1004751-01-2Relevant academic research and scientific papers
Synthesis of caprazamycin analogues and their structure - Activity relationship for antibacterial activity
Hirano, Shinpei,Ichikawa, Satoshi,Matsuda, Akira
, p. 569 - 577 (2008/09/17)
(Chemical Equation Presented) 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′-β-O-aminoribosyl-glycyluridine derivative, installation of the palmitoyl side chain to the cyclization precursor, and the construction of the diazepanone by an intramolecular reductive animation. The second generation synthesis of (+)-caprazol was also established. Palmitoyl caprazol 7 exhibited antibacterial activity against Mycobacterium smegmatis ATCC607 (MIC = 6.25 μg/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 μg/mL).
