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Volumn 53, Issue 21, 2010, Pages 7699-7708

Structure-based design, synthesis, and structure-activity relationship studies of HIV-1 protease inhibitors incorporating phenyloxazolidinones

Author keywords

[No Author keywords available]

Indexed keywords

3 (3 AMINOPHENYL) N [3 [(6 BENZOTHIAZOLYLSULFONYL)(2 METHYLPROPYL)AMINO] 2 HYDROXY 1 (PHENYLMETHYL)PROPLYL] 2 OXOOXAZOLIDINE 5 CARBOXAMIDE; ANTIVIRUS AGENT; ETHANOLAMINE DERIVATIVE; HUMAN IMMUNODEFICIENCY VIRUS PROTEINASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 78149278849     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm1008743     Document Type: Article
Times cited : (56)

References (42)
  • 4
    • 0035958773 scopus 로고    scopus 로고
    • Overview of the effectiveness of triple combination therapy in antiretroviral-naive HIV-1 infected adults
    • Bartlett, J. A.; DeMasi, R.; Quinn, J.; Moxham, C.; Rousseau, F. Overview of the effectiveness of triple combination therapy in antiretroviral-naive HIV-1 infected adults AIDS 2001, 15, 1369-1377
    • (2001) AIDS , vol.15 , pp. 1369-1377
    • Bartlett, J.A.1    Demasi, R.2    Quinn, J.3    Moxham, C.4    Rousseau, F.5
  • 5
    • 2642709177 scopus 로고    scopus 로고
    • Declining morbidity and mortality among patients with advanced human immunodeficiency virus infection
    • HIV Outpatient Study Investigators
    • Palella, F. J., Jr.; Delaney, K. M.; Moorman, A. C.; Loveless, M. O.; Fuhrer, J.; Satten, G. A.; Aschman, D. J.; Holmberg, S. D.; HIV Outpatient Study Investigators. Declining morbidity and mortality among patients with advanced human immunodeficiency virus infection N. Engl. J. Med. 1998, 338, 853-860
    • (1998) N. Engl. J. Med. , vol.338 , pp. 853-860
    • Palella, Jr.F.J.1    Delaney, K.M.2    Moorman, A.C.3    Loveless, M.O.4    Fuhrer, J.5    Satten, G.A.6    Aschman, D.J.7    Holmberg, S.D.8
  • 7
    • 77249134151 scopus 로고    scopus 로고
    • Twenty-six years of anti-HIV drug discovery: Where do we stand and where do we go?
    • Mehellou, Y.; De Clercq, E. Twenty-six years of anti-HIV drug discovery: where do we stand and where do we go? J. Med. Chem. 2010, 53, 521-538
    • (2010) J. Med. Chem. , vol.53 , pp. 521-538
    • Mehellou, Y.1    De Clercq, E.2
  • 9
    • 0346025675 scopus 로고    scopus 로고
    • Pharmacological and therapeutic properties of ritonavir-boosted protease inhibitor therapy in HIV-infected patients
    • Zeldin, R. K.; Petruschke, R. A. Pharmacological and therapeutic properties of ritonavir-boosted protease inhibitor therapy in HIV-infected patients J. Antimicrob. Chemother. 2004, 53, 4-9
    • (2004) J. Antimicrob. Chemother. , vol.53 , pp. 4-9
    • Zeldin, R.K.1    Petruschke, R.A.2
  • 10
    • 36549014231 scopus 로고    scopus 로고
    • Overview of boosted protease inhibitors in treatment-experienced HIV-infected patients
    • Youle, M. Overview of boosted protease inhibitors in treatment- experienced HIV-infected patients J. Antimicrob. Chemother. 2007, 60, 1195-1205
    • (2007) J. Antimicrob. Chemother. , vol.60 , pp. 1195-1205
    • Youle, M.1
  • 13
    • 19544386471 scopus 로고    scopus 로고
    • TMC114, a novel human immunodeficiency virus type 1 protease inhibitor active against protease inhibitor-resistant viruses, including a broad range of clinical isolates
    • De Meyer, S.; Azijn, H.; Surleraux, D.; Jochmans, D.; Tahri, A.; Pauwels, R.; Wigerinck, P.; de Bethune, M. P. TMC114, a novel human immunodeficiency virus type 1 protease inhibitor active against protease inhibitor-resistant viruses, including a broad range of clinical isolates Antimicrob. Agents Chemother. 2005, 49, 2314-2321
    • (2005) Antimicrob. Agents Chemother. , vol.49 , pp. 2314-2321
    • De Meyer, S.1    Azijn, H.2    Surleraux, D.3    Jochmans, D.4    Tahri, A.5    Pauwels, R.6    Wigerinck, P.7    De Bethune, M.P.8
  • 15
    • 73549089480 scopus 로고    scopus 로고
    • Current status and challenges of antiretroviral research and therapy
    • Esté, J. A.; Cihlar, T. Current status and challenges of antiretroviral research and therapy Antiviral Res. 2010, 85, 25-33
    • (2010) Antiviral Res. , vol.85 , pp. 25-33
    • Esté, J.A.1    Cihlar, T.2
  • 17
    • 33750338185 scopus 로고    scopus 로고
    • Genotypic changes in human immunodeficiency virus type 1 protease associated with reduced susceptibility and virologic response to the protease inhibitor tipranavir
    • Baxter, J. D.; Schapiro, J. M.; Boucher, C. A. B.; Kohlbrenner, V. M.; Hall, D. B.; Scherer, J. R.; Mayers, D. L. Genotypic changes in human immunodeficiency virus type 1 protease associated with reduced susceptibility and virologic response to the protease inhibitor tipranavir J. Virol. 2006, 80, 10794-10801
    • (2006) J. Virol. , vol.80 , pp. 10794-10801
    • Baxter, J.D.1    Schapiro, J.M.2    Boucher, C.A.B.3    Kohlbrenner, V.M.4    Hall, D.B.5    Scherer, J.R.6    Mayers, D.L.7
  • 19
    • 48449083017 scopus 로고    scopus 로고
    • HIV-1 drug resistance mutations: An updated framework for the second decade of HAART
    • Shafer, R. W.; Schaprio, J. M. HIV-1 drug resistance mutations: an updated framework for the second decade of HAART AIDS Rev. 2008, 10, 67-84
    • (2008) AIDS Rev. , vol.10 , pp. 67-84
    • Shafer, R.W.1    Schaprio, J.M.2
  • 20
    • 33845492104 scopus 로고    scopus 로고
    • Discovery of HIV-1 protease inhibitors with picomolar affinities incorporating N -aryl-oxazolidinone-5-carboxamides as novel P2 ligands
    • Ali, A.; Reddy, G. S. K. K.; Cao, H.; Anjum, S. G.; Nalam, M. N. L.; Schiffer, C. A.; Rana, T. M. Discovery of HIV-1 protease inhibitors with picomolar affinities incorporating N -aryl-oxazolidinone-5-carboxamides as novel P2 ligands J. Med. Chem. 2006, 49, 7342-7356
    • (2006) J. Med. Chem. , vol.49 , pp. 7342-7356
    • Ali, A.1    Reddy, G.S.K.K.2    Cao, H.3    Anjum, S.G.4    Nalam, M.N.L.5    Schiffer, C.A.6    Rana, T.M.7
  • 21
    • 34548475074 scopus 로고    scopus 로고
    • Design and synthesis of HIV-1 protease inhibitors incorporating oxazolidinones as P2/P2' ligands in pseudosymmetric dipeptide isosteres
    • Reddy, G. S. K. K.; Ali, A.; Nalam, M. N. L.; Anjum, S. G.; Cao, H.; Nathans, R. S.; Schiffer, C. A.; Rana, T. M. Design and synthesis of HIV-1 protease inhibitors incorporating oxazolidinones as P2/P2' ligands in pseudosymmetric dipeptide isosteres J. Med. Chem. 2007, 50, 4316-4328
    • (2007) J. Med. Chem. , vol.50 , pp. 4316-4328
    • Reddy, G.S.K.K.1    Ali, A.2    Nalam, M.N.L.3    Anjum, S.G.4    Cao, H.5    Nathans, R.S.6    Schiffer, C.A.7    Rana, T.M.8
  • 24
    • 0030027833 scopus 로고    scopus 로고
    • Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant Gram-positive bacterial infections
    • Brickner, S. J.; Hutchinson, D. K.; Barbachyn, M. R.; Manninen, P. R.; Ulanowicz, D. A.; Garmon, S. A.; Grega, K. C.; Hendges, S. K.; Toops, D. S.; Ford, C. W.; Zurenko, G. E. Synthesis and antibacterial activity of U-100592 and U-100766, two oxazolidinone antibacterial agents for the potential treatment of multidrug-resistant Gram-positive bacterial infections J. Med. Chem. 1996, 39, 673-679
    • (1996) J. Med. Chem. , vol.39 , pp. 673-679
    • Brickner, S.J.1    Hutchinson, D.K.2    Barbachyn, M.R.3    Manninen, P.R.4    Ulanowicz, D.A.5    Garmon, S.A.6    Grega, K.C.7    Hendges, S.K.8    Toops, D.S.9    Ford, C.W.10    Zurenko, G.E.11
  • 26
    • 52049123291 scopus 로고    scopus 로고
    • Do enthalpy and entropy distinguish first in class from best in class?
    • Freire, E. Do enthalpy and entropy distinguish first in class from best in class? Drug Discovery Today 2008, 13, 869-874
    • (2008) Drug Discovery Today , vol.13 , pp. 869-874
    • Freire, E.1
  • 27
    • 77953631827 scopus 로고    scopus 로고
    • A medicinal chemist's guide to molecular interactions
    • Bissantz, C.; Kuhn, B.; Stahl, M. A medicinal chemist's guide to molecular interactions J. Med. Chem. 2010, 53, 5061-5084
    • (2010) J. Med. Chem. , vol.53 , pp. 5061-5084
    • Bissantz, C.1    Kuhn, B.2    Stahl, M.3
  • 28
    • 0025099455 scopus 로고
    • Novel fluorogenic substrates for assaying retroviral proteases by resonance energy transfer
    • Matayoshi, E. D.; Wang, G. T.; Krafft, G. A.; Erickson, J. Novel fluorogenic substrates for assaying retroviral proteases by resonance energy transfer Science 1990, 247, 954-958
    • (1990) Science , vol.247 , pp. 954-958
    • Matayoshi, E.D.1    Wang, G.T.2    Krafft, G.A.3    Erickson, J.4
  • 30
    • 0018787723 scopus 로고
    • Evaluation of methods for estimating the dissociation constant of tight binding enzyme inhibitors
    • Greco, W. R.; Hakala, M. T. Evaluation of methods for estimating the dissociation constant of tight binding enzyme inhibitors J. Biol. Chem. 1979, 254, 12104-12109
    • (1979) J. Biol. Chem. , vol.254 , pp. 12104-12109
    • Greco, W.R.1    Hakala, M.T.2
  • 32
    • 0005839617 scopus 로고
    • Purdue University: West Lafayette, IN
    • Minor, W. XdisplayF; Purdue University: West Lafayette, IN, 1993.
    • (1993) XdisplayF
    • Minor, W.1
  • 33
    • 0031059866 scopus 로고    scopus 로고
    • Processing of X-ray diffraction Data Collected in Oscillation Mode
    • In;, Eds.; Academic Press: San Diego, CA
    • Otwinowski, Z.; Minor, W. Processing of X-ray diffraction Data Collected in Oscillation Mode. In Methods in Enzymology; Carter, C. W., Jr.; Sweet, R. M., Eds.; Academic Press: San Diego, CA, 1997; Vol. 276, pp 307 - 326.
    • (1997) Methods in Enzymology , vol.276 , pp. 307-326
    • Otwinowski, Z.1    Minor, W.2    Carter, Jr.C.W.3    Sweet, R.M.4
  • 34
    • 0028103275 scopus 로고
    • Collaborative Computational Project, Number 4. The CCP4 suite: Programs for protein crystallography
    • Collaborative Computational Project, Number 4. The CCP4 suite: programs for protein crystallography. Acta Crystallogr. 1994, D50, 760 - 763.
    • (1994) Acta Crystallogr. , vol.50 , pp. 760-763
  • 35
    • 84920325457 scopus 로고
    • AMoRe: An automated package for molecular replacement
    • Navaza, J. AMoRe: an automated package for molecular replacement Acta Crystallogr. 1994, A50, 157-163
    • (1994) Acta Crystallogr. , vol.50 , pp. 157-163
    • Navaza, J.1
  • 36
    • 0034283345 scopus 로고    scopus 로고
    • How does a symmetric dimer recognize an asymmetric substrate? A substrate complex of HIV-1 protease
    • Prabu-Jeyabalan, M.; Nalivaika, E.; Schiffer, C. A. How does a symmetric dimer recognize an asymmetric substrate? A substrate complex of HIV-1 protease J. Mol. Biol. 2000, 301, 1207-1220
    • (2000) J. Mol. Biol. , vol.301 , pp. 1207-1220
    • Prabu-Jeyabalan, M.1    Nalivaika, E.2    Schiffer, C.A.3
  • 37
    • 0036077402 scopus 로고    scopus 로고
    • ARP/wARP's model-building algorithms. I. The main chain
    • Morris, R. J.; Perrakis, A.; Lamzin, V. S. ARP/wARP's model-building algorithms. I. The main chain Acta Crystallogr. 2002, D58, 968-975
    • (2002) Acta Crystallogr. , vol.58 , pp. 968-975
    • Morris, R.J.1    Perrakis, A.2    Lamzin, V.S.3
  • 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. 2004, D60, 2126-2132
    • (2004) Acta Crystallogr. , vol.60 , pp. 2126-2132
    • Emsley, P.1    Cowtan, K.2
  • 39
    • 0030924992 scopus 로고    scopus 로고
    • Refinement of macromolecular structures by the maximum-likelihood method
    • Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Refinement of macromolecular structures by the maximum-likelihood method Acta Crystallogr. 1997, D53, 240-255
    • (1997) Acta Crystallogr. , vol.53 , pp. 240-255
    • Murshudov, G.N.1    Vagin, A.A.2    Dodson, E.J.3
  • 40
    • 0001841380 scopus 로고
    • On the rigid-body motion of molecules in crystals
    • Schomaker, V.; Trueblood, K. N. On the rigid-body motion of molecules in crystals Acta Crystallogr. 1968, B24, 63-76
    • (1968) Acta Crystallogr. , vol.24 , pp. 63-76
    • Schomaker, V.1    Trueblood, K.N.2
  • 41
    • 0025904209 scopus 로고
    • Rigid protein motion as a model for crystallographic temperature factors
    • Kuriyan, J.; Weis, W. I. Rigid protein motion as a model for crystallographic temperature factors Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 2773-2777
    • (1991) Proc. Natl. Acad. Sci. U.S.A. , vol.88 , pp. 2773-2777
    • Kuriyan, J.1    Weis, W.I.2
  • 42
    • 34548508518 scopus 로고    scopus 로고
    • Modeling Rigid-Body Thermal Motion in Macromolecular Crystal Structure Refinement
    • In; IUCr: London
    • Tickle, I. J.; Moss, D. S. Modeling Rigid-Body Thermal Motion in Macromolecular Crystal Structure Refinement. In IUCr99 Computing School; IUCr: London, 1999.
    • (1999) IUCr99 Computing School
    • Tickle, I.J.1    Moss, D.S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.