Zusammenfassung
An indolo[3,2-d]pyrrolo[3,2-g]azecine and a benzo[d]pyrrolo[3,2-glazecine analogue of the potent dopamine receptor antagonist LE 300 {7-methyl-6,7,8,9,14,15-hexahydro-5H-benz[d]indolo[2,3-g]azecine) have been prepared in mufti-step reactions via C-N bond cleavage of corresponding quaternary N-methylquinolizinium iodides. LE 300, the target compounds and two precursor quinolizines have been tested ...
Zusammenfassung
An indolo[3,2-d]pyrrolo[3,2-g]azecine and a benzo[d]pyrrolo[3,2-glazecine analogue of the potent dopamine receptor antagonist LE 300 {7-methyl-6,7,8,9,14,15-hexahydro-5H-benz[d]indolo[2,3-g]azecine) have been prepared in mufti-step reactions via C-N bond cleavage of corresponding quaternary N-methylquinolizinium iodides. LE 300, the target compounds and two precursor quinolizines have been tested in vitro for antagonist activity at 5-HT2A receptors (rat tail artery) and Hl receptors {guinea-pig ileum), respectively. LE 300 and compound 19 {3,6-dimethyl-4,5,6,7,8,13-hexahydro-3H-benzo[d]pyrrolo[3,2-glazecine) competitively inhibited S-HT-induced contractions with similar nanomolar potency (pA(2) = 8.32 and 8.01, respectively) but were less active than the reference antagonist ketanserin (pA(2) = 9.55). Compound 19 displayed moderate H-1-antihistaminic activity in the guinea-pig ileum assay (pA(2) = 7.37).
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