title: C4 phenyl aporphines with selective h5-HT(2B) receptor affinity.
abstract: A group of aporphine alkaloids related to (±)-nantenine (1) and bearing a C4 phenyl and various C1 or N-substituents, was synthesized and evaluated for affinity to h5-HT receptors. In general, unlike nantenine, the analogs lack affinity for the h5-HT(2A) receptor and other 5-HT receptors but bind selectively to the h5-HT(2B) receptor. With regards to 5-HT(2B) affinity, there appears to be a low tolerance for bulky C1 or N-substituents when the C4 phenyl moiety is present. Compound 5a had the highest 5-HT(2B) affinity of the compounds tested, was found to be an antagonist and is selective vs other CNS receptors.
authors.affiliation: Chemistry Dept., Hunter College, CUNY, 695 Park Avenue, NY 10065, USA; The Graduate Center, City University of New York, 365 5th Avenue, NY 10016, USA.
authors.forename: Nirav
authors.initials: N
authors.lastname: Kapadia
authors.affiliation: Chemistry Dept., Hunter College, CUNY, 695 Park Avenue, NY 10065, USA; The Graduate Center, City University of New York, 365 5th Avenue, NY 10016, USA. Electronic address: whardi@hunter.cuny.edu.
authors.forename: Wayne W
authors.initials: WW
authors.lastname: Harding
mesh_terms: D001060:Aporphines / Q000737:chemistry* / Q000494:pharmacology; D015394:Molecular Structure; D044402:Receptor, Serotonin, 5-HT2A / Q000378:metabolism*; D058830:Serotonin 5-HT2 Receptor Antagonists / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship
chemical_list: D001060:Aporphines; D044402:Receptor, Serotonin, 5-HT2A; D058830:Serotonin 5-HT2 Receptor Antagonists; C041615:nantenine
keywords: 5-HT(2A); 5-HT(2B); Aporphine; CNS; Nantenine