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 (IC50 100 nM).
MeSH terms
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AMP Deaminase / antagonists & inhibitors*
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Adenosine / analogs & derivatives
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Adenosine / chemistry
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Adenosine Triphosphate / metabolism
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Coformycin / analogs & derivatives
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Coformycin / chemistry
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Drug Design
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Drug Evaluation, Preclinical
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Enzyme Inhibitors / chemical synthesis
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Enzyme Inhibitors / chemistry*
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Enzyme Inhibitors / pharmacology*
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Formycins / chemistry*
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Formycins / pharmacology*
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Herbicides / chemistry*
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Herbicides / pharmacology
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Inhibitory Concentration 50
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Phosphorylation
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Purine Nucleosides / chemistry
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Purine Nucleosides / metabolism
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Ribonucleosides / chemistry
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Ribonucleosides / metabolism
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Structure-Activity Relationship
Substances
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Enzyme Inhibitors
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Formycins
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Herbicides
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Purine Nucleosides
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Ribonucleosides
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deamineformycin
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Coformycin
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aristeromycin
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Adenosine Triphosphate
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nebularine
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AMP Deaminase
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Adenosine