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Volumn 39, Issue 1, 1996, Pages 267-276

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

Author keywords

[No Author keywords available]

Indexed keywords

4 (3 BROMOANILINO) 6,7 DIMETHOXYQUINAZOLINE; DRUG ANALOG; ENZYME INHIBITOR; EPIDERMAL GROWTH FACTOR RECEPTOR; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE;

EID: 0030039555     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9503613     Document Type: Article
Times cited : (340)

References (36)
  • 1
    • 0028017791 scopus 로고
    • Signalling targets for the development of cancer drugs
    • Powis, G.; Workman, P. Signalling targets for the development of cancer drugs. Anti-Cancer Drug Des. 1994, 5, 263-277.
    • (1994) Anti-Cancer Drug Des. , vol.5 , pp. 263-277
    • Powis, G.1    Workman, P.2
  • 3
    • 0026005833 scopus 로고
    • Evidence for the involvement of transforming growth factor a and epidermal growth factor receptor autocrine growth mechanism in primary human ovarian cancers in vitro
    • Morishige, K.; Kurachi, H.; Amemiya, K.; Fujita, Y.; Yamamoto, T.; Miyake, A.; Tanizawa, O. Evidence for the involvement of transforming growth factor a and epidermal growth factor receptor autocrine growth mechanism in primary human ovarian cancers in vitro. Cancer Res. 1991, 51, 5322-5328.
    • (1991) Cancer Res. , vol.51 , pp. 5322-5328
    • Morishige, K.1    Kurachi, H.2    Amemiya, K.3    Fujita, Y.4    Yamamoto, T.5    Miyake, A.6    Tanizawa, O.7
  • 4
    • 0027787632 scopus 로고
    • Neu (c-erbB-2/ HER2) and the epidermal growth factor receptor (EGFR) in breast cancer
    • Jardines, L.; Weiss, M.; Fowble, B.; Greene, M. Neu (c-erbB-2/ HER2) and the epidermal growth factor receptor (EGFR) in breast cancer. Pathobiology 1993, 61, 268-282.
    • (1993) Pathobiology , vol.61 , pp. 268-282
    • Jardines, L.1    Weiss, M.2    Fowble, B.3    Greene, M.4
  • 5
    • 0027930576 scopus 로고
    • Expression of epidermal growth factor receptor and proliferating cell nuclear antigen predicts response of esophageal squamous cell carcinoma to chemoradiotherapy
    • Hickey, K.; Grehan, D.; Reid, I. M.; O'Brian, S.; Walsh, T. N.; Hennessy, T. P. J. Expression of epidermal growth factor receptor and proliferating cell nuclear antigen predicts response of esophageal squamous cell carcinoma to chemoradiotherapy. Cancer 1994, 74, 1693-1698.
    • (1994) Cancer , vol.74 , pp. 1693-1698
    • Hickey, K.1    Grehan, D.2    Reid, I.M.3    O'Brian, S.4    Walsh, T.N.5    Hennessy, T.P.J.6
  • 6
    • 77956809966 scopus 로고
    • Protein tyrosine kinases and cancer
    • Dobrusin, E. M.; Fry, D. W. Protein tyrosine kinases and cancer. Annu. Rep. Med. Chem. 1992, 27, 169-178.
    • (1992) Annu. Rep. Med. Chem. , vol.27 , pp. 169-178
    • Dobrusin, E.M.1    Fry, D.W.2
  • 7
    • 0026454471 scopus 로고
    • Protein-tyrosine kinase inhibition: Mechanism-based discovery of antitumor agents
    • Chang, C.-J.; Geahlen, R. L. Protein-tyrosine kinase inhibition: mechanism-based discovery of antitumor agents. J. Nat. Prod. 1992, 55, 1529-1560.
    • (1992) J. Nat. Prod. , vol.55 , pp. 1529-1560
    • Chang, C.-J.1    Geahlen, R.L.2
  • 8
    • 0028968949 scopus 로고
    • Tyrosine kinase inhibition; An approach to drug development
    • Levitski, A.; Gazit, A. Tyrosine kinase inhibition; An approach to drug development. Science 1995, 267, 1782-1788.
    • (1995) Science , vol.267 , pp. 1782-1788
    • Levitski, A.1    Gazit, A.2
  • 9
    • 0029035467 scopus 로고
    • Tyrosine kinase inhibitors. 4. Structure-activity relationships among N- and 3-substituted 2,2′-dithiobis(1H-indoles) for in vitro inhibition of receptor and nonreceptor protein tyrosine kinases
    • Palmer, B. D.; Rewcastle, G. W.; Thompson, A. M.; Boyd, M.; Showalter, H. D. H.; Sercel, A. D.; Fry, D. W.; Kraker, A. J.; Denny, W. A. Tyrosine kinase inhibitors. 4. Structure-activity relationships among N- and 3-substituted 2,2′-dithiobis(1H-indoles) for in vitro inhibition of receptor and nonreceptor protein tyrosine kinases. J. Med. Chem. 1995, 38, 58-67.
    • (1995) J. Med. Chem. , vol.38 , pp. 58-67
    • Palmer, B.D.1    Rewcastle, G.W.2    Thompson, A.M.3    Boyd, M.4    Showalter, H.D.H.5    Sercel, A.D.6    Fry, D.W.7    Kraker, A.J.8    Denny, W.A.9
  • 10
    • 85033835618 scopus 로고    scopus 로고
    • Eur. Patent Appl. No. 0 520 722 A1, 1992
    • Barker, A. J.; Davies, D. H. Eur. Patent Appl. No. 0 520 722 A1, 1992.
    • Barker, A.J.1    Davies, D.H.2
  • 11
    • 85033837319 scopus 로고    scopus 로고
    • Eur. Patent Appl. No. 0 566 226 A1, 1993
    • Barker, A. J. Eur. Patent Appl. No. 0 566 226 A1, 1993.
    • Barker, A.J.1
  • 12
    • 0028106163 scopus 로고
    • Epidermal growth factor receptor. Investigation of catalytic mechanism, structure-based searching and discovery of a potent inhibitor
    • Ward, W. H. J.; Cook, P. N.; Slater, A. M.; Davies, D. H.; Holdgate, G. A.; Green, L. R. Epidermal growth factor receptor. Investigation of catalytic mechanism, structure-based searching and discovery of a potent inhibitor. Biochem. Pharmacol. 1994, 48, 659-666.
    • (1994) Biochem. Pharmacol. , vol.48 , pp. 659-666
    • Ward, W.H.J.1    Cook, P.N.2    Slater, A.M.3    Davies, D.H.4    Holdgate, G.A.5    Green, L.R.6
  • 14
    • 0029130763 scopus 로고
    • Tyrosine kinase inhibitors. 5. Synthesis and structure-activity relationships for 4-(phenylmethyl)amino- and 4-phenylaminoquinazolines as potent adenosine 5′-triphosphate binding site inhibitors of the tyrosine kinase domain of the epidermal growth factor receptor
    • 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-phenylaminoquinazolines 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.
    • (1995) J. Med. Chem. , vol.38 , pp. 3482-3487
    • Rewcastle, G.W.1    Denny, W.A.2    Bridges, A.J.3    Zhou, H.4    Cody, D.R.5    McMichael, A.6    Fry, D.W.7
  • 15
    • 0023885305 scopus 로고
    • The protein kinase family; conserved features and deduced phylogeny of the catalytic domains
    • Hanks, S. K.; Quinn, A. M.; Hunter, T. The protein kinase family; conserved features and deduced phylogeny of the catalytic domains. Science 1988, 241, 42-52.
    • (1988) Science , vol.241 , pp. 42-52
    • Hanks, S.K.1    Quinn, A.M.2    Hunter, T.3
  • 16
    • 0016636632 scopus 로고
    • Linear benzoadenine. A stretched-out analog of adenine
    • Leonard, N. J.; Morrice, A. G.; Sprecker, M. A. Linear benzoadenine. A stretched-out analog of adenine. J. Org. Chem. 1975, 40, 356-363.
    • (1975) J. Org. Chem. , vol.40 , pp. 356-363
    • Leonard, N.J.1    Morrice, A.G.2    Sprecker, M.A.3
  • 17
    • 0025988512 scopus 로고
    • The antiproliferative effects of tyrosine kinase inhibitors tyrphostins on a human squamous cell carcinoma in vitro and in nude mice
    • Yoneda, T.; Lyall, R. M.; Alsina, M. M.; Persons, P. E.; Spada, A. P.; Levitski, A.; Zilberstein, A.; Mundy, G. R. The antiproliferative effects of tyrosine kinase inhibitors tyrphostins on a human squamous cell carcinoma in vitro and in nude mice. Cancer Res. 1991, 51, 4430-4435.
    • (1991) Cancer Res. , vol.51 , pp. 4430-4435
    • Yoneda, T.1    Lyall, R.M.2    Alsina, M.M.3    Persons, P.E.4    Spada, A.P.5    Levitski, A.6    Zilberstein, A.7    Mundy, G.R.8
  • 20
    • 37049175131 scopus 로고
    • The chemistry of simple heterocyclic systems. Part 1. Reactions of 6- and 7-nitro-4-hydroxyquinazoline and their derivatives
    • Morley, J. S.; Simpson, J. C. E. The chemistry of simple heterocyclic systems. Part 1. Reactions of 6- and 7-nitro-4-hydroxyquinazoline and their derivatives. J. Chem. Soc. 1948, 360-366.
    • (1948) J. Chem. Soc. , pp. 360-366
    • Morley, J.S.1    Simpson, J.C.E.2
  • 21
    • 0018735516 scopus 로고
    • Statistical analysis of enzyme kinetic data
    • Cleland, W. W. Statistical analysis of enzyme kinetic data. Methods Emzymol. 1979, 103-138.
    • (1979) Methods Emzymol. , pp. 103-138
    • Cleland, W.W.1
  • 22
    • 0017924320 scopus 로고
    • Potential Antitumor Agents. 26. Anionic congeners of the 9-anilinoacridines
    • Denny, W. A.; Atwell, G. J.; Cain, B. F. Potential Antitumor Agents. 26. Anionic congeners of the 9-anilinoacridines. J. Med. Chem. 1978, 21, 5-10.
    • (1978) J. Med. Chem. , vol.21 , pp. 5-10
    • Denny, W.A.1    Atwell, G.J.2    Cain, B.F.3
  • 23
    • 0028582185 scopus 로고
    • Crystal structure of the tyrosine kinase domain of the human insulin receptor
    • Hubbard, S. R.; Wei, L.; Ellis, L.; Hendrickson, W. A. Crystal structure of the tyrosine kinase domain of the human insulin receptor. Nature 1994, 372, 746-754.
    • (1994) Nature , vol.372 , pp. 746-754
    • Hubbard, S.R.1    Wei, L.2    Ellis, L.3    Hendrickson, W.A.4
  • 26
    • 0028157664 scopus 로고
    • Atomic structure of the MAP kinase ERK2 at 2.3 Å resolution
    • Zhang, F.; Strand, A.; Robbins, D.; Cobb, M. H.; Goldsmith, E. J. Atomic structure of the MAP kinase ERK2 at 2.3 Å resolution. Nature 1994, 367, 704-711.
    • (1994) Nature , vol.367 , pp. 704-711
    • Zhang, F.1    Strand, A.2    Robbins, D.3    Cobb, M.H.4    Goldsmith, E.J.5
  • 27
    • 0027408171 scopus 로고
    • Crystal structure of the catalytic subunit of cAMP-dependent protein kinase complexed with MgATP and peptide inhibitor
    • (a) Zheng, J.; Knighton, D. R.; Ten Eyck, L. F.; Karlsson, R.; Xuong, N.-H.; Taylor, S. S.; Sowadski, J. M. Crystal structure of the catalytic subunit of cAMP-dependent protein kinase complexed with MgATP and peptide inhibitor. Biochemistry 1993, 32, 2154-2161.
    • (1993) Biochemistry , vol.32 , pp. 2154-2161
    • Zheng, J.1    Knighton, D.R.2    Ten Eyck, L.F.3    Karlsson, R.4    Xuong, N.-H.5    Taylor, S.S.6    Sowadski, J.M.7
  • 29
    • 0347180008 scopus 로고
    • 3H-Quinazolin-4-one derivatives with antiinflammatory activity. II. Derivatives substituted in the aromatic nucleus, and related compounds
    • (a) Maillard, J.; Benard, M.; Vincent, M.; Vo-Van-Tri; Jolly, R.; Morin, R.; Benharkarte, Mrs.; Menillet, C. 3H-Quinazolin-4-one derivatives with antiinflammatory activity. II. Derivatives substituted in the aromatic nucleus, and related compounds. Chim. Ther. 1967, 2, 231-239.
    • (1967) Chim. Ther. , vol.2 , pp. 231-239
    • Maillard, J.1    Benard, M.2    Vincent, M.3    Vo-Van-Tri4    Jolly, R.5    Morin, R.6    Benharkarte, Mrs.7    Menillet, C.8
  • 30
    • 0014850623 scopus 로고
    • Structural modification of febrifugine. Some methylenedioxy analogs
    • (b) Chien, P.-L.; Cheng, C. C. Structural modification of febrifugine. Some methylenedioxy analogs. J. Med. Chem. 1970, 13, 867-870.
    • (1970) J. Med. Chem. , vol.13 , pp. 867-870
    • Chien, P.-L.1    Cheng, C.C.2
  • 31
    • 85033858510 scopus 로고
    • Bi-4-[l-(quinazolinyl-4)piperidyls] and bis4-[1-(quinazolinyl-4)piperidyl-] alkanes
    • U.S. Patent 4,011,323, 1977
    • (c) Simpson, W. R. J. Bi-4-[l-(quinazolinyl-4)piperidyls] and bis4-[1-(quinazolinyl-4)piperidyl-] alkanes. U.S. Patent 4,011,323, 1977; Chem. Abstr. 1977, 87, 6013z.
    • (1977) Chem. Abstr. , vol.87
    • Simpson, W.R.J.1
  • 32
    • 0028038279 scopus 로고
    • Cyclic GMP phosphodiesterase inhibitors. 2. Requirement of 6-substitution of quinazoline derivatives for potent and selective inhibitory activity
    • (d) Takase, Y.; Saeki, T.; Watanabe, N.; Adachi, H.; Souda, S.; Saito, I. Cyclic GMP phosphodiesterase inhibitors. 2. Requirement of 6-substitution of quinazoline derivatives for potent and selective inhibitory activity. J. Med. Chem. 1994, 37, 2106-2111.
    • (1994) J. Med. Chem. , vol.37 , pp. 2106-2111
    • Takase, Y.1    Saeki, T.2    Watanabe, N.3    Adachi, H.4    Souda, S.5    Saito, I.6
  • 33
    • 37049114082 scopus 로고
    • Quinazolines. Part IX. Covalent hydration in the neutral species of substituted quinazolines
    • Armarego, W. L. F.; Smith, J. I. C. Quinazolines. Part IX. Covalent hydration in the neutral species of substituted quinazolines. J. Chem. Soc. B 1967, 449-454.
    • (1967) J. Chem. Soc. B , pp. 449-454
    • Armarego, W.L.F.1    Smith, J.I.C.2
  • 34
    • 84986483839 scopus 로고
    • The chemistry of 2H-3,1-benzoxazine-2,4(1H)-dione (isatoic anhydride). 21. Amild process for the preparation of 10-alkyl-9-acridanones and it's application to the synthesis of acridone alkaloids
    • Coppola, G. M.; Schuster, H. F. The chemistry of 2H-3,1-benzoxazine-2,4(1H)-dione (isatoic anhydride). 21. Amild process for the preparation of 10-alkyl-9-acridanones and it's application to the synthesis of acridone alkaloids. J. Heterocycl. Chem. 1989, 26, 957-964.
    • (1989) J. Heterocycl. Chem. , vol.26 , pp. 957-964
    • Coppola, G.M.1    Schuster, H.F.2
  • 35
    • 0015312372 scopus 로고
    • Ringschluss zum chinazolon-(4)-system durch aminomethinylierung
    • Kreutzberger, A.; Uzbek, M. U. Ringschluss zum chinazolon-(4)-system durch aminomethinylierung. (Synthesis of the 4(3H)-quinazolinone ring system through aminomethenylation.) Arch. Pharmacol. 1972, 305, 171-175.
    • (1972) Arch. Pharmacol. , vol.305 , pp. 171-175
    • Kreutzberger, A.1    Uzbek, M.U.2
  • 36
    • 0023587983 scopus 로고
    • Purification of functionally active epidermal growth factor receptor protein using a competitive antagonist monoclonal antibody and competitive elution with epidermal growth factor
    • Gill, G. N.; Weber, W. Purification of functionally active epidermal growth factor receptor protein using a competitive antagonist monoclonal antibody and competitive elution with epidermal growth factor. Methods Enzymol. 1987, 146, 82-88.
    • (1987) Methods Enzymol. , vol.146 , pp. 82-88
    • Gill, G.N.1    Weber, W.2


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