Microwave synthesis of novel chenodeoxycholic acid esters and comparative study of chromatographic behavior and lipophilicity
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 wi...
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| Format: | Article |
| Language: | English |
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Society of Chemists and Technologists of Macedonia
2023-12-01
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| Series: | Macedonian Journal of Chemistry and Chemical Engineering |
| Subjects: | |
| Online Access: | https://mjcce.org.mk/index.php/MJCCE/article/view/2707 |
| _version_ | 1797378821340528640 |
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| author | Ksenija Pavlović Ljubica Grbović Milica Karadžić Banjac Strahinja Kovačević Anamarija Mandić Sanja Podunavac-Kuzmanović Bojana Vasiljević |
| author_facet | Ksenija Pavlović Ljubica Grbović Milica Karadžić Banjac Strahinja Kovačević Anamarija Mandić Sanja Podunavac-Kuzmanović Bojana Vasiljević |
| author_sort | Ksenija Pavlović |
| collection | DOAJ |
| description |
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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| first_indexed | 2024-03-08T20:13:09Z |
| format | Article |
| id | doaj.art-882b9a27da694b0fb720805716679f0b |
| institution | Directory Open Access Journal |
| issn | 1857-5552 1857-5625 |
| language | English |
| last_indexed | 2024-03-08T20:13:09Z |
| publishDate | 2023-12-01 |
| publisher | Society of Chemists and Technologists of Macedonia |
| record_format | Article |
| series | Macedonian Journal of Chemistry and Chemical Engineering |
| spelling | doaj.art-882b9a27da694b0fb720805716679f0b2023-12-23T03:05:19ZengSociety of Chemists and Technologists of MacedoniaMacedonian Journal of Chemistry and Chemical Engineering1857-55521857-56252023-12-0142210.20450/mjcce.2023.2707Microwave synthesis of novel chenodeoxycholic acid esters and comparative study of chromatographic behavior and lipophilicity Ksenija Pavlović0Ljubica Grbović1Milica Karadžić Banjac2Strahinja Kovačević3Anamarija Mandić4Sanja Podunavac-Kuzmanović5Bojana Vasiljević6Department of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences, University of Novi Sad, Trg Dositeja Obradovića 3, Novi Sad, SerbiaDepartment of Chemistry, Biochemistry and Environmental Protection, Faculty of Sciences,University of Novi Sad, Trg DositejaObradovića 3, Novi Sad, SerbiaFaculty of Technology Novi Sad, University of Novi Sad, Bulevar Cara Lazara 1, Novi Sad, SerbiaFaculty of Technology Novi Sad, University of Novi Sad, Bulevar Cara Lazara 1, Novi Sad, SerbiaUniversity of Novi Sad, Bulevar Cara Lazara 1, Novi Sad, SerbiaFaculty of Technology Novi Sad, University of Novi Sad, Bulevar Cara Lazara 1, Novi Sad, SerbiaUniversity of Belgrade, Mike Petrovića Alasa 12-14, Vinča, Serbia 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. https://mjcce.org.mk/index.php/MJCCE/article/view/2707chenodeoxycholic acid estersdiolslipophilicityliquid chromatographymicrowaves |
| spellingShingle | Ksenija Pavlović Ljubica Grbović Milica Karadžić Banjac Strahinja Kovačević Anamarija Mandić Sanja Podunavac-Kuzmanović Bojana Vasiljević Microwave synthesis of novel chenodeoxycholic acid esters and comparative study of chromatographic behavior and lipophilicity Macedonian Journal of Chemistry and Chemical Engineering chenodeoxycholic acid esters diols lipophilicity liquid chromatography microwaves |
| title | Microwave synthesis of novel chenodeoxycholic acid esters and comparative study of chromatographic behavior and lipophilicity |
| title_full | Microwave synthesis of novel chenodeoxycholic acid esters and comparative study of chromatographic behavior and lipophilicity |
| title_fullStr | Microwave synthesis of novel chenodeoxycholic acid esters and comparative study of chromatographic behavior and lipophilicity |
| title_full_unstemmed | Microwave synthesis of novel chenodeoxycholic acid esters and comparative study of chromatographic behavior and lipophilicity |
| title_short | Microwave synthesis of novel chenodeoxycholic acid esters and comparative study of chromatographic behavior and lipophilicity |
| title_sort | microwave synthesis of novel chenodeoxycholic acid esters and comparative study of chromatographic behavior and lipophilicity |
| topic | chenodeoxycholic acid esters diols lipophilicity liquid chromatography microwaves |
| url | https://mjcce.org.mk/index.php/MJCCE/article/view/2707 |
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