Abstract
A novel method for the synthesis of bile acid derivatives has been developed using “click chemistry”. Intermolecular 1,3-dipolar cycloaddition of the propargyl ester of bile acids and azide groups of 1,3,5-tris(azidomethyl)benzene gave a new quasi-podands with 1,2,3-triazole rings. The structures of the products were confirmed by spectral (1H-NMR, 13C-NMR, and FT-IR) analysis, mass spectrometry and PM5 semiempirical methods. Estimation of the pharmacotherapeutic potential has been accomplished for synthesized compounds on the basis of Prediction of Activity Spectra for Substances (PASS).
Highlights
Bile acids were isolated from the bile of mammals in 1828 by L
Much attention was given to the synthesis of molecular pockets, molecular umbrellas and quasi-podands from bile acids [11,12,13,14,15,16,17]
We reported the synthesis and physicochemical properties of new bile acid esters of 1,3,5-tris(bromomethyl)benzene or
Summary
Bile acids were isolated from the bile of mammals in 1828 by L. To get new quasi-podands we decided to modify the structure of bile acids by introduction of additional 1,2,3-triazole rings using “click chemistry” methods. “Click chemistry” is a relatively new and very attractive trend in modern organic synthesis It includes a broad spectrum of carbon–heteroatom bond forming reactions that fulfil specified requirements such as high efficiency and selectivity, simple reaction conditions and easy product isolation [28]. The possible “click” reaction pathways occurring between terminal alkynes and azides Compounds of this type are very resistant to the hydrolysis, oxidation and reduction conditions of metabolic degradation. The Cu(I)-catalyzed “click” reaction is an extremely useful method to obtain new 1,2,3-triazole derivatives of bile acids [33,34,35,36,37,38,39]
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