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

Carbocylic coformycin (4) is a potent herbicide whose primary mode of actio n involves inhibition of adenosine 5'-monophosphate deaminase (AMPDA) follo wing phosphorylation of the 5'-hydroxyl group in vivo. The search for more stable and accessible structures led to the synthesis of carbocyclic nebula rine (8) and deaminoformycin (10). The latter compound is a good herbicide and its corresponding 5'-monophosphate 14 is a strong inhibitor of plant AM PDA (IC50 100 nM). (C) 1999 Elsevier Science Ltd. All rights reserved.