2-aminothiazole-derived opioids. Bioisosteric replacement of phenols.

Article Details


Zhang A, Xiong W, Hilbert JE, DeVita EK, Bidlack JM, Neumeyer JL

2-aminothiazole-derived opioids. Bioisosteric replacement of phenols.

J Med Chem. 2004 Apr 8;47(8):1886-8.

PubMed ID
15055988 [ View in PubMed

A series of aminothiazole-derived morphinans, benzomorphans, and morphine were synthesized. Although their affinities were somewhat lower than their phenol prototypes, one compound (9a, ATPM) has been identified possessing high affinity and selectivity at the kappa receptor. Functional assays showed that 9a was a full kappa but partial mu agonist; the efficacy at kappa was significantly greater than at mu receptors. This novel compound may be valuable for the development of long-acting analgesics and drug abuse medication.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
LevorphanolKappa-type opioid receptorKi (nM)2.3N/AN/ADetails
LevorphanolMu-type opioid receptorKi (nM)0.21N/AN/ADetails
MorphineKappa-type opioid receptorKi (nM)24N/AN/ADetails
MorphineMu-type opioid receptorKi (nM)0.88N/AN/ADetails