54557-00-5Relevant academic research and scientific papers
Palladium-Catalyzed Ylidyl-Carbonylation of Aryl Halides to Produce α-Acylphosphoranes
Guo, Xiaojun,Ma, Wei,Xue, Dong,Wang, Chao,Xiao, Jianliang
supporting information, p. 4824 - 4827 (2016/10/14)
An efficient synthesis of α-acylphosphoranes by palladium-catalyzed carbonylation of aryl iodides with carbon monoxide and stabilized phosphonium ylides has been developed. Featuring 44 examples, the protocol displayed a wide substrate scope under mild reaction conditions, showcasing its potential in synthetic organic chemistry.
Pyranone, thiopyranone, and pyridone inhibitors of phosphatidylinositol 3-kinase related kinases. Structure-activity relationships for DNA-dependent protein kinase inhibition, and identification of the first potent and selective inhibitor of the ataxia telangiectasia mutated kinase
Hollick, Jonathan J.,Rigoreau, Laurent J. M.,Cano-Soumillac, Celine,Cockcroft, Xiaoling,Curtin, Nicola J.,Frigerio, Mark,Golding, Bernard T.,Guiard, Sophie,Hardcastle, Ian R.,Hickson, Ian,Hummersone, Marc G.,Menear, Keith A.,Martin, Niall M. B.,Matthews, Ian,Newell, David R.,Ord, Rachel,Richardson, Caroline J.,Smith, Graeme C. M.,Griffin, Roger J.
, p. 1958 - 1972 (2008/02/02)
Structure-activity relationships have been investigated for inhibition of DNA-dependent protein kinase (DNA-PK) and ATM kinase by a series of pyran-2-ones, pyran-4-ones, thiopyran-4-ones, and pyridin-4-ones. A wide range of IC50 values were observed for pyranones and thiopyranones substituted at the 6-position, with the 3- and 5-positions proving intolerant to substitution. Related pyran-2-ones, pyran-4-ones, and thiopyran-4-ones showed similar IC50 values against DNA-PK, whereas the pyridin-4-one system proved, in general, ineffective at inhibiting DNA-PK. Extended libraries exploring the 6-position of 2-morpholinopyran-4-ones and 2-morpholino- thiopyrano-4-ones identified the first highly potent and selective ATM inhibitor 2-morpholin-4-yl-6-thianthren-1-yl-pyran-4-one (151C; ATM; IC50 = 13 nM) and revealed constrained SARs for ATM inhibition compared with DNA-PK. One of the most potent DNA-PK inhibitors identified, 2-(4-methoxyphenyl)-6- (morpholin-4-yl)pyran-4-one (16; DNA-PK; IC50 = 220 nM) effectively sensitized HeLa cells to the topoisomerase II inhibitor etoposide in vitro.
Selective Oxidation of Phosphorus Ylides by Dimethyldioxirane. Application to the Formation of Vicinal Tricarbonyls
Wasserman, Harry H.,Baldino, Carmen M.,Coats, Steven J.
, p. 8231 - 8235 (2007/10/03)
Dimethyldioxirane (DMD) has proven to be an effective reagent for the selective conversion of phosphoranylidene intermediates 4 to the corresponding vicinal tricarbonyls 5.Unlike existing oxidation protocols which employ relatively vigorous conditions, th
The Conversion of Carboxylic Acids to Keto Phosphorane Precursors of 1,2,3-Vicinal Tricarbonyl Compounds
Wasserman, Harry H.,Ennis, David S.,Blum, Charles A.,Rotello, Vincent M.
, p. 6003 - 6006 (2007/10/02)
Acyl phosphoranylidines react with acid chlorides or anhydrides in the presence of bis(trimethylsilyl)acetamide (BSA), or couple directly with carboxylic acids activated by EDCI to give keto phosphoranes 1.
