Design, synthesis and biological evaluation of novel 3,4,5-trisubstituted aminothiophenes as inhibitors of p53-MDM2 interaction. Part 2

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 11, 2013, Pages 2886-2894

  Wang, Weisi ^a   Lv, Dan ^a   Qiu, Ni ^a   Zhang, Lei ^a   Hu, Chunqi ^a   Hu, Yongzhou ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

3,4,5 Trisubstituted aminothiophenes; Anti cancer; P53 MDM2 interaction; SARs

Indexed keywords

(2 AMINO 4 (4 CHLOROPHENYL) 5 (4 FLUOROPHENYL)THIOPHEN 3 YL)(MORPHOLINO)METHANONE; (2 AMINO 4 (4 CHLOROPHENYL) 5 (4 FLUOROPHENYL)THIOPHEN 3 YL)(PYRROLIDIN 1 YL)METHANONE; (2 AMINO 4 (4 CHLOROPHENYL) 5 PHENYLTHIOPHEN 3 YL)(MORPHOLINO)METHANONE; (2 AMINO 4 (4 CHLOROPHENYL) 5 PHENYLTHIOPHEN 3 YL)(PYRROLIDIN 1 YL)METHANONE; 2 AMINO 4 (4 CHLOROPHENYL) N CYCLOHEXY 5 (4 NITROPHENYL)THIOPHENE 3 CARBOXAMIDE; 2 AMINO 4 (4 CHLOROPHENYL) N CYCLOPROPYL 5 (4 FLUOROPHENYL)THIOPHENE 3 CARBOXAMIDE; 2 AMINO 4 (4 CHLOROPHENYL) N CYCLOPROPYL 5 (4 NITROPHENYL)THIOPHENE 3 CARBOXAMIDE; 2 AMINO 4 (4 CHLOROPHENYL) N CYCLOPROPYL 5 PHENYLTHIOPHENE 3 CARBOXAMIDE; 2 AMINO 4,5 BIS(4 CHLOROPHENYL) N CYCLOHEXYLTHIOPHENE 3 CARBOTHIOAMIDE; 2 AMINO 4,5 BIS(4 CHLOROPHENYL) N CYCLOPENTYLTHIOPHENE 3 CARBOTHIOAMIDE; 2 AMINO 4,5 BIS(4 CHLOROPHENYL) N CYCLOPROPYL 1H PYRROLE 3 CARBOXAMIDE; 2 AMINO 4,5 BIS(4 CHLOROPHENYL) N CYCLOPROPYLTHIOPHENE 3 CARBOTHIOAMIDE; 2 AMINO 5 (4 BROMOPHENYL) 4 (4 CHLOROPHENYL) N CYCLOPROPYLTHIOPHENE 3 CARBOXAMIDE; 2 AMINO 5 (4 BROMOPHENYL) 4 (4 CHLOROPHENYL)N CYCLOHEXYLTHIOPHENE 3 CARBOXAMIDE; 2 AMINO N (TERT BUTYL) 4,5 BIS(4 CHLOROPHENYL)THIOPHENE 3 CARBOTHIOAMIDE; 2 AMINO N BENZYL 4 (4 CHLOROPHENYL) 5 (4 FLUOROPHENYL)THIOPHENE 3 CARBOXAMIDE; 2 AMINO N BENZYL 4 (4 CHLOROPHENYL) 5 PHENYLTHIOPHENE 3 CARBOXAMIDE; 2 AMINO N BENZYL 5 (4 BROMOPHENYL) 4 (4 CHLOROPHENYL)THIOPHENE 3 CARBOXAMIDE; 3,4,5 TRISUBSTITUTED AMINOTHIOPHENE DERIVATIVE; [2 AMINO 4 (4 CHLOROPHENYL) 5 (4 NITROPHENYL)THIOPHEN 3 YL](MORPHOLINO)METHANONE; [2 AMINO 4 (4 CHLOROPHENYL) 5 (4 NITROPHENYL)THIOPHEN 3 YL](PIPERIDIN 1 YL)METHANONE; [2 AMINO 4 (4 CHLOROPHENYL) 5 (4 NITROPHENYL)THIOPHEN 3 YL](PYRROLIDIN 1 YL)METHANONE; [2 AMINO 5 (4 BROMOPHENYL) 4 (4 CHLOROPHENYL)THIOPHEN 3 YL](MORPHOLINO)METHANONE; [2 AMINO 5 (4 BROMOPHENYL) 4 (4 CHLOROPHENYL)THIOPHEN 3 YL](PYRROLIDIN 1 YL)METHANONE; ANTINEOPLASTIC AGENT; ETHYL 2 AMINO 4,5 BIS(4 CHLOROPHENYL) 1H PYRROLE 3 CARBOXYLATE; MCL 0527; NUTLIN 3; PROTEIN MDM2; PROTEIN P53; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIPROLIFERATIVE ACTIVITY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; MOLECULAR DOCKING; PREDICTION; PROTEIN EXPRESSION; PROTEIN PROTEIN INTERACTION;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; KINETICS; MOLECULAR DOCKING SIMULATION; PROTEIN BINDING; PROTO-ONCOGENE PROTEINS C-MDM2; SENSITIVITY AND SPECIFICITY; STRUCTURE-ACTIVITY RELATIONSHIP; THIOPHENES; TUMOR SUPPRESSOR PROTEIN P53;

EID: 84877800856     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.03.070     Document Type: Article

References (20)

1. A. Efeyan, and M. Serrano Cell Cycle 6 2007 1006
2. A.J. Levine Cell 88 1997 323
3. B. Vogelstein, D. Lane, and A.J. Levine Nature 408 2000 307
4. P. Hainaut, and M. Hollstein Adv. Cancer Res. 77 2000 81
5. S.S. Fakharzadeh, S.P. Trusko, and D.L. George EMBO J. 10 1991 1565
6. J.D. Oliner, K.W. Kinzler, P.S. Meltzer, D.L. George, and B. Vogelstein Nature 358 1992 80
7. J.D. Oliner, J.A. Pietenpol, S. Thiagalingam, J. Gyuris, K.W. Kinzler, and B. Vogelstein Nature 362 1993 857
8. M.P. Dickens, R. Fitzgerald, and P.M. Fischer Semin. Cancer Biol. 20 2010 10
9. S. Shangary, and S. Wang Annu. Rev. Pharmacol. Toxicol. 49 2009 223
10. W. Wang, and Y. Hu Med. Res. Rev. 32 2012 1159
11. W. Wang, X. Zhu, X. Hong, L. Zheng, H. Zhu, and Y. Hu Med. Chem. Commun. 4 2013 411
12. Wang, W.; Shangguan, S.; Qiu, N.; Hu, C.; Zhang, L.; Hu, Y. Bioorg. Med. Chem. http://dx.doi.org/10.1016/j.bmc.2013.03.061.
13. K. Gewald, E. Schinke, and H. Böttcher Chemische Berichte 99 1966 94
14. R.H. Rynbrandt, E.E. Nishizawa, D.P. Balogoyen, A.R. Mendoza, and K.A. Annis J. Med. Chem. 24 1981 1507
15. T. Kobayashi, T. Inoue, Z. Kita, H. Yoshiya, S. Nishino, K. Oizumi, and T. Kimura Chem. Pharm. Bull. (Tokyo) 43 1995 788
16. K. Ding, Y. Lu, Z. Nikolovska-Coleska, S. Qiu, Y. Ding, W. Gao, J. Stuckey, K. Krajewski, P.P. Roller, Y. Tomita, D.A. Parrish, J.R. Deschamps, and S. Wang J. Am. Chem. Soc. 127 2005 10130
17. K. Ding, Y. Lu, Z. Nikolovska-Coleska, G. Wang, S. Qiu, S. Shangary, W. Gao, D. Qin, J. Stuckey, K. Krajewski, P.P. Roller, and S. Wang J. Med. Chem. 49 2006 3432
18. H. Lutjens, A. Zickgraf, H. Figler, J. Linden, R.A. Olsson, and P.J. Scammells J. Med. Chem. 2003 1870 46
19. K. Wang, K. Nguyen, Y. Huang, and A. Domling J. Comb. Chem. 11 2009 920
20. Z. Nikolovska-Coleska, R. Wang, X. Fang, H. Pan, Y. Tomita, P. Li, P.P. Roller, K. Krajewski, N.G. Saito, J.A. Stuckey, and S. Wang Anal. Biochem. 332 2004 261