메뉴 건너뛰기




Volumn 52, Issue 4, 2009, Pages 1219-1223

Novel indazole non-nucleoside reverse transcriptase inhibitors using molecular hybridization based on crystallographic overlays

Author keywords

[No Author keywords available]

Indexed keywords

5 (3 METHYL 1H INDAZOL 4 YLOXY) ISOPHTHALONITRILE; 5 (5 CHLORO 3 METHYL 1H INDAZOL 4 YLOXY) ISOPHTHALONITRILE; 5 (5 FLUORO 3 METHYL 1H INDAZOL 4 YLOXY) ISOPHTHALONITRILE; CAPRAVIRINE; EFAVIRENZ; INDAZOLE DERIVATIVE; RNA DIRECTED DNA POLYMERASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 64349086788     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm801322h     Document Type: Article
Times cited : (51)

References (24)
  • 2
    • 12144265244 scopus 로고    scopus 로고
    • De Clercq, E. Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTIs): Past, Present and Future. Chem. Biodiversity 2004, 1, 44-64.
    • De Clercq, E. Non-Nucleoside Reverse Transcriptase Inhibitors (NNRTIs): Past, Present and Future. Chem. Biodiversity 2004, 1, 44-64.
  • 7
    • 1642288258 scopus 로고    scopus 로고
    • Novel Inhibitors of DNA Gyrase: 3D Structure Based Biased Needle Screening, Hit Validation by Biophysical Methods, and 3D Guided Optimization. A Promising Alternative to Random Screening
    • Boehm, H.-J.; Boehringer, M.; Bur, D.; Gmuender, H.; Huber, W.; Klaus, W.; Kostrewa, D.; Kuehne, H.; Luebbers, T.; Meunier-Keller, N.; Mueller, F. Novel Inhibitors of DNA Gyrase: 3D Structure Based Biased Needle Screening, Hit Validation by Biophysical Methods, and 3D Guided Optimization. A Promising Alternative to Random Screening. J. Med. Chem. 2000, 43, 2664-2674.
    • (2000) J. Med. Chem , vol.43 , pp. 2664-2674
    • Boehm, H.-J.1    Boehringer, M.2    Bur, D.3    Gmuender, H.4    Huber, W.5    Klaus, W.6    Kostrewa, D.7    Kuehne, H.8    Luebbers, T.9    Meunier-Keller, N.10    Mueller, F.11
  • 8
    • 0017756526 scopus 로고
    • Inhibitors of Hepatic Mixed Function Oxidase. 3. Inhibition of Hepatic Microsomal Aniline Hydroxylase and Aminopyrine Demethylase by 2,6-and 2,4-Dihy-droxyphenyl Alkyl Ketones and Related Compounds
    • Bobik, A.; Holder, G. M.; Ryan, A. Inhibitors of Hepatic Mixed Function Oxidase. 3. Inhibition of Hepatic Microsomal Aniline Hydroxylase and Aminopyrine Demethylase by 2,6-and 2,4-Dihy-droxyphenyl Alkyl Ketones and Related Compounds. J. Med. Chem. 1977, 20, 1194-1199.
    • (1977) J. Med. Chem , vol.20 , pp. 1194-1199
    • Bobik, A.1    Holder, G.M.2    Ryan, A.3
  • 9
    • 0034640387 scopus 로고    scopus 로고
    • Binding of the Second Generation Non-Nucleoside Inhibitor S-1153 to HIV-1 Reverse Transcriptase Involves Extensive Main Chain Hydrogen Bonding
    • Ren, J.; Nichols, C.; Bird, L. E.; Fujiwara, T.; Sugimoto, H.; Stuart, D. I.; Stammers, D. K. Binding of the Second Generation Non-Nucleoside Inhibitor S-1153 to HIV-1 Reverse Transcriptase Involves Extensive Main Chain Hydrogen Bonding. J. Biol. Chem. 2000, 275, 14316-14320.
    • (2000) J. Biol. Chem , vol.275 , pp. 14316-14320
    • Ren, J.1    Nichols, C.2    Bird, L.E.3    Fujiwara, T.4    Sugimoto, H.5    Stuart, D.I.6    Stammers, D.K.7
  • 10
    • 0034435564 scopus 로고    scopus 로고
    • Structural Basis for the Resilience of Efavirenz (DMP-266) to Drug Resistance Mutations in HIV-1 Reverse Transcriptase
    • Ren, J.; Milton, J.; Weaver, K. L.; Short, S. A.; Stuart, D. I.; Stammers, D. K. Structural Basis for the Resilience of Efavirenz (DMP-266) to Drug Resistance Mutations in HIV-1 Reverse Transcriptase. Structure 2000, 8, 1089-1094.
    • (2000) Structure , vol.8 , pp. 1089-1094
    • Ren, J.1    Milton, J.2    Weaver, K.L.3    Short, S.A.4    Stuart, D.I.5    Stammers, D.K.6
  • 11
    • 0034094041 scopus 로고    scopus 로고
    • Mutational Analysis of Trp-229 of Human Immunodeficiency Virus Type 1 Reverse Transcriptase (RT) Identifies This Amino Acid Residue as a Prime Target for the Rational Design of New Non-Nucleoside RT Inhibitors
    • Pelemans, H.; Esnouf, R.; De Clercq, E.; Balzarini, J. Mutational Analysis of Trp-229 of Human Immunodeficiency Virus Type 1 Reverse Transcriptase (RT) Identifies This Amino Acid Residue as a Prime Target for the Rational Design of New Non-Nucleoside RT Inhibitors. Mol. Pharm. 2000, 57, 954-960.
    • (2000) Mol. Pharm , vol.57 , pp. 954-960
    • Pelemans, H.1    Esnouf, R.2    De Clercq, E.3    Balzarini, J.4
  • 12
    • 28544440834 scopus 로고    scopus 로고
    • Fattorusso, C.; Gemma, S.; Butini, S.; Huleatt, P.; Catalanotti, B.; Persico, M.; De Angelis, M.; Fiorini, I.; Nacci, V.; Ramunno, A.; Rodriquez, M.; Greco, G.; Novellino, E.; Bergamini, A.; Marini, S.; Coletta, M.; Maga, G.; Spadari, S.; Campiani, G. Specific Targeting Highly Conserved Residues in the HIV-1 Reverse Transcriptase Primer Grip Region. Design, Synthesis and Biological Evaluation of Novel, Potent and Broad Spectrum NNRTIs with Antiviral Activity. J. Med. Chem. 2005, 48, 7153-7165.
    • Fattorusso, C.; Gemma, S.; Butini, S.; Huleatt, P.; Catalanotti, B.; Persico, M.; De Angelis, M.; Fiorini, I.; Nacci, V.; Ramunno, A.; Rodriquez, M.; Greco, G.; Novellino, E.; Bergamini, A.; Marini, S.; Coletta, M.; Maga, G.; Spadari, S.; Campiani, G. Specific Targeting Highly Conserved Residues in the HIV-1 Reverse Transcriptase Primer Grip Region. Design, Synthesis and Biological Evaluation of Novel, Potent and Broad Spectrum NNRTIs with Antiviral Activity. J. Med. Chem. 2005, 48, 7153-7165.
  • 14
    • 35348879113 scopus 로고    scopus 로고
    • Synthetic chemistry-led creation of a difluorinated biaryl ether non-nucleoside reverse transcriptase inhibitor
    • (b) Jones, L. H.; Randall, A.; Barba, O.; Selby, M. Synthetic chemistry-led creation of a difluorinated biaryl ether non-nucleoside reverse transcriptase inhibitor. Org. Biomol. Chem. 2007, 5, 3431-3433.
    • (2007) Org. Biomol. Chem , vol.5 , pp. 3431-3433
    • Jones, L.H.1    Randall, A.2    Barba, O.3    Selby, M.4
  • 15
    • 33646461680 scopus 로고    scopus 로고
    • A Concise and Selective Synthesis of Novel 5-Aryloxyimidazole NNRTIs
    • (c) Jones, L. H.; Dupont, T.; Mowbray, C. E.; Newman, S. A Concise and Selective Synthesis of Novel 5-Aryloxyimidazole NNRTIs. Org. Lett. 2006, 8, 1725-1727.
    • (2006) Org. Lett , vol.8 , pp. 1725-1727
    • Jones, L.H.1    Dupont, T.2    Mowbray, C.E.3    Newman, S.4
  • 16
    • 33745386374 scopus 로고    scopus 로고
    • A concise synthesis of trifluormethyl-substituted 4-aryloxy pyrazoles
    • (d) Jones, L. H.; Mowbray, C. E. A concise synthesis of trifluormethyl-substituted 4-aryloxy pyrazoles. Synlett 2006, 9, 1404-1406.
    • (2006) Synlett , vol.9 , pp. 1404-1406
    • Jones, L.H.1    Mowbray, C.E.2
  • 18
    • 3042554700 scopus 로고    scopus 로고
    • Metabolism and excretion of capravirine, a new non-nucleoside reverse transcriptase inhibitor, alone and in combination with ritonavir in healthy volunteers
    • Bu, H.-Z.; Pool, W. F.; Wu, E. Y.; Raber, S. R.; Amantea, M. A.; Shetty, B. V. Metabolism and excretion of capravirine, a new non-nucleoside reverse transcriptase inhibitor, alone and in combination with ritonavir in healthy volunteers. Drug Metab. Dispos. 2004, 32, 689.
    • (2004) Drug Metab. Dispos , vol.32 , pp. 689
    • Bu, H.-Z.1    Pool, W.F.2    Wu, E.Y.3    Raber, S.R.4    Amantea, M.A.5    Shetty, B.V.6
  • 19
    • 1642281756 scopus 로고    scopus 로고
    • Drug-Protein Adducts: An Industry Perspective on Minimizing the Potential for Drug Bioactivation in Drug Discovery and Development
    • Evans, D. C.; Watt, A. P.; Nicoll-Griffith, D. A.; Baille, T. A. Drug-Protein Adducts: An Industry Perspective on Minimizing the Potential for Drug Bioactivation in Drug Discovery and Development. Chem. Res. Toxicol. 2004, 17, 3-16.
    • (2004) Chem. Res. Toxicol , vol.17 , pp. 3-16
    • Evans, D.C.1    Watt, A.P.2    Nicoll-Griffith, D.A.3    Baille, T.A.4
  • 21
    • 64349092940 scopus 로고    scopus 로고
    • Coordinates have been deposited with the PDB and have the assigned code 2JLE.
    • Coordinates have been deposited with the PDB and have the assigned code 2JLE.
  • 22
    • 64349110907 scopus 로고    scopus 로고
    • The crystallographic overlay of 6 with capravirine and efavirenz fits perfectly the predicted binding mode: see Supporting Information.
    • The crystallographic overlay of 6 with capravirine and efavirenz fits perfectly the predicted binding mode: see Supporting Information.
  • 23
    • 43049147306 scopus 로고    scopus 로고
    • Tucker, T. J, Saggar, S, Sisko, J. T, Tynebor, R. M, Williams, T. M, Felock, P. J, Flynn, J. A, Lai, M.-T, Liang, Y, McGaughey, G, Liu, M, Miller, M, Moyer, G, Munshi, V, Perlow-Poehnelt, R, Prasad, S, Sanchez, R, Torrent, M, Vacca, J. P, Wan, B.-L, Yan, Y. The design and synthesis of diaryl ether second generation HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) with enhanced potency versus key clinical mutations Bioorg. Med. Chem. Lett. 2008, 18, 2959-2966. These authors observed a notable reduction in potency for their lead compound against the clinically rare mutation Y181L, presumably due to interactions between the compound and the Y188 residue. We cannot rule out a similar mutant vulnerability as we have not measured Y188 mutant potencies
    • Tucker, T. J.; Saggar, S.; Sisko, J. T.; Tynebor, R. M.; Williams, T. M.; Felock, P. J.; Flynn, J. A.; Lai, M.-T.; Liang, Y.; McGaughey, G.; Liu, M.; Miller, M.; Moyer, G.; Munshi, V.; Perlow-Poehnelt, R.; Prasad, S.; Sanchez, R.; Torrent, M.; Vacca, J. P.; Wan, B.-L.; Yan, Y. The design and synthesis of diaryl ether second generation HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs) with enhanced potency versus key clinical mutations Bioorg. Med. Chem. Lett. 2008, 18, 2959-2966. These authors observed a notable reduction in potency for their lead compound against the clinically rare mutation Y181L, presumably due to interactions between the compound and the Y188 residue. We cannot rule out a similar mutant vulnerability as we have not measured Y188 mutant potencies.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.