SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF JUVENOIDS DERIVED FROM 2-(4-HYDROXYBENZYL)CYCLOALKAN-1-ONES

Juvenoids 16-30, 32, 36, 38-41, 44-46, and 49-56 containing carbamate, carbonate, and urea moieties in the molecule were synthesized and subjected to a biological screening (Schemes 2-7, Table 2). Carbamate juvenoids 1-4 were used as reference compounds for a derailed structure-activity study of their analogues. A clear relationship between the nature of the side chain functional group and the biological activity was found. Surprisingly, not only the juvenoids 1-4 but also 38-41, the compounds with a reversed carabamate N,O-substitution pattern, showed very promising biological activity. In contrast, the carbonate and urea derivatives displayed a remarkably low activity. The relationship between the size and substitution at atoms C(2) and C(3) of the saturated ring and the biological activity is very complex and is still not completely understood.