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The Azulene Framework as a Novel Arene Bioisostere: Design of Potent Dopamine D4 Receptor Ligands Inducing Penile Erection
Author(s) -
Löber Stefan,
Tschammer Nuska,
Hübner Harald,
Melis Maria Rosaria,
Argiolas Antonio,
Gmeiner Peter
Publication year - 2009
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200800395
Subject(s) - apomorphine , azulene , bioisostere , chemistry , derivative (finance) , bicyclic molecule , dopamine , dopamine receptor , stereochemistry , combinatorial chemistry , receptor , pharmacology , biochemistry , neuroscience , medicine , chemical synthesis , organic chemistry , biology , in vitro , economics , financial economics , agonist
Blue makes it happen : The non‐uniform charge distribution of the blue colored azulene framework is highly suitable for the bioisosteric replacement of bicyclic heteroarene moieties. Showing an analogous binding mode as heterocyclic dopamine D4 receptor‐selective lead compounds, the induction of penile erection in rats over a greater range of doses indicates a putative advantage of the rationally developed azulene derivative 2 b over apomorphine.