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 sub jected to a biological screening (Schemes 2-7, Table 2). Carbamate juv enoids 1-4 were used as reference compounds for a derailed structure-a ctivity study of their analogues. A clear relationship between the nat ure of the side chain functional group and the biological activity was found. Surprisingly, not only the juvenoids 1-4 but also 38-41, the c ompounds with a reversed carabamate N,O-substitution pattern, showed v ery promising biological activity. In contrast, the carbonate and urea derivatives displayed a remarkably low activity. The relationship bet ween 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 com pletely understood.