Abstract
The synthesis and pharmacological evaluation of cis- and trans-6-amino-6,7,8,9-tetrahydro-5 H-benzocyclohepten-5-ols 4a– c and 5a– c and cis- and trans-4-amino-2,3,4,5-tetrahydro-1-benzoxepin-5-ols 4d– f and 5d– f were carried out. Chemo- and stereoselective synthesis of 5a– f was achieved by reduction of corresponding α-amino ketones 3a– f with LiAl( t-BuO) 3H. cis-4-Amino-2,3,4,5-tetrahydro-1-benzoxepin-5-ol 4d and trans-4-amino-2,3,4,5-tetrahydro-1-benzoxepin-5-ol 5d exhibited marked anorexigenic activity in mice at a dose of LD 50 800 and 500 mg/kg and ED 50 75 and 55 mg/kg, respectively, while the analog cis-2,3-dihydroxy-6-amino-6,7,8,9-tetrahydro-5 H-benzocyclohepten-5-ol 8 showed typical α-sympathomimetic activity.
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