Rapid hydrolysis of amides under physiological conditions: influence of the microenvironment on the stability of the amide bond.
A new class of bicyclic carboxyamides 1a-9a differing with respect to substitution patterns and exo-endo geometry has been synthesized. These amides are characterized by a structure-dependent unusual rapid hydrolysis rate at physiological conditions. The corresponding bicyclic anhydrides might be used as tools for masking and modifying therapeutic agents containing amine functionalities.
Glüsenkamp
K H
KH
Institute of Cell Biology (Cancer Research), University of Essen Medical School, Germany.
Mengede
C
C
Drosdziok
W
W
Jähde
E
E
Rajewsky
M F
MF
D000577:Amides / Q000737:chemistry*; D006207:Half-Life; D006868:Hydrolysis; D013329:Structure-Activity Relationship
D000577:Amides