A series of mixed thiophene/furan oligomers have been synthesized via organometallic Stille coupling. In some cases, beside cross-coupling products, symmetrical coupling products were isolated. Oligomers consisting of up to 11 rings were obtained. Attempts to prepare macrocycles with 10 thiophene and furan units were not successful.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/jo981159l | DOI Listing |
J Med Chem
November 2006
Human BioMolecular Research Institute, 5310 Eastgate Mall, San Diego, California 92121, USA.
A series of 3-heteroaromatic analogues of nicotine were synthesized to delineate structural and mechanistic requirements for selectively inhibiting human cytochrome P450 (CYP) 2A6. Thiophene, substituted thiophene, furan, substituted furan, acetylene, imidazole, substituted imidazole, thiazole, pyrazole, substituted pyrazole, and aliphatic and isoxazol moieties were used to replace the N-methylpyrrolidine ring of nicotine. A number of potent inhibitors were identified, and several exhibited high selectivity for CYP2A6 relative to CYP2E1, -3A4, -2B6, -2C9, -2C19, and -2D6.
View Article and Find Full Text PDFJ Med Chem
January 2005
Human BioMolecular Research Institute, 5310 Eastgate Mall, San Diego, California 92121, USA.
A series of 5- and 6-substituted and unsubstituted 3-heteroaromatic analogues of nicotine were synthesized in an effort to delineate the structural requirements for selectively inhibiting human cytochrome P-450 (CYP) 2A6, the major nicotine metabolizing enzyme. Thiophene, substituted thiophene, furan, substituted furan, imidazole, substituted imidazole, pyridine, substituted pyridine, thiazole, and quinoline moieties were used to replace the N-methylpyrrolidine ring of nicotine. Bromo and methyl groups were introduced at the 5-position of the pyridine ring and fluoro, chloro, and methoxy groups were placed at the 6-position of the pyridine ring in order to explore the structure-activity relationship (SAR) of inhibition of CYP2A6.
View Article and Find Full Text PDFJ Org Chem
October 1998
Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, Alabama 35487-0336.
A series of mixed thiophene/furan oligomers have been synthesized via organometallic Stille coupling. In some cases, beside cross-coupling products, symmetrical coupling products were isolated. Oligomers consisting of up to 11 rings were obtained.
View Article and Find Full Text PDFEnter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!