메뉴 건너뛰기




Volumn 49, Issue 9, 2006, Pages 2750-2757

Discovery of SCH446211 (SCH6): A new ketoamide inhibitor of the HCV NS3 serine protease and HCV subgenomic RNA replication

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIMETHYLETHYL [1 [[2 [[[1 [2 [[2 [[2 (DIMETHYLAMINO) 2 OXO 1 PHENYLETHYL]AMINO] 2 OXOETHYL]AMINO] 1,2 DIOXOETHYL] 4,4,4 TRIFLUOROBUTYL]AMINO]CARBONYL] 6,6 DIMETHYL 3 AZABICYCLO[3.1.0]HEXAN 3 YL]CARBONYL] 2,2 DIMETHYLPROPYL]CARBAMATE; ANTIVIRUS AGENT; INTERFERON REGULATORY FACTOR 3; KETOAMIDE INHIBITOR; NONSTRUCTURAL PROTEIN 3; NONSTRUCTURAL PROTEIN 3 INHIBITOR; PROLINE DERIVATIVE; SCH 446211; SCH 6; SERINE PROTEINASE INHIBITOR; UNCLASSIFIED DRUG; VIRUS RNA;

EID: 33646449468     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm060077j     Document Type: Article
Times cited : (58)

References (32)
  • 1
    • 0033516384 scopus 로고    scopus 로고
    • The scientific challenge of Hepatitis C
    • (a) Cohen, J. The Scientific Challenge of Hepatitis C. Science 1999, 285, 26-30.
    • (1999) Science , vol.285 , pp. 26-30
    • Cohen, J.1
  • 3
    • 0027942956 scopus 로고
    • Hepatitis C: Progress and problems
    • (c) Cuthbert, J. A. Hepatitis C: Progress and Problems. Clin. Microbiol. Rev. 1994, 7, 505-532. 0
    • (1994) Clin. Microbiol. Rev. , vol.7 , pp. 505-532
    • Cuthbert, J.A.1
  • 4
    • 0037315296 scopus 로고    scopus 로고
    • Recent developments in the discovery of hepatitis C virus serine protease inhibitors-towards a new class of antiviral agents
    • Narjes, F.; Koch, U.; Steinküler, C. Recent developments in the discovery of hepatitis C virus serine protease inhibitors-towards a new class of antiviral agents. Expert Opin. Investig. Drugs 2003, 12, 153-16
    • (2003) Expert Opin. Investig. Drugs , vol.12 , pp. 153-216
    • Narjes, F.1    Koch, U.2    Steinküler, C.3
  • 5
    • 0033920304 scopus 로고    scopus 로고
    • Hepatitis C virus-encoded enzymatic activities and conserved RNA elements in the 3′ nontranslated region are essential for virus replication in vivo
    • (a) Kolykhalov, A. A.; Mihalik, K.; Feinstone, S. M.; Rice, C. M. Hepatitis C virus-encoded enzymatic activities and conserved RNA elements in the 3′ nontranslated region are essential for virus replication in vivo. J. Virol. 2000, 74, 2046-2051.
    • (2000) J. Virol. , vol.74 , pp. 2046-2051
    • Kolykhalov, A.A.1    Mihalik, K.2    Feinstone, S.M.3    Rice, C.M.4
  • 6
    • 0033920795 scopus 로고    scopus 로고
    • Replication of hepatitis C virus
    • (b) Bartenschlager, R.; Lohmann, V. Replication of hepatitis C virus. J. Gen. Virol. 2000, 81, 1631-48.
    • (2000) J. Gen. Virol. , vol.81 , pp. 1631-1648
    • Bartenschlager, R.1    Lohmann, V.2
  • 7
    • 0034940307 scopus 로고    scopus 로고
    • Hepatitis C virus serine protease inhibitors: Current progress and future challenges
    • (a) Steinkuhler, C.; Koch, U.; Narjes, F.; Matassa, V. G. Hepatitis C virus serine protease inhibitors: current progress and future challenges. Curr. Med. Chem. 2001, 8, 919-932.
    • (2001) Curr. Med. Chem. , vol.8 , pp. 919-932
    • Steinkuhler, C.1    Koch, U.2    Narjes, F.3    Matassa, V.G.4
  • 11
    • 7044269387 scopus 로고    scopus 로고
    • Novel 2-oxoimidazolidine-4-carboxylic acid derivatives as Hepatitis C virus NS3-4A serine protease inhibitors: Synthesis, activity, and X-ray crystal structure of an enzyme inhibitor complex
    • Arasappan, A.; Njoroge, F. G.; Parekh, T. N.; Yang, X.; Pichardo, J.; Butkiewicz, N.; Prongay, A.; Yao, N.; Girijavallabhan, V. Novel 2-oxoimidazolidine-4-carboxylic acid derivatives as Hepatitis C virus NS3-4A serine protease inhibitors: synthesis, activity, and X-ray crystal structure of an enzyme inhibitor complex. Bioorg. Med. Chem. Lett. 2004, 14, 5751-5755
    • (2004) Bioorg. Med. Chem. Lett. , vol.14 , pp. 5751-5755
    • Arasappan, A.1    Njoroge, F.G.2    Parekh, T.N.3    Yang, X.4    Pichardo, J.5    Butkiewicz, N.6    Prongay, A.7    Yao, N.8    Girijavallabhan, V.9
  • 13
    • 0034678789 scopus 로고    scopus 로고
    • α-keto amides, a-keto esters, and α-diketones as HCV NS3 protease inhibitors
    • (b) Han, W.; Hu, Z.; Jiang, X.; Decicco, C. P. α-Keto amides, a-keto esters, and α-diketones as HCV NS3 protease inhibitors. Bioorg. Med. Chem. Lett. 2000, 10, 711-713.
    • (2000) Bioorg. Med. Chem. Lett. , vol.10 , pp. 711-713
    • Han, W.1    Hu, Z.2    Jiang, X.3    Decicco, C.P.4
  • 16
    • 26444615182 scopus 로고    scopus 로고
    • Design, synthesis and biological activity of m-Tyrosine-Based 16- And 17-Membered macrocyclic inhibitors of hepatitis C virus NS3 serine protease
    • Boc-protected α-hydroxyacid were prepared via modification of the following procedures. (a) Chen, K.; Njoroge, F. G.; Pichardo, J.; Prongay, A.; Butkiewicz, N.; Yao, N.; Madison, V.; Girijavallabhan, V. Design, Synthesis and Biological Activity of m-Tyrosine-Based 16- and 17-Membered Macrocyclic Inhibitors of Hepatitis C Virus NS3 Serine Protease. J. Med. Chem. 2005, 48, 6229-6235.
    • (2005) J. Med. Chem. , vol.48 , pp. 6229-6235
    • Chen, K.1    Njoroge, F.G.2    Pichardo, J.3    Prongay, A.4    Butkiewicz, N.5    Yao, N.6    Madison, V.7    Girijavallabhan, V.8
  • 17
    • 33646450491 scopus 로고    scopus 로고
    • Process and intermediates for the preparation of 3-amino-3- (cyclobutylmethyl)-2-hydroxypropionamide or its salts. WO 2004113272
    • (b) Chen, M.; Green, M. D.; Zhang, F. Process and intermediates for the preparation of 3-amino-3-(cyclobutylmethyl)-2-hydroxypropionamide or its salts. WO 2004113272.
    • Chen, M.1    Green, M.D.2    Zhang, F.3
  • 18
    • 0038288730 scopus 로고    scopus 로고
    • Asymmetric hydrogenations for the synthesis of boc-protected 4-alkylprolinols and prolines
    • (a) Del Valle, J. R.; Goodman, M. Asymmetric Hydrogenations for the Synthesis of Boc-Protected 4-Alkylprolinols and Prolines. J. Org. Chem. 2003, 68, 3923-3931.
    • (2003) J. Org. Chem. , vol.68 , pp. 3923-3931
    • Del Valle, J.R.1    Goodman, M.2
  • 21
    • 3142712837 scopus 로고    scopus 로고
    • Carboxy mediated stereoselective reduction of ketones with sodium triacetoxyborohydride: Synthesis of novel 3,4-fused tetrahydropyran and tetrahydrofuran prolines
    • (d) Liu, Y. T.; Wong, J. K.; Tao, M.; Osterman, R.; Sannigrahi, M.; Girijavallabhan, V. M.; Saksena, A. Carboxy mediated stereoselective reduction of ketones with sodium triacetoxyborohydride: synthesis of novel 3,4-fused tetrahydropyran and tetrahydrofuran prolines. Tetrahedron Lett. 2004, 45, 6097-6100.
    • (2004) Tetrahedron Lett. , vol.45 , pp. 6097-6100
    • Liu, Y.T.1    Wong, J.K.2    Tao, M.3    Osterman, R.4    Sannigrahi, M.5    Girijavallabhan, V.M.6    Saksena, A.7
  • 22
    • 0037842854 scopus 로고    scopus 로고
    • [3+2] Cycloaddition of trimethylenemethane (TMM) to α,β- unsaturated γ-lactam. Preparation of 5,5-fused proline surrogates
    • (e) Jao, E.; Bogen, S.; Saksena, A. K.; Girijavallabhan, V. [3+2] Cycloaddition of trimethylenemethane (TMM) to α,β-unsaturated γ-lactam. Preparation of 5,5-fused proline surrogates. Tetrahedron Lett. 2003, 44, 5033-5035.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 5033-5035
    • Jao, E.1    Bogen, S.2    Saksena, A.K.3    Girijavallabhan, V.4
  • 23
    • 0033593515 scopus 로고    scopus 로고
    • Cyclopropanation reactions of pyroglutamic acid-derived synthons with alkylidene transfer Reagents
    • (f) Zhang, R.; Mamai, A.; Madalengoitia, J. S. Cyclopropanation Reactions of Pyroglutamic Acid-Derived Synthons with Alkylidene Transfer Reagents. J. Org. Chem. 1999, 64, 547-555.
    • (1999) J. Org. Chem. , vol.64 , pp. 547-555
    • Zhang, R.1    Mamai, A.2    Madalengoitia, J.S.3
  • 24
    • 3042741556 scopus 로고
    • A useful triacetoxyperiodinane for the selective oxidation of primary or secondary alcohols and a variety of related species
    • Dess, D. B.; Martin, J. C. A Useful Triacetoxyperiodinane for the Selective Oxidation of Primary or Secondary Alcohols and a Variety of Related Species. J. Am. Chem. Soc. 1991, 113, 7277-7287.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 7277-7287
    • Dess, D.B.1    Martin, J.C.2
  • 25
    • 33947481504 scopus 로고
    • New and selective oxidation of alcohols
    • Pfitzner, K. E.; Moffatt, J. G. New and selective oxidation of alcohols. J. Am. Chem. Soc. 1963, 85, 3027-3028.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 3027-3028
    • Pfitzner, K.E.1    Moffatt, J.G.2
  • 26
    • 0033151691 scopus 로고    scopus 로고
    • A continuous spectrophotometric assay for the hepatitis C virus serine protease
    • Zhang, R.; Beyer, B. M.; Durkin, J.; Ingram, R.; Njoroge, F. G.; Windsor, W. T.; Malcolm, B. A. A Continuous Spectrophotometric Assay for the Hepatitis C Virus Serine Protease. Anal. Biochem. 1999, 270, 268-275. The substrate Ac-DTEDVVP(Nva)-O-PAP was used in the present study.
    • (1999) Anal. Biochem. , vol.270 , pp. 268-275
    • Zhang, R.1    Beyer, B.M.2    Durkin, J.3    Ingram, R.4    Njoroge, F.G.5    Windsor, W.T.6    Malcolm, B.A.7
  • 29
    • 0035951555 scopus 로고    scopus 로고
    • Poly-L-proline type II peptide mimics based on the 3-Azabicyclo[3.1.0]- hexane system
    • Mamai, A.; Zhang, R.; Natarajan, A.; Madalengoitia, J. S. Poly-L-proline Type II Peptide Mimics Based on the 3-Azabicyclo[3.1.0]-hexane System. J. Org. Chem. 2001, 66, 455-460.
    • (2001) J. Org. Chem. , vol.66 , pp. 455-460
    • Mamai, A.1    Zhang, R.2    Natarajan, A.3    Madalengoitia, J.S.4
  • 32
    • 0037687422 scopus 로고    scopus 로고
    • Regulation of interferon regulatory factor-3 by the hepatitis C virus serine protease
    • Foy, E.; Li, K.; Wang, C.; Sumpter, R., Jr.; Ikeda, M.; Lemon, S. M.; Gale, M. J. Regulation of Interferon Regulatory Factor-3 by the Hepatitis C Virus Serine Protease. Science 2003, 300, 1145-1148.
    • (2003) Science , vol.300 , pp. 1145-1148
    • Foy, E.1    Li, K.2    Wang, C.3    Sumpter Jr., R.4    Ikeda, M.5    Lemon, S.M.6    Gale, M.J.7


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.