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Bioorg Med Chem Lett. 2015 Sep 1;25(17):3451-4. doi: 10.1016/j.bmcl.2015.07.012. Epub 2015 Jul 11.

C4 phenyl aporphines with selective h5-HT(2B) receptor affinity.

Author information

1
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.
2
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.

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.

KEYWORDS:

5-HT(2A); 5-HT(2B); Aporphine; CNS; Nantenine

PMID:
26227772
PMCID:
PMC4523491
DOI:
10.1016/j.bmcl.2015.07.012
[Indexed for MEDLINE]
Free PMC Article

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