Resolution and absolute configuration of an ergoline-related dopamine agonist, trans-4,4a,5,6,7,8,8a,9-Octahydro-5-propyl-1H(or 2H)-pyrazolo[3,4-g]quinoline.
The title compound (+/-)-5 (R = Pro) (LY141865) has been resolved into a (-) isomer and a (+) isomer as the D- and L-tartrate salts, respectively. Biological studies have shown that dopamine agonist activity is a property of only the (-) isomer. Crystallographic analysis has proven that the absolute configuration of the active (-) isomer is the same as that of the natural ergolines.
D015102:3,4-Dihydroxyphenylacetic Acid / Q000494:pharmacology; D000818:Animals; D001794:Blood Pressure / Q000187:drug effects; D003345:Corticosterone / Q000494:pharmacology; D003461:Crystallography; D004298:Dopamine / Q000378:metabolism*; D004873:Ergolines / Q000494:pharmacology; D006719:Homovanillic Acid / Q000494:pharmacology; D051379:Mice; D008958:Models, Molecular; D008961:Models, Structural; D011187:Posture; D011388:Prolactin / Q000097:blood; D019257:Quinpirole; D012726:Sexual Behavior, Animal / Q000187:drug effects
D004873:Ergolines; D015102:3,4-Dihydroxyphenylacetic Acid; D019257:Quinpirole; D011388:Prolactin; D004298:Dopamine; D003345:Corticosterone; D006719:Homovanillic Acid