Identification of Thiazolidinones Spiro-Fused to IndoIin-2-ones as Potent and Selective Inhibitors of the Mycobacterium tuberculosis Protein Tyrosine Phosphatase B

Angewandte Chemie - International Edition

Volumn 49, Issue 34, 2010, Pages 5902-5905

  Vintonyak, Viktor V ^a   Warburg, Karin ^a,b   Kruse, Holger ^d   Grimme, Stefan ^d   Hübet, Katja ^a   Rauh, Daniel ^c   Waldmann, Herbert ^a,b  

^a MAX PLANCK INSTITUTE OF MOLECULAR PHYSIOLOGY   (Germany)

^b TU DORTMUND UNIVERSITY   (Germany)

^c CHEMICAL GENOMICS CENTRE OF THE MAX PLANCK SOCIETY   (Germany)

^d UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Chemical biology circular dichroism enzyme inhibitors; Phosphatases; Tuberculosis

Indexed keywords

CHEMICAL BIOLOGY; CIRCULAR DICHROISM; ENZYME INHIBITORS; INHIBITORY ACTIVITY; MYCOBACTERIUM TUBERCULOSIS; PROTEIN-TYROSINE PHOSPHATASE; SELECTIVE INHIBITORS; STRUCTURAL ELEMENTS; STRUCTURE-ACTIVITY; TUBERCULOSIS;

AMINO ACIDS; ENZYMES; PHOSPHATASES;

DICHROISM;

BACTERIAL PROTEIN; ENZYME INHIBITOR; INDOLE DERIVATIVE; INDOLIN 2 ONE; INDOLIN-2-ONE; PROTEIN TYROSINE PHOSPHATASE; SPIRO COMPOUND; THIAZOLIDINE DERIVATIVE;

ARTICLE; CHEMISTRY; CIRCULAR DICHROISM; DRUG ANTAGONISM; ENZYMOLOGY; METABOLISM; MYCOBACTERIUM TUBERCULOSIS;

BACTERIAL PROTEINS; CIRCULAR DICHROISM; ENZYME INHIBITORS; INDOLES; MYCOBACTERIUM TUBERCULOSIS; PROTEIN TYROSINE PHOSPHATASES; SPIRO COMPOUNDS; THIAZOLIDINES;

EID: 77955574023     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201002138     Document Type: Article

References (33)

1. A. Koul, T. Herget, B. Klebl, A. Ullrich, Nat. Rev. Microbiol. 2004, 2,189-202.
2. R. Singh, V. Rao, H. Shakila, R. Gupta, A. Khera, N. Dhar, A. Singh, A. Koul, Y. Singh, M. Naseema, P. R. Narayanan, C. N. Paramasivan, V. D. Ramanathan, A. K. Tyagi, Mol. Microbiol. 2003,50,751-762.
3. a) N. J. Beresford, D. Mulhearn, B. Szczepankiewicz, G. Liu, M. E. Johnson, A. Fordham-Skelton, C. Abad-Zapatero, J. S. Cavet, L. Tabernero, J. Antimicrob. Chemother. 2009, 63, 928-936;
4. b) B. Zhou, Y. He, X. Zhang, J. Xu, Y. Luo, Y. Wang, S. G. Franzblau, Z. Yang, R. J. Chan, Y. Liu, J. Zheng, Z.-Y. Zhang, Proc. Natl. Acad. ScL USA 2010, 107, 4573-4578.
5. For recent reviews, see: a) V. V. Vintonyak, A. P. Antonchick, D. Rauh, H. Waldmann, Curr. Opin. Chem. Biol. 2009, 13, 272-283;
6. b) L. Bialy, H. Waldmann, Angew. Chem. 2005,117, 3880-3906;
7. Angew. Chem. Int. Ed. 2005, 44, 3814-3839.
8. For selected examples, see: a) A. Nören-Müller, I. Reis-Corrêa, Jr., H. Prinz, C. Rosenbaum, K. Saxena, H. J. Schwalbe, D. Vestweber, G. Cagna, S. Schunk, O. Schwarz, H. Schiewe, H. Waldmann, Proc. Natl. Acad. Sci. USA 2006,103,10606-10611;
9. b) I. R. Corrêa, Jr., A. Nören-Müller, H.-D. Ambrosi, S. Jakupovic, K. Saxena, H. Schwalbe, M. Kaiser, H. Waldmann, Chem. Asian J. 2007, 2, 1109-1126;
10. c) A. Nören-Müller, W WiIk, K. Saxena, H. Schwalbe, M. Kaiser, H. Waldmann, Angew. Chem. 2008,120, 6061-6066;
11. Angew. Chem. Int. Ed 2008, 47, 5973-5977;
12. C. Grundner, D. Perrin, R. Hooft van Huijsduijnen, D. Swinnen, J. Gonzalez, C. L. Gee, T. N. Wells, T. Alber, Structure 2007,15,499-509;
13. e) M. B. Soellner, K. A. Rawls, C Grundner, T. Alber, J. A. Ellman, J. Am. Chem. Soc. 2007, 129, 9613-9615;
14. f) L. P. Tan, H. Wu, P. Y. Yang, K. A. Kalesh, X. Zhang, M. Hu, R. Srinivasan, S. Q. Yao, Org. Lett. 2009,11, 5102-5105.
15. a) J. S. Bindra in The Alkaloids, Vol. 14 (Eds.: R. H. F. Manske), Academic Press, New York, 1973, pp. 84-121;
16. b) R. T. Brown in The Chemistry of Heterocyclic Compounds, Part 4, Vol. 25 (Ed.: J. E. Saxton), John Wiley and Sons, New York, 1983;
17. c) C. V. Galliford, K. A. Scheldt, Angew. Chem. 2007,119, 8902-8912;
18. Angew. Chem. Int. Ed. 2007, 46, 8748-8758.
19. M. A. Koch, L. O. Wittenberg, S. Basu, D. A. Jeyaraj, E. Gourzoulidou, K. Reinecke, A. Odermatt, H. Waldmann, Proc. Natl. Acad. Sci. USA 2004,101,16721-16726.
20. M. A. Koch, A. Schuffenhauer, M. Scheck, S. Wetzel, M. Casaulta, A. Odermatt, P. Ertl, H. Waldmann, Proc. Natl. Acad. Sci. USA 2005, 102,17272-17277.
21. M. Kansy, F. Senner, K. Gubernator, J. Med, Chem. 1998, 41, 1007-1010.
22. A. Avdeef in Pharmacokinetic Optimization in Drug Research (Eds.: B. Testa, H. van de Waterbeemd, G. Folkers, R. Guy), Verlag Helvetica Chimica Acta, Zürich and Wiley-VCH, Weinheim, 2001, pp. 305-326.
23. M. A. Marques, C. A. Ullrich, F. Nogueira, A. Rubio, K. Burke, E. K. U. Gross, Time-Dependent Density Functional Theory, Springer, Berlin, 2006.
24. For a recent review, see: G. Bringmann, T. Brunn, K. Maksimenka, Y. Hemberger, Eur. J. Org. Chem. 2009, 2717-2727;
25. for representative applications, see : a) P. J. Stephens, J.-J. Pan, F. J. Devlin, M. Urbanová, J. Hájíček, J. Org. Chem. 2007, 72,2508-2524;
26. b) P. J. Stephens, J.-J. Pan, F. J. Devlin, M. Urbanová, O. Julínek, J. Hájíček, Chirality 2008,20,454 - 470;
27. c) S. Grimme, A. Bahlmann in. Modem Cyclophane Chemistry (Eds.: R. Gleiter, H. Hopf), Wiley, Chichester, 2004, p. 311;
28. d) T. Mori, Y. Inoue, S. Grimme, J. Phys. Chem. A 2007, 111, 7995-8006;
29. e) C Diedrich, S. Grimme, J. Phys Chem. A 2003, 107, 2524-2539;
30. f) L. Autschbach, J. Jensen, G. C Schatz, Y. C. E. Tse, M. Krykunov, J. Phys. Chem. A 2006,110,2461 -2473;
31. g) T. D. Crawford, M. C. Tarn, M. L. Abrams, Mol. Phys. 2007,105, 2607-2617;
32. h) M. C. Tarn, M. L. Abrams, T. D. Crawford, J. Phys. Chem. A 2007, 111, 11232-11241.
33. L. Goerigk, S. Grimme, J. Phys. Chem A 2009,113, 767-776.