Synthesis and in vitro activity of oleanolic acid derivatives against Chlamydia trachomatis and Staphylococcus aureus

Казакова, О. Б.; Rubanik, Liudmila; Смирнова, И. Е.; Poleschuk, Nikolay; Petrova, А. V.; Kapustsina, Yuliya; Байкова, И. П.; Tret’yakova, E. V.; Khusnutdinova, É. F.

doi:10.1007/s00044-021-02741-6

Cited by 14 publications

(10 citation statements)

References 42 publications

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“…All chemicals were of reagent grade (Sigma‐Aldrich). Compounds 1–3 were synthesized as described previously (Finlay, Honda & Gribble, 2002; Kazakova et al., 2021).…”

Section: Methodsmentioning

confidence: 99%

Antiviral opportunities of Mannich bases derived from triterpenic N‐propargylated indoles

Petrova,

Tretyakova,

Khusnutdinova

et al. 2023

Chem Biol Drug Des

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Oleanolic and glycyrrhetic acids alkyne derivatives were synthesized as a result of propargylation of the indole NH‐group condensed with the triterpene A‐ring, the following aminomethylation led to a series of Mannich bases. The synthesized compounds were tested for their potential inhibition of influenza A/PuertoRico/8/34 (H1N1) virus in Madin‐Darby canine kidney (MDCK) cell culture and SARS‐CoV‐2 pseudovirus in baby hamster kidney‐21‐human angiotensin‐converting enzyme 2 (BHK‐21‐hACE2) cells. Mannich bases of oleanolic and glycyrrhetic acids N‐propargylated indoles 7, 8, and 12 were the most efficacious against influenza virus A with IC50 7–10 μM together with a low toxicity (CC50 > 145 μM) and high selectivity index SI value 20. Indolo‐oleanolic acid morpholine amide Mannich base holding N‐methylpiperazine moiety 9 showed anti‐SARS‐CoV‐2 pseudovirus activity with EC50 value of 14.8 μM. Molecular docking and dynamics modeling investigated the binding mode of the compounds 7 and 12 into the binding pocket of influenza A virus M2 protein and compound 9 into the RBD domain of SARS‐CoV‐2 spike glycoprotein.

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“…All chemicals were of reagent grade (Sigma‐Aldrich). Compounds 1–3 were synthesized as described previously (Finlay, Honda & Gribble, 2002; Kazakova et al., 2021).…”

Section: Methodsmentioning

confidence: 99%

Antiviral opportunities of Mannich bases derived from triterpenic N‐propargylated indoles

Petrova,

Tretyakova,

Khusnutdinova

et al. 2023

Chem Biol Drug Des

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“…Oleanolic acid conjugate with diethylenetriamine 302 (Figure 13) demonstrated high inhibitory activity against C. trachomatis with chemotherapeutic index 8 and >8. Compounds 302 and 303 exhibited remarkable activities against the NCI-60 subpanel (GI 50 ranges from 0.18 to 2.21 µM) exceeding the activity of sorafenib with compound 302 as a lead (GI 50 0.17 µM for melanoma LOX IMVI) [306]. A series of oleanolic acid derivatives holding oxo-or 3-N-polyamino-3-deoxy-substituents at C3 as well as carboxamide function at C28 with different long chain polyamines have been synthesized and showed good antimicrobial activities against Gram-positive S. aureus, S. faecalis and B. cereus (MIC values from 3.125 to 200 µg/mL) and Gram-negative E. coli, P. aeruginosa, and S. enterica (MIC ranging from 6.25 to 200 µg/mL) [307].…”

Section: Terpene-and Triterpene-based Polyamine Derivativesmentioning

confidence: 99%

From Marine Metabolites to the Drugs of the Future: Squalamine, Trodusquemine, Their Steroid and Triterpene Analogues

Казакова

Giniyatullina

Babkov

et al. 2022

IJMS

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This review comprehensively describes the recent advances in the synthesis and pharmacological evaluation of steroid polyamines squalamine, trodusquemine, ceragenins, claramine, and their diverse analogs and derivatives, with a special focus on their complete synthesis from cholic acids, as well as an antibacterial and antiviral, neuroprotective, antiangiogenic, antitumor, antiobesity and weight-loss activity, antiatherogenic, regenerative, and anxiolytic properties. Trodusquemine is the most-studied small-molecule allosteric PTP1B inhibitor. The discovery of squalamine as the first representative of a previously unknown class of natural antibiotics of animal origin stimulated extensive research of terpenoids (especially triterpenoids) comprising polyamine fragments. During the last decade, this new class of biologically active semisynthetic natural product derivatives demonstrated the possibility to form supramolecular networks, which opens up many possibilities for the use of such structures for drug delivery systems in serum or other body fluids.

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“…140 In a separate study by , the authors tested the antibacterial activity of different oleanolic acid derivatives. 141 39 is a derivative of oleanolic acid, a compound found in over 1600 plant species and found in many members of the Oleaceae family. 142 39 was found to have anti-MRSA activity and also displayed anti-chlamydial activity.…”

Section: Reviewmentioning

confidence: 99%

Recent advances in the discovery of plant-derived antimicrobial natural products to combat antimicrobial resistant pathogens: insights from 2018–2022

et al. 2023

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Synthesis and in vitro activity of oleanolic acid derivatives against Chlamydia trachomatis and Staphylococcus aureus

Cited by 14 publications

References 42 publications

Antiviral opportunities of Mannich bases derived from triterpenic N‐propargylated indoles

Antiviral opportunities of Mannich bases derived from triterpenic N‐propargylated indoles

From Marine Metabolites to the Drugs of the Future: Squalamine, Trodusquemine, Their Steroid and Triterpene Analogues

Recent advances in the discovery of plant-derived antimicrobial natural products to combat antimicrobial resistant pathogens: insights from 2018–2022

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