Covalent bonding of azoles to quaternary protoberberine alkaloids

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Authors	GRYCOVÁ Lenka HULOVÁ Dagmar MAIER Lukáš STANDARA Stanislav NEČAS Marek LEMIÉRE Filip KAREŠ Radovan DOSTÁL Jiří MAREK Radek
Year of publication	2008
Type	Article in Periodical
Magazine / Source	Magnetic Resonance in Chemistry
MU Faculty or unit	Faculty of Medicine
Citation
web	DOI: 10.1002/mrc.2325
Doi	https://doi.org/10.1002/mrc.2325
Field	Organic chemistry
Keywords	NMR; 1H; 13C; 15N; berberine; palmatine; coptisine; protoberberine alkaloid; nucleophilic addition; X-ray diffraction
Attached files	MRC08_46_1127.pdf
Description	Adducts of the quaternary protoberberine alkaloids (QPA) berberine, palmatine, and coptisine were prepared with nucleophiles derived from pyrrole, pyrazole, imidazole, and 1,2,4-triazole. The products, 8-substituted 7,8-dihydroprotoberberines, were identified by mass spectrometry and 1D and 2D NMR spectroscopy, including 1H-15N shift correlations at natural abundance. In addition, two adducts of QPA with chloroform and methanethiolate were characterized by using NMR data. Single-crystal X-ray structures of 8-pyrrolyl-7,8-dihydroberberine, 8-pyrazolyl-7,8-dihydroberberine, and 8-imidazolyl-7,8-dihydroberberine are also presented.
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