Aqueous degradation of N-(hydroxymethyl)phthalimide in the presence of specific and general bases. Kinetic assessment of N-hydroxymethyl derivatives of nitrogen heterocycles as possible prodrugs.
The conversion of N-(hydroxymethyl)phthalimide (NHPH) to phthalimide could not be detected within 300 s at pH 9.0, whereas in 0.18 M NaOH complete conversion of NHPH to phthalimide was observed within 50 s. In the presence of 0.2-0.4 M 1,4-diazabicyclo[2.2.2]octane buffer solutions (pH 9.30-9.54), 40-60% conversion of NHPH to phthalimide occurred within 90-120 s. The initial concentration of NHPH affected the extent of conversion of NHPH to phthalimide.
Khan
M N
MN
Department of Chemistry, Bayero University, Kano, Nigeria.
D000468:Alkalies; D002021:Buffers; D003959:Diamines; D006868:Hydrolysis; D007700:Kinetics; D015394:Molecular Structure; D010797:Phthalimides / Q000737:chemistry*; D010879:Piperazines; D011355:Prodrugs; D014867:Water
D000468:Alkalies; D002021:Buffers; D003959:Diamines; D010797:Phthalimides; D010879:Piperazines; D011355:Prodrugs; D014867:Water; C037431:phthalimide; C070006:1,2-diaminopropane; C039968:N-hydroxymethylphthalimide; C007306:triethylenediamine