5745-75-5Relevant articles and documents
Allylic C-H acetoxylation with a 4,5-diazafluorenone-ligated palladium catalyst: A ligand-based strategy to achieve aerobic catalytic turnover
Campbell, Alison N.,White, Paul B.,Guzei, Ilia A.,Stahl, Shannon S.
supporting information; experimental part, p. 15116 - 15119 (2011/01/06)
Pd-catalyzed C-H oxidation reactions often require the use of oxidants other than O2. Here we demonstrate a ligand-based strategy to replace benzoquinone with O2 as the stoichiometric oxidant in Pd-catalyzed allylic C-H acetoxylation. Use of 4,5-diazafluorenone (1) as an ancillary ligand for Pd(OAc)2 enables terminal alkenes to be converted to linear allylic acetoxylation products in good yields and selectivity under 1 atm O 2. Mechanistic studies have revealed that 1 facilitates C-O reductive elimination from a π-allyl-PdII intermediate, thereby eliminating the requirement for benzoquinone in this key catalytic step.
αvβ3 integrin-targeting Arg-Gly-Asp (RGD) peptidomimetics containing oligoethylene glycol (OEG) spacers
Rerat, Vincent,Dive, Georges,Cordi, Alex A.,Tucker, Gordon C.,Bareille, Reine,Amédée, Jo?lle,Bordenave, Laurence,Marchand-Brynaert, Jacqueline
supporting information; experimental part, p. 7029 - 7043 (2010/07/05)
RGD peptides are used in biomaterials science for surface modifications with a view to elicit selective cellular responses. Our objective is to replace peptides by small peptidomimetics acting similarly. We designed novel molecules targeting αvβ3 integrin and featuring spacer-arms (for surface grafting), which do not disturb the biological activity, from (L) N-(3-(trifluoromethyl)benzenesulfonyl) tyrosine used as scaffold. Various Arg-mimics were fixed on the phenol function, and the ortho position was used for the coupling of OEG spacers. All peptidomimetics were active in the nM range in a binding test toward human αvβ 3 integrin (IC50 = 0.1 to 1.7 nM) and selective versus platelet integrin αIIbβ3. Selected compounds revealed excellent ability to inhibit bone cells adhesion on vitronectin. Modeling and docking studies were performed for comparing the most active RGD peptidomimetic to cilengitide, i.e., cyclo-[RGDfN(Me)V]-. Lastly, the adhesion of endothelial cells on a cultivation support grafted with RGD peptidomimetics was significantly improved. 2009 American Chemical Society.
The DDQ mediated cyclization products of some 2-hydroxy-3(1′-alkenyl)-1,4-naphthoquinones
Ameer, Farouk,Giles, Robin G.F.,Green, Ivan R.,Nagabhushana, Kyatanahalli S.
, p. 369 - 380 (2007/10/03)
The DDQ mediated cyclisation products derived from 2-hydroxy-3-(1′-alkenyl)-1,4-napthoquinones viz. 17 were found to be temperature dependent. At 60°C the naphthofuranquinone 19 was the predominant isomer whereas at 8°C the naphthopyranquinone 18 was exclusively formed.