Md. Ennis et al., 4-AMINOMETHYL CHROMANS - DEPENDENCE OF SEROTONIN AND DOPAMINE BINDINGUPON AROMATIC RING SUBSTITUTION, Bioorganic & medicinal chemistry letters, 3(6), 1993, pp. 1131-1136
The synthesis of two series of methoxy-substituted 4-aminomethyl chrom
ans is described. The formation of the pyran ring is achieved via an i
ntramolecular Friedel-Crafts reaction of the appropriate epoxide. Ther
e is a profound dependence between the position of the aromatic methox
y substituent and the binding affinity for the 5-HT1A and dopamine D-2
receptors.