Next Article in Journal
Antioxidant and Anticancer Constituents from the Leaves of Liriodendron tulipifera
Previous Article in Journal
Antiprotozoal Activities of Millettia richardiana (Fabaceae) from Madagascar
Article Menu

Export Article

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

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
*
Authors to whom correspondence should be addressed.
Received: 12 February 2014 / Revised: 19 March 2014 / Accepted: 21 March 2014 / Published: 3 April 2014
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [820 KB, uploaded 18 June 2014]   |  

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 sterols; bile acids; quaternary ammonium salt; conjugates; N,N-dimethyl-3-phthalimidopropylamine; PASS; PM5 calculations; B3LYP ab initio methods
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top