Discovering novel 3-nitroquinolines as a new class of anticancer agents

Acta Pharmacologica Sinica

Volumn 29, Issue 12, 2008, Pages 1529-1538

  Li, Hai Hong ^a   Huang, He ^a   Zhang, Xiu Hua ^b   Luo, Xiao Min ^a   Lin, Li Ping ^b   Jiang, Hua Liang ^a   Ding, Jian ^b   Chen, Kai Xian ^a   Liu, Hong ^a  

^a INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

3 nitroquinoline; Epidermal growth factor receptor; Inhibitor; Molecular modeling; Tyrosine kinase

Indexed keywords

3 NITROQUINOLINE DERIVATIVE; 4 (3 BROMOANILINO) 6,7 DIMETHOXYQUINAZOLINE; ANTINEOPLASTIC AGENT; EPIDERMAL GROWTH FACTOR RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; ERLOTINIB; GEFITINIB; LAPATINIB; NITROQUINOLINE DERIVATIVE; NQ 10; NQ 11; NQ 12; NQ 13; NQ 14; NQ 15; NQ 16; NQ 17; NQ 18; NQ 19; NQ 2; NQ 20; NQ 21; NQ 3; NQ 4; NQ 5; NQ 6; NQ 7; SULFORHODAMINE B; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BREAST CANCER; CANCER CELL; CARCINOMA CELL; CELL PROLIFERATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG DESIGN; DRUG DETERMINATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME BINDING; HUMAN; HUMAN CELL; IC 50; PROTEIN EXPRESSION; RECEPTOR BLOCKING; SQUAMOUS CELL CARCINOMA; STRUCTURE ACTIVITY RELATION; TUMOR CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYME ACTIVE SITE; METABOLISM; PROTEIN CONFORMATION; SYNTHESIS;

ANTINEOPLASTIC AGENTS; CATALYTIC DOMAIN; CELL LINE, TUMOR; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NITROQUINOLINES; PROTEIN CONFORMATION; RECEPTOR, EPIDERMAL GROWTH FACTOR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 64549100779     PISSN: 16714083     EISSN: 17457254     Source Type: Journal    
DOI: 10.1111/j.1745-7254.2008.00907.x     Document Type: Article

References (28)

1. David WF. Inhibition of the epidermal growth factor receptor family of tyrosine kinases as an approach to cancer chemotherapy: progression from reversible to irreversible inhibitors. Pharmacol Ther 1999; 82: 207-18.
2. Hickey K, Grehan D, Reid IM, O'Briain S, Walsh TN, Hennessy TPJ. Expression of epidermal growth factor receptor and proliferating cell nuclear antigen predicts response of esophageal squamous cell carcinoma to chemoradiotherapy. Cancer 1994; 74: 1693-8.
3. Wells A. EGF receptor. Int J Biochem Cell Biol 1999; 31: 637-43.
4. Delarue JC, Terrier P, Terrier-Lacombe MJ, Mouriesse H, Gotteland M, May-Levin F. Combined overexpression of c-erbB-2 protein and epidermal growth factor receptor (EGFR) could be predictive of early and long-term outcome in human breast cancer: a pilot study. Bull Cancer 1994; 81: 1067-77.
5. Antonello A, Tarozzi A, Morroni F, Cavalli A, Rosini M, Hrelia P, et al. Multitarget-directed drug design strategy: a novel molecule designed to block epidermal growth factor receptor (EGFR) and to exert proapoptotic effects. J Med Chem 2006; 49: 6642-5.
6. Fry DW, Kraker AJ, McMichael A, Ambroso LA, Nelson JM, Leopold WR, et al. Specifc inhibitor of the epidermal growth factor receptor tyrosine kinase. Science 1994; 265: 1093-5.
7. Ward WHJ, Cook PN, Slater AM, Davies DH, Holdgate GA, Green LR. Epidermal growth factor receptor tyrosine kinase. Investigation of catalytic mechanism, structure based searching and discovery of a potent inhibitor. Biochem Pharmacol 1994; 48: 659-66.
8. Rusnak DW, Lackey K, Affeck K, Wood ER, Alligood KJ, Rhodes N, et al. The effects of the novel, reversible epidermal growth factor receptor/erbB-2 tyrosine kinase inhibitor, GW2016, on the growth of human normal and tumor-derived cell lines in vitro and in vivo. Mol Cancer Ther 2001; 1: 85-94.
9. Domarkas J, Dudouit F, Williams C, Qiyu Q, Banerjee R, Brahimi F, et al. The combi-targeting concept: synthesis of stable nitrosoureas designed to inhibit the epidermal growth factor receptor (EGFR). J Med Chem 2006; 49: 3544-52.
10. Mishani E, Abourbeh G, Jacobson O, Dissoki S, Daniel RB, Rozen Y, et al. High-affinity epidermal growth factor receptor (EGFR) irreversible inhibitors with diminished chemical reactivities as positron emission tomography (PET)-imaging agent candidates of EGFR overexpressing tumors. J Med Chem 2005; 48: 5337-48.
11. Rewcastle GW, Palmer BD, Thompson AM, Bridges AJ, Cody DR, Zhou H, et al. 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: 1823-35.
12. Rewcastle GW, Bridges AJ, Fry DW, Rubin JR, Denny WA. 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: 1820-6.
13. Norman MH, Kelly JL, Hollingsworth EB. Conformationally restricted analogues of remoxipride as potential antipsychotic agents. J Med Chem 1993; 36: 3417-23.
14. Hodge CN, Pierce J. A diazine heterocycle replaces a six-membered hydrogen-bonded array in the active site of scytalone dehydratase. Bioorg Med Chem Lett 1993; 3: 1605-8.
15. Asano T, Yoshikawa T, Usui T, Yamamoto H, Yamamoto Y, Uehara Y, et al. Benzamides and benzamidines as specific inhibitors of epidermal growth factor receptor and v-Src protein tyrosine kinases. Bioorg Med Chem 2004; 12: 3529-42.
16. erbB) tyrosine kinases. Bioorg Med Chem Lett 2002; 12: 2153-7.
17. Hunt JT, Mitt T, Borzilleri R, Gullo-Brown J, Fargnoli J, Fink B, et al. Discovery of the pyrrolo[2,1-f][1,2,4]triazine nucleus as a new kinase inhibitor template. J Med Chem 2004; 47: 4054-9.
18. Thompson AM, Bridges AJ, Fry DW, Kraker AJ, Denny WA. Tyrosine kinase inhibitors 7: 7-amino-4-(phenylamino)- and 7-amino- 4-[(phenylmethyl)amin-o]- 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: 3780-8.
19. Rewcastle GW, Palmer BD, Bridges AJ, Showalter HDH, Sun L, Nelson J, et al. Tyrosine kinase inhibitors 9: Synthesis and evaluation of fused tricyclic quinazoline analogues as ATP site inhibitors of the tyrosine kinase activity of the epidermal growth factor receptor. J Med Chem 1996; 39: 918-28.
20. Cohen MH, Williams GA, Sridhara R, Chen G, McGuinn WD Jr, Morse D, et al. United States Food and Drug Administration Drug Approval summary: geftinib (ZD1839; Iressa) tablets. Clin Cancer Res 2004; 10: 1212-8.
21. Johnson JR, Cohen M, Sridhara R, Chen YF, Williams GM, Duan J, et al. Approval summary for erlotinib for treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of at least one prior chemotherapy regimen. Clin Cancer Res 2005; 11: 6414-21.
22. Harari PM, Allen GW, Bonner JA. Biology of interactions: antiepidermal growth factor receptor agents. J Clin Oncol 2007; 25: 4057-65.
23. Stamos J, Sliwkowski MX, Eigenbrot C. Structure of the epidermal growth factor receptor kinase domain alone and in complex with a 4-anilinoquinazoline inhibitor. J Biol Chem 2002; 277: 265-72.
24. Wissner A, Berger DM, Boschelli DH, Floyd MBJ, Greenberger LM, Gruber BC, et al. 4-Anilino-6,7-dialkoxyquinoline-3-carbonitrile inhibitors of epidermal growth factor receptor kinase and their bioisosteric relationship to the 4-anilino-6,7-dialkoxyquinazoline inhibitors. J Med Chem 2000; 43: 3244-56.
25. Shewchuk L, Hassell A, Wisely B, Rocque W, Holmes W, Veal J, et al. Binding mode of the 4-anilinoquinazoline class of protein kinase inhibitor: X-ray crystallographic studies of 4-anilinoquinazolines bound to cyclin-dependent kinase 2 and p38 kinase. J Med Chem 2000; 43: 133-8.
26. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, et al. Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function. J Comput Chem 1998; 19: 1639-62.
27. Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, et al. Autodock. Version 3.0.3. La Jolla, CA: The Scripps Research Institute; 1999.
28. Althuis TH, Hess HJ. Synthesis and identification of the major metabolites of prazosin formed in dog and rat. J Med Chem 1977; 20: 146-9.