Publication details

Covalent bonding of azoles to quaternary protoberberine alkaloids

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 http://dx.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
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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