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

被引：1
|
作者：
Mancuso, Raffaella [1 ]
Ferlazzo, Nadia [2 ]
De Luca, Giorgio [3 ]
Amuso, Roberta [1 ]
Piccionello, Antonio Palumbo [4 ]
Giofre, Salvatore V. [2 ]
Navarra, Michele [2 ]
Gabriele, Bartolo [1 ]
机构：
[1] Univ Calabria, Dept Chem & Chem Technol, LISOC, Via Pietro Bucci 12-C, I-87036 Arcavacata Di Rende, CS, Italy
[2] Univ Messina, Dept Chem Biol Pharmaceut & Environm Sci, Viale SS Annunziata, I-98168 Messina, Italy
[3] Natl Res Council ITM CNR, Inst Membrane Technol, Via Pietro Bucci 17-C, I-87036 Arcavacata Di Rende, CS, Italy
[4] Univ Palermo, Dept Biol Chem & Pharmaceut Sci & Technol STEBICE, Viale Sci Ed 17, I-90128 Palermo, Italy
来源：
MEDICINAL CHEMISTRY RESEARCH | 2019年 / 28卷 / 03期
关键词：
Acetylsalicylic acid; Acetylsalicylic esters; Anti-inflammatory activity; Aspirin; Computational study; ASPIRIN; ACID;
D O I：
10.1007/s00044-018-02284-3
中图分类号：
R914 [药物化学];
学科分类号：
100701 ;
摘要：
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.
引用
收藏
页码：292 / 299
页数：8
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