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Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from th

Benzyl derivatives with in vitro binding affinity for human opioid and cannabinoid receptors from th

  1. Porvata
    Gao J, León F, Radwan MM, Dale OR, Husni AS, Manly SP, Lupien S, Wang X, Hill RA, Dugan FM, Cutler HG, Cutler SJ.
    Department of Medicinal Chemistry, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.


    Bioassay-guided fractionation of the fungus Eurotium repens resulted in the isolation of two new benzyl derivatives, (E)-2-(hept-1-enyl)-3-(hydroxymethyl)-5-(3-methylbut-2-enyl)benzene-1,4-diol (1) and (E)-4-(hept-1-enyl)-7-(3-methylbut-2-enyl)-2,3-dihydrobenzofuran-2,5-diol (2), along with seven known compounds (3-9) including five benzaldehyde compounds, flavoglaucin (3), tetrahydroauroglaucin (4), dihydroauroglaucin (5), auroglaucin (6), and 2-(2',3-epoxy-1',3'- heptadienyl)-6-hydroxy-5-(3-methyl-2-butenyl)benzaldehyde (7), one diketopiperazine alkaloid, echinulin (8), and 5,7-dihydroxy-4-methylphthalide (9). The chemical structures of these compounds were established on the basis of extensive 1D and 2D NMR and HRMS data. Compounds 1-4 and 6 showed good binding affinity for human opioid or cannabinoid receptors. These findings have important implications for psychoactive studies with this class of compounds.