Molecules 2014, 19(4), 4212-4233; doi:10.3390/molecules19044212
Article

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

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Received: 12 February 2014; in revised form: 19 March 2014 / Accepted: 21 March 2014 / Published: 3 April 2014
(This article belongs to the Section Organic Synthesis)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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).
Keywords: sterols; bile acids; quaternary ammonium salt; conjugates; N,N-dimethyl-3-phthalimidopropylamine; PASS; PM5 calculations; B3LYP ab initio methods
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MDPI and ACS Style

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.

AMA Style

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(4):4212-4233.

Chicago/Turabian Style

Brycki, Bogumil; Koenig, Hanna; Kowalczyk, Iwona; Pospieszny, Tomasz. 2014. "Synthesis, Spectroscopic and Theoretical Studies of New Quaternary N,N-Dimethyl-3-phthalimidopropylammonium Conjugates of Sterols and Bile Acids." Molecules 19, no. 4: 4212-4233.


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