156300-02-6Relevant articles and documents
CARBOXY SUBSTITUTED CARBOXAMIDE DERIVATIVES AS TACHYKININ RECEPTOR ANTAGONISTS
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Page/Page column 19, (2010/02/10)
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Antagonists of the human CCR5 receptor as anti-HIV-1 agents. Part 1: Discovery and initial structure-activity relationships for 1-amino-2-phenyl-4-(piperidin-1-yl) butanes
Dorn, Conrad P.,Finke, Paul E.,Oates, Bryan,Budhu, Richard J.,Mills, Sander G.,MacCoss, Malcolm,Malkowitz, Lorraine,Springer, Martin S.,Daugherty, Bruce L.,Gould, Sandra L.,DeMartino, Julie A.,Siciliano, Salvatore J.,Carella, Anthony,Carver, Gwen,Holmes, Karen,Danzeisen, Renee,Hazuda, Daria,Kessler, Joseph,Lineberger, Janet,Miller, Michael,Schleif, William A.,Emini, Emilio A.
, p. 259 - 264 (2007/10/03)
Screening of the Merck sample collection for compounds with CCR5 receptor binding afforded (2S)-2-(3,4-dichlorophenyl)-1-[N-(methyl)-N-(phenylsulfonyl)amino]-4-[spiro(2 ,3-dihydrobenzthiophene-3,4′-piperidin-1′-yl)]butane S-oxide (4) as a potent lead structure having an IC50 binding affinity of 35 nM. Herein, we describe the discovery of this lead structure and our initial structure-activity relationship studies directed toward the requirement for and optimization of the 1-amino fragment.
Addition of transiently-generated methyl o-lithiobenzoate to imines. An isoindolone annulation
Campbell, James B.,Dedinas, Robert F.,Trumbower-Walsh, Sally A.
, p. 6205 - 6211 (2007/10/03)
Addition of phenyllithium to a mixture of an imine, methyl o-iodobenzoate, and BF3-etherate at -105°C gives good to excellent yields of isoindolones. The transient formation of methyl o-lithiobenzoate is proposed, which is formed by a rapid lithium/iodide exchange reaction of the phenyllithium with methyl o-iodobenzoate in the presence of the imine. The transiently generated anions can then be captured by the BF3-activated imines to form the isoindolones in good to high yield. The reactions conditions are sufficiently mild, and selective, to permit functional groups such carbmethoxy and aryl bromide, which could otherwise react with the added PhLi, to be tolerated.