Cyclic homopentapeptides 2. Synthetic modifications of viomycin

• Published in: Bioorganic & medicinal chemistry letters Vol. 7; no. 9; pp. 1145 - 1148
• Main Authors: Lyssikatos, J.P., Chang, S.-P., Clancy, J., Dirlam, J.P., Finegan, S.M., Girard, A.E., Hayashi, S.F., Larson, D.P., Lee, A.S., Linde, R.G., MacLelland, C.P., Petitpas, J.W., Seibel, S.B., Vu, C.B.
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 06.05.1997; Elsevier
• Subjects: Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Biological and medical sciences; Medical sciences; Pharmacology. Drug treatments; Cyclic peptides; Escherichia coli; Benzene derivatives; Guanidines; Organic carbamate; In vitro; Meticillin; Pasteurella multocida; Pasteurellaceae; Sulfur containing aminoacid; Resistance; Antibiotic; Chemical modification; Structure activity relation; Viomycin; Bacteria; Micrococcales; Ureas; Micrococcaceae; Antibacterial agent; Chemical synthesis; Pentapeptide; Staphylococcus aureus; Enterobacteriaceae
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(97)00187-X

This paper describes synthetic modifications of the C-19 position of tuberactinomycin B (viomycin) and related analogs. The in vitro antibacterial activity of selected analogs against Pasteurella multocida, Escherichia coli and methicillin-resistant Staphylococcus aureus is also discussed. Although C-19 arylation and thiolation did not improve antibacterial activity, C-19 benzyl carbamates, benzyl- and phenyl ureas were found to be more potent than the parent antibiotic. This paper describes synthetic modifications of the C-19 position of tuberatino-mycin B (viomycin) and related analogs. The in vitro antibacterial activity of selected analogs against Pasteurella multocida, Escherichia coli and methicillin-resistant Staphylococcus aureus is also discussed.