5497-12-1Relevant academic research and scientific papers
Discovery of +(2-{4-[2-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)ethoxy]phenyl}-cyclopropyl)acetic acid as potent and selective αvβ3 inhibitor: Design, synthesis, and optimization
Nagarajan, Srinivasan R.,Lu, Hwang-Fun,Gasiecki, Alan F.,Khanna, Ish K.,Parikh, Mihir D.,Desai, Bipinchandra N.,Rogers, Thomas E.,Clare, Michael,Chen, Barbara B.,Russell, Mark A.,Keene, Jeffery L.,Duffin, Tiffany,Engleman, V. Wayne,Finn, Mary B.,Freeman, Sandra K.,Klover, Jon A.,Nickols, G. Alan,Nickols, Maureen A.,Shannon, Kristen E.,Steininger, Christina A.,Westlin, William F.,Westlin, Marisa M.,Williams, Melanie L.
, p. 3390 - 3412 (2008/02/08)
The integrin αvβ3 is expressed in a number of cell types and is thought to play a major role in several pathological conditions. Various small molecules that inhibit the integrin have been shown to suppress tumor growth and retinal a
Enolate Ions as ss-Activators of ortho-metalation: Direct Synthesis of 3-Aminoindenones
Kayaleh, Nadim E.,Gupta, Ramesh C.,Johnson, Francis
, p. 4515 - 4522 (2007/10/03)
ss-Ketonitriles derived from a Claisen condensation of benzoate esters with alkyl- or phenylacetonitriles lead to 3-aminoindenones in the presence of excess LDA. This new reaction is also applicable to pyridine carboxylic esters. All of the 3-aminoindenones and their aza analogues can be hydrolyzed by acid to give the corresponding 1,3-indandiones. The mechanism of the reaction falls into the directed-ortho-metalation class in which the initial enolate ion of the keto-nitrile directs self-metalation at an ortho position. The new anion then cyclizes onto the nitrile group to generate an aminoindenone. Surprisingly the simplest member of the series, benzoylacetonitrile, does not undergo cyclization. Mechanistic isotope studies revealed that this substance preferentially and directly forms a dianion on the side chain, which is not further deprotonated at the ortho position of the aromatic ring.
