메뉴 건너뛰기




Volumn 50, Issue 17, 2007, Pages 4162-4176

Design, synthesis, and biological activity of 5,10-dihydro-dibenzo[b,e][1, 4]diazepin-11-one-based potent and selective Chk-1 inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

2 [3 (3 METHOXY 4 NITROPHENYL) 11 OXO 10,11 DIHYDRO 5H DIBENZO[B,E][1,4] DIAZEPIN 7 YL] 2 METHYL N (4 MORPHOLIN 4 YLPHENYL)PROPANAMIDE; 2 [3 (3 METHOXY 4 NITROPHENYL) 11 OXO 10,11 DIHYDRO 5H DIBENZO[B,E][1,4] DIAZEPIN 7 YL] N,N DIMETHYLACETAMIDE; 2 [3 (3 METHOXY 4 NITROPHENYL) 11 OXO 10,11 DIHYDRO 5H DIBENZO[B,E][1,4] DIAZEPIN 8 YL] 2 METHYL N (4 MORPHOLIN 4 YLPHENYL)PROPANAMIDE; 2 [3 (3 METHOXY 4 NITROPHENYL) 11 OXO 10,11 DIHYDRO 5H DIBENZO[B,E][1,4] DIAZEPIN 8 YL] N,N DIMETHYLACETAMIDE; 3 [3 (3 METHOXY 4 NITROPHENYL) 11 OXO 10,11 DIHYDRO 5H DIBENZO[B,E][1,4] DIAZEPIN 8 YL] N,N DIMETHYLPROPANAMIDE; AMIDE; CAMPTOTHECIN; CHECKPOINT KINASE 1; CISPLATIN; DIAZEPINE DERIVATIVE; DOXORUBICIN; LYSINE; PHOSPHOTRANSFERASE INHIBITOR; UNCLASSIFIED DRUG;

EID: 34548118639     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm070105d     Document Type: Article
Times cited : (46)

References (35)
  • 2
    • 0030867582 scopus 로고    scopus 로고
    • Conservation of the Chk1 checkpoint pathway in mammals: Linkage of DNA damage to Cdk regulation through Cdc25
    • (b) Sanchez, Y.; Wong, C.; Thoma, R. S.; Richman, R.; Wu, Z.; Piwinca-Worms, H.; Elledge, S. J. Conservation of the Chk1 checkpoint pathway in mammals: Linkage of DNA damage to Cdk regulation through Cdc25. Science 1997, 277, 1497-1501.
    • (1997) Science , vol.277 , pp. 1497-1501
    • Sanchez, Y.1    Wong, C.2    Thoma, R.S.3    Richman, R.4    Wu, Z.5    Piwinca-Worms, H.6    Elledge, S.J.7
  • 3
    • 0035449355 scopus 로고    scopus 로고
    • Cell cycle checkpoint signaling through the ATM and ATR kinases
    • Abraham, R. T. Cell cycle checkpoint signaling through the ATM and ATR kinases. Genes Dev. 2001, 15, 2177-2196.
    • (2001) Genes Dev , vol.15 , pp. 2177-2196
    • Abraham, R.T.1
  • 6
    • 0028985932 scopus 로고
    • Abrogation of the G2 checkpoint results in differential radiosensitization of G1 checkpoint-deficient and G1 checkpoint-competent cells
    • (a) Russell, K. J.; Wiens, L. W.; Demers, G. W.; Galloway, D. A.; Plon, S. E.; Groudine, M. Abrogation of the G2 checkpoint results in differential radiosensitization of G1 checkpoint-deficient and G1 checkpoint-competent cells. Cancer Res. 1995, 55, 1639-1642.
    • (1995) Cancer Res , vol.55 , pp. 1639-1642
    • Russell, K.J.1    Wiens, L.W.2    Demers, G.W.3    Galloway, D.A.4    Plon, S.E.5    Groudine, M.6
  • 7
    • 0028936626 scopus 로고
    • Differential sensitivity of p53-(-) and p53(+) cells to caffeine-induced radiosensitization and override of G2 delay
    • (b) Powell, S, N.; DeFrank, J. S.; Connell, P.; Eogan, M.; Preffer, F.; Dombkowski, D.; Tang, W.; Friend, S. Differential sensitivity of p53-(-) and p53(+) cells to caffeine-induced radiosensitization and override of G2 delay. Cancer Res. 1995, 55, 1643-1648.
    • (1995) Cancer Res , vol.55 , pp. 1643-1648
    • Powell, S.N.1    DeFrank, J.S.2    Connell, P.3    Eogan, M.4    Preffer, F.5    Dombkowski, D.6    Tang, W.7    Friend, S.8
  • 8
    • 0030811613 scopus 로고    scopus 로고
    • 7-Hydroxystaurosporine (UCN-01) causes redistribution of proliferating cell nuclear antigen and abrogates cisplatin-induced S-phase arrest in Chinese hamster ovary cells
    • (c) Bunch, R. T.; Eastman, A. 7-Hydroxystaurosporine (UCN-01) causes redistribution of proliferating cell nuclear antigen and abrogates cisplatin-induced S-phase arrest in Chinese hamster ovary cells. Cell Growth Differ. 1997, 8, 779-88.
    • (1997) Cell Growth Differ , vol.8 , pp. 779-788
    • Bunch, R.T.1    Eastman, A.2
  • 10
    • 0028788952 scopus 로고
    • Tumor suppressor p53 mutations and breast cancer: A critical analysis
    • (a) Ozbun, M. A.; Butel, J. S. Tumor suppressor p53 mutations and breast cancer: A critical analysis. Adv. Cancer Res. 1995, 66, 71-141.
    • (1995) Adv. Cancer Res , vol.66 , pp. 71-141
    • Ozbun, M.A.1    Butel, J.S.2
  • 11
    • 0035545996 scopus 로고    scopus 로고
    • Mammalian G1- and S-phase checkpoints in response to DNA damage
    • (b) Bartek, J.; Lukas, J. Mammalian G1- and S-phase checkpoints in response to DNA damage. Curr. Opin. Cell Biol. 2001, 13, 738-47.
    • (2001) Curr. Opin. Cell Biol , vol.13 , pp. 738-747
    • Bartek, J.1    Lukas, J.2
  • 12
    • 0034614637 scopus 로고    scopus 로고
    • The hallmarks of cancer
    • (c) Hanahan, D.; Weinberg, R.A. The hallmarks of cancer. Cell 2000, 100, 57-70.
    • (2000) Cell , vol.100 , pp. 57-70
    • Hanahan, D.1    Weinberg, R.A.2
  • 13
    • 0028936626 scopus 로고
    • Differential sensitivity of p53(-•) and p53(+) cells to caffeine-induced radiosensitization and override of G2 delay
    • (a) Powell, S. N.; DeFrank, J. S.; Connell, P.; Eogan, M.; Preffer, F.; Domkowski, D.; Tang, W.; Friend, S. Differential sensitivity of p53(-•) and p53(+) cells to caffeine-induced radiosensitization and override of G2 delay. Cancer Res. 1995, 55, 1643-1648.
    • (1995) Cancer Res , vol.55 , pp. 1643-1648
    • Powell, S.N.1    DeFrank, J.S.2    Connell, P.3    Eogan, M.4    Preffer, F.5    Domkowski, D.6    Tang, W.7    Friend, S.8
  • 14
    • 4444344407 scopus 로고    scopus 로고
    • G2 checkpoint abrogators as anticancer drugs
    • (b) Kawabe, T. G2 checkpoint abrogators as anticancer drugs. Mol. Cancer Ther. 2004, 3, 513-519.
    • (2004) Mol. Cancer Ther , vol.3 , pp. 513-519
    • Kawabe, T.1
  • 15
    • 0036569855 scopus 로고    scopus 로고
    • Wang, H.; Wang, X.; Zhou, X.-Y.; Chen, D. J.; Li, G. C.; Iliakis, G.; Wang, Y. Ku Affects Ataxia and Rad 3-releated/Chk1-dependent S phase checkpoint response after camptothecin treatment. Cancer Res. 2002, 62, 2483-2487.
    • (a) Wang, H.; Wang, X.; Zhou, X.-Y.; Chen, D. J.; Li, G. C.; Iliakis, G.; Wang, Y. Ku Affects Ataxia and Rad 3-releated/Chk1-dependent S phase checkpoint response after camptothecin treatment. Cancer Res. 2002, 62, 2483-2487.
  • 16
    • 1542754615 scopus 로고    scopus 로고
    • Human Chk1 expression is dispensable for somatic cell death and critical for sustaining G2 DNA damage checkpoint
    • (b) Chen, Z.; Xiao, Z.; Chen, J.; Ng, S. C.; Sowin, T.; Sham, H. L.; Rosenberg, S. H.; Fesik, S.; Zhang, H. Human Chk1 expression is dispensable for somatic cell death and critical for sustaining G2 DNA damage checkpoint. Mol. Cancer Ther. 2003, 2, 543-548.
    • (2003) Mol. Cancer Ther , vol.2 , pp. 543-548
    • Chen, Z.1    Xiao, Z.2    Chen, J.3    Ng, S.C.4    Sowin, T.5    Sham, H.L.6    Rosenberg, S.H.7    Fesik, S.8    Zhang, H.9
  • 17
    • 0036718911 scopus 로고    scopus 로고
    • Targeting serine/threonine protein kinase B/Akt and cell-cycle checkpoint kinases for treating cancer
    • (a) Li, Q.; Zhu, G.-D. Targeting serine/threonine protein kinase B/Akt and cell-cycle checkpoint kinases for treating cancer. Curr. Top. Med. Chem. 2002, 2, 939-971.
    • (2002) Curr. Top. Med. Chem , vol.2 , pp. 939-971
    • Li, Q.1    Zhu, G.-D.2
  • 19
    • 0033975054 scopus 로고    scopus 로고
    • An indolocarbazole inhibitor of human checkpoint kinase (Chk1) abrogates cell cycle arrest caused by DNA damage
    • Jackson, J. R.; Gilmartin, A.; Imburgia, C.; Winkler, J. D.; Marshall, L. A.; Roshak, A. An indolocarbazole inhibitor of human checkpoint kinase (Chk1) abrogates cell cycle arrest caused by DNA damage. Cancer Res. 2000, 60, 566-572.
    • (2000) Cancer Res , vol.60 , pp. 566-572
    • Jackson, J.R.1    Gilmartin, A.2    Imburgia, C.3    Winkler, J.D.4    Marshall, L.A.5    Roshak, A.6
  • 22
    • 0034053130 scopus 로고    scopus 로고
    • The Chk1 protein kinase and the Cdc25C regulatory pathways are targets of the anticancer agent UCN-01
    • (a) Graves, P. R.; Yu, L.; Schwarz, J. K.; Gales, J.; Sausville, E. A.; O'Connor, P. M.; Piwinca-Worms, H. The Chk1 protein kinase and the Cdc25C regulatory pathways are targets of the anticancer agent UCN-01. J. Biol. Chem. 2000, 275, 5600-5605.
    • (2000) J. Biol. Chem , vol.275 , pp. 5600-5605
    • Graves, P.R.1    Yu, L.2    Schwarz, J.K.3    Gales, J.4    Sausville, E.A.5    O'Connor, P.M.6    Piwinca-Worms, H.7
  • 23
    • 0034655281 scopus 로고    scopus 로고
    • The radiosensitizing agent 7-hydroxystaurosporine (UCN-01) inhibits the DNA damage checkpoint kinase hChk1
    • (b) Busby, E. C.; Leistritz, D. F.; Abraham, R. T.; Karnitz, L. M.; Sarkaria, J. N. The radiosensitizing agent 7-hydroxystaurosporine (UCN-01) inhibits the DNA damage checkpoint kinase hChk1. Cancer Res. 2000, 60, 2108-2112.
    • (2000) Cancer Res , vol.60 , pp. 2108-2112
    • Busby, E.C.1    Leistritz, D.F.2    Abraham, R.T.3    Karnitz, L.M.4    Sarkaria, J.N.5
  • 24
    • 34548126731 scopus 로고    scopus 로고
    • Ninkvoic, S.; Bennett, M. J.; Rui, E. Y.; Wang, F.; Benedict, S. P.; Teng, M. WO 2004/063198, 2004.
    • (a) Ninkvoic, S.; Bennett, M. J.; Rui, E. Y.; Wang, F.; Benedict, S. P.; Teng, M. WO 2004/063198, 2004.
  • 26
    • 34548126726 scopus 로고    scopus 로고
    • Gesner, T. G.; Barsanti, P. A.; Harrison, S. D.; Ni, Z.-J.; Brammeier, N. M.; Zhou, Y.; Le, V. P. Combination therapy with Chk1 inhibitors. U.S. 2005/0256157, 2005.
    • Gesner, T. G.; Barsanti, P. A.; Harrison, S. D.; Ni, Z.-J.; Brammeier, N. M.; Zhou, Y.; Le, V. P. Combination therapy with Chk1 inhibitors. U.S. 2005/0256157, 2005.
  • 27
    • 34548135065 scopus 로고    scopus 로고
    • Boyle, R. G.; Imogai, H. J.; Cherry, M.; Humphries, A. J.; Navarro, E. F.; Owen, D. R.; Dales, N. A.; Lamarche, M.; Cullis, C.; Gould, A. E. WO 2005/028474, 2005.
    • Boyle, R. G.; Imogai, H. J.; Cherry, M.; Humphries, A. J.; Navarro, E. F.; Owen, D. R.; Dales, N. A.; Lamarche, M.; Cullis, C.; Gould, A. E. WO 2005/028474, 2005.
  • 28
    • 20944439528 scopus 로고    scopus 로고
    • 1-(5-Chloro-2-alkoxyphenyl)-3-(5-cyano-pyrazi-2-yl)ureas as potent and selective inhibitors of Chk1 kinase: Synthesis, preliminary SAR, and biological activities
    • (a) Wang, G. T.; Li, G.; Mantei, R. A.; Chen, Z.; Kovar, P.; Gu, W.; Xiao, Z.; Zhang, H.; Sham, H. L.; Sowin, T.; Rosenberg, S. H.; Lin, N.-H. 1-(5-Chloro-2-alkoxyphenyl)-3-(5-cyano-pyrazi-2-yl)ureas as potent and selective inhibitors of Chk1 kinase: Synthesis, preliminary SAR, and biological activities. J. Med. Chem. 2005, 48, 3118-3121.
    • (2005) J. Med. Chem , vol.48 , pp. 3118-3121
    • Wang, G.T.1    Li, G.2    Mantei, R.A.3    Chen, Z.4    Kovar, P.5    Gu, W.6    Xiao, Z.7    Zhang, H.8    Sham, H.L.9    Sowin, T.10    Rosenberg, S.H.11    Lin, N.-H.12
  • 29
    • 34548140359 scopus 로고    scopus 로고
    • Diaryl urea compounds and derivatives as Chk1 inhibitors for the treatment of cancer
    • WO 03/101444
    • (b) Boyle, R. G.; Imogai, H. J.; Cherry, M. Diaryl urea compounds and derivatives as Chk1 inhibitors for the treatment of cancer. WO 03/101444, 2003.
    • (2003)
    • Boyle, R.G.1    Imogai, H.J.2    Cherry, M.3
  • 32
    • 0021840018 scopus 로고
    • A new facile synthesis of 11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines
    • Giani, R. P.; Borsa, M.; Parini, E.; and Tonon, G. C. A new facile synthesis of 11-oxo-10,11-dihydro-5H-dibenzo[b,e][1,4]diazepines Synthesis 1985, 5, 550-552.
    • (1985) Synthesis , vol.5 , pp. 550-552
    • Giani, R.P.1    Borsa, M.2    Parini, E.3    Tonon, G.C.4
  • 33
    • 0035802895 scopus 로고    scopus 로고
    • Synthesis of pinacol arylboronates via cross-coupling reaction of bis(pinacolato)diboron with chloroarenes catalyzed by palladium(0)-tricyclohexylphosphine complexes
    • Ishiyama, T.; Ishida, K.; Miyaura, N. Synthesis of pinacol arylboronates via cross-coupling reaction of bis(pinacolato)diboron with chloroarenes catalyzed by palladium(0)-tricyclohexylphosphine complexes. Tetrahedron 2001, 57, 9813-9816.
    • (2001) Tetrahedron , vol.57 , pp. 9813-9816
    • Ishiyama, T.1    Ishida, K.2    Miyaura, N.3
  • 35
    • 27944448722 scopus 로고    scopus 로고
    • Synthesis and biological evaluation of 3-ethylidene-1,3- dihydro-indol-2-ones as novel checkpoint 1 inhibitors
    • Lin, N.-H.; Xia, P.; Kovar, P.; Park, C.; Chen, Z.; Zhang, H.; Rosenberg, S. H.; Sham, H. L. Synthesis and biological evaluation of 3-ethylidene-1,3- dihydro-indol-2-ones as novel checkpoint 1 inhibitors. Bioorg. Med. Chem. Lett. 2006, 16, 421-426.
    • (2006) Bioorg. Med. Chem. Lett , vol.16 , pp. 421-426
    • Lin, N.-H.1    Xia, P.2    Kovar, P.3    Park, C.4    Chen, Z.5    Zhang, H.6    Rosenberg, S.H.7    Sham, H.L.8


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.