Microwave-Assisted Synthesis of Bile Acids Derivatives: An Overview

Abstract

: The first attempts at microwave-assisted (MW) syntheses of bile acid derivatives were performed in domestic MW appliances. However, the reproducibility of these syntheses, which were performed in uncontrolled conditions, was very low. In the first part of this overview, compounds synthesized under such conditions are presented. Consequently, with the development of MW technology, MW-assisted reactions in MW reactors became reproducible. Thus, in the second part of this review, syntheses of bile acidsbased compounds in MW reactors are presented. Among others, publications dealing with the following topics will be covered: : − Chemical transformations of hydroxyl and/or carboxyl functions of bile acids into esters or amides, : − Hydroxyl group oxidations, : − Derivatization of oxo-compounds with different nitrogen-containing compounds (e.g. 4-amino-3- substituted-1H-1,2,4-triazole-5-thiones, thiocarbohydrazides and thiosemicarbazides) : Bile acid-based molecular tweezers, capable of stereospecific molecular recognition : Reactions of hydroxyl functions to give chlorine derivatives, presenting reactive intermediates in substitution reactions with N- or O-containing nucleophilic arylhydrazides, urea derivatives, substituted thiadiazoles or triazoles or amino acid methyl esters, mainly in solvent-free conditions. : Some of the synthesized compounds expressed antimicrobial potential and/or good recognition properties as artificial receptors for specific amino acids or anions. : Detailed comparisons between conventional and MW-assisted procedures for chemical transformations of bile acids are given in most of the presented publications. Based on these results, MW irradiation methods are simpler, more efficient, cleaner and faster than conventional synthetic methods, meeting the requirements of green chemistry.

Microwave synthesis of novel chenodeoxycholic acid esters and comparative study of chromatographic behavior and lipophilicity

“…Recently many laboratories, including our own, have described microwave-assisted reactions of bile acids. 15,[18][19][20] Synthesis of bile acid derivatives proceeded in a highly-accelerated manner and the yields and purity of the final products were excellent. These results encouraged us to move forward in the synthesis of potentially biologically active bile acid esters with a slightly longer carbon chain, in contrast to common bile acid esters.…”