Antonio

AU - Giofrè, Salvatore V.

AU - Ferlazzo, Nadia

AU - Navarra, Michele

AU - Amuso, Roberta

AU - Gabriele, Bartolo

AU - Mancuso, Raffaella

AU - De Luca, Giorgio

PY - 2019

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AB - 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.

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