208402-01-1

Upstream product

• 14864-24-5 (Z)-2-(3-hydroxyprop-1-en-1-yl)phenol 
• 91-64-5 coumarin 
• 185995-96-4 (Z)-2-(3-(tert-butyldimethylsilyloxy)propenyl)phenol 
• 208401-84-7 Acetic acid 2-[(Z)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-phenyl ester 
• 208401-91-6 1-((Z)-3-hydroxy-1-propenyl)phenyl acetate 

Downstream Products

• 19878-96-7 (Z)-3-<2-(acetyloxy)phenyl>-2-propenoic acid 
• 208402-14-6 2-<(Z)-3-(benzylamino)-3-oxo-1-propenyl>phenyl acetate 
• 208402-19-1 Acetic acid 2-[(Z)-2-(benzyl-methyl-carbamoyl)-vinyl]-phenyl ester 
• 208402-18-0 2-[(Z)-3-(4-methoxyanilino)-3-oxo-1-propenyl]phenyl acetate 
• 208402-20-4 Acetic acid 2-((Z)-2-diethylcarbamoyl-vinyl)-phenyl ester 

Relevant academic research and scientific papers

Coumarin-based prodrugs. Part 3: Structural effects on the release kinetics of esterase-sensitive prodrugs of amines

To study the structural effects on the release kinetics of a coumarin- based esterase-sensitive prodrug system, two series of compounds with varying structural features of the ester 'trigger' part and the amine 'drug' part were synthesized. The half-lives of the nine model prodrugs in the presence of porcine liver esterase ranged from about 2 min to 190 min. The steric bulkiness of the acyl group seems to have only a very minor effect on the half-lives of the esterase-triggered release of amines from the model prodrugs. The rate of the lactonization depends on the steric and electronic properties of the amine moiety.

Chemical feasibility studies of a potential coumarin-based prodrug system

By using model amines, several amides of coumarinic acid with the phenolic hydroxyl group protected as an ester were prepared. These model amides underwent a facile (t( 1/2 ) 1.5-31 min) lactonization to release the original amine compounds upon esterase catalyzed hydrolysis of the phenolic ester. Such a system can be used for the preparation of esterase-sensitive prodrugs of amine-containing compounds or peptids.