Synthesis, spectroscopic and theoretical studies of new quaternary N,N-dimethyl-3-phthalimidopropylammonium conjugates of sterols and bile acids

Bogumil Brycki; Hanna Koenig; Iwona Kowalczyk; Tomasz Pospieszny

doi:10.3390/molecules19044212

Synthesis, spectroscopic and theoretical studies of new quaternary N,N-dimethyl-3-phthalimidopropylammonium conjugates of sterols and bile acids

Molecules. 2014 Apr 3;19(4):4212-33. doi: 10.3390/molecules19044212.

Authors

Bogumil Brycki¹, Hanna Koenig², Iwona Kowalczyk³, Tomasz Pospieszny⁴

Affiliations

¹ Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, Poland. brycki@amu.edu.pl.
² Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, Poland. koenig@amu.edu.pl.
³ Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, Poland. iwkow@amu.edu.pl.
⁴ Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, Poland. tposp@amu.edu.pl.

Abstract

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).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Bile Acids and Salts / chemistry*
Enzyme Inhibitors / chemical synthesis*
Enzyme Inhibitors / chemistry
Molecular Structure
Phthalimides / chemistry
Quaternary Ammonium Compounds / chemical synthesis*
Quaternary Ammonium Compounds / chemistry
Software*
Sterols / chemistry*
Structure-Activity Relationship
User-Computer Interface

Substances

Bile Acids and Salts
Enzyme Inhibitors
Phthalimides
Quaternary Ammonium Compounds
Sterols