Synthesis of Pyranmycin Derivatives with N-1 and O-6 Modifications
Bioorganic & Medicinal Chemistry
Continuing from our ongoing effort in modifying aminoglycoside antibiotics with the goal of counteracting drug resistant bacteria, we have further derivatized pyranmycin, a neomycin class aminoglycoside antibiotic, with modifications at O-6 and N-1 positions. The revealed SAR results demonstrated that the antibacterial activity of pyranmycin can be modulated by different acylic substituents at O-6. Among these results, the 6-O-aminoethyl derivative, JT050, showed effective activity against resistant strain Escherichia coli (pTZ19U-3) and E. coli (pSF815), which provides insight into further structural modifications.
Li, J.; Wang, J.; Chiang, F.-I.; Chen, H.-N.; Chang, C.-W. T. “Synthesis of Pyranmycin Derivatives with N-1 and O-6 Modifications.” Bioorg. Med. Chem. 2007, 15, 7711-7719. PubMed PMID: 17870543; PubMed Central PMCID: PMC2692305.