Covalent bonding of azoles to quaternary protoberberine alkaloids

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 s...

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Published in:Magnetic resonance in chemistry 2008-12, Vol.46 (12), p.1127-1134
Main Authors: Grycová, Lenka, Hulová, Dagmar, Maier, Lukáš, Standara, Stanislav, Nečas, Marek, Lemière, Filip, Kareš, Radovan, Dostál, Jiří, Marek, Radek
Format: Article
Language:English
Subjects:
13C
15N
Alkaloids - chemistry
Azoles - chemistry
berberine
Berberine - analogs & derivatives
Berberine - chemistry
Berberine Alkaloids - chemical synthesis
Berberine Alkaloids - chemistry
Chemistry, Organic - methods
coptisine
Crystallography, X-Ray
Magnetic Resonance Spectroscopy
Mass Spectrometry
NMR
nucleophilic addition
palmatine
protoberberine alkaloid
X-ray diffraction
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Summary: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. Copyright © 2008 John Wiley & Sons, Ltd.
ISSN:0749-1581
1097-458X
DOI:10.1002/mrc.2325