메뉴 건너뛰기




Volumn 56, Issue 13, 2013, Pages 5407-5421

Synthesis, in vitro, and in cell studies of a new series of [Indoline-3,2′-thiazolidine]-based p53 modulators

Author keywords

[No Author keywords available]

Indexed keywords

5 BROMO 3' (CYCLOHEXANECARBONYL) 1 METHYL 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ANTINEOPLASTIC AGENT; ETHYL 1 (4 CHLOROBENZOYL) 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 1 (4 CHLOROBENZOYL) 5 METHYL 2 OXO 5' H SPIRO[INDOLINE 3,2' THIAZOLE] 4 CARBOXYLATE; ETHYL 1 (4 CHLOROBENZOYL) 5 METHYL 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 3' (2 (4 CHLOROPHENYLACETYL) 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE 4 CARBOXYATE; ETHYL 3' (4 CHLOROBENZOYL) 1 METHYL 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 3' (4 CHLOROBENZOYL) 1,5 DIMETHYL 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 3' (4 CHLOROBENZOYL) 2 OXOSPIRO[INDOLINE 3,2 THIAZOLIDINE] 4' CARBOXYLATE; ETHYL 3' (4 CHLOROBENZOYL) 5 METHYL 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 3' (CYCLOHEXANECARBONYL) 1 METHYL 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 5 BROMO 1 (4 CHLOROBENZOYL) 2 OXO 5 H SPIRO[INDOLINE 3,2' THIAZOLE] 4 CARBOXYLATE; ETHYL 5 BROMO 1 (4 CHLOROBENZOYL) 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 5 BROMO 1 (CYCLOHEXANECARBONYL) 2 OXO 5 H SPIRO[INDOLINE 3,2' THIAZOLE] 4 CARBOXYLATE; ETHYL 5 BROMO 1 (CYCLOHEXANECARBONYL) 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 5 BROMO 1 METHYL 3' (4 METHYLBENZOYL) 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 5 BROMO 3 (4 CHLOROBENZOYL) 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4' CARBOXYLATE; ETHYL 5 BROMO 3 BROMO 3' BENZOYL 1 METHYL 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 5 BROMO 3' (2 (4 CHLOROPHENYL)ACETYL) 1 METHYL 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 5 BROMO 3' (2 (4 CHLOROPHENYL)ACETYL) 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 5 BROMO 3' (4 CHLOROBENZOYL) 1 METHYL 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 5 BROMO 3' (CYCLOHEXANECARBONYL) 1 METHYL 2 OXOSPIRO[INDOLINE 3,2 THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 5 BROMO 3' (CYCLOHEXANECARBONYL) 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 5 METHYL 3' (2 (4 CHLOROPHENYL)ACETYL) 2 OXOSPIRO[INDOLINE 3,2 THIAZOLIDINE] 4 CARBOXYLATE; ETHYL 5 METHYL 3' (CYCLOHEXANECARBONYL) 1 METHYL 2 OXOSPIRO[INDOLINE 3,2' THIAZOLIDINE] 4 CARBOXYLATE; PROTEIN P53; THIAZOLIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84880165688     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm400311n     Document Type: Article
Times cited : (74)

References (54)
  • 1
    • 70349442548 scopus 로고    scopus 로고
    • The first 30 years of p53: Growing ever more complex
    • Levine, J.; Oren, M. The first 30 years of p53: Growing ever more complex Nat. Rev. Cancer 2009, 9, 749-758
    • (2009) Nat. Rev. Cancer , vol.9 , pp. 749-758
    • Levine, J.1    Oren, M.2
  • 3
    • 65349103899 scopus 로고    scopus 로고
    • Blinded by the light: The growing complexity of p53
    • Vousden, K. H.; Prives, C. Blinded by the light: the growing complexity of p53 Cell 2009, 137, 413-431
    • (2009) Cell , vol.137 , pp. 413-431
    • Vousden, K.H.1    Prives, C.2
  • 4
    • 79251648704 scopus 로고    scopus 로고
    • Tumor suppressor p53: New functions of an old protein
    • Feng, Z.; Wu, R.; Lin, M.; Hu, W. Tumor suppressor p53: new functions of an old protein Front. Biol. 2011, 6, 58-68
    • (2011) Front. Biol. , vol.6 , pp. 58-68
    • Feng, Z.1    Wu, R.2    Lin, M.3    Hu, W.4
  • 6
    • 78951475020 scopus 로고    scopus 로고
    • P53 and its mutants in tumor cell migration and invasion
    • references therein
    • Muller, P. A. J.; Vousden, K. H.; Norman, J. C. p53 and its mutants in tumor cell migration and invasion J. Cell Biol. 2011, 192, 209-218 and references therein
    • (2011) J. Cell Biol. , vol.192 , pp. 209-218
    • Muller, P.A.J.1    Vousden, K.H.2    Norman, J.C.3
  • 7
    • 1942437663 scopus 로고    scopus 로고
    • Regulating the p53 system through ubiquitination
    • Yang, Y.; Li, C. C.; Weissman, A. M. Regulating the p53 system through ubiquitination Oncogene 2004, 23, 2096-2106
    • (2004) Oncogene , vol.23 , pp. 2096-2106
    • Yang, Y.1    Li, C.C.2    Weissman, A.M.3
  • 8
    • 0026649648 scopus 로고
    • The mdm-2 oncogene product forms a complex with p53 protein and inhibits p53-mediated transactivation
    • Momand, J.; Zambetti, G. P.; Olson, D. C.; George, D.; Levine, A. The mdm-2 oncogene product forms a complex with p53 protein and inhibits p53-mediated transactivation Cell 1992, 69, 1237-1245
    • (1992) Cell , vol.69 , pp. 1237-1245
    • Momand, J.1    Zambetti, G.P.2    Olson, D.C.3    George, D.4    Levine, A.5
  • 9
    • 0034282220 scopus 로고    scopus 로고
    • The MDM2 RING-finger domain is required to promote p53 nuclear export
    • Geyer, R. K.; Yu, Z. K.; Maki, C. G. The MDM2 RING-finger domain is required to promote p53 nuclear export Nat. Cell Biol. 2000, 2, 569-73
    • (2000) Nat. Cell Biol. , vol.2 , pp. 569-73
    • Geyer, R.K.1    Yu, Z.K.2    Maki, C.G.3
  • 10
    • 0030905284 scopus 로고    scopus 로고
    • Mdm2 promotes the rapid degradation of p53
    • Haupt, Y.; Maya, R.; Kazaz, A.; Oren, M. Mdm2 promotes the rapid degradation of p53 Nature 1997, 387, 296-299
    • (1997) Nature , vol.387 , pp. 296-299
    • Haupt, Y.1    Maya, R.2    Kazaz, A.3    Oren, M.4
  • 11
    • 0030941458 scopus 로고    scopus 로고
    • P53, the cellular gatekeeper for growth and division
    • Levine, A. p53, the cellular gatekeeper for growth and division Cell 1997, 88, 323-331
    • (1997) Cell , vol.88 , pp. 323-331
    • Levine, A.1
  • 12
    • 0028071555 scopus 로고
    • Mutations in the p53 tumor suppressor gene: Clues to cancer etiology and molecular pathogenesis
    • Greenblatt, M. S.; Bennett, W. P.; Hollstein, M.; Harris, C. C. Mutations in the p53 tumor suppressor gene: clues to cancer etiology and molecular pathogenesis Cancer Res. 1994, 54, 4855-4878
    • (1994) Cancer Res. , vol.54 , pp. 4855-4878
    • Greenblatt, M.S.1    Bennett, W.P.2    Hollstein, M.3    Harris, C.C.4
  • 13
    • 0025853776 scopus 로고
    • Tumorigenic potential associated with enhanced expression of a gene that is amplified in a mouse tumor cell line
    • Fakharzadeh, S. S.; Trusko, S. P.; George, D. L. Tumorigenic potential associated with enhanced expression of a gene that is amplified in a mouse tumor cell line EMBO J. 1991, 10, 1565-1569
    • (1991) EMBO J. , vol.10 , pp. 1565-1569
    • Fakharzadeh, S.S.1    Trusko, S.P.2    George, D.L.3
  • 14
    • 0026740449 scopus 로고
    • Amplification of a gene encoding a p53-associated protein in human sarcomas
    • Oliner, J. D.; Kinzler, K. W.; Meltzer, P. S.; George, D. L.; Vogelstein, B. Amplification of a gene encoding a p53-associated protein in human sarcomas Nature 1992, 358, 80-83
    • (1992) Nature , vol.358 , pp. 80-83
    • Oliner, J.D.1    Kinzler, K.W.2    Meltzer, P.S.3    George, D.L.4    Vogelstein, B.5
  • 19
    • 0037317840 scopus 로고    scopus 로고
    • Inhibiting the p53-MDM2 interaction: An important target for cancer therapy
    • Chene, P. Inhibiting the p53-MDM2 interaction: an important target for cancer therapy Nat. Rev. Cancer 2003, 3, 102-109
    • (2003) Nat. Rev. Cancer , vol.3 , pp. 102-109
    • Chene, P.1
  • 20
    • 36749026212 scopus 로고    scopus 로고
    • Inhibitors of the MDM2-p53 interaction as anticancer drugs
    • Hardcastle, I. R. Inhibitors of the MDM2-p53 interaction as anticancer drugs Drugs Future 2007, 32, 883-896
    • (2007) Drugs Future , vol.32 , pp. 883-896
    • Hardcastle, I.R.1
  • 21
    • 33645469420 scopus 로고    scopus 로고
    • Peptide, peptidomimetic, and small-molecule antagonists of the p53-HDM2 protein-protein interaction
    • Fischer, P. Peptide, peptidomimetic, and small-molecule antagonists of the p53-HDM2 protein-protein interaction Int. J. Pept. Res. Ther. 2006, 12, 3-19
    • (2006) Int. J. Pept. Res. Ther. , vol.12 , pp. 3-19
    • Fischer, P.1
  • 22
    • 65249100143 scopus 로고    scopus 로고
    • Small-molecule inhibitors of the MDM2-p53 protein-protein interaction to reactivate p53 function: A novel approach for cancer therapy
    • Shangary, S.; Wang, S. Small-molecule inhibitors of the MDM2-p53 protein-protein interaction to reactivate p53 function: a novel approach for cancer therapy Ann. Rev. Pharmacol. Toxicol 2009, 49, 223-241
    • (2009) Ann. Rev. Pharmacol. Toxicol , vol.49 , pp. 223-241
    • Shangary, S.1    Wang, S.2
  • 31
  • 33
    • 35048895357 scopus 로고    scopus 로고
    • Targeting protein-protein interactions: Lessons from p53/MDM2
    • Murray, J. K.; Gellman, S. H. Targeting protein-protein interactions: lessons from p53/MDM2 Biopolymers 2007, 88, 657-686
    • (2007) Biopolymers , vol.88 , pp. 657-686
    • Murray, J.K.1    Gellman, S.H.2
  • 34
    • 65249100143 scopus 로고    scopus 로고
    • Small-molecule inhibitors of the MDM2-p53 protein-protein interaction to reactivate p53 function: A novel approach for cancer therapy
    • Shangary, S.; Wang, S. Small-molecule inhibitors of the MDM2-p53 protein-protein interaction to reactivate p53 function: a novel approach for cancer therapy Annu. Rev. Pharmacol. Toxicol. 2009, 49, 223-241
    • (2009) Annu. Rev. Pharmacol. Toxicol. , vol.49 , pp. 223-241
    • Shangary, S.1    Wang, S.2
  • 37
    • 33845560224 scopus 로고
    • Comments on the putative stereoselectivity in cysteine-aldehyde reactions. Selective C(2) inversion and C(4) epimerization in thiazolidine-4-carboxylic acids
    • Szilagyi, L.; Gyorgydeak, Z. Comments on the putative stereoselectivity in cysteine-aldehyde reactions. Selective C(2) inversion and C(4) epimerization in thiazolidine-4-carboxylic acids J. Am. Chem. Soc. 1979, 101, 427-432
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 427-432
    • Szilagyi, L.1    Gyorgydeak, Z.2
  • 38
    • 0028808740 scopus 로고
    • Novel enantioselective syntheses of (+)-biotin
    • Deroose, F. D; De Clercq, J. Novel enantioselective syntheses of (+)-biotin J. Org. Chem. 1995, 60, 321-330
    • (1995) J. Org. Chem. , vol.60 , pp. 321-330
    • Deroose, F.D.1    De Clercq, J.2
  • 40
    • 52149098016 scopus 로고    scopus 로고
    • Disruption of the p53-Mdm2 complex by nutlin-3 reveals different cancer cell phenotypes
    • Arva, N. C.; Talbott, K. E.; Okoro, D. R.; Brekman, A.; Qiu, W. G.; Bargonetti, J. Disruption of the p53-Mdm2 complex by nutlin-3 reveals different cancer cell phenotypes Ethnicity Dis. 2008, 18 (S2) 1-8
    • (2008) Ethnicity Dis. , vol.18 , Issue.S2 , pp. 1-8
    • Arva, N.C.1    Talbott, K.E.2    Okoro, D.R.3    Brekman, A.4    Qiu, W.G.5    Bargonetti, J.6
  • 41
    • 42249102761 scopus 로고    scopus 로고
    • Nutlin-3 radiosensitizes hypoxic prostate cancer cells independent of p53
    • Supiot, S.; Hill, R. P.; Bristow, R. G. Nutlin-3 radiosensitizes hypoxic prostate cancer cells independent of p53 Mol. Cancer Ther. 2008, 7, 993-999
    • (2008) Mol. Cancer Ther. , vol.7 , pp. 993-999
    • Supiot, S.1    Hill, R.P.2    Bristow, R.G.3
  • 42
    • 77956062176 scopus 로고    scopus 로고
    • Nutlin-3 cooperates with doxorubicin to induce apoptosis of human hepatocellular carcinoma cells through p53 or p73 signaling pathways
    • Zheng, T.; Jiabei Wang, J.; Song, X.; Meng, X.; Pan, S.; Jiang, H.; Liu, L. Nutlin-3 cooperates with doxorubicin to induce apoptosis of human hepatocellular carcinoma cells through p53 or p73 signaling pathways J. Cancer Res. Clin. Oncol. 2010, 136, 1597-1604
    • (2010) J. Cancer Res. Clin. Oncol. , vol.136 , pp. 1597-1604
    • Zheng, T.1    Jiabei Wang, J.2    Song, X.3    Meng, X.4    Pan, S.5    Jiang, H.6    Liu, L.7
  • 43
    • 77953492371 scopus 로고    scopus 로고
    • Structures of low molecular weight inhibitors bound to MDMX and MDM2 reveal new approaches for p53-MDMX/MDM2 antagonist drug discovery
    • Popowicz, G. M.; Czarna, A.; Wolf, S.; Wang, K.; Wang, W.; Dömling, A.; Holak, T. A. Structures of low molecular weight inhibitors bound to MDMX and MDM2 reveal new approaches for p53-MDMX/MDM2 antagonist drug discovery Cell Cycle 2010, 9, 1104-1111
    • (2010) Cell Cycle , vol.9 , pp. 1104-1111
    • Popowicz, G.M.1    Czarna, A.2    Wolf, S.3    Wang, K.4    Wang, W.5    Dömling, A.6    Holak, T.A.7
  • 44
    • 33947716119 scopus 로고    scopus 로고
    • A semiempirical free energy force field with charge-based desolvation
    • Huey, R.; Morris, G. M.; Olson, A. J.; Goodsell, D. S. A semiempirical free energy force field with charge-based desolvation J. Comput. Chem. 2007, 28, 1145-1152
    • (2007) J. Comput. Chem. , vol.28 , pp. 1145-1152
    • Huey, R.1    Morris, G.M.2    Olson, A.J.3    Goodsell, D.S.4
  • 47
    • 0036674617 scopus 로고    scopus 로고
    • Live or let die: The cell's response to p53
    • Vousden, K. H.; Xin, Lu, X. Live or let die: the cell's response to p53 Nat. Rev. Cancer 2002, 2, 594-604
    • (2002) Nat. Rev. Cancer , vol.2 , pp. 594-604
    • Vousden, K.H.1    Xin, L.X.2
  • 50
    • 72049083694 scopus 로고    scopus 로고
    • Nutlin-3 enhances tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-induced apoptosis through up-regulation of death receptor 5 (DR5) in human sarcoma HOS cells and human colon cancer HCT116 cells
    • Hori, T.; Kondo, T.; Kanamori, M.; Tabuchi, Y.; Ogawa, R.; Zhao, Q.-L.; Ahmed, K.; Yasuda, T.; Seki, S.; Suzuki, K.; Kimura, T. Nutlin-3 enhances tumor necrosis factor-related apoptosis-inducing ligand (TRAIL)-induced apoptosis through up-regulation of death receptor 5 (DR5) in human sarcoma HOS cells and human colon cancer HCT116 cells Cancer Lett. 2010, 287, 98-108
    • (2010) Cancer Lett. , vol.287 , pp. 98-108
    • Hori, T.1    Kondo, T.2    Kanamori, M.3    Tabuchi, Y.4    Ogawa, R.5    Zhao, Q.-L.6    Ahmed, K.7    Yasuda, T.8    Seki, S.9    Suzuki, K.10    Kimura, T.11
  • 51
    • 78650439014 scopus 로고    scopus 로고
    • Contrasting effects of nutlin-3 on TRAIL- and docetaxel-induced apoptosis due to upregulation of TRAIL-R2 and Mcl-1 in human melanoma cells
    • Tseng, H.-Y.; Jiang, C. C.; Croft, A.; Tay, K. H.; Thorne, R. F.; Fan Yang, F.; Liu, H.; Hersey, P.; Zhang, X. D. Contrasting effects of nutlin-3 on TRAIL- and docetaxel-induced apoptosis due to upregulation of TRAIL-R2 and Mcl-1 in human melanoma cells Mol. Cancer Ther. 2010, 9, 3363-3374
    • (2010) Mol. Cancer Ther. , vol.9 , pp. 3363-3374
    • Tseng, H.-Y.1    Jiang, C.C.2    Croft, A.3    Tay, K.H.4    Thorne, R.F.5    Fan Yang, F.6    Liu, H.7    Hersey, P.8    Zhang, X.D.9
  • 52
    • 5144229966 scopus 로고
    • 2D ROESY with cw spinlock for mixing phase sensitive using States-TPPI method
    • Bax, A.; Davis, D. G. 2D ROESY with cw spinlock for mixing phase sensitive using States-TPPI method J. Magn. Reson. 1985, 63, 207-213
    • (1985) J. Magn. Reson. , vol.63 , pp. 207-213
    • Bax, A.1    Davis, D.G.2
  • 53
    • 2642628181 scopus 로고
    • A two-dimensional nuclear Overhauser experiment with pure absorption phase four quadrants
    • States, D. J.; Haberkorn, R. A.; Ruben, D. J. A two-dimensional nuclear Overhauser experiment with pure absorption phase four quadrants J. Magn. Reson. 1982, 48, 286-292
    • (1982) J. Magn. Reson. , vol.48 , pp. 286-292
    • States, D.J.1    Haberkorn, R.A.2    Ruben, D.J.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.