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• W2904210229 abstract "Background: A wide range of biological activity, relatively low toxicity and multiple pharmacological effects of triterpenoids are major advantages of these compounds in the prevention and treatment of various diseases. They include the lupane- type triterpenoids that proved to be a promising platform for the synthesis of analogs with a wide range of biological activities, including anti-inflammatory, antitumor, antiparasitic and antiviral properties. The main disadvantage complicating the use of all known derivatives of lupane acids in medical practice is low bioavailability associated with poor solubility in biologic fluids, limiting their effective interaction with the biological targets. Objective: The objective of this study is the synthesis of new amphiphilic betulin derivatives on the base of pyridinium salts with antifungal and antibacterial activity. Methods: In this study we have developed an effective one-pot method for the preparation of new quaternized pyridine derivatives 4-6 of the betulinic series based on the reaction of the initial triterpenes 1-3 with the Tempo+Br3 - reagent in the pyridine. The synthesized and initial compounds were tested for their antimicrobial and antifungal activity. Results: The data presented in this document indicate that all synthesized compounds 4-6 exhibited high activity against both gram-positive Staphylococcus aureus bacteria and gram-negative Pseudomonas aeruginosa strains, as well as Candida albicans and Cryptococcus neoformans fungi with the >90% coverage of the inhibition zone. The best result in a series of compounds 4-6 was found for the derivative 6 at the minimum inhibitory concentration of 1 µg/ml against S. aureus bacteria, C. albicans and C. neoformans fungi at the concentration of 8 µg/ml. Conclusion: Thus, we have demonstrated the first example of the pyridine quaternization using the betulin triterpenoids as the lipophilic substrates and Tempo+Br3 - cation. The obtained quaternized pyridine analogs of betulin triterpenes showed high antibacterial and antifungal activity in comparison with the initial compounds." @default.
• W2904210229 created "2018-12-22" @default.
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• W2904210229 date "2019-12-31" @default.
• W2904210229 modified "2023-09-26" @default.
• W2904210229 title "One-pot Synthesis of Betulin Triterpenoid Quaternized Pyridine Derivatives and their Antimicrobial Activity" @default.
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• W2904210229 doi "https://doi.org/10.2174/1570180816666181217123629" @default.
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