Covalent bonding of azoles to quaternary protoberberine alkaloids
Language English Country England, Great Britain Media print
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
18781707
DOI
10.1002/mrc.2325
Knihovny.cz E-resources
- MeSH
- Alkaloids chemistry MeSH
- Azoles chemistry MeSH
- Berberine analogs & derivatives chemistry MeSH
- Berberine Alkaloids chemical synthesis chemistry MeSH
- Mass Spectrometry MeSH
- Crystallography, X-Ray MeSH
- Magnetic Resonance Spectroscopy MeSH
- Chemistry, Organic methods MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Alkaloids MeSH
- Azoles MeSH
- Berberine MeSH
- Berberine Alkaloids MeSH
- coptisine MeSH Browser
- palmatine MeSH Browser
- protoberberine MeSH Browser
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 (1)H--(15)N 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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