Design, synthesis, and discovery of stilbene derivatives based on lithospermic acid B as potent protein tyrosine phosphatase 1B inhibitors

Bioorganic and Medicinal Chemistry Letters

Volumn 17, Issue 16, 2007, Pages 4481-4486

  Jung, Mankil ^a   Lee, Yongnam ^a   Park, Moonsoo ^a   Kim, Hanjo ^a   Kim, Heekyeong ^a   Lim, Eunyoung ^a   Tak, Jungae ^a   Sim, Minjoo ^a   Lee, Dongeun ^a   Park, Namsoo ^a   Oh, Won Keun ^c   Hur, Kyu Yeon ^b   Kang, Eun Seok ^b   Lee, Hyun Chul ^b  

^a Yonsei University   (South Korea)

^b Yonsei University College of Medicine   (South Korea)

^c Chosun University   (South Korea)

Author keywords

Lithospermic acid B (LAB); Protein tyrosine phosphatase (PTP1B); Stilbene derivatives

Indexed keywords

3,4 DIHYDROXY STIBENE CARBONYL; 4 (CHLOROMETHYL)BENZOIC ACID; BENZOIC ACID; CARBONYL DERIVATIVE; LITHOSPERMIC ACID; LITHOSPERMIC ACID B; MOLYBDIC ACID; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; STILBENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG DESIGN; DRUG STRUCTURE; DRUG SYNTHESIS;

ANTIOXIDANTS; BENZOFURANS; DEPSIDES; DRUG DESIGN; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 34447344488     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2007.06.016     Document Type: Article

References (30)

1. King H., and Rewers M. Diabetes Care 16 (1993) 157
2. McCarthy, D.; Zimmet, P. Diabetes 1994 to 2010: Global Estimates and Projections. International Diabetes Institute, Melbourne, 1994.
3. Taylor S.D., Kotoris C.C., Dinaut A.N., Wang Q., Ramachandran C., and Huang Z. Bioorg. Med. Chem. 6 (1998) 1457
4. Taylor S.I. Cell 97 (1999) 9
5. Huyer G., Liu S., Kelly J., Moffat J., Payette P., Kennedy B., Tsaprailis G., Gresser M.J., and Ramachandran C. J. Biol. Chem 272 (1997) 843
6. Shim Y.S., Kim K.C., Chi D.Y., Lee K.-H., and Cho H. Bioorg. Med. Chem. Lett. 13 (2003) 2561
7. Cheng A., Dube N., Gu F., and Tremblay M.L. Eur. J. Biochem. 269 (2002) 1050
8. Elchebly M., Payette P., Michaliszyn E., Cromlish W., Collins S., Loy A.L., Normandin D., Cheng A., Himms-Hagen J., Chan C.-C., Ramachandran C., Gresser M.J., Tremblay M.L., and Kennedy B.P. Science 283 (1999) 1544
9. Zinker B.A., Rondinone C.M., Trevillyan J.M., Gum R.J., Clampit J.E., Waring J.F., Xie N., Wilcox D., Jacobson P., Frost L., Kroeger P.E., Reilly R.M., Koterski S., Opgenorth T.J., Ulrich R.G., Crosby S., Butler M., Murray S.F., McKay R.A., Bhanot S., Monia B.P., and Jirousek M.R. Proc. Natl. Acad. Sci. U.S.A. 99 (2002) 11357
10. Blaskovich M.A., and Kim H.-O. Exp. Opin. Ther. Pat. 12 (2002) 871
11. Ockey D., and Gadek T.R. Bioorg. Med. Chem. Lett. 14 (2004) 389
12. Yasuhiro T., Rena k., Jian X.L., Purusotam B., Ken T., Tsuneo N., and Shigetoshi K. Chem. Pharm. Bull. 46 (1998) 107
13. Jung M., Lee H.C., Ahn C.W., Park W., Choi S., Kim H., Cho D., Lee G.T., and Li H.-R. Chem. Pharm. Bull. 50 8 (2002) 1135
14. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Adv. Drug Delivery Rev. 23 (1997) 3
15. Teague S.J., Davis A.M., Leeson P.D., and Oprea T. Angew. Chem. Int. Ed. 38 (1999) 3743
16. Kim S., Ko H., Park J.E., Jung S., Lee S.K., and Chun Y.-J. J. Med. Chem. 45 (2002) 160
17. Pinney K.G., Mejia M.P., Villalobos V.M., Rosenquist B.E., Pettit G.R., Verdier-Pinard P., and Hamel E. Bioorg. Med. Chem. 8 (2000) 2417
18. Pettit G.R., Grealish M.P., Jung M.K., Hamel E., Pettit R.K., Chapuis J.-C., and Schmidt J.M. J. Med. Chem. 45 (2002) 2534
19. Jung M., Lee K.H., Kendrick H., Robinson B.L., and Croft S.L. J. Med. Chem. 45 (2002) 4940
20. Maddux T., Li W., and Yu L. J. Am. Chem. Soc. 119 (1997) 844
21. All E- and Z-form were separated by using column silica gel and bioassay was performed as a single regioisomer form. Its coupling constant and chemical shift of NMR for E- and Z-form for identification and MS for the major compounds are reported in Supplementary data. Purity of each compound purified by column chromatography was confirmed by high resolution MS is and reported in attached supplementary data.
22. Maloney P.R., Parks D.J., Haffner C.D., Fivush A.M., Chandra G., Plunket K.D., Creech K.L., Moore L.B., Wilson J.G., Lewis M.C., Jones S.A., and Willson T.M. J. Med. Chem. 43 (2000) 2971
23. Pettit G.R., Anderson C.R., Herald D.L., Jung M.K., Lee D.J., Hamel E., and Pettit R.K. J. Med. Chem. 46 (2003) 525
24. Nojima T., Hirano Y., Ishiguro K., and Sawaki Y. J. Org. Chem. 62 (1997) 2387
25. Park S.-H., Kang S.-H., Lim S.-H., Oh H.-S., and Lee K.-H. Bioorg. Med. Chem. Lett. 13 (2003) 3455
26. Burke Jr. T.R., Ye B., Yan X., Wang S., Jia Z., Chen L., Zhang Z.-Y., and Barford D. Biochemistry 35 (1996) 15989
27. Roberti M., Pizzirani D., Simoni D., Rondanin R., Baruchello R., Bonora C., Buscemi F., Grimaudo S., and Tolomeo M. J. Med. Chem. 46 (2003) 3546
28. Araujo C., and Leon L. Biol. Activities of Curcuma longa L. Mem. Inst. Oswaldo Cruz 96 (2001) 723
29. Hamaguchi T., Sudo T., and Osada H. FEBS Lett. 372 (1995) 54
30. Rajan P., Vedernikova I., Cos P., Berghe D.V., Augustyns K., and Haemers A. Bioorg. Med. Chem. Lett. 11 (2001) 215