Synthesis, spectroscopic and theoretical studies of new dimeric quaternary alkylammonium conjugates of sterols

Bogumił Brycki; Hanna Koenig; Iwona Kowalczyk; Tomasz Pospieszny

doi:10.3390/molecules19079419

Synthesis, spectroscopic and theoretical studies of new dimeric quaternary alkylammonium conjugates of sterols

Molecules. 2014 Jul 3;19(7):9419-34. doi: 10.3390/molecules19079419.

Authors

Bogumił 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 dimeric quaternary alkylammonium conjugates of sterols were obtained by two step reactions of ergosterol, cholesterol and cholestanol with bromoacetic acid bromide, followed by bimolecular nucleophilic substitution with N,N,N',N'-tetramethyl-1,3-propanediamine, N,N,N',N'',N''-pentamethyldiethylenetriamine and 3,3'-iminobis- (N,N-dimethylpropylamine). The product structures were conﬁrmed by spectral (1H-NMR, 13C-NMR, FT-IR) analysis, mass spectrometry (ESI-MS) and PM5 semiempirical methods. Additionally in silico studies have been conducted for the synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASS).

Publication types

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

MeSH terms

Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Conformation
Quaternary Ammonium Compounds / chemical synthesis*
Quaternary Ammonium Compounds / chemistry
Spectrometry, Mass, Electrospray Ionization
Spectroscopy, Fourier Transform Infrared

Substances

Quaternary Ammonium Compounds