Synthesis, spectroscopic and theoretical studies of new dimeric quaternary alkylammonium conjugates of sterols.

Bogumił Brycki,Hanna Koenig,Tomasz Pospieszny,Iwona Kowalczyk

doi:10.3390/molecules19079419

Bogumił Brycki, Hanna Koenig + Show 2 more

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https://doi.org/10.3390/molecules19079419

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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 (1 H-NMR, 13 C-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).

Highlights

Steroids are very important natural products which play a crucial role in living organisms
To the best of our knowledge, no work has been published on the synthesis and physicochemical properties of dimeric quaternary alkylammonium conjugates of sterols
These new conjugates were obtained by reaction of sterols (ergosterol (1), cholesterol (2), cholestanol (3)) with bromoacetic acid bromide to give ergosteryl 3β-bromoacetate, cholesteryl 3β-bromoacetate and dihydrocholesteryl 3β-bromoacetate [41,42]

Summary

Introduction

Steroids are very important natural products which play a crucial role in living organisms. This class of compounds comprises hormones, bile acids, steroidal saponins, cardioactive glycosides, steroid alkaloids and sterols [1,2,3]. (2) phytosterols—the plant or algae sterols (e.g., sitosterol, stigmasterol); and (3) mycosterols—the sterols found in fungi (e.g., ergosterol, fungisterol) [4,5,6].

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