56979-61-4Relevant academic research and scientific papers
Reliable and versatile synthesis of 2-aryl-substituted cinnamic acid esters
Ianni, Alen,Waldvogel, Siegfried R.
, p. 2103 - 2112 (2008/02/02)
2-Aryl-substituted phosphono acetates can be readily synthesized by a four-step sequence from the respective arenes. Succeeding Horner-Wadsworth- Emmons olefinations provide stereoselectively the 2-aryl cinnamic acid esters even when sensitive moieties are involved. Georg Thieme Verlag Stuttgart.
Lipophilic versus hydrogen-bonding effect in P3 on potency and selectivity of valine aspartyl ketones as caspase 3 inhibitors
Mellon, Christophe,Aspiotis, Renee,Black, Cameron W.,Bayly, Christopher I.,Grimm, Erich L.,Giroux, Andre,Han, Yongxin,Isabel, Elise,McKay, Daniel J.,Nicholson, Donald W.,Rasper, Dita M.,Roy, Sophie,Tam, John,Thornberry, Nancy A.,Vaillancourt, John P.,Xanthoudakis, Steven,Zamboni, Robert
, p. 3886 - 3890 (2007/10/03)
Caspase 3 is a cysteinyl protease that mediates apoptotic cell death. Its inhibition may have an important impact in the treatment of several degenerative diseases. The P1 aspartic acid residue is a required element of recognition for this enzy
Ester Enolates from α-Acetoxy Esters. Synthesis of Aryl Malonic and α-Aryl Alkanoic Esters from Aryl Nucleophiles and α-Keto Esters
Ghosh, Subrata,Pardo, Simon N.,Salomon, Robert G.
, p. 4692 - 4702 (2007/10/02)
Ester enolates are generated by reductive α-deacetoxylation of α-acetoxy-α-arylmalonic esters or α-acetoxy-α-arylalkanoic esters with lithium in liquid ammonia or sodium α-(dimethylamino)naphthalenide in hexamethylphosphoramide-benzene.Since the requisite α-acetoxy esters are available from aryl nucleophiles, the reductions provide effective new synthetic routes to arylmalonic esters and α-arylalkanoic esters.For example, 2-(p-isobutylphenyl)propionic acid (ibuprofen, a commercially important nonsteroidal antiinflammatory agent) is obtained in 73percent yield overall from isobutylbenzene.Arenes, aryllithiums, or arylmagnesium halides react with α-keto esters, e.g., diethyl oxomalonate, ethyl pyruvate, methyl phenylglyoxalate, or alkyl glyoxylates, to afford α-hydroxy esters.These are acetylated with acetic anhydride-triethylamine and p-(dimethylamino)pyridine as a catalyst.Reductive α-deoxygenation then allows replacement of the acetoxy group by hydrogen or an alkyl group.
