메뉴 건너뛰기




Volumn 53, Issue 8, 2010, Pages 3075-3085

Cyclic sulfones as novel P3-caps for hepatitis C virus NS3/4A (HCV NS3/4A) protease inhibitors: Synthesis and evaluation of inhibitors with improved potency and pharmacokinetic profiles

Author keywords

[No Author keywords available]

Indexed keywords

ANTIVIRUS AGENT; BETA METHYLCYCLOHEXYLGLYCINE; BOCEPREVIR; CYCLOHEXYLMETHYLUREA; CYCLOPROPANE DERIVATIVE; GLYCINE DERIVATIVE; N [1 [2 (CYCLOPROPYLAMINO) 1,2 DIOXOETHYL]BUTYL] 6,6 DIMETHYL 3 [2 (1 METHYLCYCLOHEXYL) 2 [[[[1 (TETRAHYDRO 1,1DIOXIDO 2 THIENYL)CYCLOHEXYL]AMINO]CARBONYL]AMINO]ACETYL] 3 AZABICYCLO[3.1.0]HEXANE 2 CARBOXAMIDE; N [1 [2 (CYCLOPROPYLAMINO) 1,2 DIOXOETHYL]PENTYL] 6,6 DIMETHYL 3 [2 (1 METHYLCYCLOHEXYL) 2 [[[[1 (TETRAHYDRO 1,1 DIOXIDO 2 THIENYL)CYCLOHEXYL]AMINO]CARBONYL]AMINO]ACETYL] 3 AZABICYCLO[3.1.0]HEXANE 2 CARBOXAMIDE; NONSTRUCTURAL PROTEIN 3; NONSTRUCTURAL PROTEIN 4A; PROTEINASE INHIBITOR; SULFONE DERIVATIVE; TERT BUTYLUREA; UNCLASSIFIED DRUG; UREA DERIVATIVE; VIRUS PROTEIN;

EID: 77951143463     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm9016027     Document Type: Article
Times cited : (54)

References (30)
  • 1
    • 1642288430 scopus 로고    scopus 로고
    • World Health Organization (WHO) (revised October)
    • World Health Organization (WHO). Hepatitis C. Fact Sheet No. 164. http://www.who.int/mediacentre/factsheets/fs164/en/ (revised October 2000).
    • (2000) Hepatitis C. Fact Sheet No. 164
  • 2
    • 0033916804 scopus 로고    scopus 로고
    • Epidemiology of hepatitis C: Geographic differences and temporal trends
    • Wasley, A.; Alter, M. J. Epidemiology of hepatitis C: geographic differences and temporal trends Semin. Liver Dis. 2000, 20, 1-16
    • (2000) Semin. Liver Dis. , vol.20 , pp. 1-16
    • Wasley, A.1    Alter, M.J.2
  • 3
    • 0242456086 scopus 로고    scopus 로고
    • Scope of worldwide hepatitis C problem
    • Brown, R. S., Jr.; Gaglio, P. J. Scope of worldwide hepatitis C problem Liver Transpl. 2003, 9, S10-S13
    • (2003) Liver Transpl. , vol.9
    • Brown Jr., R.S.1    Gaglio, P.J.2
  • 6
    • 0024509701 scopus 로고
    • Isolation of a cDNA clone derived from a blood-borne non-A, non-B viral hepatitis genome
    • Choo, Q. L.; Kuo, G.; Weiner, A. J.; Overby, L. R.; Bradley, D. W.; Houghton, M. Isolation of a cDNA clone derived from a blood-borne non-A, non-B viral hepatitis genome Science 1989, 244, 359-362
    • (1989) Science , vol.244 , pp. 359-362
    • Choo, Q.L.1    Kuo, G.2    Weiner, A.J.3    Overby, L.R.4    Bradley, D.W.5    Houghton, M.6
  • 7
    • 23944476834 scopus 로고    scopus 로고
    • Unraveling hepatitis C virus replication from genome to function
    • Lindenbach, B. D.; Rice, C. M. Unraveling hepatitis C virus replication from genome to function Nature 2005, 436, 933-938
    • (2005) Nature , vol.436 , pp. 933-938
    • Lindenbach, B.D.1    Rice, C.M.2
  • 8
    • 0027287798 scopus 로고
    • Nonstructural protein 3 of the hepatitis C virus encodes a serine-type proteinase required for cleavage at the NS3/4 and NS4/5 junctions
    • Bartenschlager, R.; Ahlborn-Laake, L.; Mous, J.; Jacobsen, H. Nonstructural protein 3 of the hepatitis C virus encodes a serine-type proteinase required for cleavage at the NS3/4 and NS4/5 junctions J. Virol. 1993, 67, 3835-3844
    • (1993) J. Virol. , vol.67 , pp. 3835-3844
    • Bartenschlager, R.1    Ahlborn-Laake, L.2    Mous, J.3    Jacobsen, H.4
  • 23
    • 77951143476 scopus 로고    scopus 로고
    • Unless otherwise indicated, the following parameters were used for rat PK evaluations: rats were orally administered at a dose of 10 mg/kg in 0.4% methylcellulose in water. Blood samples were withdrawn periodically and pooled. AUC was calculated over 0-6 h
    • Unless otherwise indicated, the following parameters were used for rat PK evaluations: rats were orally administered at a dose of 10 mg/kg in 0.4% methylcellulose in water. Blood samples were withdrawn periodically and pooled. AUC was calculated over 0-6 h.
  • 24
    • 33644785717 scopus 로고    scopus 로고
    • Stereoselective synthesis of β-substituted β-amino sulfones and sulfonamides via addition of sulfonyl anions to chiral N -sulfinyl imines
    • Velázquez, F.; Arasappan, A.; Chen, K.; Sannigrahi, M.; Venkatraman, S.; McPhail, A. T.; Chan, T.-M.; Shih, N.-Y.; Njoroge, F. G. Stereoselective synthesis of β-substituted β-amino sulfones and sulfonamides via addition of sulfonyl anions to chiral N -sulfinyl imines Org. Lett. 2006, 8, 789-792
    • (2006) Org. Lett. , vol.8 , pp. 789-792
    • Velázquez, F.1    Arasappan, A.2    Chen, K.3    Sannigrahi, M.4    Venkatraman, S.5    McPhail, A.T.6    Chan, T.-M.7    Shih, N.-Y.8    Njoroge, F.G.9
  • 25
    • 0033582571 scopus 로고    scopus 로고
    • Synthesis of enantiomerically pure N - Tert -butanesulfinyl imines (tert -butanesulfinimines) by the direct condensation of tert -butanesulfinamide with aldehydes and ketones
    • Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. Synthesis of enantiomerically pure N-tert -butanesulfinyl imines (tert -butanesulfinimines) by the direct condensation of tert -butanesulfinamide with aldehydes and ketones J. Org. Chem. 1999, 64, 1278-1284
    • (1999) J. Org. Chem. , vol.64 , pp. 1278-1284
    • Liu, G.1    Cogan, D.A.2    Owens, T.D.3    Tang, T.P.4    Ellman, J.A.5
  • 26
    • 77951124013 scopus 로고    scopus 로고
    • Crystal structure of compound 19 has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 763018
    • Crystal structure of compound 19 has been deposited at the Cambridge Crystallographic Data Centre and allocated the deposition number CCDC 763018.
  • 27
    • 77951130169 scopus 로고    scopus 로고
    • On the basis of our previous experience in the development of 1, we decided to use enantiomerically pure P1-groups in all target compounds presented herein to avoid problems associated with handling diastereomeric mixtures
    • On the basis of our previous experience in the development of 1, we decided to use enantiomerically pure P1-groups in all target compounds presented herein to avoid problems associated with handling diastereomeric mixtures.
  • 28
    • 77951137834 scopus 로고    scopus 로고
    • To perform a thorough SAR investigation, selected five- and six-membered analogues having the S -configuration in the cyclic sulfone moiety were prepared for potency and PK comparison. The data collected always favored the analogues having R -configuration in the cyclic sulfone moiety
    • To perform a thorough SAR investigation, selected five- and six-membered analogues having the S -configuration in the cyclic sulfone moiety were prepared for potency and PK comparison. The data collected always favored the analogues having R -configuration in the cyclic sulfone moiety.
  • 29
    • 33747031401 scopus 로고    scopus 로고
    • Rapid in vivo oral screening in rats: Reliability, acceptance criteria, and filtering efficiency
    • Mei, H; Korfmacher, W; Morrison, R. Rapid in vivo oral screening in rats: reliability, acceptance criteria, and filtering efficiency AAPS J. 2006, 8 (3) E493-E500
    • (2006) AAPS J. , vol.8 , Issue.3
    • Mei, H.1    Korfmacher, W.2    Morrison, R.3
  • 30
    • 34547652788 scopus 로고    scopus 로고
    • Practical and efficient method for amino acid derivatives containing β-quaternary center: Application toward synthesis of hepatitis C virus NS3 serine protease inhibitors
    • Arasappan, A.; Venkatraman, S.; Padilla, A. I.; Wu, W.; Meng, T.; Jin, Y.; Wong, J.; Prongay, A.; Girijavallabhan, V.; Njoroge, F. G. Practical and efficient method for amino acid derivatives containing β-quaternary center: application toward synthesis of hepatitis C virus NS3 serine protease inhibitors Tetrahedron Lett. 2007, 48, 6343-6347
    • (2007) Tetrahedron Lett. , vol.48 , pp. 6343-6347
    • Arasappan, A.1    Venkatraman, S.2    Padilla, A.I.3    Wu, W.4    Meng, T.5    Jin, Y.6    Wong, J.7    Prongay, A.8    Girijavallabhan, V.9    Njoroge, F.G.10


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.