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1.
Bioorg Med Chem Lett ; 13(16): 2709-13, 2003 Aug 18.
Article in English | MEDLINE | ID: mdl-12873499

ABSTRACT

Structural modifications to the peptide deformylase inhibitor BB-3497 are described. In this paper, we describe the initial SAR around this lead for modifications to the methylene spacer and the P1' side chain. Enzyme inhibition and antibacterial activity data revealed that the optimum distance between the N-formyl hydroxylamine metal binding group and the P1' side chain is one unsubstituted methylene unit. Additionally, lipophilic P1' side chains that closely mimic the methionine residue in the substrate provided compounds with the best microbiological profile.


Subject(s)
Amidohydrolases/antagonists & inhibitors , Anti-Bacterial Agents/chemical synthesis , Hydroxamic Acids/chemistry , Methane/analogs & derivatives , Anti-Bacterial Agents/pharmacology , Enzyme Inhibitors/chemical synthesis , Enzyme Inhibitors/pharmacology , Hydrocarbons , Hydroxamic Acids/pharmacology , Hydroxylamine/chemistry , Inhibitory Concentration 50 , Metals/chemistry , Methane/chemistry , Microbial Sensitivity Tests , Molecular Mimicry , Oligopeptides/chemistry , Oligopeptides/pharmacology , Structure-Activity Relationship
2.
Bioorg Med Chem Lett ; 12(24): 3595-9, 2002 Dec 16.
Article in English | MEDLINE | ID: mdl-12443784

ABSTRACT

A series of analogues of the potent peptide deformylase (PDF) inhibitor BB-3497 containing alternative metal binding groups was synthesised. Enzyme inhibition and antibacterial activity data for these compounds revealed that the bidentate hydroxamic acid and N-formyl hydroxylamine structural motifs represent the optimum chelating groups on the pseudopeptidic BB-3497 backbone.


Subject(s)
Amidohydrolases , Aminopeptidases/antagonists & inhibitors , Hydroxamic Acids/chemical synthesis , Hydroxamic Acids/pharmacology , Metals/chemistry , Bacteria/drug effects , Binding Sites , Enzyme Inhibitors/chemical synthesis , Enzyme Inhibitors/pharmacology , Escherichia coli Proteins/antagonists & inhibitors , Inhibitory Concentration 50 , Microbial Sensitivity Tests , Structure-Activity Relationship
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