570419-61-3Relevant academic research and scientific papers
Superacid-catalyzed intramolecular cyclization reaction of arylcyanopropionate: Geminal substitution effect on superelectrophilicity
Nakamura, Satoshi,Sugimoto, Hiromichi,Ohwada, Tomohiko
, p. 4219 - 4224 (2008/09/20)
(Chemical Equation Presented) We present superacid-catalyzed intramolecular cyclization reactions of arylcyanopropionates to give cyclized five- and six-membered β-enamino esters in moderate to high yields. Known intramolecular ring-closing reactions of protonated nitrile to aromatic carbon atom are limited to the 6-membered case. Interestingly, a significant synergistic increase of reactivity of the cyano functionality was observed, and the cyano nitrogen atom was converted into an amino group, when an ester group was present in a geminal arrangement. Deuterium exchange experiments excluded the involvement of deprotonation of the α-proton in the cyclization process. The acidity dependence of the cyclization reactions and 13C NMR studies of a model compound, methyl cyanoacetate, in various acidic media were consistent with the involvement of the O,N-diprotonated dication of methyl cyanoacetate, a distonic dication, in strong acid, and this is considered to be the de facto electrophile in the present cyclization reaction of arylcyanopropionates.
Discovery of a novel class of 2-ureido thiophene carboxamide checkpoint kinase inhibitors
Janetka, James W.,Almeida, Lynsie,Ashwell, Susan,Brassil, Patrick J.,Daly, Kevin,Deng, Chun,Gero, Thomas,Glynn, Roberta E.,Horn, Candice L.,Ioannidis, Stephanos,Lyne, Paul,Newcombe, Nicholas J.,Oza, Vibha B.,Pass, Martin,Springer, Stephanie K.,Su, Mei,Toader, Dorin,Vasbinder, Melissa M.,Yu, Dingwei,Yu, Yan,Zabludoff, Sonya D.
body text, p. 4242 - 4248 (2009/04/10)
Checkpoint kinase-1 (Chk1, CHEK1) is a Ser/Thr protein kinase that mediates the cellular response to DNA-damage. A novel class of 2-ureido thiophene carboxamide urea (TCU) Chk1 inhibitors is described. Inhibitors in this chemotype were optimized for cellular potency and selectivity over Cdk1.
