154083-67-7Relevant academic research and scientific papers
Effect of Substituents and Stability of Transient Aluminum-Aminals in the Presence of Nucleophiles
Barrios, Francis J.,Springer, Brannon C.,Hazlitt, Robert A.,Colby, David A.
, p. 175 - 180 (2015/05/05)
Disubstituted hydroxylamines are synthesized and used to form aluminum-amide complexes. These reagents mask carbonyl groups in situ via nucleophilic addition. The stability and utility of the aluminum-aminals are presented in the context of selectively controlling nucleophilic addition on substrates with multiple carbonyl groups.
N-O chemistry for antibiotics: Discovery of N-alkyl-N-(pyridin-2-yl) hydroxylamine scaffolds as selective antibacterial agents using nitroso diels-alder and ene chemistry
Wencewicz, Timothy A.,Yang, Baiyuan,Rudloff, James R.,Oliver, Allen G.,Miller, Marvin J.
experimental part, p. 6843 - 6858 (2011/12/04)
The discovery, syntheses, and structure-activity relationships (SAR) of a new family of heterocyclic antibacterial compounds based on N-alkyl-N-(pyridin- 2-yl)hydroxylamine scaffolds are described. A structurally diverse library of ～100 heterocyclic molecules generated from Lewis acid-mediated nucleophilic ring-opening reactions with nitroso Diels-Alder cycloadducts and nitroso ene reactions with substituted alkenes was evaluated in whole cell antibacterial assays. Compounds containing the N-alkyl-N-(pyridin-2-yl)hydroxylamine structure demonstrated selective and potent antibacterial activity against the Gram-positive bacterium Micrococcus luteus ATCC 10240 (MIC90 = 2.0 μM or 0.41 μg/mL) and moderate activity against other Gram-positive strains including antibiotic resistant strains of Staphylococcus aureus (MRSA) and Enterococcus faecalis (VRE). A new synthetic route to the active core was developed using palladium-catalyzed Buchwald-Hartwig amination reactions of N-alkyl-O-(4-methoxybenzyl)hydroxylamines with 2-halo-pyridines that facilitated SAR studies and revealed the simplest active structural fragment. This work shows the value of using a combination of diversity-oriented synthesis (DOS) and parallel synthesis for identifying new antibacterial scaffolds.
Synthesis and antibacterial activity of cephalosporins having hydroxamic acid at C-7 position
Kim, Myoung Goo,Jung, Jae Chul,Sung, Moo Je,Choi, Young Key,An, Sang Geun,Lee, Se-Jong,Yoon, Geal-Jung,Park, Myung Hwan
, p. 2077 - 2080 (2007/10/03)
The synthesis and in vitro activity of cephalosporins with hydroxamic acid at the 7-position are described. Anti-pseudomonal activity of the compound 11a was shown to be comparable to that of ceftazidime. Especially, the compound 11a exhibited good activity against Gram-positive bacteria including Streptococcus pneumoniae and Staphylococcus aureus.
