The design and synthesis of inhibitors of adenosine 5′-monophosphate deaminase

Abstract

Carbocylic coformycin ( 4) is a potent herbicide whose primary mode of action involves inhibition of adenosine 5′-monophosphate deaminase (AMPDA) following phosphorylation of the 5′-hydroxyl group in vivo. The search for more stable and accessible structures led to the synthesis of carbocyclic nebularine ( 8) and deaminoformycin ( 10). The latter compound is a good herbicide and its corresponding 5′-monophosphate 14 is a strong inhibitor of plant AMPDA (IC 50 100 nM).