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

IF 1.1 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY

Macedonian Journal of Chemistry and Chemical Engineering Pub Date : 2023-12-24 DOI:10.20450/mjcce.2023.2707

Ksenija Pavlović, Ljubica M Grbović, Milica Ž. Karadžić Banjac, Strahinja Z. Kovačević, A. Mandic, S. Podunavac-Kuzmanovic, Bojana R. Vasiljević

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Abstract

In this study, eco-friendly microwave-assisted esterification reactions of chenodeoxycholic acid with medium-chain diols (1,2-ethanediol, 1,4-butanediol, 1,6-hexanediol, 1,8-octanediol, and 1,10-decanediol) or tetraethylene glycol were accomplished. The synthesized bile acid esters were obtained with high yields (up to 81 %) and purity in a short reaction time (15 min). It is shown that the microwave technique is a suitable method for the preparation of chenodeoxycholic acid esters. In order to obtain detailed insight into the lipophilic behavior of the studied chenodeoxycholic acid esters, a comparative study of chromatographic behavior and lipophilicity was performed. Also, the present study deals with the estimation of pH – logD profiles in order to get an overview of the changes in lipophilicity related to the pH value changes. The obtained results indicate that studied compounds have logD values in the range acceptable for potential drug candidates. Chromatographic lipophilicity of synthesized chenodeoxycholic acid esters successfully correlate with in silico lipophilicity descriptors.

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新型酚去氧胆酸酯的微波合成及其色谱行为和亲油性比较研究

本研究利用环保型微波辅助技术完成了去甲胆酸与中链二元醇（1,2-乙二醇、1,4-丁二醇、1,6-己二醇、1,8-辛二醇和 1,10-癸二醇）或四甘醇的酯化反应。在很短的反应时间（15 分钟）内，合成的胆汁酸酯的产率（高达 81%）和纯度都很高。结果表明，微波技术是制备酚去氧胆酸酯的合适方法。为了详细了解所研究的去甲氧胆酸酯的亲脂性，对其色谱行为和亲脂性进行了比较研究。此外，本研究还对 pH 值-logD 曲线进行了估算，以便全面了解亲油性随 pH 值变化而发生的变化。研究结果表明，所研究化合物的 logD 值在潜在候选药物可接受的范围内。合成的苯去氧胆酸酯的色谱亲油性成功地与硅亲脂性描述指标相关联。

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来源期刊

Macedonian Journal of Chemistry and Chemical Engineering 化学-工程：化工

CiteScore

1.60

自引率

20.00%

发文量

审稿时长

>12 weeks

期刊介绍： Macedonian Journal of Chemistry and Chemical Engineering (Maced. J. Chem. Chem. Eng.) is an official publication of the Society of Chemists and Technologists of Macedonia. It is a not-for-profit open acess journal published twice a year. The journal publishes original scientific papers, short communications, reviews and educational papers from all fields of chemistry, chemical engineering, food technology, biotechnology and material sciences, metallurgy and related fields. The papers published in the Journal are summarized in Chemical Abstracts.