Covalent bonding of azoles to quaternary protoberberine alkaloids

GRYCOVÁ, Lenka, Dagmar HULOVÁ, Lukáš MAIER, Stanislav STANDARA, Marek NEČAS, Filip LEMIÉRE, Radovan KAREŠ, Jiří DOSTÁL and Radek MAREK. Covalent bonding of azoles to quaternary protoberberine alkaloids. Magnetic Resonance in Chemistry. John Wiley & Sons, 2008, vol. 46, No 12, p. 1127-1134. ISSN 0749-1581. Available from: https://dx.doi.org/10.1002/mrc.2325.

Basic information

• Original name: Covalent bonding of azoles to quaternary protoberberine alkaloids
• Name in Czech: Kovalentní vazba azolů na kvartérní protoberberinové alkaloidy
• Authors: GRYCOVÁ, Lenka (203 Czech Republic, belonging to the institution), Dagmar HULOVÁ (203 Czech Republic), Lukáš MAIER (203 Czech Republic), Stanislav STANDARA (203 Czech Republic, belonging to the institution), Marek NEČAS (203 Czech Republic, belonging to the institution), Filip LEMIÉRE (56 Belgium), Radovan KAREŠ (203 Czech Republic, belonging to the institution), Jiří DOSTÁL (203 Czech Republic, belonging to the institution) and Radek MAREK (203 Czech Republic, guarantor, belonging to the institution).
• Edition: Magnetic Resonance in Chemistry, John Wiley & Sons, 2008, 0749-1581.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10401 Organic chemistry
• Country of publisher: United Kingdom of Great Britain and Northern Ireland
• Confidentiality degree: is not subject to a state or trade secret
• WWW: DOI: 10.1002/mrc.2325
• Impact factor: Impact factor: 1.443
• RIV identification code: RIV/00216224:14110/08:00024854
• Organization unit: Faculty of Medicine
• Doi: http://dx.doi.org/10.1002/mrc.2325
• UT WoS: 000261163000006
• Keywords (in Czech): NMR; 1H; 13C; 15N; berberin; palmatin; koptisin; protoberberiny; alkaloidy; nukleofilní adice; X-ray difrakce
• Keywords in English: NMR; 1H; 13C; 15N; berberine; palmatine; coptisine; protoberberine alkaloid; nucleophilic addition; X-ray diffraction
• Tags: 13C, 15N, 1H, berberine, coptisine, NMR, nucleophilic addition, palmatine, protoberberine alkaloid, X-ray diffraction
• Tags: International impact, Reviewed

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 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.

Abstract (in Czech)

Příprava, NMR a RTG studie 8-substituovaných 7,8-dihydroprotoberberinů s kovalentně navázaným pyrrolem, pyrazolem, imidazolem, and 1,2,4-triazolem je popsána a diskutována.

Links

• GA525/04/0017, research and development project: Name: Rostlinné zdroje benzofenanthridinových alkaloidů a účinek těchto alkaloidů na normální a nádorové buňky

Investor: Czech Science Foundation, Plant sources of benzophenanthridine alkaloids and effects of these alkaloid on normal and cancer cells

• LC06030, research and development project: Name: Biomolekulární centrum

Investor: Ministry of Education, Youth and Sports of the CR, Biomolecular centre

• MSM0021622413, plan (intention): Name: Proteiny v metabolismu a při interakci organismů s prostředím

Investor: Ministry of Education, Youth and Sports of the CR, Proteins in metabolism and interaction of organisms with the environment