메뉴 건너뛰기




Volumn 56, Issue 17, 2013, Pages 6792-6802

Highly potent HIV-1 protease inhibitors with novel tricyclic P2 ligands: Design, synthesis, and protein-ligand X-ray studies

Author keywords

[No Author keywords available]

Indexed keywords

2,3,3A,6,7,8A HEXAHYDROFURO[2,3 B]BENZOFURAN 4(5H) ONE; 2,3,3A,8A TETRAHYDRO 5H FURO[2,3 B]THIOPYRANO[4,3 D]FURAN 4(7H) ONE 6,6 DIOXIDE; 3,3A,7,8A TETRAHYDRO 2H FURO[3',2':4,5]FURO[2,3 C]PYRAN 4(5H) ONE; 4 DIAZO 2H PYRAN 3,5(4H,6H) DIONE; 4 DIAZO 2H THIOPYRAN 3,5(4H,6H) DIONE 1,1 DIOXIDE; 4 HYDROXYOCTAHYDRO 5H FURO[2,3 B]THIOPYRANO[4,3 D]FURAN 6,6 DIOXIDE; 6,6 DIMETHYL 3,3A,5,6,7,8A DECAHYDROFURO[2,3 B]BENZOFURAN 4(2H) ONE; 6,6 DIMETHYLDECAHYDROFURO[2,3 B]BENZOFURAN 4 YL(4 NITROPHENYL)CARBONATE; 6,6 DIMETHYLOCTAHYDROFURO[2,3 B]BENZOFURAN 4(2H) OL; DECAHYDRO 2H PYRANO[2,3 B]BENZOFURAN 5 YL (NITROPHENYL)CARBONATE; DECAHYDROFURO[2,3 B]BENZOFURAN 4 OL; DECAHYDROFURO[2,3 B]BENZOFURAN 4 YL CARBONATE; DECAHYDROFURO[2,3 B]BENZOFURAN 4 YL(4 NITROPHENYL)CARBONATE; HUMAN IMMUNODEFICIENCY VIRUS 1 PROTEINASE INHIBITOR; HUMAN IMMUNODEFICIENCY VIRUS PROTEINASE INHIBITOR; OCTAHYDRO 2H FURO[3',2':4,5]FURO[2,3 C]PYRAN 4 OL; OCTAHYDRO 2H PYRANO[2,3 B]BENZOFURAN 5(3H) OL; UNCLASSIFIED DRUG;

EID: 84884259096     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400768f     Document Type: Article
Times cited : (42)

References (40)
  • 1
    • 62749131195 scopus 로고    scopus 로고
    • U.K. Demonstration of Sustained Drug-Resistant Human Immunodeficiency Virus Type 1 Lineages Circulating among Treatment-Naïve Individuals
    • Hue, S.; Gifford, R. J.; Dunn, D.; Fernhill, E.; Pillay, D. U.K. Demonstration of Sustained Drug-Resistant Human Immunodeficiency Virus Type 1 Lineages Circulating among Treatment-Naïve Individuals J. Virol. 2009, 83, 2645-2654
    • (2009) J. Virol. , vol.83 , pp. 2645-2654
    • Hue, S.1    Gifford, R.J.2    Dunn, D.3    Fernhill, E.4    Pillay, D.5
  • 2
    • 70349209354 scopus 로고    scopus 로고
    • HAART in Treatment-Experienced Patients in the 21st Century: The Audacity of Hope
    • Conway, B. HAART in Treatment-Experienced Patients in the 21st Century: The Audacity of Hope Future Virol. 2009, 4, 39-41
    • (2009) Future Virol. , vol.4 , pp. 39-41
    • Conway, B.1
  • 4
    • 35348829315 scopus 로고    scopus 로고
    • Darunavir, a Conceptually New HIV-1 Protease Inhibitor for the Treatment of Drug-Resistant HIV
    • Ghosh, A. K.; Dawson, Z. L.; Mitsuya, H. Darunavir, a Conceptually New HIV-1 Protease Inhibitor for the Treatment of Drug-Resistant HIV Bioorg. Med. Chem. 2007, 15, 7576-7580
    • (2007) Bioorg. Med. Chem. , vol.15 , pp. 7576-7580
    • Ghosh, A.K.1    Dawson, Z.L.2    Mitsuya, H.3
  • 5
    • 38949203748 scopus 로고    scopus 로고
    • Design of HIV Protease Inhibitors Targeting Protein Backbone: An Effective Strategy for Combating Drug Resistance
    • Ghosh, A. K.; Chapsal, B. D.; Weber, I. T.; Mitsuya, H. Design of HIV Protease Inhibitors Targeting Protein Backbone: An Effective Strategy for Combating Drug Resistance Acc. Chem. Res. 2008, 41, 78-86
    • (2008) Acc. Chem. Res. , vol.41 , pp. 78-86
    • Ghosh, A.K.1    Chapsal, B.D.2    Weber, I.T.3    Mitsuya, H.4
  • 6
    • 33749008221 scopus 로고    scopus 로고
    • Bis-Tetrahydrofuran: A Privileged Ligand for Darunavir and a New Generation of HIV Protease Inhibitors That Combat Drug Resistance
    • Ghosh, A. K.; Sridhar, P. R.; Kumaragurubaran, N.; Koh, Y.; Weber, I. T.; Mitsuya, H. Bis-Tetrahydrofuran: A Privileged Ligand for Darunavir and a New Generation of HIV Protease Inhibitors That Combat Drug Resistance ChemMedChem. 2006, 1, 939-950
    • (2006) ChemMedChem. , vol.1 , pp. 939-950
    • Ghosh, A.K.1    Sridhar, P.R.2    Kumaragurubaran, N.3    Koh, Y.4    Weber, I.T.5    Mitsuya, H.6
  • 8
    • 84873893231 scopus 로고    scopus 로고
    • Novel P2 Tris-Tetrahydrofuran Group in Antiviral Compound 1 (GRL-0519) Fills the S2 Binding Pocket of Selected Mutants of HIV-1 Protease
    • Zhang, H.; Wang, Y. F.; Shen, C.-H.; Agniswamy, J.; Rao, K. V.; Xu, X.; Ghosh, A. K.; Harrison, R. W.; Weber, I. T. Novel P2 Tris-Tetrahydrofuran Group in Antiviral Compound 1 (GRL-0519) Fills the S2 Binding Pocket of Selected Mutants of HIV-1 Protease J. Med. Chem. 2013, 56, 1074-1083
    • (2013) J. Med. Chem. , vol.56 , pp. 1074-1083
    • Zhang, H.1    Wang, Y.F.2    Shen, C.-H.3    Agniswamy, J.4    Rao, K.V.5    Xu, X.6    Ghosh, A.K.7    Harrison, R.W.8    Weber, I.T.9
  • 9
    • 84876207904 scopus 로고    scopus 로고
    • GRL-0519, a Novel Oxatricyclic Ligand-Containing Nonpeptidic HIV-1 Protease Inhibitor (PI), Potently Suppresses Replication of a Wide Spectrum of Multi-PI-Resistant HIV-1 Variants in Vitro
    • Amano, M.; Tojo, Y.; Salcedo-Gómez, P. M.; Campbell, J. R.; Das, D.; Aoki, M.; Xu, C.-X.; Rao, K. V.; Ghosh, A. K.; Mitsuya, H. GRL-0519, a Novel Oxatricyclic Ligand-Containing Nonpeptidic HIV-1 Protease Inhibitor (PI), Potently Suppresses Replication of a Wide Spectrum of Multi-PI-Resistant HIV-1 Variants In Vitro Antimicrob. Agents Chemother. 2013, 57, 2036-2046
    • (2013) Antimicrob. Agents Chemother. , vol.57 , pp. 2036-2046
    • Amano, M.1    Tojo, Y.2    Salcedo-Gómez, P.M.3    Campbell, J.R.4    Das, D.5    Aoki, M.6    Xu, C.-X.7    Rao, K.V.8    Ghosh, A.K.9    Mitsuya, H.10
  • 10
    • 85017379143 scopus 로고    scopus 로고
    • Darunavir, a New PI with Dual Mechanism: From a Novel Drug Design Concept to New Hope Against Drug-Resistant HIV
    • Ghosh, A. Wiley-VCH: Weinheim, Germany
    • Ghosh, A. K.; Chapsal, B.; Mitsuya, H. Darunavir, a New PI with Dual Mechanism: From a Novel Drug Design Concept to New Hope Against Drug-Resistant HIV. In Aspartic Acid Proteases as Therapeutic Targets; Ghosh, A., Ed.; Wiley-VCH: Weinheim, Germany, 2010; pp 205-243.
    • (2010) Aspartic Acid Proteases As Therapeutic Targets , pp. 205-243
    • Ghosh, A.K.1    Chapsal, B.2    Mitsuya, H.3
  • 11
    • 0000498416 scopus 로고
    • Mn(III)-Promoted Annulation of Enol Ethers to Fused or Spiro 2-Cyclopentanones
    • Corey, E. J.; Ghosh, A. K. Mn(III)-Promoted Annulation of Enol Ethers to Fused or Spiro 2-Cyclopentanones Tetrahedron Lett. 1987, 28, 175-178
    • (1987) Tetrahedron Lett. , vol.28 , pp. 175-178
    • Corey, E.J.1    Ghosh, A.K.2
  • 12
    • 84884260334 scopus 로고    scopus 로고
    • CCDC 940709 (12) and CCDC 940708 (13) contain the supplementary crystallographic data for this Article. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via
    • CCDC 940709 (12) and CCDC 940708 (13) contain the supplementary crystallographic data for this Article. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via www.ccdc.cam.ac.uk/ data-request/cif.
  • 13
    • 0008954659 scopus 로고
    • Sterochemical Control of Reductions III. An Approach to Group Haptophilicities
    • Thompson, H. W.; Naipawer, R. E. Sterochemical Control of Reductions III. An Approach to Group Haptophilicities J. Am. Chem. Soc. 1973, 95, 6379-6386
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 6379-6386
    • Thompson, H.W.1    Naipawer, R.E.2
  • 14
    • 33845280102 scopus 로고
    • Anhydrides as Acylating Agents in Lipase-Catalyzed Stereoselective Esterification of Racemic Alcohols
    • Bianchi, D.; Cesti, P.; Battistel, E. Anhydrides as Acylating Agents in Lipase-Catalyzed Stereoselective Esterification of Racemic Alcohols J. Org. Chem. 1988, 53, 5531-5534
    • (1988) J. Org. Chem. , vol.53 , pp. 5531-5534
    • Bianchi, D.1    Cesti, P.2    Battistel, E.3
  • 15
    • 0028798774 scopus 로고
    • Synthesis and Optical Resolution of High Affinity P2-Ligands for HIV-1 Protease Inhibitors
    • Ghosh, A. K.; Chen, Y. Synthesis and Optical Resolution of High Affinity P2-Ligands for HIV-1 Protease Inhibitors Tetrahedron Lett. 1995, 36, 505-508
    • (1995) Tetrahedron Lett. , vol.36 , pp. 505-508
    • Ghosh, A.K.1    Chen, Y.2
  • 16
    • 0010640653 scopus 로고
    • α-Methyl-α-Trifluoromethylphenylacetic Acid, a Versatile Reagent for the Determination of Enantiomeric Composition of Alcohols and Amines
    • Dale, J. A.; Dull, D. L.; Mosher, H. S. α-Methyl-α- Trifluoromethylphenylacetic Acid, a Versatile Reagent for the Determination of Enantiomeric Composition of Alcohols and Amines J. Org. Chem. 1969, 34, 2543-2549
    • (1969) J. Org. Chem. , vol.34 , pp. 2543-2549
    • Dale, J.A.1    Dull, D.L.2    Mosher, H.S.3
  • 18
    • 80051550330 scopus 로고    scopus 로고
    • Diazo-Transfer Reactions to 1,3-Dicarbonyl Compounds with Tosyl Azide
    • Presset, M.; Mailhol, D.; Coquerel, Y.; Rodriguez, J. Diazo-Transfer Reactions to 1,3-Dicarbonyl Compounds with Tosyl Azide Synthesis 2011, 16, 2549-2552
    • (2011) Synthesis , vol.16 , pp. 2549-2552
    • Presset, M.1    Mailhol, D.2    Coquerel, Y.3    Rodriguez, J.4
  • 19
    • 33751051559 scopus 로고    scopus 로고
    • Effects of Substitution on 9-(3-Bromo-4-fluorophenyl)-5,9-dihydro-3H,4H- 2,6-dioxa-4-azacyclopenta[b]naphthalene-1,8-dione, a Dihydropyridine ATP-Sensitive Potassium Channel Opener
    • Altenbach, R. J.; Brune, M. E.; Buckner, S. A.; Coghlan, M. J.; Daza, A. V.; Fabiyi, A.; Gopalakrishnan, M.; Henry, R. F.; Khilevich, A.; Kort, M. E.; Milicic, I. Effects of Substitution on 9-(3-Bromo-4-fluorophenyl)-5,9-dihydro- 3H,4H-2,6-dioxa-4-azacyclopenta[b]naphthalene-1,8-dione, a Dihydropyridine ATP-Sensitive Potassium Channel Opener J. Med. Chem. 2006, 49, 6869-6887
    • (2006) J. Med. Chem. , vol.49 , pp. 6869-6887
    • Altenbach, R.J.1    Brune, M.E.2    Buckner, S.A.3    Coghlan, M.J.4    Daza, A.V.5    Fabiyi, A.6    Gopalakrishnan, M.7    Henry, R.F.8    Khilevich, A.9    Kort, M.E.10    Milicic, I.11
  • 20
    • 0002947731 scopus 로고
    • Novel Heterocyclic Synthons. Synthesis and Properties of Thia- and Oxacyclohexane-3,5-diones
    • Terasawa, T.; Okada, T. Novel Heterocyclic Synthons. Synthesis and Properties of Thia- and Oxacyclohexane-3,5-diones J. Org. Chem. 1977, 42, 1163-1169
    • (1977) J. Org. Chem. , vol.42 , pp. 1163-1169
    • Terasawa, T.1    Okada, T.2
  • 21
    • 79953024874 scopus 로고    scopus 로고
    • 2-Azido-1,3-dimethylimidazolinium Salts: Efficient Diazo-Transfer Reagents for 1,3-Dicarbonyl Compounds
    • Kitamura, M.; Tashiro, N.; Satoshi Miyagawa, S.; Tatsuo Okauchi, T. 2-Azido-1,3-dimethylimidazolinium Salts: Efficient Diazo-Transfer Reagents for 1,3-Dicarbonyl Compounds Synthesis 2011, 7, 1037-1044
    • (2011) Synthesis , vol.7 , pp. 1037-1044
    • Kitamura, M.1    Tashiro, N.2    Satoshi Miyagawa, S.3    Tatsuo Okauchi, T.4
  • 22
    • 43949156887 scopus 로고
    • A Mild, Inexpensive and Practical Oxidation of Sulfides
    • Webb, K. S. A Mild, Inexpensive and Practical Oxidation of Sulfides Tetrahedron Lett. 1994, 35, 3457-3460
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3457-3460
    • Webb, K.S.1
  • 23
    • 0026758555 scopus 로고
    • 2-Thioalkyl Penems: An Efficient Synthesis of Sulopenem, a (5 R,6 S)-6-(1(R)-Hydroxyethyl)-2-[(cis -1-oxo-3-thiolanyl)thio]-2-penem Antibacterial
    • Volkmann, R. A.; Kelbaugh, P. R.; Nason, D. M.; Jasys, V. 2-Thioalkyl Penems: An Efficient Synthesis of Sulopenem, a (5 R,6 S)-6-(1(R)-Hydroxyethyl)- 2-[(cis -1-oxo-3-thiolanyl)thio]-2-penem Antibacterial J. Org. Chem. 1992, 57, 4352-4361
    • (1992) J. Org. Chem. , vol.57 , pp. 4352-4361
    • Volkmann, R.A.1    Kelbaugh, P.R.2    Nason, D.M.3    Jasys, V.4
  • 24
    • 33751155388 scopus 로고
    • Reactions of a Cyclic Rhodium Carbenoid with Aromatic Compounds and Vinyl Ethers
    • Pirrung, M. C.; Zhang, J.; Lackey, K.; Sternbach, D. D.; Brown, F. Reactions of a Cyclic Rhodium Carbenoid with Aromatic Compounds and Vinyl Ethers J. Org. Chem. 1995, 60, 2112-2124
    • (1995) J. Org. Chem. , vol.60 , pp. 2112-2124
    • Pirrung, M.C.1    Zhang, J.2    Lackey, K.3    Sternbach, D.D.4    Brown, F.5
  • 25
    • 17544386507 scopus 로고    scopus 로고
    • On the Enantioselectivity of Transition Metal-Catalyzed 1,3-Cycloadditions of 2-Diazocyclohexane-1,3-diones
    • Müller, P.; Allenbach, Y. F.; Bernardinelli, G. On the Enantioselectivity of Transition Metal-Catalyzed 1,3-Cycloadditions of 2-Diazocyclohexane-1,3-diones Helv. Chim. Acta 2003, 86, 3164-3172
    • (2003) Helv. Chim. Acta , vol.86 , pp. 3164-3172
    • Müller, P.1    Allenbach, Y.F.2    Bernardinelli, G.3
  • 26
    • 78751654776 scopus 로고    scopus 로고
    • Design and Synthesis of Potent HIV-1 Protease Inhibitors Incorporating Hexahydrofuropyranol-Derived High Affinity P2 Ligands: Structure-Activity Studies and Biological Evaluation
    • Ghosh, A. K.; Chapsal, B. D.; Baldridge, A.; Steffey, M. P.; Walters, D. E.; Koh, Y.; Amano, M.; Mitsuya, H. Design and Synthesis of Potent HIV-1 Protease Inhibitors Incorporating Hexahydrofuropyranol-Derived High Affinity P2 Ligands: Structure-Activity Studies and Biological Evaluation J. Med. Chem. 2011, 54, 622-634
    • (2011) J. Med. Chem. , vol.54 , pp. 622-634
    • Ghosh, A.K.1    Chapsal, B.D.2    Baldridge, A.3    Steffey, M.P.4    Walters, D.E.5    Koh, Y.6    Amano, M.7    Mitsuya, H.8
  • 27
    • 0025663423 scopus 로고
    • A Simple Continuous Fluorometric Assay for HIV Protease
    • Toth, M. V.; Marshall, G. R. A Simple Continuous Fluorometric Assay for HIV Protease Int. J. Pept. Protein Res. 1990, 36, 544-550
    • (1990) Int. J. Pept. Protein Res. , vol.36 , pp. 544-550
    • Toth, M.V.1    Marshall, G.R.2
  • 29
    • 11144354478 scopus 로고    scopus 로고
    • High Resolution Crystal Structures of HIV-1 Protease with a Potent Non-Peptide Inhibitor (UIC-94017) Active against Multi-Drug-Resistant Clinical Strains
    • Tie, Y.; Boross, P. I.; Wang, Y.-F.; Gaddis, L.; Hussain, A. K.; Leshchenko, S.; Ghosh, A. K.; Louis, J. M.; Harrison, R. W.; Weber, I. T. High Resolution Crystal Structures of HIV-1 Protease with a Potent Non-Peptide Inhibitor (UIC-94017) Active against Multi-Drug-Resistant Clinical Strains J. Mol. Biol. 2004, 338, 341-352
    • (2004) J. Mol. Biol. , vol.338 , pp. 341-352
    • Tie, Y.1    Boross, P.I.2    Wang, Y.-F.3    Gaddis, L.4    Hussain, A.K.5    Leshchenko, S.6    Ghosh, A.K.7    Louis, J.M.8    Harrison, R.W.9    Weber, I.T.10
  • 30
    • 0035370444 scopus 로고    scopus 로고
    • Structural Implications of Drug-Resistant Mutants of HIV-1 Protease: High Resolution Crystal Structures of the Mutant Protease/Substrate Analog Complexes
    • Mahalingam, B.; Louis, J. M.; Hung, J.; Harrison, R. W.; Weber, I. T. Structural Implications of Drug-Resistant Mutants of HIV-1 Protease: High Resolution Crystal Structures of the Mutant Protease/Substrate Analog Complexes Proteins 2001, 43, 455-464
    • (2001) Proteins , vol.43 , pp. 455-464
    • Mahalingam, B.1    Louis, J.M.2    Hung, J.3    Harrison, R.W.4    Weber, I.T.5
  • 31
    • 0031059866 scopus 로고    scopus 로고
    • Processing of X-ray Diffraction Data Collected in Oscillation Mode
    • Carter, C. W. Jr. Sweet, R. M. Academic Press: New York
    • Otwinowski, Z.; Minor, W. Processing of X-ray Diffraction Data Collected in Oscillation Mode. In Methods in Enzymology: Macromolecular Crystallography, Part A; Carter, C. W., Jr.; Sweet, R. M., Eds.; Academic Press: New York, 1997; Vol. 276, pp 307-326.
    • (1997) Methods in Enzymology: Macromolecular Crystallography, Part A , vol.276 , pp. 307-326
    • Otwinowski, Z.1    Minor, W.2
  • 32
    • 77956326486 scopus 로고    scopus 로고
    • Amprenavir Complexes with HIV-1 Protease and Its Drug-Resistant Mutants Altering Hydrophobic Clusters
    • Shen, C. H.; Wang, Y. F.; Kovalevasky, A. Y.; Harrison, R. W.; Weber, I. T. Amprenavir Complexes with HIV-1 Protease and Its Drug-Resistant Mutants Altering Hydrophobic Clusters FEBS J. 2010, 277, 3699-3714
    • (2010) FEBS J. , vol.277 , pp. 3699-3714
    • Shen, C.H.1    Wang, Y.F.2    Kovalevasky, A.Y.3    Harrison, R.W.4    Weber, I.T.5
  • 34
    • 0028103275 scopus 로고
    • The CCP4 Suite: Programs for Protein Crystallography
    • Collaborative Computational Project, Number 4
    • Collaborative Computational Project, Number 4. The CCP4 Suite: Programs for Protein Crystallography. Acta Crystallogr., Sect. D 1994, 50, 760-763.
    • (1994) Acta Crystallogr., Sect. D , vol.50 , pp. 760-763
  • 38
    • 13244281317 scopus 로고    scopus 로고
    • Coot: Model-Building Tools for Molecular Graphics
    • Emsley, P.; Cowtan, K. Coot: Model-Building Tools for Molecular Graphics Acta Crystallogr., Sect. D 2004, 60, 2126-2132
    • (2004) Acta Crystallogr., Sect. D , vol.60 , pp. 2126-2132
    • Emsley, P.1    Cowtan, K.2
  • 39
    • 7544226311 scopus 로고    scopus 로고
    • PRODRG: A Tool for High-Throughput Crystallography of Protein-Ligand Complexes
    • Schuettelkopf, A. W.; van Aalten, D. M. F. PRODRG: A Tool for High-Throughput Crystallography of Protein-Ligand Complexes Acta Crystallogr., Sect. D 2004, 60, 1355-1363
    • (2004) Acta Crystallogr., Sect. D , vol.60 , pp. 1355-1363
    • Schuettelkopf, A.W.1    Van Aalten, D.M.F.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.