Abstract
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.
Highlights
N-Heterocyclic compounds represent a large class of organic molecules, many of which are biologically active substances, widely applied in medicine [1]
We reported the first case of pyridine quaternization using Tempo+Br3- cation
In continuation of our research on the synthesis of pyridinium analogue of natural compounds, method developed by us [8,9], which avoids the additional stage of halogenation and increases the
Summary
N-Heterocyclic compounds represent a large class of organic molecules, many of which are biologically active substances, widely applied in medicine [1]. Lupane triterpenoids are considered to be one of the most promising compounds, as they contain a hydrophobic carbocyclic backbone, which possesses a high affinity to lipid membranes [4,5]. The synthesis of their ammonium derivatives is a promising task for the development of targeted agents against bacterial infections and malignant neoplasms. The development of new one-pot methods and approaches to the synthesis of target derivatives would create effective and quite simple methods for their preparation, and significantly enrich the range of quaternized ammonium analogues of natural compounds
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