Inhibitors of hepatitis C virus NS3·4A protease 1. Non-Charged tetrapeptide variants
The synthesis and structure–activity relationships of a novel series of reversible covalent inhibitors of the hepatitis C NS3·4A protease are described.
References (15)
- et al.
Hepatology
(2002)et al.Hepatology
(2002) - et al.
Biochemistry
(1998)et al.Biochemistry
(1998) - et al.
Bioorg. Med. Chem. Lett.
(2003) - et al.
J. Med. Chem.
(2000) - et al.
Angew. Chem. Int. Ed.
(2003)et al.J. Org. Chem.
(2001)et al.Bioorg. Med. Chem. Lett.
(2002) - et al.
Nature Rev.
(2002)et al.Hepatology
(2002) - et al.
Exp. Op. Inves. New Drugs
(2003)Perni, R. B.; Kwong, A. D. In Progress in Medicinal Chemistry, King F. D., Oxford, A. W., Eds. Elsevier Science B.V.:...
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