127042-09-5Relevant articles and documents
2-Alkylidene-benzo[1,3]dioxin-4-ones: A new class of compounds
Babin, Pierre,Bennetau, Bernard
, p. 5231 - 5233 (2001)
A new class of compounds, 2-alkylidene-benzo[1,3]dioxin-4-ones, have been synthesised by cyclisation of the corresponding o-acyloxy benzoyl chlorides with triethylamine. The 2-methylene-benzo[1,3]dioxin-4-one acts as a prodrug for aspirin and is a useful intermediate in the synthesis of new aspirin prodrugs.
Aspirin prodrugs: synthesis and hydrolysis of 2-benzyloxy-2-methyl-4H-1,3-benzodioxin-4-ones.
Ankersen,Senning
, p. 793 - 798 (2007/10/02)
Aspirin is widely used for its analgesic, antiinflammatory and antipyretic properties. Among its disadvantages are the relatively narrow therapeutic margin, its irritancy towards the gastric mucosa, and occasionally patient hypersensitivity towards aspirin. As part of our effort to develop prodrugs without these liabilities eleven new title compounds have been isolated and characterized. These 'superaspirin' candidates were subjected to non-enzymatic hydrolysis for a first rapid screening in vitro. Only 2-(2,6-dimethoxybenzyloxy)-2-methyl-4H-1,3-benzodioxin-4-one (4c) was observed to act as an exclusive aspirin prodrug, while 2-(2-methoxybenzyloxy)-2-methyl-4H-1,3-benzodioxin-4-one (4b) and 2-(2-ethoxybenzyloxy)-2-methyl-4H-1,3- benzodioxin-4-one (4d) were shown to release both aspirin 6 and salicylic acid 7. Subsequently, these three candidates were further characterized by investigation of the pH profile of their hydrolysis rates.
