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Publications

Holzgrabe, U.; Cambareri, A.; Kuhl, U.; Siener, T.; Brandt, W.; Straßburger, W.; Friderichs, E.; Englberger, W.; Kögel, B.; Haurand, M.; Diazabicyclononanones, a potent class of kappa opioid analgesics Farmaco 57, 531-534, (2002) DOI: 10.1016/S0014-827X(02)01243-0

The 1,5-dimethyl 3,7-diaza-3,7-dimethyl-9-oxo-2,4-di-2-pyridine-bicyclo[3.3.1]nonane-1,5-dicarboxylate, HZ2, has a high and selective affinity for the kappa opioid receptor and an antinociceptive activity comparable to morphine. In addition, it is characterized by a long duration of action and a high oral bioavailability. QSAR studies within series of kappa agonists revealed a chair-boat conformation of a double protonated HZ2 characterized by an almost parallel orientation of the C9 carbonyl group and the N7-H group and at least one aromatic ring to be the pharmacophoric arrangement. Structural variations showed that the pyridine rings in 2 and 4 position can be replaced with p-methoxy-, m-hydroxy- and m-fluoro-substituted phenyl rings. However, all other substituents have to be kept the same for a high affinity to the kappa receptor.
Publications

Holzgrabe, U.; Friderichs, E.; Englberger, W.; Strassberger, W.; Maurand, M.; Brandt, W.; Camberri, A.; Kuhl, U.; Siener, T.; Diazabicyclononanones, a new class of opioid-type analgesics Sci. Cult. 68, 1-4, (2002)

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