Cephalosporins. VII. Synthesis and antibacterial activity of new cephalosporins bearing a 2-imino-3-hydroxythiazoline (2-aminothiazole N-oxide) in the C-7 acylamino side chain.

Structure-guided optimisation of N-hydroxythiazole-derived inhibitors of factor inhibiting hypoxia-inducible factor-α

“…The FIH:Zn: N -hydroxythiazole complex structures also showed that N -hydroxythiazoles can bind to the active site metal of FIH in a bidentate manner through the exocyclic nitrogen atom and nucleophilic hydroxyl group of the N -hydroxythiazole unit. Although previous studies have demonstrated the promising biological activity of N -hydroxythiazole-derived compounds, in addition to PHD2 inhibition, 33 for example antibacterial properties 99 and inhibition of metallo-β-lactamases (MBLs), 81 their ability to bind metals in this manner had not yet been observed in crystallographic studies. It is likely that this metal coordination motif may be useful in the development of inhibitors for other metal-containing enzymes, including for 2OG oxygenases and beyond.…”

Easy access to the family of thiazole N-oxides using HOF·CH3CN

“…b-Lactam antibiotics, such as cephalosporins, bearing thiazole N-oxide derivatives, display unusual and effective antibacterial properties. 2 Thiazole N-oxide analogues of epothilones A and B serve as novel anticancer agents. 3 Recent studies on the design and synthesis of oligonucleotides containing thiazole N-oxide disclose that this functionality is unique in the sense of introducing a pronounced directional dipole into molecules that is capable of forming specific and strong hydrogen bonds.…”