6639-35-6Relevant academic research and scientific papers
α-Amino Diphenyl Phosphonates as Novel Inhibitors of Escherichia coli ClpP Protease
Moreno-Cinos, Carlos,Sassetti, Elisa,Salado, Irene G.,Witt, Gesa,Benramdane, Siham,Reinhardt, Laura,Cruz, Cristina D.,Joossens, Jurgen,Van Der Veken, Pieter,Br?tz-Oesterhelt, Heike,Tammela, P?ivi,Winterhalter, Mathias,Gribbon, Philip,Windshügel, Bj?rn,Augustyns, Koen
supporting information, p. 774 - 797 (2019/01/30)
Increased Gram-negative bacteria resistance to antibiotics is becoming a global problem, and new classes of antibiotics with novel mechanisms of action are required. The caseinolytic protease subunit P (ClpP) is a serine protease conserved among bacteria that is considered as an interesting drug target. ClpP function is involved in protein turnover and homeostasis, stress response, and virulence among other processes. The focus of this study was to identify new inhibitors of Escherichia coli ClpP and to understand their mode of action. A focused library of serine protease inhibitors based on diaryl phosphonate warheads was tested for ClpP inhibition, and a chemical exploration around the hit compounds was conducted. Altogether, 14 new potent inhibitors of E. coli ClpP were identified. Compounds 85 and 92 emerged as most interesting compounds from this study due to their potency and, respectively, to its moderate but consistent antibacterial properties as well as the favorable cytotoxicity profile.
The Nitration of α- and β-Acylnaphthalenes
Barker, Steven D.,Wilson, Karen,Norris, Robert K.
, p. 1969 - 1980 (2007/10/02)
The nitration of α- and β-acylnaphthalenes with copper(II) nitrate in acetic anhydride or nitric acid/acetic acid mixtures gives high yields of the corresponding mononitro compounds.The assignment of constitution to these products is made on the basis of extensive 1H n.m.r. chemical shift and coupling constant data.In the case of α-acylnaphthalenes, with the notable exception of α-pivalonaphthone, nitration occurs in the α-positions of the unsubstituted ring to give mixtures of 5- and 8-nitro compounds. α-Pivalonaphthone gives appreciable amounts of the 4-nitro compound and also of the 8-nitro compound.This result indicates that the pivaloyl group does not shield the 8-position sterically to any significant extent and is effectively electronically neutral, unlike the other acyl substituents, in allowing attack at the α-position (position 4) of the acylated ring.This result is ascribable to the lack of coplanarity of the pivaloyl group with the naphthalene system.All of the β-acylnaphthalenes gave mixtures of 4-, 5- and 8-nitro derivatives in proportions that did not vary significantly with the nature of the acyl group.
