71925-14-9Relevant articles and documents
Studies at the ionizable position of cephalosporins and penicillins: Hydroxamates as substitutes for the traditional carboxylate group
Majewski, Mark W.,Miller, Patricia A.,Miller, Marvin J.
, p. 292 - 296 (2017)
Classically, β-lactams need an ionizable group to potentiate antibacterial activity. Sets of cephalosporins and penicillins featuring different substituted hydroxamates in place of the traditional carboxylate group have been synthesized and tested for antibiotic activity. Many of the compounds exhibited anti-bacterial activities with notable MIC values in the range of 6-0.2 μM.
N-(Diethoxyphosphoryl)-O-benzylhydroxylamine - A convenient substrate for the synthesis of N-substituted O-benzylhydroxylamines
B?azewska, Katarzyna,Gajda, Tadeusz
, p. 10249 - 10254 (2007/10/03)
Easily available N-(diethoxyphosphoryl)-O-benzylhydroxylamine was shown to be convenient, orthogonally protected substrate for regioselective N-alkylation by means of diverse halides under basic conditions (sodium hydride/ tetrabutylammonium bromide). An
Artificial Siderophores. 1. Synthesis and Microbial Iron Transport Capabilities
Lee, Byung Hyun,Miller, Marvin J.,Prody, Catherine A.,Neilands, John B.
, p. 317 - 323 (2007/10/02)
Several di- and trihydroxamate analogues of natural microbial iron chelators have been prepared.The syntheses involved linkage of core structural units, including pyridinedicarboxylic acid, benzenetricarboxylic acid, nitrilotriacetic acid, and tricarballylic acid, by amide bonds to 1-amino-ω-(hydroxyamino)alkanes to provide the polyhydroxamates 1-5.The required protected (hydroxyamino)alkanes 8, 16, and 21 were prepared by different routes. 1-Amino-3-propane di-p-toluenesulfonate (8) was prepared from the N-protected aminopropanol 6 by oxidation to the aldehyde, formation of the substituted oxime, and reduction with NaBH3CN followed by deprotection of the Boc group.The pentyl derivatives 16 and 21 were made by direct alkylation with either benzyl acetohydroxamate or N-carbobenzoxy-O-benzylhydroxylamine.In Escherichia coli RW193 most of the analogues behaved nutritionally as ferrichrome.However, in E. coli AN193, a mutant lacking the ferrichrome receptor, capacity to use other natural siderophores was retained while response to all analogues was lost.