Synthesis of quinazolines as tyrosine kinase inhibitors

Anti-Cancer Agents in Medicinal Chemistry

Volumn 9, Issue 3, 2009, Pages 246-275

  Srivastava, Sanjay K ^a   Kumar, Vivek ^a   Agarwal, Shiv K ^a   Mukherjee, Rama ^a   Burman, Anand C ^a  

^a DABUR RESEARCH FOUNDATION   (India)

Author keywords

[No Author keywords available]

Indexed keywords

3 METHYL 4 NITROBENZOIC ACID; 4 (3 BROMOPHENYL) AMINO QUINAZOLINE; 4 (PHENYLAMINO) QUINAZOLINE DERIVATIVE; 4 ANILINOPYRIDOL; 4 ANILINOQUINAZOLINE; 4 ANILINOQUINOLINE DERIVATIVE; 4 CHLORO 6,7 DIMETHOXY QUINAZOLINE; 4 CHLOROQUINAZOLINE; 6 AMINO 1H INDOLE 5 CARBOXYLIC ETHYL ESTER; 6 NITRO 4 (3 BROMOPHENYLAMINO) QUINAZOLINE; 6,7 DIMETHOXY ANTHRANILIC ACID; 6,7 DIMETHOXY QUINAZOLONE; 7 AMINO 6 NITROQUINAZOLINE; 7 BENZYLOXY 3,4 DIHYDROQUINAZOLIN 4 ONE; 7 FLUORO 6 NITROQUINAZOLINONE; CANERTINIB; CT 52923; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; GEFITINIB; GW 974; IMIDAZOLOQUINAZOLINE; KN 734; PLATELET DERIVED GROWTH FACTOR RECEPTOR; PROTEIN TYROSINE KINASE INHIBITOR; PYRIDOPYRIMIDINE DERIVATIVE; PYRROLOQUINAZOLINE DERIVATIVE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG; VASCULOTROPIN INHIBITOR; VASCULOTROPIN RECEPTOR 2;

ALKYLATION; ANTINEOPLASTIC ACTIVITY; CANCER GROWTH; CELL PROLIFERATION; CYTOTOXICITY; DRUG ABSORPTION; DRUG BIOAVAILABILITY; DRUG BLOOD LEVEL; DRUG DETERMINATION; DRUG HALF LIFE; DRUG INHIBITION; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; GROWTH INHIBITION; HUMAN; IC 50; NONHUMAN; PHOSPHORYLATION; REVIEW; STRUCTURE ACTIVITY RELATION;

EID: 65549111254     PISSN: 18715206     EISSN: None     Source Type: Journal    
DOI: 10.2174/1871520610909030246     Document Type: Review

References (53)

1. Jaracz, S.; Chen, J.; Kuznetsova, L.V.; Ojima, I. Recent advances in tumor-targeting anticancer drug conjugates. Bioorg. Med. Chem., 2005, 13, 5043.
2. http://en.wikipedia.org/wiki/Taxol
3. Mukherjee, R.; Kumar, V.; Srivastava, S.K.; Agarwal, S.K.; Burman, A.C. Betulinic acid derivatives as anticancer agents: structure activity relationship. Anti-Cancer Agents Med. Chem., 2006, 6(3), 271.
4. Morin, M.J. From oncogene to drug development of small molecule tyrosine kinase inhibitors as anti-tumor and anti-angiogenic agents. Oncogene, 2000, 19(56), 6574.
5. Bridges, A.J. Chemical inhibitors of protein kinases. Chem. Rev., 2001, 101(8), 2541.
6. Verma, A.; Panigrahi, S.K.; Rambabu, G.; Gopalakrishnan, B.; Sarma, J.A.R.P.; Desiraju, G.R. Design of EGFR kinase inhibitors: a ligand-based approach and its confirmation with structure-based studies. Bioorg. Med. Chem., 2003, 11(21), 4643.
7. Jin, Y.; Li, H.Y.; Lin, L.P.; Tan, J.; Ding, J.; Luo, X.; Long, Y.Q. Synthesis and antitumor evaluation of novel 5-substituted-4-hydroxy-8-nitroquinazolines as EGFR signaling-targeted inhibitors. Bioorg. Med. Chem., 2005, 13(19), 5613.
8. Wissner, A.; Floyd, M.B.; Johnson, B.D.; Fraser, H.; Ingalls, C.; Nittoli, T.; Dushin, R.G.; Discafani, C.; Nilakantan, R.; Marini, J.; Ravi, M.; Cheung, K.; Tan, X.; Musto, S.; Annable, T.; Siegel, M.M.; Loganzo, F. 2-(Quinazolin-4-ylamino)-[1,4]benzoquinones as covalent-binding, irreversible inhibitors of the kinase domain of vascular endothelial growth factor receptor-2. J. Med. Chem., 2005, 48(24), 7560.
9. Heath, J.A.; Mehrotra, M.M.; Chi, S.; Yu, J.C.; Hutchaleelaha, A.; Hollenbach, S.J.; Giese, N.A.; Scarborough, R.M.; Pandey, A. Identification of 4-piperazin-1-yl-quinazoline template based aryl and benzyl thioureas as potent, selective, and orally bioavailable inhibitors of platelet-derived growth factor (PDGF) receptor. Biorg. Med. Chem. Lett., 2004, 14(19), 4867.
10. Pandey, A.; Volkots, D.L.; Seroogy, J.M.; Rose, J.W.; Yu, J.C.; Lambing, J. L.; Hutchaleelaha, A.; Hollenbach, S.J.; Abe, K.; Giese, N.A.; Scarborough, R.M. Identification of orally active, potent, and selective 4-piperazinylquinazolines as antagonists of the platelet-derived growth factor receptor tyrosine kinase family. J. Med. Chem., 2002, 45, 3772.
11. Bridges, A.J.; Cody, D.R.; Zhou, H.; McMichael, A.; Fry, David W. Potent and selective inhibitors of platelet-derived growth factor receptor phosphorylation. Part 4: structure-activity relationships for substituents on the quinazoline moiety of 4-[4-(N-substituted(thio) carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives. Bioorg. Med. Chem., 1995, 3(12), 1651.
12. Bridges, A.J.; Zhou, H.; Cody, D.R.; Rewcastle, G.W.; McMichael, A.; Showalter, H.D.H.; Fry, D.W.; Kraker, A.J.; Denny, W.A. Enantioselective inhibition of the epidermal growth factor receptor tyrosine kinase by 4-(alpha-phenethylamino) quinazolines. J. Med. Chem., 1996, 39(1), 267.
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(18), 3482.
14. Fry, D.W.; Kraker, A.J.; McMichael, A.; Ambroso, L.A.; Nelson, J.M.; Leopold, W.R.; Connors, R.W.; Bridges, A.J. A specific inhibitor of the epidermal growth factor receptor tyrosine kinase. Science, 1994, 265, 1093.
15. Rewcastle, G.W.; Palmer, B.D.; Bridges, A.J.; Showalter, H.D.H.; Sun, L.; Nelson, J.; McMichael, A.; Kraker, A.J.; Fry, D.W.; Denny, W.A. 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(4), 918.
16. Palmer, B.D.; Trumpp-Kallmeyer, S.; Fry, D.W.; Nelson, J.M.; Showalter, H.D.H.; Denny, W.A. 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(10), 1519.
17. Showalter, H.D.H.; Sun, L.; Sercel, A.D.; Winters, R.T.; Denny, W.A.; Palmer, B.D. Concise syntheses of the novel 1 H-Pyrrolo[3,2-g]quinazoline ring system and its [2,3-f] angular isomer. J. Org. Chem., 1996, 61(3), 1155.
18. lck and EGF-R tyrosine kinase activity. Biorg. Med. Chem. Lett., 1997, 7(4), 417.
19. Myers, M.R.; Spada, A.P.; Maguire, M.P.; Persons, P.E.; Zilberstein, A.; Hsu, C.Y.; Johnson, S. Aryl and heteroaryl quinazoline compounds which inhibit csf-1r receptor tyrosine kinase. WO Patent 9515758, June 15, 1995.
20. Gibson, K.H.; Grundy, W.; Godfrey, A.A.; Woodburn, J.R.; Ashton, S.E.; Curry, B.J.; Scarlett, L.; Barker, A.J.; Brown, D.S. Epidermal growth factor receptor tyrosine kinase: Structure-activity relationships and antitumour activity of novel quinazolines. Bioorg. Med. Chem. Lett., 1997, 7(21), 2723.
21. Smaill, J.B.; Palmer, B.D.; Rewcastle, G.W.; Denny, W.A.; McNamara, D.J.; Dobrusin, E.M.; Bridges, A.J.; Zhou, H.; Showalter, H.D.H.; Winters, R.T.; Leopold, W.R.; Fry, D.W.; Nelson, J.M.; Slintak, V.; Elliot, W.L.; Roberts, B.J.; Vincent, P.W.; Patmore, S.J. 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.
22. Fry, D.W.; Bridges, A.J.; Denny, W.A.; Doherty, A.; Gries, K.D.; Hicks, J.L.; Hook, K.E.; Keller, P.R.; Leopold, W.R.; Loo, J.A.; McNamara, D.J.; Nelson, J.M.; Sherwood, V.; Smaill, J.B.; Trumpp-Kallmeyer, S.; Dobrusin, E.M. Specific, irreversible inactivation of the epidermal growth factor receptor and erbB2, by a new class of tyrosine kinase inhibitor. Proc. Natl. Acad. Sci. USA, 1998, 95, 12022.
23. Morley, J.S.; Simpson, J.C.E. The chemistry of simple heterocyclic systems. Part I. Reactions of 6- and 7-nitro-4-hydroxyquinazoline and their derivatives. J. Chem. Soc., 1948, 360.
24. Rewcastle, G.W.; Palmer, B.D.; Thompson, A.M.; Bridges, A.J.; Cody, D.R.; Zhou, H.; Fry, D.W.; 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(9), 1823.
25. Rewcastle, G.W.; Murray, D.K.; Elliott, W.L.; Fry, D.; Howard, C.T.; Nelson, J.M.; Roberts, B.J.; Vincent, P.W.; Showalter, H.D.H.; Winters, R. T.; Denny, W.A. Tyrosine kinase inhibitors. 14. Structure-activity relationships for methylamino-substituted derivatives of 4-[(3-bromophenyl)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(5), 742.
26. Smaill, J.B.; Rewcastle, G.W.; Loo, J.A.; Greis, K.D.; Chan, O.H.; Reyner, Eric L.; Lipka, E.; Showalter, H.D.H.; Vincent, P.W.; Elliott, W.L.; Denny, W.A. 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(7), 1380.
27. Smaill, J.B.; Showalter, H.D.H.; Zhou, H.; Bridges, A.J.; McNamara, D.J.; Fry, D.W.; Nelson, J.M.; Sherwood, V.; Vincent, P.W.; Roberts, B.J.; Elliott, W.L.; Denny, W.A. 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(3), 429.
28. Tsou, H.R.; Mamuya, N.; Johnson, B.D.; Reich, M.F.; Gruber, B.C.; Ye, F.; Nilakantan, R.; Shen, R.; Discafani, C.; DeBlanc, R.; Davis, R.; Koehn, F.E.; Greenberger, L.M.; Wang, Y.F.; Wissner, A. 6-Substituted-4-(3-bromophenylamino)quinazolines as putative irreversible inhibitors of the epidermal growth factor receptor (EGFR) and human epidermal growth factor receptor (HER-2) tyrosine kinases with enhanced antitumor activity. J. Med. Chem., 2001, 44(17), 2719.
29. Wissner, A.; Johnson, B.D.; Floyd, M.B.; Kitchen, D.B. 4-amino-quinazoline EGFR Inhibitors. US Patent 5760041, June 02, 1998.
30. Discafani, C.M.; Carroll, M.L.; Floyd, M.B., Jr.; Hollander, I.J.; Husain, Z.; Johnson, B.D.; Kitchen, D.; May, M.K.; Malo, M.S.; Minnick, A.A., Jr.; Nilakantan, R.; Shen, R.; Wang, Y.F.; Wissner, A.; Greenberger, L.M. Irreversible inhibition of epidermal growth factor receptor tyrosine kinase with in vivo activity by N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-2-butynamide (CL-387,785). Biochem. Pharmacol., 1999, 57, 917.
31. Denny, W.A.; Rewcatsle, G.W.; Bridges, A.J.; Fry, D.W.; Kraker, A.J. Structure-activity relationships for 4-anilinoquinazolines as potent inhibitors at the ATP binding site of the epidermal growth factor receptor in vitro. Clin. Exp. Pharmacol. Physiol., 1996, 23, 424.
32. Barker, A.J.; Gibson, K.H.; Grundy, W.; Godfrey, A.A.; Barlow, J.J.; Healy, M.P.; Woodburn, J.R.; Ashton, S.E.; Curry, B.J.; Scarlett, L. Studies leading to the identification of ZD1839 (IRESSA): an orally active, selective epidermal growth factor receptor tyrosine kinase inhibitor targeted to the treatment of cancer. Bioorg. Med. Chem. Lett., 2001, 11(14), 1911.
33. Barker, A.J.; Davies, J.H. Therapeutic preparations containing quinazoline derivatives. E. Patent 0520722, Dec 27, 1996.
34. Cockerill, S.; Stubberfield, C.; Stables, J.; Carter, M.; Guntrip, S.; Smith, K.; McKeown, S.; Shaw, R.; Topley, P.; Thomsen, L. Indazolylamino quinazolines and pyridopyrimidines as inhibitors of the EGFr and C-erbB-2. Bioorg. Med. Chem. Lett., 2001, 11(11), 1401.
35. Albuschat, R.; Löwe, W.; Weber, M.; Luger, P.; Jendrossek, V. 4-Anilinoquinazolines with Lavendustin A subunit as inhibitors of epidermal growth factor receptor tyrosine kinase: syntheses, chemical and pharmacological properties. E. J. Med. Chem., 2004, 39 (12), 1001.
36. Onoda, T.; Iinuma, H.; Sasaki, Y.; Hamada, M.; Isshiki, K.; Naganawa, H.; Takeuchi, T.; Tatsuta, K.; Umezawa, K. Isolation of a Novel Tyrosine Kinase Inhibitor, Lavendustin A, from Streptomyces griseolavendus. J. Nat. Prod., 1989, 52(6), 1252.
37. Wang, S.; Yang, D.; Enyedy, I. Erbb-2 selective small molecule kinase inhibitors. U.S. Patent 4023957A1, Feb 05, 2004.
38. Ballard, P.; Bradbury, R.H.; Hennequin, L.F.A.; Hickinson, D.M.; Johnson, P.D.; Kettle, J.G.; Klinowska, T.; Morgentin, R.; Ogilvie, D.J.; Olivier, A. 5-Substituted 4-anilinoquinazolines as potent, selective and orally active inhibitors of erbB2 receptor tyrosine kinase. Bioorg. Med. Chem. Lett., 2005, 15(19), 4226.
39. Brown, D.S.; Morris, J.J.; Thomas, A. P. Aniline derivatives. WO Patent 9615118, May 23, 1996.
40. Ballard, P.; Bradbury, R.H.; Harris, C.S.; Hennequin, L.F.A.; Hickinson, M.; Johnson, P.D.; Kettle, J.G.; Klinowska, T.; Leach, A.G.; Morgentin, R. Inhibitors of epidermal growth factor receptor tyrosine kinase: Novel C-5 substituted anilinoquinazolines designed to target the ribose pocket. Biorg. Med. Chem. Lett., 2006, 16(6) 1633.
41. Hennequin, L.F.; Thomas, A.P.; Johnstone, C.; Stokes, E.S.E.; Plé, P.A.; Lohmann, J.M.; Ogilvie, D.J.; Dukes, M.; Wedge, S.R.; Curwen, J.O.; Kendrew, J.; Brempt, C.L. Design and structure-activity relationship of a new class of potent VEGF receptor tyrosine kinase inhibitors. J. Med. Chem., 1999, 42(26), 5369.
42. Althuis, T.H.; Hess, H.J. Synthesis and identification of the major metabolites of prazosin formed in dog and rat. J. Med. Chem., 1977, 20, 146.
43. Hennequin, L.F.; Stokes, E.S.E.; Thomas, A.P.; Johnstone, C.; Plé, P.A.; Ogilvie, D.J.; Dukes, M.; Wedge, S.R.; Kendrew, J.; Curwen, J.O. Novel 4-anilinoquinazolines with C-7 basic side chains: design and structure activity relationship of a series of potent, orally active, VEGF receptor tyrosine kinase inhibitors. J. Med. Chem., 2002, 45(6), 1300.
44. Barker, A. J.; Brown, D.S. Quinazoline derivatives. EP602851, Oct 09, 1996.
45. Matsuno, K.; Ichimura, M.; Nakajima, T.; Tahara, K.; Fujiwara, S.; Kase, H.; Ushiki, J.; Giese, N.A.; Pandey, A.; Scarborough, R.M.; Lokker, N.A.; Yu, J.; Irie, J.; Tsukuda, E.; Ide, S.; Oda, S.; Nomoto, Y. J. Med. Chem., 2002, 45(14), 3057.
46. Matsuno, K.; Ichimura, M.; Nomoto, Y.; Fujiwara, S.; Ide, S.-i.; Tsukuda, E.; Irie, J.; Oda, S. Chem. Abstr., 1998, 128, 257447.
47. Cronin, T.H.; Hess, H.J.E. South Africa Patent Appl. No. 676512, Oct 31, 1967; Chem. Abst., 1969, 70, 68419.
48. Pandey, A.; Volkots, D.L.; Seroogy, J.M.; Rose, J.W.; Yu, J.; Lambing, J.L. Hutchaleelaha, A.; Hollenbach, S.J.; Abe, K.; Giese, N.A.; Scarborough, R.M. Identification of orally active, potent, and selective 4-piperazinylquinazolines as antagonists of the platelet-derived growth factor receptor tyrosine kinase family. J. Med. Chem., 2002, 45 (17), 3772.
49. Yu, J.C.; Lokker, N.A.; Hollenbach, S.; Apatira, M.; Li, J.; Betz, A.; Sedlock, D.; Oda, S.; Nomoto, Y.; Matsuno, K.; Ide, S.I.; Tsukuda, E.; Giese, N.A. Efficacy of the novel selective platelet-derived growth factor receptor antagonist CT52923 on cellular proliferation, migration, and suppression of neointima following vascular injury. J. Pharmacol. Exp. Ther., 2001, 298, 1172.
50. Giese, N.A.; Lokker, N.A.; Yu, J.C.; Matsuno, K.; Ichimura, M.; Oda, S.; Scarborough, R. M.; Pandey, A. Development of antagonists of the platelet-derived growth factor receptor family. Oncol. Spectr., 2001, 2, 550.
51. Matsuno, K.; Nakajima, T.; Ichimura, M.; Giese, N.A.; Yu, J.; Lokker, N.A.; Ushiki, J.; Ide, S.; Oda, S.; Nomoto, Y. Potent and selective inhibitors of PDGF receptor phosphorylation. 2. Synthesis, structure activity relationship, improvement of aqueous solubility, and biological effects of 4-[4-(N-substituted (thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives. J. Med. Chem., 2002, 45, 4513.
52. Matsuno, K.; Ushiki, J.; Seishi, T.; Ichimura, M.; Giese, N.A.; Yu, J.; Takahashi, S.; Oda, S.; Nomoto, Y. Potent and selective inhibitors of platelet-derived growth factor receptor phosphorylation. 3. replacement of quinazoline moiety and improvement of metabolic polymorphism of 4-[4-(N-substituted (thio)carbamoyl)-1-piperazinyl]-6,7-dimethoxyquinazoline derivatives. J. Med. Chem., 2003, 46(23), 4910.
53. Matsuno, K.; Seishi, T.; Nakajima, T.; Ichimura, M.; Giese, N.A.; Yu, J.; Oda, S.; Nomoto, Y. Potent and selective inhibitors of platelet-derived growth factor receptor phosphorylation. Part 4: structure-activity relationships for substituents on the quinazoline moiety of