Aspirin prodrugs: synthesis and hydrolysis of 2-acetoxybenzoate esters of various N-(hydroxyalkyl) amides
-
Add time:07/23/2019 Source:sciencedirect.com
Three new esters of aspirin were synthesized and evaluated in vitro as potential prodrug forms of aspirin with the aim of depressing the gastrotoxicity of the drug by temporarily masking the carboxylic acid function. The esters, derived from N-(hydroxymethyl)acetamide, N-(hydroxymethyl)benzamide and ga-hydroxy-N-benzoylglycine benzyl ester, were all found to undergo a facile hydrolysis in aqueous solution of pH 0–8 with a quantitative regeneration of aspirin. The compounds were very easily cleaved at pH 7.4 but were more stable at lower pH values. Due to the great lability at pH 7.4 the compounds were also found to be cleaved quantitatively or predominantly to aspirin in the presence of human plasma rather than to the corresponding salicylate esters and hence salicylic acid.
We also recommend Trading Suppliers and Manufacturers of BENZOYLGLYCINE METHYL ESTER (cas 1205-08-9). Pls Click Website Link as below: cas 1205-08-9 suppliers
Prev:4-Methylumbelliferyl esters as fluorogenic substrates for proteases
Next:Prodrugs as drug delivery systems. 65. Hydrolysis of α-hydroxy-and α-acyloxy-N-benzoylglycine derivatives and implications for the design of prodrugs of NH-acidic compounds) - 【Back】【Close 】【Print】【Add to favorite 】
- Related Information
- X-ray and vibrational studies of methyl (N-benzoylaminooxy)acetate07/26/2019
- Synthesis of novel bioactive phthalimido-4-methyl pentanoateorganotin(IV) esters with spectroscopic investigation07/25/2019
- Prodrugs as drug delivery systems. 65. Hydrolysis of α-hydroxy-and α-acyloxy-N-benzoylglycine derivatives and implications for the design of prodrugs of NH-acidic compounds07/24/2019
- 4-Methylumbelliferyl esters as fluorogenic substrates for proteases07/22/2019
- Preparation, IR and 1H NMR spectral studies of triorganotin(IV) complexes of N-benzoylglycine and N-benzoylglycylglycine07/20/2019
- Mild and effective cleavage of esters with bis(tributyltin) oxide: A useful application in the deprotection of Pom penicillanate esters07/21/2019
- Separation of electronic and hydrophobic effects for the papain hydrolysis of substituted N-benzoylglycine esters07/18/2019
-
Health and Chemical more >
-
Related Products
- Methyl 1-Benzyl-5-oxopyrrolidine-3-carboxylate
- Methyl (((methoxymethylphosphinothioyl)thio)acetyl)methylcarbamate
- Methyl (+)-(3R)-7-[4-(4-fluorophenyl)-6-isopropyl-2-(N-methyl-N-methanesulfonylamino)pyrimidin-5-yl]-3-hydroxy-5-oxo-(6E)-heptenoate
- Methyl (2-amino-5-methyl-1,3-thiazol-4-yl)acetate
- Methyl (2-chloromethyl)oxazole-4-carboxylate
- Methyl (2E)-3-(4-methylphenyl)propenoate
- Methyl (2E)-3-cyclohexylprop-2-enoate
- Methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-iodopropanoate
- Methyl (2R)-2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate
- Methyl (2R)-2-amino-2-cyclohexylethanoate hydrochloride