Stability of 2-thiophenobarbital and its N-methyl derivatives in the presence of beta-cyclodextrin.
The rates of hydrolysis of thiophenobarbital and its N-mono- and N,N'-dimethyl-derivatives were determined under different conditions of pH and temperature using UV spectroscopy. They were compared with those obtained in the presence of different concentrations of beta-cyclodextrin. It was found that the compounds degrade with different rates and beta-cyclodextrin retards the hydrolysis. The formation of complexes between the investigated compounds and beta-cyclodextrin was proved by 13C NMR and ROESY spectra and molecular modeling. The inclusion with the phenyl substituent into the beta-cyclodextrin cavity is preferred.
Zuchowski
Grzegorz
G
Department of Organic Chemistry, Medical College, Jagiellonian University, Medyczna 9, 30-688 Kraków, Poland.
Tarsa
Monika
M
Stasiewicz-Urban
Anna
A
Bojarski
Jacek
J
D004355:Drug Stability; D006868:Hydrolysis; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D010634:Phenobarbital / Q000031:analogs & derivatives* / Q000737:chemistry; D012015:Reference Standards; D013056:Spectrophotometry, Ultraviolet; D013696:Temperature; D047392:beta-Cyclodextrins / Q000737:chemistry*
C508574:2-thiophenobarbital; C481455:N-methyl-2-thiophenobarbital; D047392:beta-Cyclodextrins; D010634:Phenobarbital