CoMFA, CoMSIA and eigenvalue analysis on dibenzodioxepinone and dibenzodioxocinone derivatives as cholesteryl ester transfer protein inhibitors

Molecules

Volumn 13, Issue 8, 2008, Pages 1822-1839

  Xiong, Xu Qiong ^a   Zhao, Dong Mei ^a   Bu, Peng Fei ^a   Liu, Yang ^a   Ren, Jin Hong ^a   Wang, Jian ^a   Cheng, Mao Sheng ^a  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

Author keywords

Cholesteryl ester transfer protein inhibitors; CoMFA; CoMSIA; Dibenzodioxepinone and dibenzodioxocinone analogues; Eigenvalue analysis

Indexed keywords

CHOLESTEROL ESTER TRANSFER PROTEIN; ENZYME INHIBITOR; OXEPINE DERIVATIVE; OXOCIN DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; HYDROGEN BOND; HYDROPHOBICITY; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

CHOLESTEROL ESTER TRANSFER PROTEINS; ENZYME INHIBITORS; HYDROGEN BONDING; HYDROPHOBICITY; MODELS, MOLECULAR; OXEPINS; OXOCINS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 50949108513     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules13081822     Document Type: Article

References (27)

1. Wolfe, M. L.; Rader, D. J. Cholesteryl Ester Transfer Protein and Coronary Artery Disease: An Observation with Therapeutic Implications. Circulation 2004, 110, 1338-1340.
2. Barter, P. J.; Brewer, H. B., Jr.; Chapman, M. J.; Hennekens, C. H.; Rader, D. J.; Tall, A. R. Cholesteryl Ester Transfer Protein: A Novel Target for Raising HDL and Inhibiting Atherosclerosis. Arterioscler. Thromb. Vasc. Biol. 2003, 23, 160-167.
3. Ruggeri, R. B. Cholesteryl Ester Transfer Protein: Pharmacological Inhibition for the Modulation of Plasma Cholesterol Levels and Promising Target for the Prevention of Atherosclerosis. Cur. Top. Med. Chem. 2005, 5, 257-264.
4. Cuchel, M.; Rader, D. J. Is the Cholesteryl Ester Transfer Protein Proatherogenic or Antiatherogenic in Humans? J. Am. Coll. Cardiol. 2007, 50, 1956-1958.
5. Parini, P.; Rudel, L. L. Is There a Need for Cholesteryl Ester Transfer Protein Inhibition? Arterioscler. Thromb. Vasc. Biol. 2003, 23, 374-375.
6. Eary, C. T.; Jones, Z. S.; Groneberg, R. D.; Burgess, L. E.; Mareska, D. A.; Drew, M. D.; Blake, J. F.; Laird, E. R.; Balachari, D.; O'Sullivan, M.; Allen, A.; Marsh, V. Tetrazole and ester substituted tetrahydoquinoxalines as potent cholesteryl ester transfer protein inhibitors. Bioorg. Med. Chem. Lett. 2007, 17, 2608-2613.
7. Brückner, D.; Hafner, F.-T.; Li, V.; Schmeck, C.; Telser, J.; Vakalopoulos, A.; Wirtz, G. Dibenzodioxocinones-A new class of CETP inhibitors. Bioorg. Med. Chem. Lett. 2005, 15, 3611-3614.
8. Brousseau, M. E.; Schaefer, E. J.; Wolfe, M. L.; Bloedon, L. T.; Digenio, A. G.; Clark, R. W.; Mancuso, J. P.; Rader, D. J. Effects of an Inhibitor of Cholesteryl Ester Transfer Protein on HDL Cholesterol. N. Engl. J. Med. 2004, 350, 1505-1515.
9. Reinhard, E. J.; Wang, J. L.; Durley, R. C.; Fobian, Y. M.; Grapperhaus, M. L.; Hickory, B. S.; Massa, M. A.; Norton, M. B.; Promo, M. A.; Tollefson, M. B.; Vernier, W. F.; Connolly, D. T.; Witherbee, B. J.; Melton, M. A.; Regina, K. J.; Smith, M. E.; Sikorski, J. A. Discovery of a Simple Picomolar Inhibitor of Cholesteryl Ester Transfer Protein. J. Med. Chem. 2003, 46, 2152-2168.
10. Okamoto, H.; Fumlhiko, Y.; Korekiyo, W.; Takashi, M. A cholesteryl ester transfer protein inhibitor attenuates atherosclerosis in rabbits. Nature 2000, 46, 203-206.
11. Tomoda, H.; Matsushima, C.; Tabata, N.; Namatame, I.; Tanaka, H.; Bamberger, M. J.; Arai, H.; Fukazawa, M.; Inoue, K.; Omura, S. Structure-specific inhibition of cholesteryl ester transfer protein by azaphilones. J. Antibiot. 1999, 52, 160-170.
12. Krishna, R.; Anderson, M. S.; Bergman, A. J.; Jin, B.; Fallon, M.; Cote, J.; Rosko, K.; Chavez-Eng, C.; Lutz, R.; Bloomfield, D. M.; Gutierrez, M.; Doherty, J.; Bieberdorf, F.; Chodakewitz, J.; Gottesdiener, K. M.; Wagner, J. A. Effect of the cholesteryl ester transfer protein inhibitor, anacetrapib, on lipoproteins in patients with dyslipidaemia and on 24-h ambulatory blood pressure in healthy individuals: two double-blind, randomised placebo-controlled phase I studies. Lancet 2007, 370, 1907-1914.
13. Qiu, X.; Mistry, A.; Ammirati, M. J.; Chrunyk, B. A.; Clark, R. W.; Cong, Y.; Culp, J. S.; Danley, D. E.; Freeman, T. B.; Geoghegan, K. F.; Griffor, M. C.; Hawrylik, S. J.; Hayward, C. M.; Hensley, P.; Hoth, L. R.; Karam, G. A.; Lira, M. E.; Lloyd, D. B.; McGrath, K. M.; Stutzman-Engwall, K. J.; Subashi, A. K.; Subashi, T. A.; Thompson, J. F.; Wang, I.-K.; Zhao, H.; Seddon, A. P. Crystal structure of cholesteryl ester transfer protein reveals a long tunnel and four bound lipid molecules. Na. Struct. Mol. Biol. 2007, 14, 106-113.
14. Bayer HealthCare AG. Patent Appl. WO 2004039453; [Chem. Abstr. 2004, 140, 406830].
15. Jain, A. N.; Koile, K.; Chapman, D. Compass: predicting biological activities from molecular surface properties, performance comparisons on a steroid benchmark. J. Med. Chem. 1994, 37, 2315-2327.
16. Bush, A.; Martin-Pastor, M. Structure and conformation of complex carbohydrate of glycoproteins, glycolipids, and bacterial polysaccharides C. Annu. Rev. Biophys. Biomol. Struct. 1999, 28, 269-293.
17. Cramer, R. D.; Patterson, D. E.; Bunce, J. D. Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J. Am. Chem. Soc. 1988, 110, 5959-5967.
18. Wang, R. X.; Gao, Y.; Liu, L.; Lai, L. H. All-orientation search and all-placement search in comparative molecular field analysis. J. Mol. Model. 1998, 4, 276-283.
19. Klebe, G.; Abraham, U.; Mietzner, T. Molecular Similarity Indices in a Comparative Analysis (CoMSIA) of Drug Molecules to Correlate and Predict their Biological Activity. J. Med. Chem. 1994, 37, 4130-4146.
20. Klebe, G.; Abraham, U. Comparative Molecular Similarity Index Analysis (CoMSIA) to Study Hydrogen Bonding Properties and to Score Combinatorial Libraries. J. Comput.-Aided Mol. Des. 1999, 13, 1-10.
21. Ferguson, A. M.; Heritage, T.; Jonathon, P.; Pack, S. E.; Philips, L. EVA: A New Theoretically Based Molecular Descriptor for Use in QSAR/QSPR Analysis. J. Comput.-Aided. Mol. Des. 1997, 11, 143-152.
22. Makhija, M. T.; Kulkarni, V. M. Eigen Value Analysis of HIV-1 Integrase Inhibitors. J. Chem. Inf. Comput. Sci. 2001, 41, 1569-1577.
23. Turner, D. B.; Willett, P.; Ferguson, A. M.; Heritage, T. W. Evaluation of a Novel Molecular Vibration-Based Descriptor (EVA) for QSAR Studies. 2. Model Validation Using a Benchmark Steroid Dataset. J. Comput.-Aided. Mol. Des. 1999, 13, 271-296.
24. Agrafiotis, D. K.; Cedeno, W.; Lobanov, V. S. On the use of neural network ensembles in QSAR and QSPR. J. Chem. Inf. Comput. Sci. 2002, 42, 903-911.
25. Cramer, R. D.; Bunce, J. D.; Patterson, D. E.; Frank, I. E. Crossvalidation, bootstrapping, and partial least squares compared with multiple regression in conventional QSAR studies. Quant. Struct.-Act. Relat. 1988, 7, 18-25.
26. Wehrens, R.; van der Linden, W. E. Bootstrapping principal component regression models. J. Chemom. 1997, 11, 157-171.
27. Clark, R. D.; Sprous, D. G.; Leonard, J. M. Validating models based on large data sets. In: Rational Approaches to Drug Design; Höltje, H. D., Sippl, W., Eds.; Prous Science SA: Barcelona, Spain, 2001; pp. 475-485.