Synthesis, Spectroscopic and Theoretical Studies of New Quasi-Podands from Bile Acid Derivatives Linked by 1,2,3-Triazole Rings

Abstract

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 ( 1 H-NMR, 13 C-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).

In vitro studies on the interactions of blood lipid level‐related biological molecules with gallic acid and tannic acid

“…The symmetric CO stretching vibrations were responsible for the non‐symmetrical peaks in the range from 1716 to 1699 cm −1 in the spectra of polyphenols, while the peaks in the 1614–1615, 1532–1541, 1446–1448 cm −1 regions were assigned to the aromatic ring stretching vibrations. Furthermore, the symmetric and asymmetric –COO − stretching vibrations were associated with the bands at 1568–1576 and 1408 cm −1 in the spectra of cholates . The peaks related with the symmetric CO and aromatic ring stretching vibrations were shown in the spectra of polyphenol–cholate coprecipitates and confirmed the presence of polyphenols, however, no signal associated with the symmetric and asymmetric –COO − stretching vibrations was observed.…”

“…Figure shows the FTIR spectra of polyphenols, cholates and polyphenol–cholate coprecipitates in the range 400–4000 cm −1 . The bands in the 3441–3358 cm −1 region of the spectra of all samples were associated with the –OH stretching vibrations . Blue shifts of –OH bands were observed in the spectra of polyphenol–cholate coprecipitates, which implied that polyphenols might interact with cholates via hydrogen bonds.…”

“…The bands in the 3441-3358 cm −1 region of the spectra of all samples were associated with the -OH stretching vibrations. 27 Blue shifts of -OH bands were observed in the spectra of polyphenol-cholate coprecipitates, which implied that polyphenols might interact with cholates via hydrogen bonds. The peaks in the range from 2950 to 2850 cm −1 in the spectra of cholates and polyphenol-cholate coprecipitates were due to -CH 3 and -CH 2 vibrations of aliphatic hydrocarbon.…”

(3R,5S,7R,8R,9S,10S,12S,13R,14S)-10,13-Dimethyl-17-[5-oxo-5-(prop-2-yn-1-yloxy)pentan-2-yl]hexadecahydro-1H-cyclopenta[a]phenanthrene-3,7,12-triyl triacetate

“…The introduction of a bile acid group at the 20-position of camptochecin was found to decrease toxicity in vivo and improve selectivity for hepatoma cells (Li et al, 2014). Bile acid esters may find applications in molecular recognition, supramolecular chemistry and in pharmacology (Pospieszny et al, 2014). We report herein on the synthesis and crystal structure of the title cholic acid derivative.…”

Pd- and Cu-catalyzed approaches in the syntheses of new cholane aminoanthraquinone pincer-like ligands

“…Later, two modern synthetic approaches based on metal-catalyzed reactions were applied for the modification of bile acids – cross-coupling [28–29] (Scheme 1) and Cu(I)-catalyzed cycloaddition of azides to alkynes (Fig. 1) [11,16,30–32]. …”