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

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 (IC50 100 nM).