Derivatives of 2-arylcyclopropylamine: Synthesis and interactions with 5-HT1A receptors

Article abstract of DOI:10.1016/0960-894X(96)00045-5

A series of cis- and trans-derivatives of 2-aryl-N,N-dipropylcyclopropylamines and 1-(2-arylcyclopropyl)-N,N-dipropylmethylamines were synthesized and evaluated for affinity at the 5-HT_1A receptor. The key step in the syntheses was a cyclopropanation of cis- and trans-3-arylpropenoic esters with diazomethane which proceeds with retention of the stereochemistry. cis-1-[2-(3-Methoxyphenyl)cyclopropyl]-N,N-dipropylmethylamine (32) had the highest 5-HT_1A-receptor affinity (K_i= 58 nM) of the novel derivatives.