Pharmacophore modeling of some novel indole β-diketo acid and coumarin-based derivatives as HIV integrase inhibitors

Medicinal Chemistry Research

Volumn 21, Issue 2, 2012, Pages 165-173

  Jain, Shailesh V ^a   Sonawane, Lalit V ^a   Patil, Ravindra R ^a   Bari, Sanjaykumar B ^a  

^a R C PATEL INSTITUTE OF PHARMACEUTICAL EDUCATION AND RESEARCH   (India)

Author keywords

3D QSAR; Coumarin based inhibitors; Indole diketo acid derivatives; Pharmacophore modeling

Indexed keywords

BETA DIKETO ACID DERIVATIVE; COUMARIN DERIVATIVE; INTEGRASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; HYDROGEN BOND; PHARMACOPHORE; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

EID: 84861910179     PISSN: 10542523     EISSN: 15548120     Source Type: Journal    
DOI: 10.1007/s00044-010-9520-1     Document Type: Article

References (26)

1. ACD/Chemsketch 12.0. (2009)
2. Axe FU, Bembenek SD, Szalma S (2006) Three-dimensional models of histamine H3 receptor antagonist complexes and their pharmacophore. J Mol Graph Model 24:456-464
3. Burke TR (1997) Coumarin-based inhibitors of HIV integrase. J Med Chem 40:242-249
4. Burke TR et al (1999) Chicoric acid analogues as HIV-1 integrase inhibitors. J Med Chem 42:1401-1414
5. Burke TR et al (2008) 2, 3-Dihydro-6, 7-dihydroxy-1H-isoindol-1-one-Based HIV-1 integrase inhibitors. J Med Chem 51:251-259
6. Bushman D, Siegel JS (2000) A new class of hiv-1 integrase inhibitors: the 3,3,3′,3'-tetramethyl-1,1′-spirobi(indan)-5,5′,6,6′- tetrol family. J Med Chem 43:2031-2039 (Pubitemid 30340942)
7. Craigie R, Mizuuchi K, Bushman FD, Engleman SA (1991) A rapid in vitro assay for HIV DNA integration. Nucleic Acid Res 19:2729-2734 (Pubitemid 21896911)
8. Dixon SL, Smondyrev AM, Knoll EH, Rao SN, Shaw DE, Friesner RA (2006a) PHASE: a new engine for pharmacophore perception, 3D QSAR model development, and 3D database screening: 1. Methodology and preliminary results. J Comput-Aided Mol Des 20:647-671 (Pubitemid 46023928)
9. Dixon SL, Smondyrev AM, Rao SN (2006b) PHASE: a novel approach to pharmacophore modeling and 3D database searching. Chem Biol Drug Des 67:370-372
10. Evans DA, Doman TN, Thorner DA, Bodkin MJ (2007) 3D QSAR methods: phase and catalyst compared. J Chem Inf Model 47: 1248-1257 (Pubitemid 46973738)
11. Ghose AK, Wendoloski JJ (1998) Pharmacophore modelling: methods, experimental verification and applications. 3D QSAR Drug Des 2:253-271 (Pubitemid 128491927)
12. Jayatilleke PRN, Nair AC, Zauhar R, Welsh WJ (2000) Computational studies on HIV-1 protease inhibitors: influence of calculated inhibitor-enzyme binding affinities on the statistical quality of 3D-QSAR CoMFA models. J Med Chem 43: 4446-4451 (Pubitemid 32046869)
13. Katz RA, Merkel G, Kulkosky J, Leis J, Skalka AM (1990) The avian retroviral IN protein is both necessary and sufficient for integrative recombination in vitro. Cell 63:87-95
14. Ligprep 2.0 (2006) Schrodinger, LLC, New York, NY
15. MacroModel 9.1 (2006) Schrodinger, LLC, New York, NY
16. Michael BP et al (2009) Azaindole hydroxamic acids are potent HIV-1 integrase inhibitors. J Med Chem 52:7211-7219
17. Nair AC, Jayatilleke P, Wang X, Miertus S, Welsh WJ (2002) Computational studies on tetrahydropyrimidine-2-one hiv-1 protease inhibitors: improving three-dimensional quantitative structure-activity relationship comparative molecular field analysis models by inclusion of calculated inhibitor- and receptor-based properties. J Med Chem 45(4):973-981
18. Phase (2007) version 8.0
19. Pommier Y, Marchand C, Johnson AA, Semenova E (2006) Mechanisms and inhibition of HIV integration. Drug Discov Today: Dis Mech 3(2):253-260 (Pubitemid 44356299)
20. Prathipati P, Saxena AK (2005) Characterization of b3-adrenergic receptor: determination of pharmacophore and 3D QSAR model for b3-adrenergic receptor agonism. J Comput Aided Mol Des 19:93-110 (Pubitemid 40974010)
21. Pungpo P, Hannongbua S (2000) Three-dimensional quantitative structure-activity relationships study on HIV-1 reverse transcriptase inhibitors in the class of dipyridodiazepinone derivatives, using comparative molecular field analysis. J Mol Graph Model 18:581-590 (Pubitemid 32072138)
22. Raghavan K, Buolamwini JK, Fesen MR, Pommier Y, Kohn KW (1995) Three-dimensional quantitative structure-activity relationship (QSAR) of HIV Integrase inhibitors: a comparative molecular field analysis (CoMFA) Study. J Med Chem 38: 890-907
23. Sechi M (2004) Design and synthesis of novel indole a-diketo acid derivatives as hiv-1 integrase inhibitors. J Med Chem 47: 5298-5310 (Pubitemid 39314928)
24. Vajragupta O, Boonchoong P (2002) New leads of HIV-1 integrase inhibitors. Mahidol Univ J Pharm Sci 29(3-4):1-10
25. Vandekerckhove L, Back D, Voet A, Vogelaers D (2008) Integrase inhibitors: integration of a new class of HIV-1 drugs intoclinical practice. Rev Antiviral Therapy 2:1-19
26. Verschueren WG et al (2005) Design and optimization of tricyclic phthalimide analogues as novel inhibitors of HIV-1 integrase. J Med Chem 48:1930-1940 (Pubitemid 40396323)