Synthesis, spectroscopic and theoretical studies of new quaternary N,N-dimethyl-3-phthalimidopropylammonium conjugates of sterols and bile acids.
New quaternary 3-phthalimidopropylammonium conjugates of steroids were obtained by reaction of sterols (ergosterol, cholesterol, cholestanol) and bile acids (lithocholic, deoxycholic, cholic) with bromoacetic acid bromide to give sterol 3β-bromoacetates and bile acid 3α-bromoacetates, respectively. These intermediates were subjected to nuclephilic substitution with N,N-dimethyl-3-phthalimidopropylamine to give the final quaternary ammonium salts. The structures of products were confirmed by spectral (1H-NMR, 13C-NMR, and FT-IR) analysis, mass spectrometry (ESI-MS, MALDI) as well as PM5 semiempirical methods and B3LYP ab initio methods. Estimation of the pharmacotherapeutic potential has been accomplished for synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASS).
Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, Poland. brycki@amu.edu.pl.
Bogumil
B
Brycki
Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, Poland. koenig@amu.edu.pl.
Hanna
H
Koenig
Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, Poland. iwkow@amu.edu.pl.
Iwona
I
Kowalczyk
Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, Poland. tposp@amu.edu.pl.
Tomasz
T
Pospieszny
D001647:Bile Acids and Salts / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010797:Phthalimides / Q000737:chemistry; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012984:Software; D013261:Sterols / Q000737:chemistry*; D013329:Structure-Activity Relationship; D014584:User-Computer Interface
D001647:Bile Acids and Salts; D004791:Enzyme Inhibitors; D010797:Phthalimides; D000644:Quaternary Ammonium Compounds; D013261:Sterols