80936-65-8Relevant academic research and scientific papers
Design and synthesis of novel benzoxazole analogs as Aurora B kinase inhibitors
An, Ying,Lee, Eun,Yu, Yeongji,Yun, Jieun,Lee, Myeong Youl,Kang, Jong Soon,Kim, Woo-Young,Jeon, Raok
, p. 3067 - 3072 (2016)
A novel series of benzoxazole analogs was designed and synthesized, and their inhibitory activities against Aurora kinases were evaluated. Some of the tested compounds exhibited a promising activity with respect to the inhibition of Aurora B kinase. A structure-activity relationship study indicated that linker length, regiochemistry, and halogen substitution play important roles in kinase inhibitory potency. The binding modes between representative compounds and Aurora kinases were interpreted through a molecular docking study to explain the inhibitory activity and selectivity for Aurora A and B kinases. Compounds 13l and 13q also show an antiproliferative effect on the human tumor cell lines in a dose-dependent manner. The most potent 13q demonstrated good efficacy in the prostate cancer PC-3 tumor xenograft model.
A library approach to the development of BenzaPhos: Highly efficient chiral supramolecular ligands for asymmetric hydrogenation
Pignataro, Luca,Bovio, Chiara,Civera, Monica,Piarulli, Umberto,Gennari, Cesare
supporting information; experimental part, p. 10368 - 10381 (2012/10/08)
A library of chiral supramolecular ligands, named BenzaPhos, of straightforward preparation (two steps from commercially or readily available starting materials) and modular structure, was designed and synthesized. The ligands were screened in the search for new rhodium catalysts for the enantioselective hydrogenation of several benchmark and industrially relevant substrates. Once a series of hits were identified, structural modifications were introduced on three of the best ligands and a small second-generation library was created. Members of the latter library showed outstanding levels of activity and enantioselectivity in the hydrogenation of challenging olefins, such as enamide S4 and β-dehydroamino ester S5 (>99 % ee: best value ever reported in both cases). A series of control experiments were undertaken to clarify the role of hydrogen bonding in determining the catalytic properties of the new ligands. The results of these experiments, together with those of computational studies carried out on four dihydride complexes involved in the catalytic hydrogenation of substrate S4, strongly suggest that a substrate orientation takes place in the catalytic cycle by formation of a hydrogen bond between the ligand amide oxygen atom and the substrate amide NH atom. As simple as selective: BenzaPhos ligands, benzamide-containing chiral monophosphites of modular structure and trivial synthesis, have been screened in the Rh-catalyzed hydrogenation of olefins (see scheme), giving excellent enantioselectivities with three benchmark and two industrially relevant substrates. Control experiments and computational studies suggest an important role of ligand-substrate hydrogen bonding in the stereodiscriminating step of the catalytic cycle. Copyright
Irreversible Enzyme Inhibitors. 202. Candidate Active-Site-Directed Irreversible Inhibitors of 5-Fluoro-2'-deoxyuridine Phosphorylase from Walker 256 Rat Tumor Derived from 1-Benzyl-5-(3-ethoxybenzyl)uracil
Kelley, James L.,Baker, B. R.
, p. 600 - 603 (2007/10/02)
Six candidate irreversible inhibitors of uridine-deoxyuridine phosphorylase (EC 2.4.2.3) from Walker 256 rat tumor were synthesized.These compounds connect a terminal sulfonyl fluoride group to the 1-benzyl moiety of 1-benzyl-5-(3-ethoxybenzyl)uracil (9).
