Synthesis and pharmacological evaluation of new (E)- and (Z)-3-aryl-4-styryl-1H-pyrazoles as potential cannabinoid ligands

Abstract

New (Z)- and (E)-1-alkyl-3-(2-hydroxyphenyl)-4-styryl-1H-pyrazoles and (Z)- and (E)-3(5)-(2-alkyloxyphenyl)-4-styryl-1H-pyrazoles were prepared by alkylation of (Z)- and (E)-3(5)-(2-hydroxyphenyl)-4-styryl-1H-pyrazoles with a long chain alkyl bromide in basic medium. The affinity of these alkylated pyrazoles to both human CB1 and CB2 type cannabinoid receptors was evaluated. The results showed that some of them exhibit affinity towards CB1 cannabinoid receptors in the nanomolar range. © ARKAT USA, Inc.