메뉴 건너뛰기




Volumn 51, Issue 7, 2008, Pages 2078-2087

Structure-guided design of C2-symmetric HIV-1 protease inhibitors based on a pyrrolidine scaffold

Author keywords

[No Author keywords available]

Indexed keywords

3,4 BIS N SULFONAMIDE; PROTEINASE INHIBITOR; PYRROLIDINE DERIVATIVE; TARTARIC ACID; UNCLASSIFIED DRUG;

EID: 41849085506     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm701142s     Document Type: Article
Times cited : (46)

References (37)
  • 2
    • 0037624182 scopus 로고    scopus 로고
    • Twenty years of therapy for HIV-1 infection
    • Pomerantz, R. J.; Horn, D. L. Twenty years of therapy for HIV-1 infection. Nat. Med. 2003, 9 (7), 867-873.
    • (2003) Nat. Med , vol.9 , Issue.7 , pp. 867-873
    • Pomerantz, R.J.1    Horn, D.L.2
  • 3
    • 0027218692 scopus 로고
    • Structure-based inhibitors of HIV-1 protease
    • Wlodawer, A.; Erickson, J. W. Structure-based inhibitors of HIV-1 protease. Annu. Rev. Biochem. 1993, 62 (1), 543-585.
    • (1993) Annu. Rev. Biochem , vol.62 , Issue.1 , pp. 543-585
    • Wlodawer, A.1    Erickson, J.W.2
  • 4
    • 2942534993 scopus 로고    scopus 로고
    • HIV protease inhibition: Limited recent progress and advances in understanding current pitfalls
    • Rodríguez-Barrios, F.; Gago, F. HIV protease inhibition: limited recent progress and advances in understanding current pitfalls. Curr. Top. Med. Chem. 2004, 4, 991-1007.
    • (2004) Curr. Top. Med. Chem , vol.4 , pp. 991-1007
    • Rodríguez-Barrios, F.1    Gago, F.2
  • 5
    • 3042724872 scopus 로고    scopus 로고
    • Non-peptidic HIV protease inhibitors
    • Chrusciel, R. A.; Strohbach, J. W. Non-peptidic HIV protease inhibitors. Curr. Top. Med. Chem. 2004, 4 (10), 1097-1114.
    • (2004) Curr. Top. Med. Chem , vol.4 , Issue.10 , pp. 1097-1114
    • Chrusciel, R.A.1    Strohbach, J.W.2
  • 6
    • 3042554178 scopus 로고    scopus 로고
    • Peptidomimetic inhibitors of HIV protease
    • Randolph, J. T.; DeGoey, D. A. Peptidomimetic inhibitors of HIV protease. Curr. Top. Med. Chem. 2004, 4 (10), 1079-1095.
    • (2004) Curr. Top. Med. Chem , vol.4 , Issue.10 , pp. 1079-1095
    • Randolph, J.T.1    DeGoey, D.A.2
  • 12
    • 33746276423 scopus 로고    scopus 로고
    • Hof, F.; Schütz, A.; Fäh, C.; Meyer, S.; Bur, D.; Liu, J.; Goldberg, D. E.; Diederich, F. Starving the malaria parasite: inhibitors active against the aspartic proteases plasmepsins I, II, and IV. Angew. Chem., Int. Ed. 2006, 45 (13), 2138-2141.
    • Hof, F.; Schütz, A.; Fäh, C.; Meyer, S.; Bur, D.; Liu, J.; Goldberg, D. E.; Diederich, F. Starving the malaria parasite: inhibitors active against the aspartic proteases plasmepsins I, II, and IV. Angew. Chem., Int. Ed. 2006, 45 (13), 2138-2141.
  • 13
    • 18844441446 scopus 로고    scopus 로고
    • An old target revisited: Two new privileged skeletons and an unexpected binding mode for HIV-protease inhibitors
    • Specker, E.; Böttcher, J.; Lilie, H.; Heine, A.; Schoop, A.; Müller, G.; Griebenow, N.; Klebe, G. An old target revisited: two new privileged skeletons and an unexpected binding mode for HIV-protease inhibitors. Angew. Chem., Int. Ed. 2005, 44 (20), 3140-3144.
    • (2005) Angew. Chem., Int. Ed , vol.44 , Issue.20 , pp. 3140-3144
    • Specker, E.1    Böttcher, J.2    Lilie, H.3    Heine, A.4    Schoop, A.5    Müller, G.6    Griebenow, N.7    Klebe, G.8
  • 14
    • 33746301158 scopus 로고    scopus 로고
    • Unexpected novel binding mode of pyrrolidine-based aspartyl protease inhibitors: Design, synthesis and crystal structure in complex with HIV protease
    • Specker, E.; Böttcher, J.; Brass, S.; Heine, A.; Lilie, H.; Schoop, A.; Müller, G.; Griebenow, N.; Klebe, G. Unexpected novel binding mode of pyrrolidine-based aspartyl protease inhibitors: design, synthesis and crystal structure in complex with HIV protease. ChemMedChem 2006, 1 (1), 106-117.
    • (2006) ChemMedChem , vol.1 , Issue.1 , pp. 106-117
    • Specker, E.1    Böttcher, J.2    Brass, S.3    Heine, A.4    Lilie, H.5    Schoop, A.6    Müller, G.7    Griebenow, N.8    Klebe, G.9
  • 15
    • 34547657456 scopus 로고    scopus 로고
    • Atypical protonation states in the active site of HIV-1 protease: A computational study
    • Czodrowski, P.; Sotriffer, C. A.; Klebe, G. Atypical protonation states in the active site of HIV-1 protease: a computational study. J. Chem. Inf. Model. 2007, 47 (4), 1590-1598.
    • (2007) J. Chem. Inf. Model , vol.47 , Issue.4 , pp. 1590-1598
    • Czodrowski, P.1    Sotriffer, C.A.2    Klebe, G.3
  • 16
    • 84985633308 scopus 로고
    • Asymmetric hydrogenation of α-(acetylamino)cinnamic acid with a novel rhodium complex; the design of an optimal ligand
    • Nagel, U. Asymmetric hydrogenation of α-(acetylamino)cinnamic acid with a novel rhodium complex; the design of an optimal ligand. Angew. Chem., Int. Ed. Engl. 1984, 23 (6), 435-436.
    • (1984) Angew. Chem., Int. Ed. Engl , vol.23 , Issue.6 , pp. 435-436
    • Nagel, U.1
  • 17
    • 0000652292 scopus 로고    scopus 로고
    • Nagel, U.; Kinzel, E.; Andrade, J.; Prescher, G. Enantioselektive Katalyse, 4. Synthese N-substituierter (R,R)-3,4- Bis(diphenylphosphino)-pyrrolidine und Anwendung ihrer Rhodiumkomplexe zur asymmetrischen Hydrierung von α-(Acylamino)-acrylsäure-Derivaten. Enantioselective Catalysis, 4. Synthesis N-Substituted (R,R)-3,4-Bis(diphenylphosphino)-pyrrolidines. The Use of their Rhodium Complexes for the Asymmetric Hydrogenation of α-(Acylamino)-acrylic Acid Derivatives. Chem. Ber. 1986, 119 (11), 3326-3343.
    • Nagel, U.; Kinzel, E.; Andrade, J.; Prescher, G. Enantioselektive Katalyse, 4. Synthese N-substituierter (R,R)-3,4- Bis(diphenylphosphino)-pyrrolidine und Anwendung ihrer Rhodiumkomplexe zur asymmetrischen Hydrierung von α-(Acylamino)-acrylsäure-Derivaten. Enantioselective Catalysis, 4. Synthesis N-Substituted (R,R)-3,4-Bis(diphenylphosphino)-pyrrolidines. The Use of their Rhodium Complexes for the Asymmetric Hydrogenation of α-(Acylamino)-acrylic Acid Derivatives. Chem. Ber. 1986, 119 (11), 3326-3343.
  • 19
    • 0030920809 scopus 로고    scopus 로고
    • 2 symmetric primary vicinal diamines. Double stereospecific Mitsunobu reaction on the heterocyclic diols derived from tartaric acid
    • 2 symmetric primary vicinal diamines. Double stereospecific Mitsunobu reaction on the heterocyclic diols derived from tartaric acid. Tetrahedron: Asymmetry 1997, 8 (11), 1861-1867.
    • (1997) Tetrahedron: Asymmetry , vol.8 , Issue.11 , pp. 1861-1867
    • Skarøewski, J.1    Gupta, A.2
  • 20
    • 0038400046 scopus 로고    scopus 로고
    • Chemoenzymatic preparation of non-racemic N-Boc-pyrrolidine-3,4-dicarboxylic acid 3-ethyl esters and their 4-hydroxymethyl derivatives
    • Rodríguez Sarmiento, R. M.; Wirz, B.; Iding, H. Chemoenzymatic preparation of non-racemic N-Boc-pyrrolidine-3,4-dicarboxylic acid 3-ethyl esters and their 4-hydroxymethyl derivatives. Tetrahedron: Asymmetry 2003, 14 (11), 1547-1551.
    • (2003) Tetrahedron: Asymmetry , vol.14 , Issue.11 , pp. 1547-1551
    • Rodríguez Sarmiento, R.M.1    Wirz, B.2    Iding, H.3
  • 22
    • 0037131591 scopus 로고    scopus 로고
    • Heterogeneous Pd-catalyzed asymmetric allylic substitution using resin-supported trost-type bisphosphane ligands
    • Song, C. E.; Yang, J. W.; Roh, E. J.; Lee, S.-G.; Ahn, J. H.; Han, H. Heterogeneous Pd-catalyzed asymmetric allylic substitution using resin-supported trost-type bisphosphane ligands. Angew. Chem., Int. Ed. 2002, 41 (20), 3852-3854.
    • (2002) Angew. Chem., Int. Ed , vol.41 , Issue.20 , pp. 3852-3854
    • Song, C.E.1    Yang, J.W.2    Roh, E.J.3    Lee, S.-G.4    Ahn, J.H.5    Han, H.6
  • 23
    • 0024801485 scopus 로고
    • Efficient conversion of nitriles to amides with basic hydrogen peroxide in dimethyl sulfoxide
    • Katritzky, A. R.; Pilarski, B.; Urogdi, L. Efficient conversion of nitriles to amides with basic hydrogen peroxide in dimethyl sulfoxide. Synthesis 1989, (12), 949-950.
    • (1989) Synthesis , vol.12 , pp. 949-950
    • Katritzky, A.R.1    Pilarski, B.2    Urogdi, L.3
  • 24
    • 18744381869 scopus 로고    scopus 로고
    • Novel lead structures for antimalarial farnesyltransferase inhibitors
    • Kettler, K.; Sakowski, J.; Wiesner, J.; Ortmann, R.; Jomaa, H.; Schlitzer, M. Novel lead structures for antimalarial farnesyltransferase inhibitors. Pharmazie 2005, 60 (5), 323-327.
    • (2005) Pharmazie , vol.60 , Issue.5 , pp. 323-327
    • Kettler, K.1    Sakowski, J.2    Wiesner, J.3    Ortmann, R.4    Jomaa, H.5    Schlitzer, M.6
  • 25
    • 0026690374 scopus 로고
    • High-level expression and purification of mature HIV-1 protease in Escherichia coli under control of the araBAD promoter
    • Taylor, A.; Brown, D. P.; Kadam, S.; Maus, M.; Kohlbrenner, W. E.; Weigl, D.; Turon, M. C.; Katz, L. High-level expression and purification of mature HIV-1 protease in Escherichia coli under control of the araBAD promoter. Appl. Microbiol. Biotechnol. 1992, 37 (2), 205-210.
    • (1992) Appl. Microbiol. Biotechnol , vol.37 , Issue.2 , pp. 205-210
    • Taylor, A.1    Brown, D.P.2    Kadam, S.3    Maus, M.4    Kohlbrenner, W.E.5    Weigl, D.6    Turon, M.C.7    Katz, L.8
  • 26
    • 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 (6), 544-550.
    • (1990) Int. J. Pept. Protein Res , vol.36 , Issue.6 , pp. 544-550
    • Toth, M.V.1    Marshall, G.R.2
  • 27
    • 0031059866 scopus 로고    scopus 로고
    • Processing of X-ray Diffraction Data Collected in Oscillation Mode
    • Carter, C. W, Jr, Ed, 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., Ed.; 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
  • 28
    • 3042613550 scopus 로고    scopus 로고
    • Likelihood-enhanced fast rotation functions
    • Storoni, L. C.; McCoy, A. J.; Read, R. J. Likelihood-enhanced fast rotation functions. Acta Crystallogr. D 2004, 60 (3), 432-438.
    • (2004) Acta Crystallogr. D , vol.60 , Issue.3 , pp. 432-438
    • Storoni, L.C.1    McCoy, A.J.2    Read, R.J.3
  • 29
    • 4644366388 scopus 로고    scopus 로고
    • HKL2MAP: A graphical user interface for macromolecular phasing with SHELX programs
    • Pape, T.; Schneider, T. R. HKL2MAP: a graphical user interface for macromolecular phasing with SHELX programs. J. Appl. Crystallogr. 2004, 37 (5), 843-844.
    • (2004) J. Appl. Crystallogr , vol.37 , Issue.5 , pp. 843-844
    • Pape, T.1    Schneider, T.R.2
  • 30
    • 0038210935 scopus 로고    scopus 로고
    • Advances in direct methods for protein crystallography
    • Usón, I.; Sheldrick, G. M. Advances in direct methods for protein crystallography. Curr. Opin. Struct. Biol. 1999, 9 (5), 643-648.
    • (1999) Curr. Opin. Struct. Biol , vol.9 , Issue.5 , pp. 643-648
    • Usón, I.1    Sheldrick, G.M.2
  • 31
    • 0013054388 scopus 로고    scopus 로고
    • Macromolecular phasing with SHELXE
    • Sheldrick, G. M. Macromolecular phasing with SHELXE. Z. Kristallogr. 2002, 217 (12), 644-650.
    • (2002) Z. Kristallogr , vol.217 , Issue.12 , pp. 644-650
    • Sheldrick, G.M.1
  • 32
    • 0032872798 scopus 로고    scopus 로고
    • Density modification for macromolecular phase improvement
    • Cowtan, K. D.; Zhang, K. Y. J. Density modification for macromolecular phase improvement. Prog. Biophys. Mol. Biol. 1999, 72 (3), 245-270.
    • (1999) Prog. Biophys. Mol. Biol , vol.72 , Issue.3 , pp. 245-270
    • Cowtan, K.D.1    Zhang, K.Y.J.2
  • 33
    • 0000127585 scopus 로고
    • Automated refinement of protein models
    • Lamzin, V. S.; Wilson, K. S. Automated refinement of protein models. Acta Crystallogr. D 1993, 49 (1), 129-147.
    • (1993) Acta Crystallogr. D , vol.49 , Issue.1 , pp. 129-147
    • Lamzin, V.S.1    Wilson, K.S.2
  • 34
    • 0028103275 scopus 로고
    • The CCP4 suite: Programs for protein crystallography
    • The CCP4 suite: programs for protein crystallography. Acta Crystallogr. D 1994, 50 (5), 760-763.
    • (1994) Acta Crystallogr. D , vol.50 , Issue.5 , pp. 760-763
  • 36
    • 0030880598 scopus 로고    scopus 로고
    • High-Resolution Refinement
    • SHELXL:, Charles, W. C. J, Robert, M. S, Eds, Academic Press: San Diego, CA
    • Sheldrick, G. M.; Schneider, T. R., SHELXL: High-Resolution Refinement. In Methods in Enzymology; Charles, W. C. J., Robert, M. S., Eds.; Academic Press: San Diego, CA, 1997; Vol. 277, pp 319-343.
    • (1997) Methods in Enzymology , vol.277 , pp. 319-343
    • Sheldrick, G.M.1    Schneider, T.R.2
  • 37
    • 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. D 2004, 60 (12, Part 1), 2126-2132.
    • (2004) Acta Crystallogr. D , vol.60 , Issue.12 and PART 1 , pp. 2126-2132
    • Emsley, P.1    Cowtan, K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.