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Synthesis of N-Heterocyclic Analogues of 28-O-Methyl Betulinate, and Their Antibacterial and Antifungal Properties

Institute of Petrochemistry and Catalysis, Ufa Federal Research Center of RAS, 141 Prosp. Oktyabrya, 450075 Ufa, Republic of Bashkortostan, Russia
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Molbank 2020, 2020(1), M1100; https://doi.org/10.3390/M1100
Received: 19 November 2019 / Revised: 17 December 2019 / Accepted: 17 December 2019 / Published: 19 December 2019
(This article belongs to the Section Natural Products)
The paper presents the results on the one-pot pyridine quaternization using betulinic 28-O-methyl ester (1) and Tempo+Br3 cation followed by reduction of the resulting salt (2) to 1,2,5,6-tetrahydropyridine derivative (3). The structures of new compounds are confirmed by means of 1D and 2D-NMR spectroscopy, as well as MALDI TOF/TOF spectrometry. The derivatives 2 and 3 are active against S. aureus at the minimum inhibitory concentration (MIC) of 4 μg/mL and 16 μg/mL, correspondingly. View Full-Text
Keywords: C28-methyl ester of betulinic acid; Tempo+Br3 cation; pyridinium salts; antibacterial activity; antifungal activity C28-methyl ester of betulinic acid; Tempo+Br3 cation; pyridinium salts; antibacterial activity; antifungal activity
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MDPI and ACS Style

Shakurova, E.R.; Parfenova, L.V. Synthesis of N-Heterocyclic Analogues of 28-O-Methyl Betulinate, and Their Antibacterial and Antifungal Properties. Molbank 2020, 2020, M1100.

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