Semi-synthesis of antibacterial dialkylresorcinol derivatives

• Published in: Journal of antibiotics Vol. 74; no. 1; pp. 70 - 75
• Main Authors: Li, Jianye, Shi, Yue, Clark, Benjamin R.
• Format: Journal Article
• Language: English
• Published: London Nature Publishing Group UK 01-01-2021; Nature Publishing Group
• Subjects: 101/58; 631/326/22/1290; 631/92/613; 639/638/309/2144; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Antimicrobial agents; Bacteria - drug effects; Bacteria - ultrastructure; Bacteriology; Biomedical and Life Sciences; Bioorganic Chemistry; Drug Design; Life Sciences; Medicinal Chemistry; Microbial Sensitivity Tests; Microbiology; Molecular Structure; Organic Chemistry; Phenols; Resorcinols - chemical synthesis; Resorcinols - chemistry; Resorcinols - pharmacology
• ISSN: 0021-8820; 1881-1469
• DOI: 10.1038/s41429-020-0359-5

Dialkylresorcinols are a class of antimicrobial natural products produced by a range of bacterial species. Semi-synthetic derivatization of two microbial dialkylresorcinols isolated from a
Pseudomonas aurantiaca
strain has yielded 21 derivatives, which were tested for antimicrobial activity, revealing several trends in their activity. The presence of aromatic and phenolic hydrogen atoms was crucial for activity, with all derivatives lacking these features possessing greatly reduced activity. On the other hand, derivatives with shorter alkyl chains at C-5 possessed lower MIC values, while one mono-fluorosulfated derivative showed significantly improved activity against several of the test strains.