- Kinetic Resolution of 2-Substituted Indolines by N-Sulfonylation using an Atropisomeric 4-DMAP-N-oxide Organocatalyst
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The first catalytic kinetic resolution by N-sulfonylation is described. 2-Substituted indolines are resolved (s=2.6–19) using an atropisomeric 4-dimethylaminopyridine-N-oxide (4-DMAP-N-oxide) organocatalyst. Use of 2-isopropyl-4-nitrophenylsulfonyl chloride is critical to the stereodiscrimination and enables facile deprotection of the sulfonamide products with thioglycolic acid. A qualitative model that accounts for the stereodiscrimination is proposed.
- Murray, James I.,Flodén, Nils J.,Bauer, Adriano,Fessner, Nico D.,Dunklemann, Daniel L.,Bob-Egbe, Opetoritse,Rzepa, Henry S.,Bürgi, Thomas,Richardson, Jeffery,Spivey, Alan C.
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supporting information
p. 5760 - 5764
(2017/05/12)
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- Synthesis and pharmacological evaluation of peptide-mimetic protease-activated receptor-1 antagonists containing novel heterocyclic scaffolds
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Protease-activated receptor-1 (PAR-1) is a G-coupled receptor activated by α-thrombin and other proteases. In this paper we describe the synthesis and the pharmacological evaluation of novel peptide-mimetic antagonists (compounds 1-16) characterized by th
- Severino, Beatrice,Fiorino, Ferdinando,Perissutti, Elisa,Frecentese, Francesco,Cirino, Giuseppe,Roviezzo, Fiorentina,Santagada, Vincenzo,Caliendo, Giuseppe
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p. 6009 - 6020
(2008/12/21)
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- New nonsteroidal androgen receptor modulators based on 4-(trifluoromethyl)-2(1H)-pyrrolidino[3,2-g]quinolinone
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A series of 2(1H)-pyrrolidino[3,2-g]quinolinones was prepared and tested for the ability to modulate the transcriptional activity of the human androgen receptor (hAR). The parent compound, 4-(trifluoromethyl)-2(1H)-pyrrolidino[3,2-g]quinolinone, displayed moderate interaction with hAR, but more substituted analogues, particularly 6,7-disubstituted compounds, were potent hAR agonists in vitro.
- Edwards, James P.,West, Sarah J.,Pooley, Charlotte L. F.,Marschke, Keith B.,Farmer, Luc J.,Jones, Todd K.
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p. 745 - 750
(2007/10/03)
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