title: Application of ring-closing metathesis for the synthesis of macrocyclic peptidomimetics as inhibitors of HCV NS3 protease.
abstract: An efficient synthetic approach for the preparation of macrocyclic peptidomimetics for inhibition of HCV NS3 is presented. The macrocyclic core is built using ring-closing metathesis (RCM) of a tripeptidic diene. The presented approach allows the introduction of heteroatoms in strategic places along the macrocyclic ring. The methyl ester moiety in the RCM products was synthetically manipulated to install a keto-amide moiety via a Passerini reaction.
authors.affiliation: Schering-Plough Research Institute, 2015 Galloping Hill Road, K-15-3 3545, Kenilworth, New Jersey 07033-1300, USA. francisco.velazquez@spcorp.com
authors.forename: Francisco
authors.initials: F
authors.lastname: Velázquez
authors.forename: Srikanth
authors.initials: S
authors.lastname: Venkatraman
authors.forename: Wanli
authors.initials: W
authors.lastname: Wu
authors.forename: Melissa
authors.initials: M
authors.lastname: Blackman
authors.forename: Andrew
authors.initials: A
authors.lastname: Prongay
authors.forename: Viyyoor
authors.initials: V
authors.lastname: Girijavallabhan
authors.forename: Neng-Yang
authors.initials: NY
authors.lastname: Shih
authors.forename: F George
authors.initials: FG
authors.lastname: Njoroge
mesh_terms: D002384:Catalysis; D003500:Cyclization; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D016174:Hepacivirus / Q000201:enzymology*; D018716:Molecular Mimicry; D015394:Molecular Structure; D010455:Peptides / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
chemical_list: D004791:Enzyme Inhibitors; D010455:Peptides; D011758:Pyrroles