title: Rapid hydrolysis of amides under physiological conditions: influence of the microenvironment on the stability of the amide bond.
abstract: 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.
authors.affiliation: Institute of Cell Biology (Cancer Research), University of Essen Medical School, Germany.
authors.forename: K H
authors.initials: KH
authors.lastname: Glüsenkamp
authors.forename: C
authors.initials: C
authors.lastname: Mengede
authors.forename: W
authors.initials: W
authors.lastname: Drosdziok
authors.forename: E
authors.initials: E
authors.lastname: Jähde
authors.forename: M F
authors.initials: MF
authors.lastname: Rajewsky
mesh_terms: D000577:Amides / Q000737:chemistry*; D006207:Half-Life; D006868:Hydrolysis; D013329:Structure-Activity Relationship
chemical_list: D000577:Amides