Synthesis and biological evaluation of novel quinazoline-derived human Pin1 inhibitors

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 9, 2011, Pages 2797-2807

  Zhu, Lina ^a,b   Jin, Jing ^a   Liu, Chang ^a,b   Zhang, Chongjing ^a   Sun, Yan ^a   Guo, Yanshen ^a   Fu, Decai ^b   Chen, Xiaoguang ^a   Xu, Bailing ^a  

^a INSTITUTE OF MATERIA MEDICA   (China)

^b HEBEI UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

Author keywords

Anti cancer agents; Pin1; Pin1 inhibitor; PPIase; Quinazoline

Indexed keywords

(6 NITRO 2 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)BENZOIC ACID; 2 (2 (BENZYLAMINO) 6 NITROQUINAZOLIN 4 YLAMINO)ETHYLDIHYDROGEN PHOSPHATE; 2 (2 CHLORO 6 QUINAZOLIN 4 YLAMINO)ETHANOL; 2 (6 NITRO 2 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)ACETIC ACID; 2 (6 NITRO 2 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)ETHANOL; 2 (6 NITRO 2 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)ETHYLDIHYDROGEN PHOSPHATE; 2,4 DICHLORO 6 NITROQUINAZOLINE; 2,4 DICHLOROQUINAZOLINE; 3 (2 (3,5 BIS(TRIFLUOROMETHYL)BENZYLAMINO) 6 NITROQUINAZOLIN 4 YLAMINO)PROPANOIC ACID; 3 (6 NITRO 2 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)PROPANOIC ACID; 4 (2 (3 (4 CHLOROPHENYL)UREIDO) 6 NITROQUINAZOLIN 4 YLAMINO)BENZOIC ACID; 4 (2 (3,5 BIS(TRIFLUOROMETHYL)BENZYLAMINO) 6 NITROQUINAZOLIN 4 YLAMINO)BUTANOIC ACID; 4 (2 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)BENZOIC ACID; 4 (6 AMINO 2 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)BENZOIC ACID; 4 (6 NITRO 2 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)BENZOIC ACID; 4 (6 NITRO 4 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)BENZOIC ACID; DIBENZYL 2 (2 (BENZYLAMINO) 6 NITROQUINAZOLIN 4 YLAMINO)ETHYLPHOSPHATE; DIBENZYL 2 (6 NITRO 2 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)ETHYLPHOSPHATE; ETHYL 4 (2 (3,5 BIS(TRIFLUOROMETHYL)BENZYLAMINO) 6 NITROQUINAZOLIN 4 YLAMINO)BUTANOATE; METHYL 2 (6 AMINO 2 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)ACETATE; METHYL 2 (6 NITRO 2 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)PROPANOATE; METHYL 3 (2 (3,5 BIS(TRIFLUOROMETHYL)BENZYLAMINO) 6 NITROQUINAZOLIN 4 YLAMINO)PROPANOATE; METHYL 4 (2 CHLORO 6 NITROQUINAZOLIN 4 YLAMINO)BENZOATE; METHYL 4 (2 CHLOROQUINAZOLIN 4 YLAMINO)BENZOATE; METHYL 4 (6 AMINO 2 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)BENZOATE; METHYL 4 (6 NITRO 2 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)BENZOATE; METHYL 4 (6 NITRO 4 (4 PHENOXYPHENYLAMINO)QUINAZOLIN 4 YLAMINO)BENZOATE; PEPTIDYLPROLYL ISOMERASE PIN1; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ARTICLE; BIOLOGICAL ACTIVITY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG DETERMINATION; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50; STRUCTURE ACTIVITY RELATION;

ALGORITHMS; BINDING SITES; CATALYTIC DOMAIN; ENZYME INHIBITORS; HUMANS; PEPTIDYLPROLYL ISOMERASE; PROTEIN STRUCTURE, TERTIARY; QUINAZOLINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79955379962     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.03.058     Document Type: Article

References (20)

1. K.P. Lu, S.D. Hanes, and T. Hunter Nature 380 1996 544
2. M.B. Yaffe, M. Schutkowski, M. Shen, X.Z. Zhou, P.T. Stukenberg, J.U. Rahfeld, J. Xu, J. Kuang, M.W. Kirschner, G. Fischer, L.C. Cantley, and K.P. Lu Science 278 1997 1957
3. M. Shen, P.T. Stukenberg, M.W. Kirschner, and K.P. Lu Genes Dev. 12 1998 706
4. K.P. Lu, and X.Z. Zhou Nat. Rev. Mol. Cell Biol. 8 2007 904
5. L. Bao, A. Kimzey, G. Sauter, J.M. Sowadski, K.P. Lu, and D.G. Wang Am. J. Pathol. 164 2004 1727
6. G. Ayala, D.G. Wang, G. Wulf, A. Frolov, R. Li, J. Sowadski, T.M. Wheeler, K.P. Lu, and L. Bao Cancer Res. 63 2003 6244
7. J.F. Rippmann, S. Hobbie, C. Daiber, B. Guilliard, M. Bauer, J. Birk, H. Nar, P. Garin-Chesa, W.J. Pettig, and A. Schnapp Cell Growth Differ. 11 2000 409
8. A. Ryo, H. Uemura, H. Ishiguro, T. Saitoh, A. Yamaguchi, K. Perrem, Y. Kubota, K.P. Lu, and I. Aoki Clin. Cancer Res. 11 2005 7523
9. C.J. Zhang, Z.H. Zhang, B.L. Xu, and Y.L. Wang Acta Pharm. Sinica 43 2008 9
10. G.G. Xu, and F.A. Etzkorn Drug News Perspect. 22 2009 399
11. T. Mori, and T. Uchida Curr. Enzyme Inhib. 6 2010 46
12. C. Guo, X. Hou, L. Dong, E. Dagostino, S. Greasley, R. Ferre, J. Marakovits, M.C. Johnson, D. Matthews, B. Mroczkowski, H. Parge, T. VanArsdale, I. Popoff, J. Piraino, S. Margosiak, J. Thomson, G. Los, and B.W. Murry Bioorg. Med. Chem. Lett. 19 2009 5613
13. L. Dong, J. Marakovits, X. Hou, C. Guo, S. Greasley, E. Dagostino, R. Ferre, M.C. Johnson, E. Kraynov, J. Thomson, V. Pathak, and B.W. Murry Bioorg. Med. Chem. Lett. 20 2010 2210
14. A.J. Potter, S. Ray, L. Gueritz, C.L. Nunns, C.J. Bryant, S.F. Scrace, N. Matassova, L. Baker, P. Dokurno, D.A. Robinson, A.E. Surgenor, B. Davis, J.B. Murry, C.M. Richardson, and J.D. Moore Bioorg. Med. Chem. Lett. 20 2010 586
15. A.J. Potter, V. Oldfield, C. Nunns, C. Fromont, S. Ray, C.J. Northfield, C.J. Bryant, S.F. Scrace, D. Robinson, N. Matossova, L. Baker, P. Dokurno, A.E. Surgenor, B. Davis, C.M. Richardson, J.B. Murray, and J.D. Moore Bioorg. Med. Chem. Lett. 20 2010 6483
16. R. Ranganathan, K.P. Lu, T. Hunter, and J.P. Noel Cell 89 1997 875
17. X.J. Wang, B. Xu, A.B. Mullins, F.K. Neiler, and F.A. Etzkorn J. Am. Chem. Soc. 126 2004 15533
18. J.L. Kofron, P. Kuzmič, V. Kishore, E. Colón-Bonilla, and D.H. Rich Biochemistry 30 1991 6127
19. sybyl 7.2, Tripos Inc., 1699 South Hanley Road, St. Louis, MO 631444, USA.
20. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin J. Comput. Chem. 25 2004 1605