Indole Derivatives of Fusidane Triterpenoids: Synthesis and the Antibacterial Activity

Салимова, Е. В.; Magafurova, Aygul A.; Tret’yakova, E. V.; Куковинец, О. С.; Parfenova, Lyudmila V.

doi:10.1007/s10593-020-02733-1

Cited by 16 publications

(5 citation statements)

References 16 publications

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“…In 2020, Salimova et al synthesized two new indole derivatives (10 and 11) of FA by the Fischer reaction. The antimicrobial activity of the derivatives was tested against MRSA (strain ATCC 43300), and the compounds showed comparable activity to FA (Salimova et al, 2020).…”

Section: Anti-gram-positive Bacterial Activitymentioning

confidence: 99%

Bioactivities and Structure–Activity Relationships of Fusidic Acid Derivatives: A Review

Long

Zhang

et al. 2021

Front. Pharmacol.

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Fusidic acid (FA) is a natural tetracyclic triterpene isolated from fungi, which is clinically used for systemic and local staphylococcal infections, including methicillin-resistant Staphylococcus aureus and coagulase-negative staphylococci infections. FA and its derivatives have been shown to possess a wide range of pharmacological activities, including antibacterial, antimalarial, antituberculosis, anticancer, tumor multidrug resistance reversal, anti-inflammation, antifungal, and antiviral activity in vivo and in vitro. The semisynthesis, structural modification and biological activities of FA derivatives have been extensively studied in recent years. This review summarized the biological activities and structure–activity relationship (SAR) of FA in the last two decades. This summary can prove useful information for drug exploration of FA derivatives.

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Section: Anti-gram-positive Bacterial Activitymentioning

confidence: 99%

Bioactivities and Structure–Activity Relationships of Fusidic Acid Derivatives: A Review

Long

Zhang

et al. 2021

Front. Pharmacol.

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“…Terpenoids isolated from plant sources remain the starting material for various chemical transformations in terms of obtaining compounds with useful properties [1][2][3][4][5][6][7][8]. Terpenoid derivatives with cytotoxic, anti-inflammatory, analgesic, et al activity have been synthesized by chemical transformation [9][10][11][12][13][14][15][16].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Investigation of Biological Activity of a Number of New Betulonic Acid Derivatives Containing 1,2,3-Triazole Fragments

Jalmakhanbetova,

Mukusheva,

Abdugalimov

et al. 2024

Preprint

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A number of chemical modifications were carried out in order to synthesize new compounds based on the triterpenoid betulonic acid. Triazolation reactions were carried out for the synthesis of new 1,2,3-triazole derivatives based on betulonic acid. Chemical changes were made on the carbonyl group at the C-3 position of the initial molecule and on the carboxyl and hydroxyl groups at the C-28 position. Chromatographic methods were used to separate and purify the formed products. Spectroscopic (NMR-, mass-) methods were used to establish the structure of synthesized compounds. As a result of the chemical transformations carried out, a number of new derivatives of betulonic acid were obtained. All synthesized compounds were tested for antimicrobial and cytotoxic activity. As a result, compounds with pronounced antimicrobial activity were identified.

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“…In continuation of our previous research on the synthesis and biological activity of novel fusidane triterpenoid analogues [ 19 , 20 , 21 , 22 ], the present work is aimed both at the study of the antimicrobial effect of a number of FA amines and at the identification of their potential biological targets, including cell membranes. For this purpose, FA derivatives containing linear, aromatic, and heterocyclic amino groups or polyamine and pyrazinecarboxamide moieties at the C-3 atom of the molecule were synthesized.…”

Section: Introductionmentioning

confidence: 99%

3-Amino-Substituted Analogues of Fusidic Acid as Membrane-Active Antibacterial Compounds

et al. 2023

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Fusidic acid (FA) is an antibiotic with high activity against Staphylococcus aureus; it has been used in clinical practice since the 1960s. However, the narrow antimicrobial spectrum of FA limits its application in the treatment of bacterial infections. In this regard, this work aims both at the study of the antimicrobial effect of a number of FA amines and at the identification of their potential biological targets. In this way, FA analogues containing aliphatic and aromatic amino groups and biogenic polyamine, spermine and spermidine, moieties at the C-3 atom, were synthesized (20 examples). Pyrazinecarboxamide-substituted analogues exhibit a high antibacterial activity against S. aureus (MRSA) with MIC ≤ 0.25 μg/mL. Spermine and spermidine derivatives, along with activity against S. aureus, also inhibit the growth and reproduction of Gram-negative bacteria Escherichia coli, Acinetobacter baumannii, and Pseudomonas aeruginosa, and have a high fungicidal effect against Candida albicans and Cryptococcus neoformans. The study of the membrane activity demonstrated that the spermidine- and spermine-containing compounds are able to immerse into membranes and disorder the lipidsleading to a detergent effect. Moreover, spermine-based compounds are also able to form ion-permeable pores in the lipid bilayers mimicking the bacterial membranes. Using molecular docking, inhibition of the protein synthesis elongation factor EF-G was proposed, and polyamine substituents were shown to make the greatest contribution to the stability of the complexes of fusidic acid derivatives with biological targets. This suggests that the antibacterial effect of the obtained compounds may be associated with both membrane activity and inhibition of the elongation factor EF-G.

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Indole Derivatives of Fusidane Triterpenoids: Synthesis and the Antibacterial Activity

Cited by 16 publications

References 16 publications

Bioactivities and Structure–Activity Relationships of Fusidic Acid Derivatives: A Review

Bioactivities and Structure–Activity Relationships of Fusidic Acid Derivatives: A Review

Synthesis and Investigation of Biological Activity of a Number of New Betulonic Acid Derivatives Containing 1,2,3-Triazole Fragments

3-Amino-Substituted Analogues of Fusidic Acid as Membrane-Active Antibacterial Compounds

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