Title
Covalent bonding of azoles to quaternary protoberberine alkaloids Covalent bonding of azoles to quaternary protoberberine alkaloids
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Chichester ,
Subject
Chemistry
Source (journal)
Magnetic resonance in chemistry. - Chichester
Volume/pages
46(2008) :12 , p. 1127-1134
ISSN
0749-1581
ISI
000261163000006
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
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 1H15N 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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