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

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'...

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Main Authors:	Bogumił Brycki, Hanna Koenig, Iwona Kowalczyk, Tomasz Pospieszny
Format:	Article
Language:	English
Published:	MDPI AG 2014-07-01
Series:	Molecules
Subjects:	sterols dimeric quaternary alkylammonium salt conjugates prediction of activity spectra for substances quantum chemical calculations
Online Access:	http://www.mdpi.com/1420-3049/19/7/9419

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spelling	doaj-e76e66b9d7c14faeba1448d52c7be9182020-11-24T22:51:54ZengMDPI AGMolecules1420-30492014-07-011979419943410.3390/molecules19079419molecules19079419Synthesis, Spectroscopic and Theoretical Studies of New Dimeric Quaternary Alkylammonium Conjugates of SterolsBogumił Brycki0Hanna Koenig1Iwona Kowalczyk2Tomasz Pospieszny3Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, PolandLaboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, PolandLaboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, PolandLaboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, PolandNew 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).http://www.mdpi.com/1420-3049/19/7/9419sterolsdimeric quaternary alkylammonium saltconjugatesprediction of activity spectra for substancesquantum chemical calculations
collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Bogumił Brycki Hanna Koenig Iwona Kowalczyk Tomasz Pospieszny
spellingShingle	Bogumił Brycki Hanna Koenig Iwona Kowalczyk Tomasz Pospieszny Synthesis, Spectroscopic and Theoretical Studies of New Dimeric Quaternary Alkylammonium Conjugates of Sterols Molecules sterols dimeric quaternary alkylammonium salt conjugates prediction of activity spectra for substances quantum chemical calculations
author_facet	Bogumił Brycki Hanna Koenig Iwona Kowalczyk Tomasz Pospieszny
author_sort	Bogumił Brycki
title	Synthesis, Spectroscopic and Theoretical Studies of New Dimeric Quaternary Alkylammonium Conjugates of Sterols
title_short	Synthesis, Spectroscopic and Theoretical Studies of New Dimeric Quaternary Alkylammonium Conjugates of Sterols
title_full	Synthesis, Spectroscopic and Theoretical Studies of New Dimeric Quaternary Alkylammonium Conjugates of Sterols
title_fullStr	Synthesis, Spectroscopic and Theoretical Studies of New Dimeric Quaternary Alkylammonium Conjugates of Sterols
title_full_unstemmed	Synthesis, Spectroscopic and Theoretical Studies of New Dimeric Quaternary Alkylammonium Conjugates of Sterols
title_sort	synthesis, spectroscopic and theoretical studies of new dimeric quaternary alkylammonium conjugates of sterols
publisher	MDPI AG
series	Molecules
issn	1420-3049
publishDate	2014-07-01
description	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).
topic	sterols dimeric quaternary alkylammonium salt conjugates prediction of activity spectra for substances quantum chemical calculations
url	http://www.mdpi.com/1420-3049/19/7/9419
work_keys_str_mv	AT bogumiłbrycki synthesisspectroscopicandtheoreticalstudiesofnewdimericquaternaryalkylammoniumconjugatesofsterols AT hannakoenig synthesisspectroscopicandtheoreticalstudiesofnewdimericquaternaryalkylammoniumconjugatesofsterols AT iwonakowalczyk synthesisspectroscopicandtheoreticalstudiesofnewdimericquaternaryalkylammoniumconjugatesofsterols AT tomaszpospieszny synthesisspectroscopicandtheoreticalstudiesofnewdimericquaternaryalkylammoniumconjugatesofsterols
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Synthesis, Spectroscopic and Theoretical Studies of New Dimeric Quaternary Alkylammonium Conjugates of Sterols

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