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Volumn 2, Issue 3, 2011, Pages 224-229

Inhibitors of HCV NS5A: From iminothiazolidinones to symmetrical stilbenes

Author keywords

HCV NS5A inhibitor; iminothiazolidinone; stilbene

Indexed keywords

ALANINE; BMS 790052; BMS 824; BMS 858; DIMETHYL SULFOXIDE; NONSTRUCTURAL PROTEIN 5A; PROLINE; STILBENE; THIAZOLE DERIVATIVE; THIOHYDANTOIN DERIVATIVE; UNCLASSIFIED DRUG;

EID: 79952682354     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml1002647     Document Type: Article
Times cited : (83)

References (32)
  • 1
    • 0036815962 scopus 로고    scopus 로고
    • Global epidemiology and burden of hepatitis C
    • DOI 10.1016/S1286-4579(02)01649-0, PII S1286457902016490
    • Kim, W. R. Global Epidemiology and Burden of Hepatitis C Microbes Infection 2002, 4, 1219-1225 (Pubitemid 35435276)
    • (2002) Microbes and Infection , vol.4 , Issue.12 , pp. 1219-1225
    • Kim, W.R.1
  • 2
    • 33845449051 scopus 로고    scopus 로고
    • Peginterferon and ribavirin for chronic hepatitis C
    • DOI 10.1056/NEJMct061675
    • Hoofnagle, J. H.; Seeff, L. B. Peginterferon and Ribavirin for Chronic Hepatitis C N. Engl. J. Med. 2006, 355, 2444-2451 (Pubitemid 44903748)
    • (2006) New England Journal of Medicine , vol.355 , Issue.23 , pp. 2444-2451
    • Hoofnagle, J.H.1    Seeff, L.B.2
  • 3
    • 54349107459 scopus 로고    scopus 로고
    • Extended-Therapy Duration for Chronic Hepatitis C, Genotype 1: The Long and the Short of It
    • Pearlman, B. L. Extended-Therapy Duration for Chronic Hepatitis C, Genotype 1: The Long and the Short of It World J. Gastroenterol. 2008, 14, 3621-3627
    • (2008) World J. Gastroenterol. , vol.14 , pp. 3621-3627
    • Pearlman, B.L.1
  • 4
    • 23944482649 scopus 로고    scopus 로고
    • Challenges and successes in developing new therapies for hepatitis C
    • DOI 10.1038/nature04080
    • De Francesco, R.; Migliaccio, G. Challenges and Successes in Developing New Therapies for Hepatitis C Nature 2005, 436, 953-960 (Pubitemid 41191671)
    • (2005) Nature , vol.436 , Issue.7053 , pp. 953-960
    • De Francesco, R.1    Migliaccio, G.2
  • 6
    • 16244415844 scopus 로고    scopus 로고
    • Development of a cell-based high-throughput specificity screen using a hepatitis C virus-bovine viral diarrhea virus dual replicon assay
    • DOI 10.1128/AAC.49.4.1346-1353.2005
    • O'Boyle, D. R.; Nower, P. T.; Lemm, J. A.; Valera, L.; Sun, J.-H.; Rigat, K.; Colonno, R.; Gao, M. Development of a Cell-Based High-Throughput Specificity Screen Using a Hepatitis C Virus-Bovine Viral Diarrhea Virus Dual Replicon Assay Antimicrob. Agents Chemother. 2005, 49, 1346-1353 (Pubitemid 40463360)
    • (2005) Antimicrobial Agents and Chemotherapy , vol.49 , Issue.4 , pp. 1346-1353
    • O'Boyle II, D.R.1    Nower, P.T.2    Lemm, J.A.3    Valera, L.4    Sun, J.-H.5    Rigat, K.6    Colonno, R.7    Gao, M.8
  • 8
    • 34047228579 scopus 로고    scopus 로고
    • Axially chiral 2-arylimino-3-aryl-thiazolidine-4-one derivatives: Enantiomeric separation and determination of racemization barriers by chiral HPLC
    • DOI 10.1021/jo0625554
    • Erol, S.; Dogan, I. Axially Chiral 2-Arylimino-3-aryl-thiazolidine-4-one Derivatives: Enantiomeric Separation and Determination of Racemization Barriers by Chiral HPLC J. Org. Chem. 2007, 72, 2494-2500 (Pubitemid 46536180)
    • (2007) Journal of Organic Chemistry , vol.72 , Issue.7 , pp. 2494-2500
    • Erol, S.1    Dogan, I.2
  • 9
    • 0000966065 scopus 로고
    • Influence of Substituents on the Synthesis of Thiazolidinones
    • 781.
    • Garnaik, M. B. K.; Behera, R. Influence of Substituents on the Synthesis of Thiazolidinones. Indian J. Chem. 1987, 26B, 779 - 781.
    • (1987) Indian J. Chem. , vol.26 , pp. 779
    • Garnaik, M.B.K.1    Behera, R.2
  • 10
    • 1242316307 scopus 로고    scopus 로고
    • Regioselective Synthesis of 3-(Heteroaryl)-iminothiazolindin-4-ones
    • St. Laurent, D. R.; Gao, Q.; Wu, D.; Serrano-Wu, M. H. Regioselective Synthesis of 3-(Heteroaryl)-iminothiazolindin-4-ones Tetrahedron Lett. 2004, 45, 1907-1910
    • (2004) Tetrahedron Lett. , vol.45 , pp. 1907-1910
    • St. Laurent, D.R.1    Gao, Q.2    Wu, D.3    Serrano-Wu, M.H.4
  • 12
    • 34250189143 scopus 로고    scopus 로고
    • Discovery of a rhodanine class of compounds as inhibitors of Plasmodium falciparum enoyl-acyl carrier protein reductase
    • DOI 10.1021/jm061257w
    • Kumar, G.; Parasuraman, P.; Sharma, S. K.; Banerjee, T.; Karmodiya, K.; Surolia, N.; Surolia, A. Discovery of a Rhodanine Class of Compounds as Inhibitors of Plasmodium falciparum Enoyl-Acyl Carrier Protein Reductase J. Med. Chem. 2007, 50, 2665-2675 (Pubitemid 46896074)
    • (2007) Journal of Medicinal Chemistry , vol.50 , Issue.11 , pp. 2665-2675
    • Kumar, G.1    Parasuraman, P.2    Sharma, S.K.3    Banerjee, T.4    Karmodiya, K.5    Surolia, N.6    Surolia, A.7
  • 13
    • 79952666614 scopus 로고    scopus 로고
    • The diastereomers at the C-5 position of 2 were separated by chiral prep HPLC but observed to rapidly equilibrate due to facile keto-enol tautomerism (see Supporting Information for LC trace).
    • The diastereomers at the C-5 position of 2 were separated by chiral prep HPLC but observed to rapidly equilibrate due to facile keto-enol tautomerism (see Supporting Information for LC trace).
  • 14
    • 79952680950 scopus 로고    scopus 로고
    • Compounds 2 - 15 were prepared in library format using parallel synthesis methodology and subject to minimal purification. All compounds were of at least 70% purity, and MWs were confirmed by LCMS.
    • Compounds 2 - 15 were prepared in library format using parallel synthesis methodology and subject to minimal purification. All compounds were of at least 70% purity, and MWs were confirmed by LCMS.
  • 16
    • 79952644186 scopus 로고    scopus 로고
    • See Supporting Information for HPLC stability studies and experimental details. In DMSO, compounds 2 and 18 underwent complete conversion to 46 and 47, respectively. All compounds were dissolved and diluted in DMSO prior to evaluation in replicon and preincubation in media.
    • See Supporting Information for HPLC stability studies and experimental details. In DMSO, compounds 2 and 18 underwent complete conversion to 46 and 47, respectively. All compounds were dissolved and diluted in DMSO prior to evaluation in replicon and preincubation in media.
  • 20
    • 77953652929 scopus 로고    scopus 로고
    • Metal-Free, Aerobic Dioxygenation of Alkenes Using Hydroxamic Acids
    • Schmidt, V. A.; Alexanian, E. J. Metal-Free, Aerobic Dioxygenation of Alkenes Using Hydroxamic Acids Angew. Chem., Int. Ed. 2010, 49, 4491-4494
    • (2010) Angew. Chem., Int. Ed. , vol.49 , pp. 4491-4494
    • Schmidt, V.A.1    Alexanian, E.J.2
  • 21
    • 69949102328 scopus 로고    scopus 로고
    • Radicals in Organic Synthesis. Part 1
    • Rowlands, G. J. Radicals in Organic Synthesis. Part 1 Terahedron 2009, 65, 8603-8655
    • (2009) Terahedron , vol.65 , pp. 8603-8655
    • Rowlands, G.J.1
  • 22
    • 33751553881 scopus 로고
    • Manganese(III)-Based Oxidative Free-Radical Cyclization of Unsaturated β-Keto Esters, 1,3-Diketones, and Malonate Diesters
    • Kates, S. A.; Dombroski, M. A.; Snider, B. B. Manganese(III)-Based Oxidative Free-Radical Cyclization of Unsaturated β-Keto Esters, 1,3-Diketones, and Malonate Diesters J. Org. Chem. 1990, 55, 2427-2436
    • (1990) J. Org. Chem. , vol.55 , pp. 2427-2436
    • Kates, S.A.1    Dombroski, M.A.2    Snider, B.B.3
  • 23
    • 7044286458 scopus 로고    scopus 로고
    • Manganese(III)-based oxidative free-radical cyclizations
    • Snider, B. B. Manganese(III)-Based Oxidative Free-Radical Cyclizations Chem. Rev. 1996, 96, 339-363 (Pubitemid 126637724)
    • (1996) Chemical Reviews , vol.96 , Issue.1 , pp. 339-363
    • Snider, B.B.1
  • 24
    • 79952679269 scopus 로고    scopus 로고
    • Chemical shifts were consistent with the presence of an imine bond (not present in 51), while H-N long-range correlation indicated an amide nitrogen (see Supporting Information).
    • Chemical shifts were consistent with the presence of an imine bond (not present in 51), while H-N long-range correlation indicated an amide nitrogen (see Supporting Information).
  • 25
    • 79952651842 scopus 로고    scopus 로고
    • 50 = 2 nM. Dimer and acetates 52 and 53 were formed as single compounds with no evidence of diastereomers being formed (see Supporting Information).
    • 50 = 2 nM. Dimer and acetates 52 and 53 were formed as single compounds with no evidence of diastereomers being formed (see Supporting Information).
  • 26
    • 37049101309 scopus 로고
    • Oxidative Dehydrodimerization of N -Acyl α-Amino-acids: Synthesis of Novel Di-αα′-amino-acid Derivatives
    • For the radical dimerization process, see
    • For the radical dimerization process, see: Obata, N.; Niimura, K. Oxidative Dehydrodimerization of N -Acyl α-Amino-acids: Synthesis of Novel Di-αα′-amino-acid Derivatives Chem. Commun. 1977, 238-239
    • (1977) Chem. Commun. , pp. 238-239
    • Obata, N.1    Niimura, K.2
  • 27
    • 79952687354 scopus 로고    scopus 로고
    • Thiohydantoins hydrolyze under these conditions to the thioureas if not isolated promptly.
    • Thiohydantoins hydrolyze under these conditions to the thioureas if not isolated promptly.
  • 29
    • 79952657906 scopus 로고    scopus 로고
    • The alanine analogue of stilbene 55 proved to be too insoluble in DMSO to evaluate in the replicon assay.
    • The alanine analogue of stilbene 55 proved to be too insoluble in DMSO to evaluate in the replicon assay.
  • 30
    • 19644393931 scopus 로고    scopus 로고
    • Structure of the zinc-binding domain of an essential component of the hepatitis C virus replicase
    • DOI 10.1038/nature03580
    • Tellinghuisen, T. L.; Marcotrigiano, J.; Rice, C. M. Structure of the Zinc-Binding Domain of an Essential Component of the Hepatitis C Virus Replicase Nature 2005, 435, 374-379 (Pubitemid 40745549)
    • (2005) Nature , vol.435 , Issue.7040 , pp. 374-379
    • Tellinghuisen, T.L.1    Marcotrigiano, J.2    Rice, C.M.3
  • 31
    • 66149115122 scopus 로고    scopus 로고
    • Crystal Structure of a Novel Dimeric Form of NS5A Domain i Protein from Hepatitis C Virus
    • Love, R. A.; Brodsky, O.; Hickey, M. J.; Wells, P. A.; Cronin, C. N. Crystal Structure of a Novel Dimeric Form of NS5A Domain I Protein from Hepatitis C Virus J. Virol. 2009, 83, 4395-4403
    • (2009) J. Virol. , vol.83 , pp. 4395-4403
    • Love, R.A.1    Brodsky, O.2    Hickey, M.J.3    Wells, P.A.4    Cronin, C.N.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.