Synthesis and in vitro activity of oleanolic acid derivatives against Chlamydia trachomatis and Staphylococcus aureus
| Autor: | Liudmila Rubanik, E. F. Khusnutdinova, Elena V. Tretyakova, I. P. Baikova, Anastasia Petrova, Irina Smirnova, Yuliya Kapustsina, Oxana B. Kazakova, Nikolay Poleschuk |
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| Rok vydání: | 2021 |
| Předmět: |
010405 organic chemistry
Organic Chemistry medicine.disease_cause 01 natural sciences In vitro 0104 chemical sciences Microbiology 010404 medicinal & biomolecular chemistry chemistry.chemical_compound chemistry Staphylococcus aureus Amide Diethylenetriamine medicine Bioorganic chemistry General Pharmacology Toxicology and Pharmaceutics Chlamydia trachomatis Oleanolic acid Conjugate |
| Zdroj: | Medicinal Chemistry Research. 30:1408-1418 |
| ISSN: | 1554-8120 1054-2523 |
| DOI: | 10.1007/s00044-021-02741-6 |
| Popis: | A series of nitrogen-containing modificants with amide, arylidene or heterocyclic fragments of oleanolic, oleanonic and 2,3-indolo-oleanolic acids have been synthesized and evaluated for activity against C. trachomatis and key ESKAPE pathogens. Oleanolic acid conjugates with homopyperazine 3, N-hydroxymethyl-homopyperazine 4, and diethylenetriamine 23 demonstrated a high inhibitory activity against C. trachomatis with chemotherapeutic index (CTI) 8 and >8, while 3-amino-3,4-seco-4(23)-en-erythrodiol 22 was found to be a leader compound with significant activity (MIC 3.125 μg/mL). Compounds 3 and 22 showed a moderate activity against MRSA with MICs of 8 and 4 μg/mL. Compounds 2, 3, and 23 exhibited remarkable activities against NCI-60 subpanel (GI50 ranges from 0.18 to 2.21 μM) exceeding the activity of sorafenib with compound 23 as a leader (GI50 0.17 μM for melanoma LOX IMVI). |
| Databáze: | OpenAIRE |
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