Synthesis of new linearly annulated tricycles as rigid dopamine congeners.
A simple synthetic route that leads to three isosters of octahydrobenzo[g]quinolines (IA), in which the carbon atom in 4-position is replaced by an oxygen, a sulfur or a nitrogen atom, to give hexahydronaphth-[1,4]oxazine (VIII a) and -[1,4]thiazine (VIII b), and octahydrobenzo[g]quinoxaline (VIII c) respectively, is here reported. These compounds can be considered as new structural models of dopamine agonists.
Perrone
R
R
Dipartimento Farmacochimico, Università di Bari, Italy.
Berardi
F
F
Bettoni
G
G
Tortorella
V
V
D055598:Chemical Phenomena; D002621:Chemistry; D008968:Molecular Conformation; D010078:Oxazines / Q000138:chemical synthesis* / Q000494:pharmacology; D010084:Oxidation-Reduction; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000494:pharmacology; D011954:Receptors, Dopamine / Q000187:drug effects*; D013843:Thiazines / Q000138:chemical synthesis* / Q000494:pharmacology
D010078:Oxazines; D011810:Quinoxalines; D011954:Receptors, Dopamine; D013843:Thiazines; C056631:6,9-dimethoxy-4-n-propyl-2,3,4a,5,10,10a-hexahydro-4H-naphth(2,3-b)(1,4)oxazine; C056632:6,9-dimethoxy-4-propyl-2,3,4a,5,10,10a-hexahydro-4H-naphtho(2,3-b)(1,4)thiazine; C056633:VICO 81