185995-96-4

Upstream product

• 91-64-5 coumarin 
• 14864-24-5 (Z)-2-(3-hydroxyprop-1-en-1-yl)phenol 
• 18162-48-6 tert-butyldimethylsilyl chloride 

Downstream Products

• 208401-87-0 Isobutyric acid 2-[(Z)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-phenyl ester 
• 208401-89-2 2,2-Dimethyl-propionic acid 2-[(Z)-3-(tert-butyl-dimethyl-silanyloxy)-propenyl]-phenyl ester 
• 208402-17-9 2,2-Dimethyl-propionic acid 2-((Z)-2-benzylcarbamoyl-vinyl)-phenyl ester 
• 208402-16-8 2-<(Z)-3-(benzylamino)-3-oxo-1-propenyl>phenyl 2-methylpropanoate 
• 208402-15-7 Propionic acid 2-((Z)-2-benzylcarbamoyl-vinyl)-phenyl ester 
• 208402-20-4 Acetic acid 2-((Z)-2-diethylcarbamoyl-vinyl)-phenyl ester 
• 208402-12-4 (Z)-3-(2-Isobutyryloxy-phenyl)-acrylic acid 
• 208402-13-5 (Z)-3-[2-(2,2-Dimethyl-propionyloxy)-phenyl]-acrylic acid 
• 208402-07-7 Isobutyric acid 2-((Z)-3-oxo-propenyl)-phenyl ester 
• 208401-99-4 2,2-Dimethyl-propionic acid 2-((Z)-3-hydroxy-propenyl)-phenyl ester 
• 208402-09-9 2,2-Dimethyl-propionic acid 2-((Z)-3-oxo-propenyl)-phenyl ester 
• 208401-96-1 Isobutyric acid 2-((Z)-3-hydroxy-propenyl)-phenyl ester 
• 208402-18-0 2-[(Z)-3-(4-methoxyanilino)-3-oxo-1-propenyl]phenyl acetate 
• 208402-19-1 Acetic acid 2-[(Z)-2-(benzyl-methyl-carbamoyl)-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.

Design, synthesis, and bioavailability evaluation of coumarin-based prodrug of meptazinol

Based on the known coumarin-based prodrug system, a new meptazinol (Z)-3-[2-(propionyloxy) phenyl]-2-propenoic ester (3) was designed and synthesized as prodrug to minimize the first-pass effect of meptazinol (1) and improve the oral bioavailability. The

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.