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Eur J Pharmacol. 2003 Dec 15;482(1-3):335-7.

Spiro[9,10-dihydroanthracene]-9,3'-pyrrolidine-a structurally unique tetracyclic 5-HT2A receptor antagonist.

Author information

1
Department of Medicinal Chemistry, School of Pharmacy, Virginia Commonwealth University, Box 980540, Richmond, VA 23298-0540, USA.

Abstract

Structural elaboration of phenylethylamine to spiro[9,10-dihydroanthracene]-9,3'-pyrrolidine (SpAMDA) produces an agent with unexpectedly high affinity (K(i)=4 nM) at 5-HT(2A) receptors. It was shown that SpAMDA acts as a 5-HT(2A) receptor antagonist. The structure and molecular geometry of SpAMDA are not consistent with existing pharmacophore features, and a novel 5-HT(2A) antagonist pharmacophore model is proposed for the binding of aminomethyl-9,10-dihydroanthracene analogs. Thus, SpAMDA may be a structurally novel parent of a new class of 5-HT(2A) receptor antagonists that binds to the receptor in a unique fashion that is distinct from the binding topology of existing 5-HT(2A) receptor antagonists.

PMID:
14660041
DOI:
10.1016/j.ejphar.2003.09.059
[Indexed for MEDLINE]

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