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Molecules 2014, 19(7), 9419-9434; doi:10.3390/molecules19079419

Synthesis, Spectroscopic and Theoretical Studies of New Dimeric Quaternary Alkylammonium Conjugates of Sterols

Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, Poland
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Received: 10 June 2014 / Revised: 30 June 2014 / Accepted: 1 July 2014 / Published: 3 July 2014
(This article belongs to the Section Organic Synthesis)
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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). View Full-Text
Keywords: sterols; dimeric quaternary alkylammonium salt; conjugates; prediction of activity spectra for substances; quantum chemical calculations sterols; dimeric quaternary alkylammonium salt; conjugates; prediction of activity spectra for substances; quantum chemical calculations
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Brycki, B.; Koenig, H.; Kowalczyk, I.; Pospieszny, T. Synthesis, Spectroscopic and Theoretical Studies of New Dimeric Quaternary Alkylammonium Conjugates of Sterols. Molecules 2014, 19, 9419-9434.

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