Synthesis of Amide Derivatives of Glycyrrhizic Acid

Glycyrrhizic acid (GL) is the main active ingredient of licorice, which is widely used as a traditional medicine in many countries, especially in the East Asia region (China, Japan). Many studies have shown that GL has a wide range of anti-inflammatory and antiviral effects. The GA aglycone and the...

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Bibliographic Details
Published in:Pharmaceutical chemistry journal 2023-09, Vol.57 (6), p.885-898
Main Authors: Mohammed, Eyad Abdulwhab H., Yijie, Peng, Yuan, Wang Zong, Xin, Qiang, Quanyi, Zhao
Format: Article
Language:English
Subjects:
Amino acids
Antiviral agents
Medicine
Organic Chemistry
Pharmacology/Toxicology
Pharmacy
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Summary:Glycyrrhizic acid (GL) is the main active ingredient of licorice, which is widely used as a traditional medicine in many countries, especially in the East Asia region (China, Japan). Many studies have shown that GL has a wide range of anti-inflammatory and antiviral effects. The GA aglycone and the glucuronate fraction of its structure play an important role in the design of derivatives with the target molecules during the activation process. In the present study, the amine derivatives of GL were designed and synthesized as promising derivatives with high efficacy and important physicochemical properties. GL was treated with HCl-CH 3 OH solution to obtain dimethyl glycyrrhizate. In the activation process, the carboxyl groups in glucuronic acid exhibited higher reactivity than those in C30. Second, in the presence of coupling agents HOBt/EDCI and organic bases, GL reacted with various amino acids in solvents such as DMF or dioxane to obtain seven glycyrrhizate diamide derivatives, which were characterized by IR and 1 H NMR spectra.
ISSN:0091-150X
1573-9031
DOI:10.1007/s11094-023-02964-4