Aminoglycosides. V. Synthesis of glucopyranoside derivatives of neamine modified in the 2-deoxystreptamine ring.
trans-4-Aminocyclohexanol-2'-amino-alpha-D-glucopyranosides were prepared which are derivatives of neamine having the 3-amino and 5 and 6 hydroxyl groups of the 2-deoxystreptamine ring replaced with hydrogen. The 2'-amino-alpha-glycosides were synthesized by the method of LEMIEUX using a chloro nitroso dimer of a glucal and appropriately substituted cyclohexanols. Reductive deblocking of the intermediate 2-oximino derivatives afforded paromamine and neamine analogues. Two examples of 2'-amino-alpha-glycosides with ring-opened variations of the 2-deoxystreptamine aglycone are described. None of the compounds exhibited better in vitro antibacterial activity than neamine when compared against Gram-positive and Gram-negative bacteria.
D001419:Bacteria / Q000187:drug effects; D004352:Drug Resistance, Microbial; D009355:Neomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D013329:Structure-Activity Relationship
D009355:Neomycin