Modeling of diarylalkyl-imidazole and diarylalkyl-triazole derivatives as potent aromatase inhibitors for treatment of hormone-dependent cancer

Journal of Computational Chemistry

Volumn 31, Issue 12, 2010, Pages 2342-2353

  Nagar, Shuchi ^a   Saha, Achintya ^a  

^a UNIVERSITY OF CALCUTTA   (India)

Author keywords

Aromatase inhibitors; CoMFA; CoMSIA; Pharmacophore; QSAR

Indexed keywords

AROMATASE; COMFA; COMSIA; PHARMACOPHORES; QSAR;

ELECTROSTATICS; ENZYMES; HYDROGEN; HYDROGEN BONDS; HYDROPHOBICITY; MOLECULAR MODELING; NITROGEN COMPOUNDS; PHARMACODYNAMICS; VAN DER WAALS FORCES;

ENZYME ACTIVITY;

ANTINEOPLASTIC HORMONE AGONISTS AND ANTAGONISTS; AROMATASE INHIBITOR; HYDROGEN; IMIDAZOLE DERIVATIVE; LIGAND; TRIAZOLE DERIVATIVE;

CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER SIMULATION; CONFERENCE PAPER; CONFORMATION; ENERGY TRANSFER; METABOLISM; NEOPLASM; QUANTITATIVE STRUCTURE ACTIVITY RELATION; NEOPLASMS;

ANTINEOPLASTIC AGENTS, HORMONAL; AROMATASE INHIBITORS; COMPUTER SIMULATION; ENERGY TRANSFER; HYDROGEN; IMIDAZOLES; LIGANDS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR CONFORMATION; NEOPLASMS; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 77955558315     PISSN: 01928651     EISSN: 1096987X     Source Type: Journal    
DOI: 10.1002/jcc.21528     Document Type: Conference Paper

References (47)

1. Early Breast Cancer Trialists' Collaborative Group. Lancet 1998, 351, 1451.
2. Chang, J.; Elledge, R. M.; Osborne, C. K. Semin. Breast Dis 2000, 3, 62.
3. Diab, S. G.; Elledge, R. M.; Clark, G. M. J Natl Cancer Inst 2000, 92, 550.
4. Chetrite, G. S.; Pasqualini, J. R. J Steroid Biochem Mol Biol 2001, 76, 95.
5. Chetrite, G. S.; Cortes-Prieto, J.; Philippe, J. C.; Wright, F.; Pasqualini, J. R. J Steroid Biochem. Mol Biol 2000, 72, 23.
6. Coombes, R. C.; Wilkinson, J. R.; Bliss, J. M.; Shah, P.; Easton, D. F.; Dowsett, M. Br J Cancer 1991, 64, 247.
7. Recanatini, M.; Cavalli, A.; Valenti, P. Med Res Rev 2002, 22, 282.
8. Oprea, T. I.; Garcia, A. E. J Comput-Aided Mol Des .1996, 10, 186.
9. Recanatini, M. J. Comput Aided Mol Des 1996, 10, 74.
10. Nagar, S.; Islam, A.; Das, S.; Mukherjee, A.; Saha, A. Mol Div 2008, 12, 65.
11. Nagar, S.; Islam, A.; Das, S.; Mukherjee, A.; Saha, A. Lett Drug Des Discov 2009, 6, 38.
12. Cramer, R, D., III; Patterson, D. E.; Bunce, J. D. Prog Clin Biol Res 1989, 291, 161,
13. Allen, M. S.; Tan, Y. C.; Tradell, M. L.; Narayanan, K.; Schindler, L. R.; Martin, M. J.; Schultz, C.; Hagen, T. J.; Koehler, K. F. J Med Chem 1990, 33, 2343.
14. Cramer, R. D., III; Patterson, D. E.; Bunce, J. D. J Am Chem Soc 1988, 110, 5959.
15. Green, S. M.; Marshall, G. R. Trends Pharmacol Sci 1995, 16, 285.
16. Klebe, G.; Abraham, U.; Mietzner, T. J Med Chem 1994, 37, 4130.
17. Waller, C. L.; Oprea, T. I.; Giolitti, A.; Marshall, G. R. J Med Chem 1993, 36, 4152.
18. Depriest, S. A.; Mayer, D.; Naylor, C. B.; Marshall, G. R. J Am Chem Soc 1993, 115, 5372.
19. Karjalainen, A.; Kalapudas, A.; Sodervall, M.; Pelkonen, O.; Lammintausta, R. Eur J Pharm Sci 2000, 11, 109.
20. Snedecor, G. W.; Cochran, W. G. Statistical Methods, 6th ed.; Iowa State University Press: Iowa, 1967.
21. Wold, S.; Albano, C. In CHEMOMETRICS: Mathematics and Statistics in Chemistry; Kowalski, B., Ed.; Reidel Dordrecht: The Netherlands, 1984.
22. Hoskuldsson, A. J Chemom 1.987, 2, 211.
23. CS Chem3D Pro and CS MOPAC Pro 7.0.1, Cambridge Soft., Cambridge, 2002. Available at: www.camsoft.com.
24. Kier, L. B.; Hall, L. H. Pharm Res 1990, 7, 801,
25. ESI-MS, Chemical Technology, Calcutta University, Kolkata, 2007.
26. Fujitsu Systems Business of America Inc. CAChe 6.1, ComputerAided Chemistry for Macintosh and Windows, Fujitsu Systems Business of America Inc., Chiba, Japan, 2004. Available at: www. CACheSoftware.com.
27. Accelrys. TSAR 3D 3.3, Oxford Molecular Limited, Accelrys, San Diego, 2006. Available at: www.accelrys.com.
28. Talete srl. DRAGON 5.4, Talete srl., 2006. Available at: www. talete.mi.it.
29. MdlconnZ version 4.05, Electronic Citation, 2006. Available at: http://www.edusoft-lc.com/mo.lco.nnZ/.
30. Chemical Computing Group Inc. MOE 2006.08, Molecular Operating Environment. Chemical Computing Group Inc., Montreal, Canada, 2006. Available at: www.chemcomp.com.
31. Statistica 7.1, StatSoft Inc., Tulsa, 2005. Available at: www.statsoft. com.
32. Wold, S.; Eriksson, L. In Chemometric Methods, Vol. 2; De Waterbeemd, H. V., Ed.; VCH. Verlagsgesellschaft mbh: Weinheim, 1995; p. 312.
33. Tripos Inc. SYBYL 7.3; Tripos Inc.: St. Louis, 2006. Available at: www.tripos.com.
34. Viswanadhan, V. N.; Ghose, A. K.; Revankar, G. R.; Robins, R. K. J Chem Inf Comput Sci 1989, 29, 163.
35. Kirkpatrick, S.; Gelatt, C. D.; Vecchi, M. P. Science 1983, 220, 671.
36. Streitwieser, A. Molecular Orbital Theory for Organic Chemists; Wiley: New York, 1961.
37. Vinter, J. G.; Davis, A.; Saunders, M. R. J Comput-Aided Mol Des 1987, 1, 31.
38. White, D. N. J. Comput. Chem 1977, 1, 225.
39. . Accelrys. Catalyst 4.11; Accelrys Inc.: San Diego, CA. Available at: www.accelrys.com.
40. Sutter, J.; Guüner, O.; Hoffmann, R.; Li, H.; Waldman, M. In. Pharmacophore Perception, Development, and Use in Drug Design; International University Line: La Jolla, CA, 2000; pp. 499-511.
41. Schuster, D.; Laggner, C.; Steindl, T. M. J Chem Inf Model 2006, 46, 1301.
42. Gasteiger, J.; Marsili, M. Tetrahedron 1980, 36, 3219.
43. Wildman, S. A.; Grippen, G. M. J Chem Inf Comput Sci 1999, 39, 868.
44. Godden, J. W.; Bajorath, J. J Chem Inf Comput Sci 2002, 42, 87.
45. Saberi, M. R.; Vinh, T. K.; Yee, S. W.; Griffiths, B. J. N.; Evans, P. J.; Simons, C. J Med Chem 2006, 49, 1016.
46. Karkola, S.; Wahala, K. Mol Cell Endocrinol 2009, 301, 235.
47. Polanski, J. Curr Med Chem 2009, 16, 3243.