메뉴 건너뛰기




Volumn 52, Issue 14, 2009, Pages 4380-4390

Cell division cycle 7 kinase inhibitors: 1H-pyrrolo[2,3-b]pyridines, synthesis and structure-activity relationships

Author keywords

[No Author keywords available]

Indexed keywords

1H PYRROLO[2,3 B]PYRIDINE DERIVATIVE; 2 (BENZYLAMINO) 5 (1H PYRROLO[2,3 B]PYRIDIN 3 YLMETHYLENE) 1,3 THIAZOL 4(5H) ONE; 2 PHENYL 5 (1H PYRROLO[2,3 B]PYRIDIN 3 YLMETHYLENE) 3,5 DIHYDRO 4H IMIDAZOL 4 ONE DERIVATIVE; 7 AZAINDOLE DERIVATIVE; ANTINEOPLASTIC AGENT; CDC 7 KINASE; CDC 7 KINASE INHIBITOR; ENZYME INHIBITOR; PROTEIN SERINE THREONINE KINASE; UNCLASSIFIED DRUG;

EID: 67650754045     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm900248g     Document Type: Article
Times cited : (53)

References (36)
  • 1
    • 0035997368 scopus 로고    scopus 로고
    • DNA replication in eukaryotic cells
    • Bell, S. P.; Dutta, A. DNA replication in eukaryotic cells. Annu. Rev. Biochem. 2002, 71, 333-374.
    • (2002) Annu. Rev. Biochem , vol.71 , pp. 333-374
    • Bell, S.P.1    Dutta, A.2
  • 2
    • 0033026068 scopus 로고    scopus 로고
    • A novel growth- and cell cycle-regulated protein, ASK, activates human Cdc7-related kinase and is essential for G1/S transition in mammalian cells
    • Kumagai, H.; Sato, N.; Yamada, M.; Mahony, D.; Seghezzi, W.; Lees, E.; Arai, K.; Masai, H. A novel growth- and cell cycle-regulated protein, ASK, activates human Cdc7-related kinase and is essential for G1/S transition in mammalian cells. Mol. Cell. Biol. 1999, 19, 5083-5095.
    • (1999) Mol. Cell. Biol , vol.19 , pp. 5083-5095
    • Kumagai, H.1    Sato, N.2    Yamada, M.3    Mahony, D.4    Seghezzi, W.5    Lees, E.6    Arai, K.7    Masai, H.8
  • 4
    • 0032574671 scopus 로고    scopus 로고
    • A human homologue of the yeast CDC7 gene is overexpressed in some tumors and transformed cell lines
    • Hess, G. F.; Drong, R. F.; Weiland, K. L.; Slightom, J. L.; Sclafani, R. A.; Hollingsworth, R. E. A human homologue of the yeast CDC7 gene is overexpressed in some tumors and transformed cell lines. Gene 1998, 211 (1), 133-140.
    • (1998) Gene , vol.211 , Issue.1 , pp. 133-140
    • Hess, G.F.1    Drong, R.F.2    Weiland, K.L.3    Slightom, J.L.4    Sclafani, R.A.5    Hollingsworth, R.E.6
  • 5
    • 50949102890 scopus 로고    scopus 로고
    • Bonte, D.; Lindvall, C.; Liu, H.; Dykema, K.; Furge, K.; Weinreich, M. Cdc7-Dbf4 kinase overexpression in multiple cancers and tumor cell lines is correlated with p53 inactivation. Neoplasia (Ann Arbor, MI, U.S.) 2008, 10 (9), 920-931.
    • Bonte, D.; Lindvall, C.; Liu, H.; Dykema, K.; Furge, K.; Weinreich, M. Cdc7-Dbf4 kinase overexpression in multiple cancers and tumor cell lines is correlated with p53 inactivation. Neoplasia (Ann Arbor, MI, U.S.) 2008, 10 (9), 920-931.
  • 6
    • 0033569906 scopus 로고    scopus 로고
    • Mammalian Cdc7-Dbf4 protein kinase complex is essential for initiation of DNA replication
    • Jiang, W.; McDonald, D.; Hope, T. J.; Hunter, T. Mammalian Cdc7-Dbf4 protein kinase complex is essential for initiation of DNA replication. EMBO J. 1999, 18, 5703-5713.
    • (1999) EMBO J , vol.18 , pp. 5703-5713
    • Jiang, W.1    McDonald, D.2    Hope, T.J.3    Hunter, T.4
  • 7
    • 4944256913 scopus 로고    scopus 로고
    • Cdc7 inhibition reveals a p53-dependent replication checkpoint that is defective in cancer cells
    • Montagnoli, A.; Tenca, P.; Sola, F.; Carpani, D.; Brotherton, D.; Albanese, C.; Santocanale, C. Cdc7 inhibition reveals a p53-dependent replication checkpoint that is defective in cancer cells. Cancer Res. 2004, 64, 7110-7116.
    • (2004) Cancer Res , vol.64 , pp. 7110-7116
    • Montagnoli, A.1    Tenca, P.2    Sola, F.3    Carpani, D.4    Brotherton, D.5    Albanese, C.6    Santocanale, C.7
  • 9
    • 45149124103 scopus 로고    scopus 로고
    • Inhibition of Cdc7/Dbf4 kinase activity affects specific phosphorylation sites on MCM2 in cancer cells
    • Charych, D.; Coyne, M.; Yabannavar, A.; Narberes, J.; Chow, S.; Wallroth, M.; Shafer, C. M.; Walter, A. Inhibition of Cdc7/Dbf4 kinase activity affects specific phosphorylation sites on MCM2 in cancer cells. J. Cell. Biochem. 2008, 104 (3), 1075-1086.
    • (2008) J. Cell. Biochem , vol.104 , Issue.3 , pp. 1075-1086
    • Charych, D.1    Coyne, M.2    Yabannavar, A.3    Narberes, J.4    Chow, S.5    Wallroth, M.6    Shafer, C.M.7    Walter, A.8
  • 11
    • 43749097854 scopus 로고    scopus 로고
    • Montagnoli, A.; Valsasina, B.; Croci, V.; Menichincheri, M.; Rainoldi, S.; Marchesi, V.; Tibolla, M.; Tenca, P.; Brotherton, D.; Albanese, C.; Patton, V.; Alzani, R.; Ciavolella, A.; Sola, F.; Molinari, A.; Volpi, D.; Avanzi, N.; Fiorentini, F.; Cattoni, M.; Healy, S.; Ballinari, D.; Pesenti, E.; Isacchi, A.; Moll, J.; Bensimon, A.; Vanotti, E.; Santocanale, C. A Cdc7 kinase inhibitor restricts initiation of DNA replication and has antitumor activity. Nat. Chem. Biol. 2008, 4 (6), 357-365.
    • (a) Montagnoli, A.; Valsasina, B.; Croci, V.; Menichincheri, M.; Rainoldi, S.; Marchesi, V.; Tibolla, M.; Tenca, P.; Brotherton, D.; Albanese, C.; Patton, V.; Alzani, R.; Ciavolella, A.; Sola, F.; Molinari, A.; Volpi, D.; Avanzi, N.; Fiorentini, F.; Cattoni, M.; Healy, S.; Ballinari, D.; Pesenti, E.; Isacchi, A.; Moll, J.; Bensimon, A.; Vanotti, E.; Santocanale, C. A Cdc7 kinase inhibitor restricts initiation of DNA replication and has antitumor activity. Nat. Chem. Biol. 2008, 4 (6), 357-365.
  • 12
    • 43749093435 scopus 로고    scopus 로고
    • Stopping replication, at the beginning
    • (b) Jackson, P. K. Stopping replication, at the beginning. Nat. Chem. Biol. 2008, 4 (6), 331-332.
    • (2008) Nat. Chem. Biol , vol.4 , Issue.6 , pp. 331-332
    • Jackson, P.K.1
  • 13
    • 60549104083 scopus 로고    scopus 로고
    • Menichincheri, M.; Bargiotti, A.; Berthelsen, J.; Bertrand, J. A.; Bossi, R.; Ciavolella, A.; Cirla, A.; Cristiani, C.; Croci, V.; D0Alessio, R.; Fasolini, M.; Fiorentini, F.; Forte, B.; Isacchi, A.; Martina, K.; Molinari, A.; Montagnoli, A.; Orsini, P.; Orzi, F.; Pesenti, E.; Pezzetta, D.; Pillan, A.; Poggesi, I.; Roletto, F.; Scolaro, A.; Tato, M.; Tibolla, M.; Valsasina, B.; Varasi, M.; Volpi, D.; Santocanale, C.; Vanotti, E. First Cdc7 Kinase Inhibitors: Pyrrolopyridinones as Potent and Orally Active Antitumor Agents. 2. Lead Discovery. J. Med. Chem. 2009, 52, 293-307.
    • Menichincheri, M.; Bargiotti, A.; Berthelsen, J.; Bertrand, J. A.; Bossi, R.; Ciavolella, A.; Cirla, A.; Cristiani, C.; Croci, V.; D0Alessio, R.; Fasolini, M.; Fiorentini, F.; Forte, B.; Isacchi, A.; Martina, K.; Molinari, A.; Montagnoli, A.; Orsini, P.; Orzi, F.; Pesenti, E.; Pezzetta, D.; Pillan, A.; Poggesi, I.; Roletto, F.; Scolaro, A.; Tato, M.; Tibolla, M.; Valsasina, B.; Varasi, M.; Volpi, D.; Santocanale, C.; Vanotti, E. First Cdc7 Kinase Inhibitors: Pyrrolopyridinones as Potent and Orally Active Antitumor Agents. 2. Lead Discovery. J. Med. Chem. 2009, 52, 293-307.
  • 14
    • 67650719017 scopus 로고    scopus 로고
    • Drug design with Cdc7 kinase: A potential novel cancer therapy target
    • For a review: a
    • For a review: (a) Sawa, M.; Masai, H. Drug design with Cdc7 kinase: a potential novel cancer therapy target. Drug Des. Dev. Ther. 2008, 2, 255-264.
    • (2008) Drug Des. Dev. Ther , vol.2 , pp. 255-264
    • Sawa, M.1    Masai, H.2
  • 15
    • 61849163877 scopus 로고    scopus 로고
    • Cdc7 as a potential new target for cancer therapy
    • (b) Ito, S.; Taniyama, C.; Arai, N.; Masai, H. Cdc7 as a potential new target for cancer therapy. Drug News Perspect. 2008, 21 (9), 481-488.
    • (2008) Drug News Perspect , vol.21 , Issue.9 , pp. 481-488
    • Ito, S.1    Taniyama, C.2    Arai, N.3    Masai, H.4
  • 16
    • 67650724350 scopus 로고    scopus 로고
    • Identification of XL413, a Selective Cdc7 Kinase Inhibitor Which Induces Cell Cycle Arrest and Exhibits Potent Antitumor Activity
    • Geneva, Switzerland, Oct. 21-24
    • Robertson, S. Identification of XL413, a Selective Cdc7 Kinase Inhibitor Which Induces Cell Cycle Arrest and Exhibits Potent Antitumor Activity. In AARC-NCI-EORTC International Conference, Geneva, Switzerland, Oct. 21-24, 2008.
    • (2008) AARC-NCI-EORTC International Conference
    • Robertson, S.1
  • 17
    • 57749119173 scopus 로고    scopus 로고
    • Synthesis and evaluation of pyrido-thieno-pyrimidines as potent and selective Cdc7 kinase inhibitors
    • Zhao, C.; Tovar, C.; Yin, X.; Xu, Q.; Todorov, I. T.; Vassilev, L. T.; Chen, L. Synthesis and evaluation of pyrido-thieno-pyrimidines as potent and selective Cdc7 kinase inhibitors. Bioorg. Med. Chem. Lett. 2009, 19, 319-323.
    • (2009) Bioorg. Med. Chem. Lett , vol.19 , pp. 319-323
    • Zhao, C.1    Tovar, C.2    Yin, X.3    Xu, Q.4    Todorov, I.T.5    Vassilev, L.T.6    Chen, L.7
  • 18
    • 48649100754 scopus 로고    scopus 로고
    • Shafer, C. M.; Lindvall, M.; Bellamacina, C.; Gesner, T. G.; Yabannavar, A.; Jia, W.; Lin, S.; Walter, A. 4-(1H-Indazol-5-yl)-6-phenylpyrimidin- 2(1H)-one analogs as potent CDC7 inhibitors. Bioorg. Med. Chem. Lett. 2008, 18, 4482-4485.
    • Shafer, C. M.; Lindvall, M.; Bellamacina, C.; Gesner, T. G.; Yabannavar, A.; Jia, W.; Lin, S.; Walter, A. 4-(1H-Indazol-5-yl)-6-phenylpyrimidin- 2(1H)-one analogs as potent CDC7 inhibitors. Bioorg. Med. Chem. Lett. 2008, 18, 4482-4485.
  • 20
    • 2942522534 scopus 로고    scopus 로고
    • Pevarello, P.; Brasca, M. G.; Amici, R.; Orsini, P.; Traquandi, G.; Corti, L.; Piutti, C.; Sansonna, P.; Villa, M.; Pierce, B. S.; Pulici, M.; Giordano, P.; Martina, K.; Fritzen, E. L.; Nugent, R. A.; Casale, E.; Cameron, A.; Ciomei, M.; Roletto, F.; Isacchi, A.; Fogliatto, G.; Pesenti, E.; Pastori, W.; Marsiglio, A.; Leach, K. L.; Clare, P. M.; Fiorentini, F.; Varasi, M.; Vulpetti, A.; Warpehoski, M. A. 3-Aminopyrazole Inhibitors of CDK2/Cyclin A as Antitumor Agents. 1. Lead Finding. J. Med. Chem. 2004, 47, 3367-3380.
    • Pevarello, P.; Brasca, M. G.; Amici, R.; Orsini, P.; Traquandi, G.; Corti, L.; Piutti, C.; Sansonna, P.; Villa, M.; Pierce, B. S.; Pulici, M.; Giordano, P.; Martina, K.; Fritzen, E. L.; Nugent, R. A.; Casale, E.; Cameron, A.; Ciomei, M.; Roletto, F.; Isacchi, A.; Fogliatto, G.; Pesenti, E.; Pastori, W.; Marsiglio, A.; Leach, K. L.; Clare, P. M.; Fiorentini, F.; Varasi, M.; Vulpetti, A.; Warpehoski, M. A. 3-Aminopyrazole Inhibitors of CDK2/Cyclin A as Antitumor Agents. 1. Lead Finding. J. Med. Chem. 2004, 47, 3367-3380.
  • 23
    • 33645802169 scopus 로고    scopus 로고
    • Cyclin-dependent kinase pathways as targets for cancer treatment
    • Shapiro, G. I. Cyclin-dependent kinase pathways as targets for cancer treatment. J. Clin. Oncol. 2006, 24, 1770-1783.
    • (2006) J. Clin. Oncol , vol.24 , pp. 1770-1783
    • Shapiro, G.I.1
  • 24
    • 0141815505 scopus 로고    scopus 로고
    • Investigating RNA polymerase II carboxyl-terminal domain (CTD) phosphorylation
    • Palancade, B.; Bensaude, O. Investigating RNA polymerase II carboxyl-terminal domain (CTD) phosphorylation. Eur. J. Biochem. 2003, 270, 3859-3870.
    • (2003) Eur. J. Biochem , vol.270 , pp. 3859-3870
    • Palancade, B.1    Bensaude, O.2
  • 25
    • 33749503799 scopus 로고    scopus 로고
    • Combined Depletion of Cell Cycle and Transcriptional Cyclin-Dependent Kinase Activities Induces Apoptosis in Cancer Cells
    • Cai, D.; Vaughan, M. L., Jr.; Zhang, X.; Shapiro, I. G. Combined Depletion of Cell Cycle and Transcriptional Cyclin-Dependent Kinase Activities Induces Apoptosis in Cancer Cells. Cancer Res. 2006, 66 (18), 9270-9280.
    • (2006) Cancer Res , vol.66 , Issue.18 , pp. 9270-9280
    • Cai, D.1    Vaughan Jr., M.L.2    Zhang, X.3    Shapiro, I.G.4
  • 27
    • 0043123574 scopus 로고
    • The reaction of phenylpyruvic acid and related compounds with ammonia
    • Galat, A. The reaction of phenylpyruvic acid and related compounds with ammonia. J. Am. Chem. Soc. 1950, 72, 4436-4439.
    • (1950) J. Am. Chem. Soc , vol.72 , pp. 4436-4439
    • Galat, A.1
  • 28
    • 0031696894 scopus 로고    scopus 로고
    • Synthesis, spectral, and antimicrobial properties of 5-chloroarylidene aromatic derivatives of imidazolin-4-one
    • Kiec-Kononowicz, K.; Szymanska, E.; Motyl, M.; Holzer, W.; Bialecka, A.; Kasprowicz, A. Synthesis, spectral, and antimicrobial properties of 5-chloroarylidene aromatic derivatives of imidazolin-4-one. Pharmazie 1998, 53, 680-684.
    • (1998) Pharmazie , vol.53 , pp. 680-684
    • Kiec-Kononowicz, K.1    Szymanska, E.2    Motyl, M.3    Holzer, W.4    Bialecka, A.5    Kasprowicz, A.6
  • 29
    • 44549087848 scopus 로고    scopus 로고
    • Cyclin-dependent kinase 9: A key transcriptional regulator and potential drug target in oncology, virology and cardiology
    • Wang, S.; Fischer, P. M. Cyclin-dependent kinase 9: a key transcriptional regulator and potential drug target in oncology, virology and cardiology. Trends Pharmacol. Sci. 2008, 29 (6), 302-313.
    • (2008) Trends Pharmacol. Sci , vol.29 , Issue.6 , pp. 302-313
    • Wang, S.1    Fischer, P.M.2
  • 30
    • 24944497371 scopus 로고    scopus 로고
    • Features of selective kinase inhibitors
    • Knight, Z. A.; Shokat, K. M. Features of selective kinase inhibitors. Chem. Biol. 2005, 12, 621-637.
    • (2005) Chem. Biol , vol.12 , pp. 621-637
    • Knight, Z.A.1    Shokat, K.M.2
  • 32
    • 0032568397 scopus 로고    scopus 로고
    • Physicochemical High Throughput Screening: Parallel Artificial Membrane Permeation Assay in the Description of Passive Absorption Processes
    • Kansy, M.; Senner, F.; Gubernator, K. Physicochemical High Throughput Screening: Parallel Artificial Membrane Permeation Assay in the Description of Passive Absorption Processes. J. Med. Chem. 1998, 41, 1007-1010.
    • (1998) J. Med. Chem , vol.41 , pp. 1007-1010
    • Kansy, M.1    Senner, F.2    Gubernator, K.3
  • 33
    • 2642527944 scopus 로고    scopus 로고
    • Combined application of parallel artificial membrane permeability assay and Caco-2 permeability assays in drug discovery
    • Kerns, E. H.; Di, L.; Petusky, S.; Farris, M.; Ley, R.; Jupp, P. Combined application of parallel artificial membrane permeability assay and Caco-2 permeability assays in drug discovery. J. Pharm. Sci. 2004, 93 (6), 1440-1453.
    • (2004) J. Pharm. Sci , vol.93 , Issue.6 , pp. 1440-1453
    • Kerns, E.H.1    Di, L.2    Petusky, S.3    Farris, M.4    Ley, R.5    Jupp, P.6
  • 34
    • 1242316994 scopus 로고    scopus 로고
    • A fully automated method for accurate mass determination using high-performance liquid chromatography with a quadrupole/orthogonal acceleration time-of-flight mass spectrometer
    • Colombo, M.; Sirtori, F. R.; Rizzo, V. A fully automated method for accurate mass determination using high-performance liquid chromatography with a quadrupole/orthogonal acceleration time-of-flight mass spectrometer. Rapid Commun. Mass Spectrom. 2004, 18, 511-517.
    • (2004) Rapid Commun. Mass Spectrom , vol.18 , pp. 511-517
    • Colombo, M.1    Sirtori, F.R.2    Rizzo, V.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.