Evaluation of glycolamide esters and various other esters of aspirin as true aspirin prodrugs was written by Moerk Nielsen, Niels;Bundgaard, Hans. And the article was included in Journal of Medicinal Chemistry in 1989.COA of Formula: C17H15NO5 The following contents are mentioned in the article:
A series of glycolamide, glycolate, (acyloxy)methyl, alkyl, and aryl esters of aspirin) were synthesized and evaluated as potential prodrug forms of aspirin, N,N-disubstituted glycolamide esters were rapidly hydrolyzed in human plasma, resulting in the formation of aspirin as well as the corresponding salicylate esters. These in turn hydrolyzed rapidly to salicylic acid. The largest amount of aspirin formed from the esters were 50 and 55% in case of the N,N-dimethyl- and N,N-diethylglycolamide esters, resp. Similar results were obtained in blood with the N,N-dimethyl- and N,N-diethylglycolamide esters. Unsubstituted and monosubstituted glycolamide esters as well as most other esters previously suggested to be aspirin prodrugs hydrolyzed exclusively to the corresponding salicylic acid esters. Lipophilicity parameters and water solubilities of the esters were determined, and structural factors favoring ester prodrug hydrolysis at the expense of deacetylation to yield salicylate ester are discussed. The properties of some N,N-disubstituted glycolamide esters of aspirin are highlighted with respect to their use as potential aspirin prodrugs. This study involved multiple reactions and reactants, such as 4-Acetamidophenyl 2-acetoxybenzoate (cas: 5003-48-5COA of Formula: C17H15NO5).
4-Acetamidophenyl 2-acetoxybenzoate (cas: 5003-48-5) belongs to esters. Esters are also usually derived from carboxylic acids. It may also be obtained by reaction of acid anhydride or acid halides with alcohols or by the reaction of salts of carboxylic acids with alkyl halides. Cyclic esters are called lactones, regardless of whether they are derived from an organic or inorganic acid. One example of an organic lactone is γ-valerolactone.COA of Formula: C17H15NO5
Referemce:
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics