300832-84-2Relevant articles and documents
Sulfone-Mediated SNAr Reaction as a Powerful Tool for the Synthesis of 4-Quinolinyl Ethers and More-Application to the Synthesis of HCV NS3/4a Protease Inhibitor BI 201420
Patel, Nitinchandra D.,Wei, Xudong,Byrne, Denis,Narayanan, Bikshandarkoil A.,Pennino, Scott,Sarvestani, Max,Saha, Anjan,Haddad, Nizar,Kapadia, Suresh,Lorenz, Jon C.,Decroos, Philomen,Ye, Andrew,Lee, Heewon,Grinberg, Nelu,Hossain, Azad,Busacca, Carl A.,Yee, Nathan K.,Senanayake, Chris H.
, p. 8339 - 8351 (2020/07/16)
An efficient general methodology for the synthesis of 4-quinolinyl ethers is demonstrated via a highly reactive SNAr reaction of 4-quinolinyl sulfones with a range of structurally diversified 1°, 2°, and 3° alcohols with a wide substrate scope and high yields. By adapting this methodology, a convergent synthesis of a complex target of HCV NS3/4a protease inhibitor BI 201420 was accomplished.
Efficient large-scale synthesis of BILN 2061, a potent HCV protease inhibitor, by a convergent approach based on ring-closing metathesis
Yee, Nathan K.,Farina, Vittorio,Houpis, Ioannis N.,Haddad, Nizar,Frutos, Rogelio P.,Gallou, Fabrice,Wang, Xiao-Jun,Wei, Xudong,Simpson, Robert D.,Feng, Xuwu,Fuchs, Victor,Xu, Yibo,Tan, Jonathan,Zhang, Li,Xu, Jinghua,Smith-Keenan, Lana L.,Vitous, Jana,Ridges, Michael D.,Spinelli, Earl M.,Johnson, Michael,Donsbach, Kai,Nicola, Thomas,Brenner, Michael,Winter, Eric,Kreye, Paul,Samstag, Wendelin
, p. 7133 - 7145 (2007/10/03)
A multistep scalable synthesis of the clinically important hepatitis C virus (HCV) protease inhibitor BILN 2061 (1) is described. The synthesis is highly convergent and consists of two amide bond formations, one etherification, and one ring-closing metath
Structure-Activity Study on a Novel Series of Macrocyclic Inhibitors of the Hepatitis C Virus NS3 Protease Leading to the Discovery of BILN 2061
Llinàs-Brunet, Montse,Bailey, Murray D.,Bolger, Gordon,Brochu, Christian,Faucher, Anne-Marie,Ferland, Jean Marie,Garneau, Michel,Ghiro, Elise,Gorys, Vida,Grand-Ma?tre, Chantal,Halmos, Ted,Lapeyre-Paquette, Nicole,Liard, Francine,Poirier, Martin,Rhéaume, Manon,Tsantrizos, Youla S.,Lamarre, Daniel
, p. 1605 - 1608 (2007/10/03)
From the discovery of competitive hexapeptide inhibitors, potent and selective HCV NS3 protease macrocyclic inhibitors have been identified. Structure-activity relationship studies were performed focusing on optimizing the N-terminal carbamate and the aromatic substituent on the (4R) -hydroxyproline moiety. Inhibitors meeting the potency criteria in the cell-based assay and with improved oral bioavailability in rats were identified. BILN 2061 was selected as the best compound, the first NS3 protease inhibitor reported with antiviral activity in man.
