Synthesis and structure–activity relationships of thiotetronic acid analogues of thiolactomycin

• Published in: Bioorganic & medicinal chemistry letters Vol. 11; no. 20; pp. 2751 - 2754
• Main Authors: Sakya, Subas M, Suarez-Contreras, Melani, Dirlam, John P, O'Connell, Thomas N, Hayashi, Shigeru F, Santoro, Sheryl L, Kamicker, Barbara J, George, David M, Ziegler, Carl B
• Format: Journal Article
• Language: English
• Published: Oxford Elsevier Ltd 22.10.2001; Elsevier
• Subjects: Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antibacterial agents; Antibiotics. Antiinfectious agents. Antiparasitic agents; Biological and medical sciences; Medical sciences; Microbial Sensitivity Tests; Pharmacology. Drug treatments; Staphylococcus aureus - drug effects; Structure-Activity Relationship; Thiophenes - chemical synthesis; Thiophenes - chemistry; Thiophenes - pharmacology; Five membered ring; Thiolactone; Enol; In vitro; Pasteurella multocida; Pasteurellaceae; Lipophilic compound; Thiophene derivatives; Sulfur heterocycle; Side chain; Synthetic product; Structure activity relation; Bacteria; Micrococcales; Micrococcaceae; Antibacterial agent; Staphylococcus aureus; Hemisynthesis
• ISSN: 0960-894X; 1464-3405
• DOI: 10.1016/S0960-894X(01)00567-4

3-Acetyl analogues of thiolactomycin, a thiotetronic acid natural product, were synthesized and profiled against livestock pathogens. Some analogues showed improved activity over thiolactomycin against Staphylococcus aureus and comparable activity against Pasteurella multocida. Several semisynthetically modified analogues of thiolactomycin showed no improvement in activity over thiolactomycin. 3-Acetyl analogues of thiolactomycin, a thiotetronic acid natural product, were synthesized and profiled against livestock pathogens.