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  • Title: Synthesis of caprazamycin analogues and their structure--activity relationship for antibacterial activity.
    Author: Hirano S, Ichikawa S, Matsuda A.
    Journal: J Org Chem; 2008 Jan 18; 73(2):569-77. PubMed ID: 18092805.
    Abstract:
    Synthesis of palmitoyl caprazol 7, which possesses a simple fatty acyl side chain at the 3' ''-position of the diazepanone moiety, was carried out and their antibacterial activity was evaluated. The key elements of our approach include the improved synthesis of the key 5'-beta-O-aminoribosyl-glycyluridine derivative, installation of the palmitoyl side chain to the cyclization precursor, and the construction of the diazepanone by an intramolecular reductive amination. The second generation synthesis of (+)-caprazol was also established. Palmitoyl caprazol 7 exhibited antibacterial activity against Mycobacterium smegmatis ATCC607 (MIC = 6.25 microg/mL) with potency similar to that of the caprazamycins (CPZs). Palmitoyl caprazol 7 and N6'-desmethyl palmitoyl caprazol 28 also exhibited antibacterial activity against drug-resistant bacteria including methyciline-resistant Staphylococcus aureus (MRSA) and vancomycin-resistant Enterococcus (VRE) strains (MIC = 3.13-12.5 microg/mL).
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