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Volumn 6, Issue 9, 2015, Pages 987-992

Oxopyrido[2,3-d]pyrimidines as Covalent L858R/T790M Mutant Selective Epidermal Growth Factor Receptor (EGFR) Inhibitors

Author keywords

EGFR; EGFR T790M mutant; Epidermal growth factor receptor; irreversible inhibitor; kinase inhibitor; nonsmall cell lung cancer

Indexed keywords

ANTINEOPLASTIC AGENT; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; GEFITINIB; OXOPYRIDO[2,3 D]PYRIMIDINE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84941564103     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/acsmedchemlett.5b00193     Document Type: Article
Times cited : (19)

References (35)
  • 1
    • 33847323129 scopus 로고    scopus 로고
    • Epidermal growth factor receptor mutations in lung cancer
    • Sharma, S. V.; Bell, D. W.; Settleman, J.; Haber, D. A. Epidermal growth factor receptor mutations in lung cancer Nat. Rev. Cancer 2007, 7, 169-181 10.1038/nrc2088
    • (2007) Nat. Rev. Cancer , vol.7 , pp. 169-181
    • Sharma, S.V.1    Bell, D.W.2    Settleman, J.3    Haber, D.A.4
  • 2
    • 84875950992 scopus 로고    scopus 로고
    • Epidermal growth factor receptor tyrosine kinase inhibitor-resistant disease
    • Ohashi, K.; Maruvka, Y. E.; Michor, F.; Pao, W. Epidermal growth factor receptor tyrosine kinase inhibitor-resistant disease J. Clin. Oncol. 2013, 31, 1070-1080 10.1200/JCO.2012.43.3912
    • (2013) J. Clin. Oncol. , vol.31 , pp. 1070-1080
    • Ohashi, K.1    Maruvka, Y.E.2    Michor, F.3    Pao, W.4
  • 3
    • 84887497121 scopus 로고    scopus 로고
    • The quest to overcome resistance to EGFR-targeted therapies in cancer
    • Chong, C. R.; Jänne, P. A. The quest to overcome resistance to EGFR-targeted therapies in cancer Nat. Med. 2013, 19, 1389-1400 10.1038/nm.3388
    • (2013) Nat. Med. , vol.19 , pp. 1389-1400
    • Chong, C.R.1    Jänne, P.A.2
  • 4
    • 84864246491 scopus 로고    scopus 로고
    • Irreversible protein kinase inhibitors: Balancing the benefits and risks
    • Barf, T.; Kaptein, A. Irreversible protein kinase inhibitors: balancing the benefits and risks J. Med. Chem. 2012, 55, 6243-6262 10.1021/jm3003203
    • (2012) J. Med. Chem. , vol.55 , pp. 6243-6262
    • Barf, T.1    Kaptein, A.2
  • 5
    • 64349093749 scopus 로고    scopus 로고
    • Covalent modifiers: An orthogonal approach to drug design
    • Potashman, M. H.; Duggan, M. E. Covalent modifiers: an orthogonal approach to drug design J. Med. Chem. 2009, 52, 1231-1246 10.1021/jm8008597
    • (2009) J. Med. Chem. , vol.52 , pp. 1231-1246
    • Potashman, M.H.1    Duggan, M.E.2
  • 6
    • 84858669035 scopus 로고    scopus 로고
    • Second-generation irreversible epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors (TKIs): A better mousetrap? A review of the clinical evidence
    • Ou, S.-H. Second-generation irreversible epidermal growth factor receptor (EGFR) tyrosine kinase inhibitors (TKIs): A better mousetrap? A review of the clinical evidence Crit. Rev. Onc./Hematol. 2012, 83, 407-421 10.1016/j.critrevonc.2011.11.010
    • (2012) Crit. Rev. Onc./Hematol. , vol.83 , pp. 407-421
    • Ou, S.-H.1
  • 10
    • 0034611617 scopus 로고    scopus 로고
    • 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
    • Smaill, J. B.; Rewcastle, G. W.; Loo, J. A.; Greis, K. D.; Chan, O. H.; Reyner, E. 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, 1380-1397 10.1021/jm990482t
    • (2000) J. Med. Chem. , vol.43 , pp. 1380-1397
    • Smaill, J.B.1    Rewcastle, G.W.2    Loo, J.A.3    Greis, K.D.4    Chan, O.H.5    Reyner, E.L.6    Lipka, E.7    Showalter, H.D.H.8    Vincent, P.W.9    Elliott, W.L.10    Denny, W.A.11
  • 14
    • 84884640384 scopus 로고    scopus 로고
    • Afatinib: First global approval
    • Dungo, R. T.; Keating, G. M. Afatinib: first global approval Drugs 2013, 73, 1503-1515 10.1007/s40265-013-0111-6
    • (2013) Drugs , vol.73 , pp. 1503-1515
    • Dungo, R.T.1    Keating, G.M.2
  • 25
    • 84863341925 scopus 로고    scopus 로고
    • Design, synthesis, and biological evaluation of novel conformationally constrained inhibitors targeting epidermal growth factor receptor threonine790 methionine790 mutant
    • Chang, S.; Zhang, L.; Xu, S.; Luo, J.; Lu, X.; Zhang, Z.; Xu, T.; Liu, Y.; Tu, Z.; Xu, Y.; Ren, X.; Geng, M.; Ding, J.; Pei, D.; Ding, K. Design, synthesis, and biological evaluation of novel conformationally constrained inhibitors targeting epidermal growth factor receptor threonine790 methionine790 mutant J. Med. Chem. 2012, 55, 2711-2723 10.1021/jm201591k
    • (2012) J. Med. Chem. , vol.55 , pp. 2711-2723
    • Chang, S.1    Zhang, L.2    Xu, S.3    Luo, J.4    Lu, X.5    Zhang, Z.6    Xu, T.7    Liu, Y.8    Tu, Z.9    Xu, Y.10    Ren, X.11    Geng, M.12    Ding, J.13    Pei, D.14    Ding, K.15
  • 26
    • 84887920359 scopus 로고    scopus 로고
    • Design, synthesis and biological evaluation of 2-oxo-3,4-dihydropyrimido[4,5-d]pyrimidinyl derivatives as new irreversible epidermal growth factor receptor inhibitors with improved pharmacokinetic properties
    • Xu, S.; Xu, T.; Zhang, L.; Zhang, Z.; Luo, J.; Liu, Y.; Lu, X.; Tu, Z.; Ren, X.; Ding, K. Design, synthesis and biological evaluation of 2-oxo-3,4-dihydropyrimido[4,5-d]pyrimidinyl derivatives as new irreversible epidermal growth factor receptor inhibitors with improved pharmacokinetic properties J. Med. Chem. 2013, 56, 8803-8813 10.1021/jm4012388
    • (2013) J. Med. Chem. , vol.56 , pp. 8803-8813
    • Xu, S.1    Xu, T.2    Zhang, L.3    Zhang, Z.4    Luo, J.5    Liu, Y.6    Lu, X.7    Tu, Z.8    Ren, X.9    Ding, K.10
  • 28
    • 84886494418 scopus 로고    scopus 로고
    • Discovery of pteridin-7(8H)-one-based irreversible inhibitors targeting the epidermal growth factor receptor (EGFR) kinase T790M/L858R mutant
    • Zhou, W.; Liu, X.; Tu, Z.; Zhang, L.; Ku, X.; Bai, F.; Zhao, Z.; Xu, Y.; Ding, K.; Li, H. Discovery of pteridin-7(8H)-one-based irreversible inhibitors targeting the epidermal growth factor receptor (EGFR) kinase T790M/L858R mutant J. Med. Chem. 2013, 56, 7821-7837 10.1021/jm401045n
    • (2013) J. Med. Chem. , vol.56 , pp. 7821-7837
    • Zhou, W.1    Liu, X.2    Tu, Z.3    Zhang, L.4    Ku, X.5    Bai, F.6    Zhao, Z.7    Xu, Y.8    Ding, K.9    Li, H.10
  • 31
    • 84898071875 scopus 로고    scopus 로고
    • Pyridin-2-one synthesis using ester enolates and aryl aminoaldehydes and ketones
    • Apsunde, T.; Wurz, R. P. Pyridin-2-one synthesis using ester enolates and aryl aminoaldehydes and ketones J. Org. Chem. 2014, 79, 3260-3266 10.1021/jo500284n
    • (2014) J. Org. Chem. , vol.79 , pp. 3260-3266
    • Apsunde, T.1    Wurz, R.P.2
  • 33
    • 40049099220 scopus 로고    scopus 로고
    • The T790M mutation in EGFR kinase causes drug resistance by increasing the affinity for ATP
    • The KM[ATP] values for EGFRWT EGFRT790M EGFRL858R and EGFRT790M/L858R are 5.2, 5.9, 148, and 8.4 ΜM, respectively; see
    • The KM[ATP] values for EGFRWT, EGFRT790M, EGFRL858R, and EGFRT790M/L858R are 5.2, 5.9, 148, and 8.4 ΜM, respectively; see: Yun, C.-H.; Mengwasser, K. E.; Toms, A. V.; Woo, M. S.; Greulich, H.; Wong, K.-K.; Meyerson, M.; Eck, M. J. The T790M mutation in EGFR kinase causes drug resistance by increasing the affinity for ATP Proc. Natl. Acad. Sci. U. S. A. 2008, 105, 2070-2075 10.1073/pnas.0709662105
    • (2008) Proc. Natl. Acad. Sci. U. S. A. , vol.105 , pp. 2070-2075
    • Yun, C.-H.1    Mengwasser, K.E.2    Toms, A.V.3    Woo, M.S.4    Greulich, H.5    Wong, K.-K.6    Meyerson, M.7    Eck, M.J.8
  • 34
    • 84925446013 scopus 로고    scopus 로고
    • A proposed screening paradigm for discovery of covalent inhibitor drugs
    • For a discussion on preclinical ADME properties of 10 clinically late stage or marketed covalent inhibitors, see
    • For a discussion on preclinical ADME properties of 10 clinically late stage or marketed covalent inhibitors, see: Moghaddam, M. F.; Tang, Y.; ÓBrien, Z.; Richardson, S. J.; Bacolod, M.; Chaturedi, P.; Apuy, J.; Kulkarni, A. A proposed screening paradigm for discovery of covalent inhibitor drugs Drug Metab. Lett. 2014, 8, 19-30 10.2174/1872312808666140317151735
    • (2014) Drug Metab. Lett. , vol.8 , pp. 19-30
    • Moghaddam, M.F.1    Tang, Y.2    Óbrien, Z.3    Richardson, S.J.4    Bacolod, M.5    Chaturedi, P.6    Apuy, J.7    Kulkarni, A.8
  • 35
    • 84882299342 scopus 로고    scopus 로고
    • High throughput glutathione and Nrf2 assays to assess chemical and biological reactivity of cysteine-reactive compounds
    • For a discussion on reactivity of acrylamides with glutathione, see
    • For a discussion on reactivity of acrylamides with glutathione, see: Naven, R. T.; Kantesaria, S.; Nadanaciva, S.; Schroeter, T.; Leach, K. L. High throughput glutathione and Nrf2 assays to assess chemical and biological reactivity of cysteine-reactive compounds Toxicol. Res. 2013, 2, 235-244 10.1039/c3tx50027f
    • (2013) Toxicol. Res. , vol.2 , pp. 235-244
    • Naven, R.T.1    Kantesaria, S.2    Nadanaciva, S.3    Schroeter, T.4    Leach, K.L.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.