153371-25-6Relevant articles and documents
Inhibitors of hepatitis C virus NS3·4A protease 2. Warhead SAR and optimization
Perni, Robert B.,Pitlik, Janos,Britt, Shawn D.,Court, John J.,Courtney, Lawrence F.,Deininger, David D.,Farmer, Luc J.,Gates, Cynthia A.,Harbeson, Scott L.,Levin, Rhonda B.,Lin, Chao,Lin, Kai,Moon, Young-Choon,Luong, Yu-Ping,O'Malley, Ethan T.,Rao, B. Govinda,Thomson, John A.,Tung, Roger D.,Van Drie, John H.,Wei, Yunyi
, p. 1441 - 1446 (2004)
The α-ketoamide warhead (e.g., 15) was found to be a practical replacement for aliphatic aldehydes in a series of HCV NS3·4A protease inhibitors. Structure-activity relationships and prime side optimization are discussed.
The synthesis of α,α-disubstituted α-amino acids via ichikawa rearrangement
Szczes?niak, Piotr,Pieczykolan, Micha?,Stecko, Sebastian
, p. 1057 - 1074 (2016/02/19)
An approach to α,α-disubstituted α-amino acids is reported. The key step is allyl cyanate-to-isocyanate rearrangement. As demonstrated, the resultant allyl isocyanates can be directly trapped with various nucleophiles, for instance, alcohols, amines, and organometallic reagents, to provide a broad range of N-functionalized allylamines. The developed method has been successfully applied in the synthesis of two bioactive peptides: 2-aminoadamantane-2-carboxylic acid derived P2X7-evoked glutamate release inhibitor and 4-amino-tetrahydropyranyl-4-carboxylic acid derived dipeptide GSK-2793660, which is currently in clinical trials as cathepsin C inhibitor for the treatment of cystic fibrosis, noncystic fibrosis bronchiectasis, ANCA-associated vasculitis and bronchiectasis.
Synthesis of proline analogues as potent and selective cathepsin S inhibitors
Kim, Mira,Jeon, Jiyoung,Song, Jiyeon,Suh, Kwee Hyun,Kim, Young Hoon,Min, Kyung Hoon,Lee, Kwang-Ok
, p. 3140 - 3144 (2013/06/26)
Cathepsin S is a potential target of autoimmune disease. A series of proline derived compounds were synthesized and evaluated as cathepsin S inhibitors. We discovered potent cathepsin S inhibitors through structure-activity relationship studies of proline analogues. In particular, compound 19-(S) showed promising in vitro/vivo pharmacological activities and properties as a selective cathepsin S inhibitor.