2-thiazolylimino/heteroarylimino-5-arylidene-4-thiazolidinones as new agents with SHP-2 inhibitory action

Journal of Medicinal Chemistry

Volumn 51, Issue 17, 2008, Pages 5221-5228

  Geronikaki, A ^a   Eleftheriou, P ^a   Vicini, P ^b   Alam, I ^c   Dixit, A ^c   Saxena, A K ^c  

^a ARISTOTLE UNIVERSITY OF THESSALONIKI   (Greece)

^b UNIVERSITY OF PARMA   (Italy)

^c CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

[No Author keywords available]

Indexed keywords

5 (4 METHOXYBENZYLIDENE) 2 (BENZO[D]THIAZOL 2 YLIMINO)THIAZOLIDIN 4 ONE; 5 (4 METHOXYBENZYLIDENE) 2 (THIAZOL 2 YLIMINO)THIAZOLIDIN 4 ONE; PROTEIN TYROSINE PHOSPHATASE SHP 2; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; DRUG ACTIVITY; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; HYDROGEN BOND; MOLECULAR DOCKING; PROTEIN INTERACTION; STRUCTURE ANALYSIS;

HUMANS; HYDROGEN BONDING; HYDROPHOBICITY; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 11; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; THIAZOLIDINEDIONES;

EID: 51849138330     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm8004306     Document Type: Article

References (37)

1. Bruce, D.; Gelb, L.; Tartaglia, M. Noonan syndrome and related disorders: dysregulated RAS-mitogen activated protein kinase signal transduction. Hum. Mol. Genet. 2006, 15, 220-226.
2. Neel, B. G.; Gu, H.; Pao, L. The "Shp"ing news: SH2 domain-containing tyrosine phosphatases in cell signaling. Trends Biochem. Sci. 2003, 28, 284-293.
3. Tartaglia, M.; Martinelli, S.; Stella, L.; Bocchinfuso, G.; Flex, E.; Cordeddu, V.; Zampino, G.; Burgt, I.; Palleschi, A.; Petrucci, T. C.; Sorcini, M.; Schoch, C.; Foa, R.; Emanuel, P. D.; Gelb, B. D. Diversity and functional consequences of germline and somatic PTPN11 mutations in human disease. Am. J. Hum. Genet. 2006, 78, 279-290.
4. Tartaglia, M.; Mehler, E. L.; Goldberg, R.; Zampino, G.; Brunner, H. G.; Kremer, H.; van der Burgt, I.; Crosby, A. H.; Ion, A.; Jeffery, S.; Kalidas, K.; Patton, M. A.; Kucherlapati, R. S.: Gelb, B. D. Mutations in PTPN11, encoding the protein tyrosine phosphatase SHP-2, cause Noonan syndrome. Nat. Genet. 2001, 29, 465-468.
5. Keilhack, H.; David, F. S.; McGregor, M.; Cantley, L. C.; Neel, B. G. Diverse biochemical properties of Shp2 mutants. Implications for disease phenotypes. J. Biol. Chem. 2005, 280, 30984-30993.
6. Tartaglia, M.; Martinelli, S.; Cazzaniga, G.; Cordeddu, V.; Iavarone, I.; Spinelli, M.; Palmi, C.; Carta, C.; Pession, A.; Aricò, M.; Masera, G.; Basso, G.; Sorcini, M.; Gelb, B. D.; Biondi, A. Genetic evidence for lineage- and differentiation stage-related contribution of somatic PTPN11 mutations to leukemogenesis in childhood acute leukemia. Blood 2004, 104, 307-313.
7. Tartaglia, M.; Niemeyer, C. M.; Fragale, A.; Song, X.; Buechner, J.; Jung, A.; Hahlen, K.; Hasle, H.; Licht, J. D.; Gelb, B. D. Somatic mutations in PTPN11 in juvenile myelomonocytic leukemia, myelodysplastic syndromes and acute myeloid leukemia. Nat. Genet. 2003, 34, 148-150.
8. Legius, E.; Schrander-Stumpel, C.; Schollen, E.; Pulles-Heintzberger, C.; Gewillig, M.; Fryns, J. P. PTPN11 mutations in LEOPARD syndrome. J. Med. Genet 2002, 39, 571-574.
9. Digilio, M. C.; Conti, E.; Sarkozy, A.; Mingarelli, R.; Dottorini, T.; Marino, B.; Pizzuti, A.; Dallapiccola, B. Grouping of multiple-lentigines/ LEOPARD and Noonan syndromes on the PTPN11 gene. Am. J. Hum. Genet. 2002, 71, 389-394.
10. Noonan, J. A. Hypertelorism with Turner phenotype. A new syndrome with associated congenital heart disease. Am. J. Dis. Child. 1968, 116, 373-380.
11. Chong, Z. Z.; Maiese, K. The Src homology 2 domain tyrosine phosphatases SHP-1 and SHP-2: diversified control of cell growth, inflammation, and injury. Histol. Histopathol. 2007, 22, 1251-1267.
12. Piovesan, E. J.; Young Blood, M. R.; Kowacs, P. A.; Mulinari, R. A.; Werneck, L. C.; Sandrini, R. Prevalence of migraine in Noonan syndrome. Cephalalgia 2007, 27, 330-335.
13. Linabery, A. M.; Ross, J. A. Trends in childhood cancer incidence in the U.S. (1992-2004). Cancer 2008, 112, 416-432.
14. Shen, K.; Keng, Y. F.; Wu, L.; Guo, X. L.; Lawrence, D. S.; Zhang, Z. Y. Acquisition of a specific and potent PTP1B inhibitor from a novel combinatorial library and screening procedure. J. Biol. Chem. 2001, 276, 47311-47319.
15. Huang, P.; Ramphal, J.; Wei, J.; Liang, C.; Jallal, B.; McMahon, G.; Tang, C. Structure-based design and discovery of novel inhibitors of protein tyrosine phosphatases. Bioorg. Med. Chem. 2003, 11, 1835-1849.
16. Szczepankiewicz, B. G.; Liu, G.; Hajduk, P. J.; Abad-Zapatero, C.; Pei, Z.; Xin, Z.; Lubben, T. H.; Trevillyan, J. M.; Stashko, M. A.; Ballaron, S. J.; Liang, H.; Huang, F.; Hutchins, C. W.; Fesik, S. W.; Jirousek, M. R. Discovery of a potent, selective protein tyrosine phosphatase 1B inhibitor using a linked-fragment strategy. J. Am. Chem. Soc. 2003, 125, 4087-4096.
17. Nören-Müller, A.; Reis-Corrêa, I.; Prinz, H., Jr.; Rosenbaum, C.; Saxena, K.; Schwalbe, H. J.; Vestweber, D.; Cagna, G.; Schunk, S.; Schwarz, O.; Schiewe, H.; Waldmann, H. Discovery of protein phosphatase inhibitor classes by biology-oriented synthesis. Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 10606-10611.
18. Chen, L.; Sung, S.; Richard Yip, M. L.; Lawrence, H. R.; Ren, Y.; Guida, W. C.; Sebti, S. M.; Lawrence, N. J.; Wu, J. Discovery of a novel Shp2 protein tyrosine phosphatase inhibitor. Mol. Pharmacol. 2006, 70, 562-570.
19. Douty, B.; Wayland, B.; Ala, P. J.; Bower, M. J.; Pruitt, J.; Bostrom, L.; Wei, M.; Klabe, R.; Gonneville, L.; Wynn, R.; Burn, T. C.; Liu, P. C.; Combs, A. P.; Yue, E. W. Isothiazolidinone inhibitors of PTP1B containing imidazoles and imidazolines. Bioorg. Med. Chem. Lett. 2008, 18, 66-71.
20. Maccari, R.; Paoli, P.; Ottanà, R.; Jacomelli, M.; Ciurleo, R.; Manao, G.; Steindl, T.; Langer, T.; Vigorita, M. G.; Camici, G. 5-Arylidene-2,4-thiazolidinediones as inhibitors of protein tyrosine phosphatases. Bioorg. Med. Chem. 2007, 15, 5137-5149.
21. Stuible, M.; Zhao, L.; Aubry, I.; Schmidt-Arras, D.; Böhmer, F. D.; Li, C. J.; Tremblay, M. L. Cellular inhibition of protein tyrosine phosphatase 1B by uncharged thioxothiazolidinone derivatives. ChemBioChem 2007, 8, 179-186.
22. Sparks, R. B.; Polam, P.; Zhu, W.; Crawley, M. L.; Takvorian, A.; McLaughlin, E.; Wei, M.; Ala, P. J.; Gonneville, L.; Taylor, N.; Li, Y.; Wynn, R.; Burn, T. C.; Liu, P. C.; Combs, A. P. Benzothiazole benzimidazole (S)-isothiazolidinone derivatives as protein tyrosine phosphatase-1B inhibitors. Bioorg. Med. Chem. Lett. 2007, 17, 736-740.
23. Ala, P. J.; Gonneville, L.; Hillman, M.; Becker-Pasha, M.; Yue, E. W.; Douty, B.; Wayland, B.; Polam, P.; Crawley, M. L.; McLaughlin, E.; Sparks, R. B.; Glass, B.; Takvorian, A.; Combs, A. P.; Burn, T. C.; Hollis, G. F.; Wynn, R. Structural insights into the design of nonpeptidic isothiazolidinone-containing inhibitors of protein-tyrosine phosphatase 1B. J. Biol. Chem. 2006, 281, 38013-38021.
24. Ala, P. J.; Gonneville, L.; Hillman, M. C.; Becker-Pasha, M.; Wei, M.; Reid, B. G.; Klabe, R.; Yue, E. W.; Wayland, B.; Douty, B.; Polam, P.; Wasserman, Z.; Bower, M.; Combs, A. P.; Burn, T. C.; Hollis, G. F.; Wynn, R. Structural basis for inhibition of protein-tyrosine phosphatase 1B by isothiazolidinone heterocyclic phosphonate mimetics. J. Biol. Chem. 2006, 281, 32784-95.
25. Combs, A. P.; Zhu, W.; Crawley, M. L.; Glass, B.; Polam, P.; Sparks, R. B.; Modi, D.; Takvorian, A.; McLaughlin, E.; Yue, E. W.; Wasserman, Z.; Bower, M.; Wei, M.; Rupar, M.; Ala, P. J.; Reid, B. M.; Ellis, D.; Gonneville, L.; Emm, T.; Taylor, N.; Yeleswaram, S.; Li, Y.; Wynn, R.; Burn, T. C.; Hollis, G.; Liu, P. C.; Metcalf, B. Potent benzimidazole sulfonamide protein tyrosine phosphatase 1B inhibitors containing the heterocyclic (S)- isothiazolidinone phosphotyrosine mimetic. J. Med. Chem. 2006, 49, 3774-3789.
26. Yue, E. W.; Wayland, B.; Douty, B.; Crawley, M. L.; McLaughlin, E.; Takvorian, A.; Wasserman, Z.; Bower, M. J.; Wei, M.; Li, Y.; Ala, P. J.; Gonneville, L.; Wynn, R.; Burn, T. C.; Liu, P. C.; Combs, A. P. Isothiazolidinone heterocycles as inhibitors of protein tyrosine phosphatases: synthesis and structure-activity relationships of a peptide scaffold. Bioorg. Med. Chem. 2006, 14, 5833-5849.
27. Combs, A. P.; Yue, E. W.; Bower, M.; Ala, P. J.; Wayland, B.; Douty, B.; Takvorian, A.; Polam, P.; Wasserman, Z.; Zhu, W.; Crawley, M. L.; Pruitt, J.; Sparks, R.; Glass, B.; Modi, D.; McLaughlin, E.; Bostrom, L.; Li, M.; Galya, L.; Blom, K.; Hillman, M.; Gonneville, L.; Reid, B. G.; Wei, M.; Becker-Pasha, M.; Klabe, R.; Huber, R.; Li, Y.; Hollis, G.; Burn, T. C.; Wynn, R.; Liu, P.; Metcalf, B. Structure-based design and discovery of protein tyrosine phosphatase inhibitors incorporating novel isothiazolidinone heterocyclic phosphotyrosine mimetics. J. Med. Chem. 2005, 48, 6544-6508.
28. Vicini, P.; Geronikaki, A.; Kitka, A.; Incerti, M.; Zani, F. Synthesis and antimicrobial activity of novel 2-thiazolylimino-5-arylidene-4- thiazolidinones. Bioorg. Med. Chem. 2006, 14, 3859-3864.
29. Vicini, P.; Amoretti, L.; Chiavarini, M.; Impicciatore, M. Synthesis and local anesthetic activity of alkylaminoacyl derivatives of 3-amino-1,2- benzisothiazoles. Farmaco 1990, 4, 933-944.
30. Geronikaki, A.; Theophilidis, G. Synthesis of 2-(aminoacetylamino) thiazole derivatives and comparison of their local anesthetic activity by method of action potential. Eur. J. Med. Chem. 1992, 27 (7), 709-716.
31. Ates, O.; Altinas, H.; Otuk, G. Synthesis and antimicrobial activity of 4-carbetoxymethyl-2[(α-haloacyl)amino]thiazoles and 5-nonsubstituted/ substituted 2-[(4-carbetoxymethylthiazol-2-ylimino]-4-thiazolidinones. Arzneim.-Forsch./Drug Res. 2000, 50, (1), N6, 569575.
32. Dhal, P. N.; Achary, T. E.; Nayak, A. J. Synthesis of thiazolidinones. II. 5-Benzal derivatives of 2-(substituted benzothiazol-2-ylimino)-4- thiazolidinones and their brominated products. J. Indian Chem. Soc. 1974, 51, 931-933.
33. Vicini, P.; Geronikaki, A.; Incerti, M.; Zani, F.; Dearden, J.; Hewitt, M. 2-Heteroaylimino-5-benzylidene-4-thiazolidinones analogues of 2-thiazolylimino-5-benzylidene-4-thiazolidinones with antimicrobial activity: synthesis and structure-activity relationship. Bioorg. Med. Chem. 2008, 16 (7), 3714-7724.
34. Geronikaki, A. A.; Lagunin, A. A.; Hadjipavlou-Litina, D. I.; Eleftheriou, P. T.; Filimonov, D. A.; Poroikov, V. V.; Alam, I.; Saxena, A. K. Computer-aided discovery of anti-inflammatory thiazolidinones with dual cyclooxygenase/lipoxygenase inhibition. J. Med. Chem. 2008, 51, 1601-1609.
35. Wang, C. Z.; Su, H. W.; Hsu, Y. C.; Shen, M. R.; Tang, M. J. A discoidin domain receptor 1/SHP-2 signaling complex inhibits alpha2beta1-integrin-mediated signal transducers and activators of transcription 1/3 activation and cell migration. Mol. Biol. Cell 2006, 17, 2839-2852.
36. Jones, G.; Willett, P.; Glen, R. C.; Leach, A. R.; Taylor, R. Development and validation of a genetic algorithm for flexible docking. J. Mol. Biol. 1997, 267, 727-748.
37. Friesner, R. A.; Banks, J. L.; Murphy, R. B.; Halgren, T. A.; Klicic, J. J.; Mainz, D. T.; Repasky, M. P.; Knoll, E. H.; Shelley, M.; Perry, J. K.; Shaw, D. E.; Francis, P.; Shenkin, P. S. Glide: a new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy. J. Med.Chem. 2004, 47, 1739-1749.