Molecular structure, spectral and thermal properties and in silico biological activity of new bis-phthalimidopropylalkylammonium conjugates of bile acids

New quaternary bis-phthalimidopropylalkylammonium conjugates of lithocholic, deoxycholic and cholic acids were obtained by reaction of bile acids with bromoacetic acid bromide to give bile acid 3 alpha-bromoacetates. These intermediates were subjected to nuclephilic substitution with N,N-bis-(phthalimidopropyl)-N-ethylamine, N,N-bis-(phthalimidopropyl)-N-decylamine and N,N-bis-(phthalimidopropyl)-N-hexadecylamine to give the final quaternary ammonium salts. The structures of products were confirmed by spectral (H-1 NMR, C-13 NMR, 2D NMR and FT-IR) analysis, mass spectrometry (ESI-MS) as well as PM5 semiempirical methods and B3LYP ab initio methods. In addition, differential scanning calorimetric (DSC) studies were performed for compounds of different hydrocarbon chain length. Estimation of the pharmacotherapeutic potential has been accomplished for synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASS). (C) 2021 Elsevier B.V. All rights reserved.

Automated summary

Novel quaternary bis-phthalimidopropylalkylammonium conjugates of bile acids were synthesized and their structures were confirmed by various spectroscopic and mass spectrometric analyses, followed by pharmacotherapeutic potential assessment.