Derivatives of 1,4-bis(3-hydroxycarbonyl-4-hydroxyl)styrylbenzene as PTP1B inhibitors with hypoglycemic activity

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 18, 2008, Pages 8643-8652

  Shrestha, Suja ^a   Bhattarai, Bharat Raj ^a   Kafle, Bhooshan ^a   Lee, Keun Hyeung ^a   Cho, Hyeongjin ^a  

^a Inha University   (South Korea)

Author keywords

Diabetes; Inhibitor; PTP1B; Salicylic acid

Indexed keywords

1,4 BIS(3 HYDROXYCARBONYL 4 HYDROXYL)STYRYLBENZENE; 5 [2 [4 [2 (5 BROMO 3 CARBOXY 4 HYDROXYPHENYL)VINYL]PHENYL]VINYL] 3 BROMO 2 HYDROXYBENZOIC ACID; ANTIDIABETIC AGENT; BENZENE DERIVATIVE; CARBONYL DERIVATIVE; GLUCOSE; HYDROXYL GROUP; PROTEIN TYROSINE PHOSPHATASE 1B; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; SALICYLIC ACID DERIVATIVE; STILBENE DERIVATIVE; STYRENE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DRUG EFFICACY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; FOOD INTAKE; GLUCOSE BLOOD LEVEL; GLUCOSE TOLERANCE; IC 50; MALE; MOUSE; NONHUMAN; OBESITY; WEIGHT GAIN;

ANIMALS; ANTI-OBESITY AGENTS; BLOOD GLUCOSE; DISEASE MODELS, ANIMAL; FASTING; GLUCOSE TOLERANCE TEST; HYPERGLYCEMIA; MICE; MICE, INBRED C57BL; MICE, OBESE; OBESITY; SALICYLIC ACIDS; STILBENES; STRUCTURE-ACTIVITY RELATIONSHIP; STYRENES; WEIGHT GAIN;

ANIMALIA; MUS;

EID: 51449106930     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.07.090     Document Type: Article

References (34)

1. In: Finkel T., and Gutkind J.S. (Eds). Signal Transduction and Human Disease (2003), Wiley, Hoboken, NJ
2. Withers D.J., and White M. Endocrinology 141 (2000) 1917
3. Saltiel A., and Pessin J.E. Trends Cell Biol. 12 (2002) 65
4. Saltiel A., and Kahn C.R. Nature 414 (2001) 799
5. Elchebly M., Cheng A., and Tremblay M.L. J. Mol. Med. 78 (2000) 473
6. Bourdeau, A.; Dube, N.; Tremblay, M. L. Curr. Opin. Cell Biol.
7. Anderson J.N., Jansen P.G., Echwald S.M., Mortensen O.H., Fukuda T., Vecchio R.D., Tonks N.K., and Møller N.P.H. FASEB J. 18 (2004) 8
8. Montalibet J., and Kennedy B.P. Drug Discovery Today Ther. Strateg. 2 (2005) 129
9. 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
10. You-Ten K.E., Muise E.S., Itié A., Michaliszyn E., Wagner J., Jothy S., Lapp W.S., and Tremblay M.L. J. Exp. Med. 186 (1997) 683
11. Galic S., Klingler-Hoffmann M., Fodero-Tavoletti M.T., Puryer M.A., Meng T.-C., Tonks N.K., and Tiganis T. Mol. Cell Biol. 23 (2003) 2096
12. Galic S., Hauser C., Kahn B.B., Haj F.G., Neel B.G., Tonks N.K., and Tiganis T. Mol. Cell Biol. 25 (2005) 819
13. Bhattarai B.R., Shrestha S., Ham S.W., Lee K.-H., Kim K.R., Cheon H.G., and Cho H. Bioorg. Med. Chem. Lett. 17 (2007) 5357
14. Shrestha S., Bhattarai B.R., Chang K.J., Lee K.-H., and Cho H. Bioorg. Med. Chem. Lett. 17 (2007) 2760
15. Shrestha S., Bhattarai B.R., Lee K.-H., and Cho H. Bioorg. Med. Chem. 15 (2007) 6535
16. Liang F., Huang Z., Lee S.Y., Liang J., Ivanov M.I., Alonso A., Bliska J.B., Lawrence D.S., Mustelin T., and Zhang Z.Y. J. Biol. Chem. 278 (2003) 41734
17. Jang M., Cai L., Udeani G.O., Slowing K.V., Thomas C.F., Beecher C.W., Fong H.H., Farnsworth N.R., Kinghorn A.D., Mehta R.G., Moon R.C., and Pezzuto J.M. Science 275 (1997) 218
18. Rimando A.M., Cuendet M., Desmarchelier C., Mehta R.G., Pezzuto J.M., and Duke S.O. J. Agric. Food Chem. 50 (2002) 3453
19. Murcia M.A., and Marti{dotless}́nez-Tomé M. J. Food Protect. 64 (2001) 379
20. Su H.-C., Hung L.-M., and Chen J.-K. Am. J. Physiol. Endocrinol. Metab. 290 (2006) E1339
21. Lagouge M., Argmann C., Gerhart-Hines Z., Meziane H., Lerin C., Daussin F., Messadeq N., Milne J., Lambert P., Elliott P., Geny B., Laakso M., Puigserver P., and Auwerx J. Cell 127 (2006) 1109
22. Skovronsky D.M., Zhang B., Kung M.-P., Kung H.F., Trojanowski J.G., and Lee V.M.-Y. Proc. Natl. Acad. Sci. USA 97 (2000) 7609
23. Styren S.D., Hamilton R.L., Styren G.C., and Klunk W.E. J. Histochem. Cytochem. 48 (2000) 1223
24. Flaherty D.P., Walsh S.M., Kiyota T., Dong Y., Ikezu T., and Vennerstrom J.L. J. Med. Chem. 50 (2007) 4986
25. Nussbaumer P., Winiski A.P., Cammisuli S., Hiestand P., Weckbecker G., and Stuetz A. J. Med. Chem. 37 (1994) 4079
26. Kim S., Ko H., Park J.E., Jung S., Lee S.K., and Chun Y.-J. J. Med. Chem. 45 (2002) 160
27. Zhuang Z.-P., Kung M.-P., Hou C., Skovronsky D.M., Gur T., Plössl K., Trojanowski J.Q., Lee V.M.-Y., and Kung H.F. J. Med. Chem. 44 (2001) 1905
28. Lee C.-W., Zhuang Z.-P., Kung M.-P., Plössl K., Skovronsky D., Gur T., Hou C., Trojanowski J.Q., Lee V.M.-Y., and Kung H.F. J. Med. Chem. 44 (2001) 2270
29. Gilbert A.M., Katz T.J., Geiger W.E., Robben M.P., and Rheingold A.L. J. Am. Chem. Soc. 115 (1993) 3199
30. Stille J.K., and Groh B.L. J. Am. Chem. Soc. 109 (1987) 813
31. Massa M.A., Spangler D.P., Durley R.C., Hickory B.S., Connolly D.T., Witherbee B.J., Smith M.E., and Sikorski J.A. Bioorg. Med. Chem. Lett. 11 (2001) 1625
32. Pei D., Neel B.G., and Walsh C.T. Proc. Natl. Acad. Sci. USA 90 (1993) 1092
33. Shim Y.S., Kim K.C., Chi D.Y., Lee K.-H., and Cho H. Bioorg. Med. Chem. Lett. 13 (2003) 2561
34. Kwon M., Oh M., Han J., and Cho H. J. Biochem. Mol. Biol. 29 (1996) 386