3D-QSAR and receptor modeling of tyrosine kinase inhibitors with flexible atom receptor model (FLARM)

Journal of Chemical Information and Computer Sciences

Volumn 43, Issue 1, 2003, Pages 298-303

  Peng, Tao ^a   Pei, Jianfeng ^a   Zhou, Jiaju ^a  

^a INSTITUTE OF PROCESS ENGINEERING   (China)

Author keywords

[No Author keywords available]

Indexed keywords

EPIDERMAL GROWTH FACTOR RECEPTOR; FLEXIBLE ATOM RECEPTOR MODEL; HYDROPHOBIC INTERACTION; TYROSINE KINASE INHIBITOR;

ATOMS; COMPUTER AIDED DESIGN; DRUG PRODUCTS; HYDROGEN BONDS; MATHEMATICAL MODELS; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE;

ENZYME INHIBITION;

ENZYME INHIBITOR; EPIDERMAL GROWTH FACTOR RECEPTOR; LIGAND;

ARTICLE; BINDING SITE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; COMPUTER AIDED DESIGN; COMPUTER SIMULATION; DRUG ANTAGONISM; DRUG DESIGN; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

BINDING SITES; COMPUTER SIMULATION; COMPUTER-AIDED DESIGN; DRUG DESIGN; ENZYME INHIBITORS; LIGANDS; MODELS, CHEMICAL; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RECEPTOR, EPIDERMAL GROWTH FACTOR;

EID: 0037208315     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci0256034     Document Type: Article

References (33)

1. Aaronson, S. A. Growth factors and cancer. Science 1991, 254, 1146-1152.
2. Fry, D. W.; Kraker, A. J.; Conners, R. C.; Elliott, W. L.; Nelson, J. M.; Showalter, H. D.; Leopold, W. R. Strategies for the discovery of novel tyrosine kinase inhibitors with anticancer activity. Anti-Cancer Drug Des. 1994, 9, 331-351.
3. Levitzki, A.; Gazit, A. Tyrosine kinase inhibition: An approach to drug development. Science 1995, 267, 1782-1788.
4. Fry, D. W. Protein tyrosine kinases as therapeutic targets in cancer chemotherapy and recent advances in the development of new inhibitors. Exp. Opin. Invest. Drugs 1994, 3, 577-595.
5. Traxler, P.; Lydon, N. Recent advances in protein tyrosine kinase inhibitors. Drugs Future 1995, 20, 1261-1274.
6. Spada, A. P.; Myers, M. R. Small molecule inhibitors of tyrosine kinase activity. Exp. Opin. Ther. Patents 1995, 5, 805-817.
7. Bridges, A. J. The current status of tyrosine kinase inhibitors: do the diarylamine inhibitors of the EGF receptor represent a new beginning? Exp. Opin. Ther. Patents 1995, 5, 1245-1257.
8. Traxler, P. Protein tyrosine kinase inhibitors in cancer treatment. Exp. Opin. Ther. Patents 1997, 7, 571-588.
9. Traxler, P.; Furet, P. Strategies toward the design of novel and selective protein tyrosine kinase inhibitors. Pharmacol. Ther. 1999, 82, 195-206.
10. Traxler, P.; Furet, P.; Mett, H.; Buchdunger, E.; Meyer, T.; Lydon, N. 4-(Phenylamino)pyrrolopyrimidines: potent and selective, ATP site directed inhibitors of the EGF-receptor protein tyrosine kinase. J. Med. Chem. 1996, 38, 2285-2292.
11. Traxler, P.; Bold, G.; Frei, J.; Lang, M.; Lydon, N.; Mett, H.; Buchdunger, E.; Meyer, T.; Mueller, M.; Furet, P. Use of a pharmacophore model for the design of EGF-R tyrosine kinase inhibitors: 4-(phenylamino)pyrazolo-pyrimidines. J. Med. Chem. 1997, 40, 3601-3616.
12. Traxler, P.; Green, J.; Mett, H.; Sequin, U.; Furet, P. Use of a pharmacophore model for the design of EGFR tyrosine kinase inhibitors: isoflavones and 3-phenyl-4(1H)-quinolones J. Med. Chem. 1999, 42, 1018-1026.
13. Rewcastle, G. W.; Denny, W. A.; Bridges, A. J.; Zhou, H.; Cody, D. R.; McMichael, A.; Fry, D. W. Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-(phenylmethyl-amino)-and 4-(phenylamino) quinazolines as potent adenosine 5'-triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth factor receptor. J. Med. Chem. 1995, 38, 3482-3487.
14. Showalter, H.; Sercel, A.; Leja, B. Tyrosine kinase inhibitors. 6. Structure- activity relationships among N- and 3-substituted 2,2'-diselenobis (1H-indoles) for inhibition of protein tyrosine kinases and comparative in vitro and in vivo studies against selected sulfur congeners. J. Med. Chem. 1997, 40, 413-426.
15. Thompson, A. M.; Bridges, A. J.; Fry, D. W.; Kraker, A. J.; Denny, W. A. Tyrosine kinase inhibitors. 7. 7-amino-4-(phenylamino)- and 7-amino-4-[(phenyl-methyl)amino-]pyrido[4,3-d] pyrimidines: A new class of inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor. J. Med. Chem. 1995, 38, 3780-3788.
16. Bridges, A.; Zhou, H.; Cody, D. Tyrosine kinase inhibitors. 8. An unusually steep structure-activity relationship for analogues of 4-(3-bromoanilino)-6, 7-dimethoxyquinazoline (PD 153035), a potent inhibitor of the epidermal growth factor receptor. J. Med. Chem. 1996, 39, 267-276.
17. Rewcastle, G. W.; Palmer, B. D.; Bridges, A. J.; Showalter, H. D.; Sun, L.; Nelson, J. M.; McMichael, A.; Kraker, A. J.; Fry, D. W.; Denny, W. A. Tyrosine kinase inhibitors. 9. Synthesis and evaluation of fused tricyclic quinazolines analogues as ATP site inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor. J. Med. Chem. 1996, 39, 918-928.
18. Rewcastle, G. W.; Palmer, B. D.; Thompson, A. M.; Bridges, A. J.; Cody, D. R.; Zhou, H.; Fry, D. W.; McMicheal, A.; Kraker, A. J.; Denny, W. A. Tyrosine kinase inhibitors. 10. Isomeric 4-[(3-bromophenyl)-amino]pyrido[d]-pyrimidines are potent ATP binding site inhibitors of the tyrosine kinase function of the epidermal growth factor receptor. J. Med. Chem. 1996, 39, 1823-1935.
19. Palmer, B.; Trumpp-Kallmeyer, S.; Fry, D. Tyrosine kinase inhibitors. 11. soluble analogues of pyrrolo- and pyrazoloquinazolines as epidermal growth factor receptor inhibitors: synthesis, biological evaluation, and modeling of the mode of binding. J. Med. Chem. 1997, 40, 1519-1529.
20. Rewcastle, G.; Bridges, A.; Fry, D. Tyrosine kinase inhibitors. 12. synthesis and structure-activity relationships for 6-substituted 4-(phenylamino)pyrimido[5, 4-d]pyrimidines designed as inhibitors of the epidermal growth factor receptor. J. Med. Chem. 1997, 40, 1820-1826.
21. Thompson, A.; Murray, D.; Elliott, W. Tyrosine kinase inhibitors. 13. structure-activity relationships for soluble 7-substituted 4-[(3-bromophenyl)amino]pyrido[4,3-d]pyrimidines designed as inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor. J. Med. Chem. 1997, 40, 3915-3925.
22. Rewcastle, G.; Murray, D.; Elliott, W. Tyrosine kinase inhibitors. 14. structure -activity relationships for methyl-amino-substituted derivatives of 4-[(3-bromo-phenyl)amino]-6-(methylamino)-pyrido[3,4-d]-pyrimidine (PD 158780), a potent and specific inhibitor of the tyrosine kinase activity of receptors for the EGF family of growth factors. J. Med. Chem. 1998, 41, 742-751.
23. Smaill, J.; Palmer, B.; Rewcastle, G. Tyrosine kinase inhibitors. 15. 4-(phenylamino)quinazoline and 4-(phenylamino)pyrido[d]pyrimidine acrylamides as irreversible inhibitors of the ATP binding site of the epidermal growth factor receptor. J. Med. Chem. 1999, 42, 1803-1815.
24. Showalter, H.; Gridges, A.; Zhou, H. Tyrosine kinase inhibitors. 16. 6,5,6-tricyclic bnzothieno[3, 2-d]pyrimidines and primido[5, 4-b]- and -[4,5-b]indoles as potent inhibitors of the epidermal growth factor receptor Tyrosine Kinase. J. Med. Chem. 1999, 42, 5464-5474.
25. Smaill, J.; Showatle, H. Tyrosine kinase inhibitors. 17. Irreversible inhibitors of the epidermal growth factor receptor: 4-(phenylamino)-quinazoline- and 4-(phenylamino)pyrido[3,2-d]pyrimidine-6-acrylamides bearing additional solubilizing functions. J. Med. Chem. 2000, 43, 1380-1397.
26. Smaill, J.; Showalte, H.; Zhou, H. Tyrosine kinase inhibitors. 18. 6-substituted 4-anilinoquinazolines and 4-anilinopyrido[3,4-d]pyrimidines as soluble, irreversible inhibitors of the epidermal growth factor receptor. J. Med. Chem. 2001, 44, 429-440.
27. Walters, D. E.; Hinds, R. M. Genetically evolved receptor models: A computational approach to construction of receptor models. J. Med. Chem. 1994, 37, 2527-2536.
28. Chen, H.; Zhou, J.; Xei, G. PARM: A genetic evolved algorithm to predict bioactivity. J. Chem. Inf. Comput. Sci. 1998, 38, 243-250.
29. Pei, J.; Zhou, J.; Xie, G.; Chen, H.; He, X. PARM: A practical utility for drug design. J. Mol. Graph. Model. 2001, 19, 448-454.
30. Pei, J.; Zhou, J. Flexible atom receptor model (FLARM). Acta Chim. Sinica 2002, 60, 973-979.
31. Sybyl, version 6.5; Tripos Associates: St. Louis, MO, 1998.
32. Furet, P.; Caravatti, G.; Lydon, N.; Priestle, J.; Sowadski, J.; Trinks, U.; Traxler, P. Modeling study of protein kinase inhibitors: binding mode of staurosporine - origin of the selectivity of CGP 52411. J. Comput. Aided Mol. Des. 1995, 9, 465-471.
33. Lawie, A. M.; Noble, M. E. M.; Tunnah, P.; Brown, N. R.; Johnson, L. N. Endicott, J. A. Protein kinase inhibition by staurosporine revealed in details of the molecular interaction with CDK2. Nature Struct. Biol. 1997, 4, 796-801.