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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)

Isochromanone-based urotensin-II receptor agonists.

A series of analogues of the selective non-peptide urotensin II (UII) receptor agonist 3-(4-chlorophenyl)-3-(2-dimethylaminoethyl)-isochroman-1-one (AC-7954, 1) was synthesized and evaluated for UII agonist activity using a functional cell-based assay. The introduction of a methyl group in the 4-position resulted in a complete loss of activity, whereas substituents in the aromatic rings were beneficial. Sterically demanding amino groups were also detrimental to the activity. Several potent agonists were identified, six compounds being equally or more potent than 1. The most potent compound in the series was the 6,7-dimethyl analogue of 1 (16, pEC50 6.87). The racemate of 16 was resolved into the pure enantiomers using preparative straight phase HPLC. It was shown that the potency resides in the (+)-enantiomer (pEC50 7.11). The synthesized compounds seem to be selective for the UII receptor as no activities were observed at the closely related SSTR3 and 5 receptors.[1]


  1. Isochromanone-based urotensin-II receptor agonists. Lehmann, F., Currier, E.A., Olsson, R., Hacksell, U., Luthman, K. Bioorg. Med. Chem. (2005) [Pubmed]
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