SYNTHESIS OF SOME COMPOUNDS OF ANTICIPATED ACTIVITY ON SOME BRAIN STIMULANT AMINES

Abstract

ABSTRACT The present work deals with the preparation of rigid analogs of the antidepressant drug, fluoxetine, a selective serotonin-reuptake inhibitor. A series of tropane derivatives, incorporating many structural features of the fluoxetine molecule, was prepared. The synthesized compounds are derivatives of 8-methyl-3-(3 · - or 4-substituted phenoxy)-3-( un )substituted phenyl-8-azabicyclo[3.2.1 ]octanes. The results of the physical and spectral microanalyses used in characterization of the synthesized compounds are cited. Five known intermediates and seven new final compounds were prepared. All of the final compounds have been evaluated for their potential activities as serotonin- and norepinephrine-reuptake inhibitors. Known starting and intermediate compounds: • Acetonedicarboxylic acid • Succindialdoxime • 8-Methyl-8-azabicyclo[3.2.1]octan-3-one (3-tropinone) (I) • 8-Methyl-3-phenyl-8-azabicyclo[3.2.1 ]octan-3-ol (3-phenyltropine) (II) • 3-(4'-Fluorophenyl)-8-methyl-8-azabicyclo[3.2 .1 ]octan-3-ol (IV) New final compounds: • 8-Methyl-3-(4-nitrophenoxy)-3-phenyl-8-azabicyclo [3.2.1] octane (Illa) • 3-{4'-Cyanophenoxy)-8-methyl-3-phenyl-8-azabicyclo [3.2.1] octane (lllb) • 8-Methyl-3-phenyl-3-{4-trifluoromethylphenoxy)- 8-azabicyclo (3. 2 .1] octane (Ille)