414863-57-3Relevant academic research and scientific papers
Identification of chemokine receptor CCR4 antagonist
Purandare, Ashok V.,Gao, Aiming,Wan, Honghe,Somerville, John,Burke, Christine,Seachord, Carrie,Vaccaro, Wayne,Wityak, John,Poss, Michael A.
, p. 2669 - 2672 (2007/10/03)
The present study reports the identification and hits to leads optimization of chemokine receptor CCR4 antagonists. Compound 12 is a high affinity, non-cytotoxic antagonist of CCR4 that blocks the functional activity mediated by the receptor.
Preparation and resolution of a modular class of axially chiral quinazoline-containing ligands and their application in asymmetric rhodium-catalyzed olefin hydroboration
Connolly, David J.,Lacey, Patrick M.,McCarthy, Mary,Saunders, Cormac P.,Carroll, Anne-Marie,Goddard, Richard,Guiry, Patrick J.
, p. 6572 - 6589 (2007/10/03)
The preparation and resolution of a series of axially chiral quinazoline-containing ligands is described in which the key steps are the metal-catalyzed naphthyl-phosphorus bond formation, the naphthalene-quinazoline Suzuki coupling, and the preparation of the Suzuki electrophilic components from the corresponding imidate and anthranilic acid. Diastereomeric palladacycles derived from the racemic phosphinamines and (+)-di-μ-chlorobis[(R)- dimethyl(1-(1-naphthyl)ethyl)-aminato-C2,N]dipalladium(II) were separated by fractional crystallization. The configuration of the resulting diastereomers was determined by X-ray crystallographic analysis. Displacement of the resolving agent by reaction with 1,2-bis(diphenylphosphino)ethane afforded enantiopure ligand in each case. Their rhodium complexes were prepared and applied in the enantioselective hydroboration of a range of vinylarenes. The quinazolinap catalysts were found to be extremely active, giving excellent conversions, good to complete regioselectivities, and the highest enantioselectivities obtained to date for several members of the vinylarene class, including cis-β-methylstyrene (97%), cis-stilbene (99%), and indene (99.5%).
A facile and versatile route to 2-substituted-4(3H)-quinazolinones and quinazolines
Connolly,Guiry
, p. 1707 - 1710 (2007/10/03)
A range of 2-aryl and 2-alkyl quinazolinones have been prepared in moderate to good yields from the reaction of anthranilic acid and the appropriately substituted imidate in a facile, mild, onepot procedure. Subsequent reaction with phosphorus oxychloride afforded the corresponding 4-chloro-2-substituted quinazolines, which are useful synthetic intermediates, in good to high yields. Product isolation was facilitated by the development of work up procedures for both reactions that did not include purification by column chromatography.
