Novel Peptide Mimetics Based on N-protected Amino Acids Derived from Isomannide as Potential Inhibitors of NS3 Serine Protease of Hepatitis C Virus

Author(s): Thalita G. Barros, Bruna C. Zorzanelli, Sergio Pinheiro, Monique A. de Brito, Amilcar Tanuri, Emmerson C.B. da Costa, Ronaldo S. Mohana-Borges, Carlos R. Rodrigues, Alessandra T.M. Souza, Vitor F. Ferreira, Estela M.F. Muri.

Journal Name: Letters in Organic Chemistry

Volume 9 , Issue 4 , 2012

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Abstract:

Hepatitis C virus (HCV) is among the most important flaviviruses. It has a serine protease which is important for viral replication and this enzyme constitutes a suitable target for new anti-retroviral drugs. Herein we disclose a series of amide and ester peptide mimetic inhibitors of serine proteases, all of them obtained via coupling reactions of isomannide derivatives with N-protected amino acids. The arginine derivative 19 showed 45% of inhibition of NS3/4A serine protease at 100 μM and molecular modeling studies had shown that 19 interacted with the active site of this enzyme.

Keywords: HCV, isomannide, peptide mimetic, serine protease, hepatocellular carcinoma, structural manipulation, bioavailability, administration, dipeptides, scaffold

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Article Details

VOLUME: 9
ISSUE: 4
Year: 2012
Page: [239 - 249]
Pages: 11
DOI: 10.2174/157017812800233787

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