Synthesis and biological activity of 2-amino-1-oxa-2,3-dihydro-1-H-phenalene derivatives.
The preparation of two 2-dialkylamino-1-oxa-2,3-dihydro-1H-phenalenes (3 and 4) is described. Lewis acid-catalyzed Baeyer-Villiger reaction of acenaphthenone (5) gave the lactone 6. Reduction afforded the lactol 7, which was reacted with amines to give the target compounds 3 and 4. Investigation of the effects of these compounds on catechol and indole metabolism revealed that they lack the dopamine antagonist or agonist and serotonin agonist properties of the respective deoxy analogues.
Wang
W Y
WY
Department of Chemistry, University of Notre Dame, Indiana 46556.
Freeman
J P
JP
Burian
M A
MA
Vonvoigtlander
P F
PF
Szmuszkovicz
J
J
D006916:5-Hydroxytryptophan / Q000378:metabolism; D000818:Animals; D014150:Antipsychotic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D001923:Brain Chemistry / Q000187:drug effects; D004295:Dihydroxyphenylalanine / Q000378:metabolism; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D006834:Hydrazines / Q000037:antagonists & inhibitors; D010084:Oxidation-Reduction; D043803:Phenalenes; D051381:Rats; D011954:Receptors, Dopamine / Q000187:drug effects; D011985:Receptors, Serotonin / Q000187:drug effects
D014150:Antipsychotic Agents; D006571:Heterocyclic Compounds; D006834:Hydrazines; D043803:Phenalenes; D011954:Receptors, Dopamine; D011985:Receptors, Serotonin; C067936:2-dimethylamino-1-oxa-2,3-dihydro-1H-phenalene; C067937:2-dipropylamino-1-oxa-2,3-dihydro-1H-phenalene; D004295:Dihydroxyphenylalanine; C004297:3-hydroxybenzylhydrazine; D006916:5-Hydroxytryptophan