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Synthesis, Spectroscopic and Theoretical Studies of New Quaternary N,N-Dimethyl-3-phthalimidopropylammonium Conjugates of Sterols and Bile Acids

Laboratory of Microbiocide Chemistry, Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, Poznań 60-780, Poland
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Molecules 2014, 19(4), 4212-4233; https://doi.org/10.3390/molecules19044212
Received: 12 February 2014 / Revised: 19 March 2014 / Accepted: 21 March 2014 / Published: 3 April 2014
(This article belongs to the Section Organic Chemistry)
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). View Full-Text
Keywords: sterols; bile acids; quaternary ammonium salt; conjugates; N,N-dimethyl-3-phthalimidopropylamine; PASS; PM5 calculations; B3LYP ab initio methods sterols; bile acids; quaternary ammonium salt; conjugates; N,N-dimethyl-3-phthalimidopropylamine; PASS; PM5 calculations; B3LYP ab initio methods
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Brycki, B.; Koenig, H.; Kowalczyk, I.; Pospieszny, T. Synthesis, Spectroscopic and Theoretical Studies of New Quaternary N,N-Dimethyl-3-phthalimidopropylammonium Conjugates of Sterols and Bile Acids. Molecules 2014, 19, 4212-4233.

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