90178-71-5Relevant articles and documents
Activity of diphenyl ether benzyl amines against Human African Trypanosomiasis
Anderson, Samuel,Belter, Bret,Cal, Monica,Darner, Grant,Davis, Paul H.,Hagen, James P.,Higgins, Katie,Kaiser, Marcel,Leas, Derek A.,Mashinson, Victoria,Mitra, Ananya,Vera-Esquivel, Carlos,Wallick, Alexander,Warner, Rosalie C.,Wol, Tasloach
, (2020/03/17)
Insect-borne parasite Trypanosoma brucei plagues humans and other animals, eliciting the disease Human African trypanosomiasis, also known as African sleeping sickness. This disease poses the biggest threat to the people in Sub-Saharan Africa. Given the high toxicity and difficulties with administration of currently available drugs, a novel treatment is needed. Building on known Human African trypanosomiasis structure–activity relationship (SAR), we now describe a number of functionally simple diphenyl ether analogs which give low micromolar activity (IC50 = 0.16–0.96 μM) against T. b. rhodesiense. The best compound shows favorable selectivity against the L6 cell line (SI = 750) and even greater selectivity (SI = 1200) against four human cell lines. The data herein provides direction for the ongoing optimization of antitrypanosomal diphenyl ethers.
4-(Phenoxy) and 4-(benzyloxy)benzamides as potent and selective inhibitors of mono-ADP-ribosyltransferase PARP10/ARTD10
Murthy, Sudarshan,Desantis, Jenny,Verheugd, Patricia,Maksimainen, Mirko M.,Venkannagari, Harikanth,Massari, Serena,Ashok, Yashwanth,Obaji, Ezeogo,Nkizinkinko, Yves,Lüscher, Bernhard,Tabarrini, Oriana,Lehti?, Lari
, p. 93 - 102 (2018/07/06)
Human Diphtheria toxin-like ADP-ribosyltranferases (ARTD) 10 is an enzyme carrying out mono-ADP-ribosylation of a range of cellular proteins and affecting their activities. It shuttles between cytoplasm and nucleus and influences signaling events in both compartments, such as nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) signaling and S phase DNA repair. Furthermore, overexpression of ARTD10 induces cell death. We recently reported on the discovery of a hit compound, OUL35 (compound 1), with 330 nM potency and remarkable selectivity towards ARTD10 over other enzymes in the human protein family. Here we aimed at establishing a structure-activity relationship of the OUL35 scaffold, by evaluating an array of 4-phenoxybenzamide derivatives. By exploring modifications on the linker between the aromatic rings, we identified also a 4-(benzyloxy)benzamide derivative, compound 32, which is potent (IC50 = 230 nM) and selective, and like OUL35 was able to rescue HeLa cells from ARTD10-induced cell death. Evaluation of an enlarged series of derivatives produced detailed knowledge on the structural requirements for ARTD10 inhibition and allowed the discovery of further tool compounds with submicromolar cellular potency that will help in understanding the roles of ARTD10 in biological systems.
Ligand-free copper-catalyzed coupling of phenols with nitroarenes by using a metal-organic framework as a robust and recoverable catalyst
Phan, Nam T. S.,Nguyen, Tung T.,Nguyen, Vu T.,Nguyen, Khoa D.
, p. 2374 - 2381 (2013/08/23)
A highly porous metal-organic framework Cu2(BDC)2(DABCO) (H2BDC=1,4-benzenedicarboxylic acid, DABCO=1,4-diazabicyclo[2.2.2]octane) was synthesized and used as an efficient recyclable heterogeneous catalyst for the coupling reaction of phenols with nitroarenes to form diaryl ethers without using a ligand. Physical characterization of the MOF was obtained by using XRD, SEM, TEM, thermogravimetric analysis (TGA), FTIR spectroscopy, atomic absorption spectrophotometry (AAS), H2 temperature-programmed reduction (H2-TPR), and N2 physisorption measurements. The Cu2(BDC)2(DABCO)-catalyzed coupling reaction offers several advantages compared to the conventional Ullmann reaction for the synthesis of unsymmetrical diaryl ethers. To the best of our knowledge, the ligand-free Cu-catalyzed O-arylation reaction of phenols with nitroarenes that uses a heterogeneous catalyst has not been mentioned previously in the literature.
