Synthesis and biological evaluation of novel indolin-2-one derivatives as protein tyrosine phosphatase 1b inhibitors

Letters in Organic Chemistry

Volumn 8, Issue 7, 2011, Pages 526-530

  Dai, Hou Ling ^a   Shen, Qiang ^b   Zheng, Jian Bin ^a   Lib, Jing Ya ^b   Wen, Ren ^a   Li, Jia ^b  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

3 substituted indolin 2 ones; Diabetes; Inhibitor; Protein tyrosine phosphatase 1B; Structure activity relationship

Indexed keywords

EID: 79961057426     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017811796504909     Document Type: Article

References (17)

1. Johnson, T.O.; Ermolieff, J.; Jirousek, M.R. Protein tyrosine phosphatase 1B inhibitors for diabetes. Nat. Rev. Drug Discov., 2002, 1(9), 696-709. (Pubitemid 37368828)
2. Barford, D.; Flint, A.J.; Tonks, N.K. Crystal structure of human protein tyrosine phosphatase 1B. Science, 1994, 263(5152), 1397-1404. (Pubitemid 24137822)
3. Zabolotny, J.M.; Haj, F.G.; Kim, Y.B.; Kim, H.J.; Shulman, G.I.; Kim, J.K.; Neel, B.G.; Kahn, B.B. Transgenic overexpression of protein-tyrosine phosphatase 1B in muscle causes insulin resistance, but overexpression with leukocyte antigen-related phosphatase does not additively impair insulin action. J. Biol. Chem., 2004, 279(23), 24844-24851. (Pubitemid 38725352)
4. Zabolotny, J.M.; Bence-Hanulec, K.K.; Stricker-Krongrad, A.; Haj, F.; Wang, Y.; Minokoshi, Y.; Kim, Y.B.; Elmquist, J.K.; Tartaglia, L.A.; Kahn, B.B.; Neel, B.G. PTP1B regulates leptin signal transduction in vivo. Dev. Cell, 2002, 2(4), 489-495. (Pubitemid 34436576)
5. Seely, B.L.; Staubs, P.A.; Reichart, D.R.; Berhanu, P.; Milarski, K.L.; Saltiel, A.R.; Kusari, J.; Olefsky, J.M. Protein tyrosine phosphatase 1B interacts with the activated insulin receptor. Diabetes, 1996, 45(10), 1379-1385. (Pubitemid 26332902)
6. Burke, T.R.; Zhang, Z.Y. Protein-tyrosine phosphatases: Structure, mechanism, and inhibitor discovery. Biopolymers, 1998, 47(3), 225-241. (Pubitemid 28530097)
7. Taylor, S.D. Inhibitors of protein tyrosine phosphatase 1B (PTP1B). Curr. Top. Med. Chem., 2003, 3(7), 759-782.
8. Wu, J.; Lawrence, N.J.; Sebti, S.M.; Lawrence, H.R. Inhibition of SHP2/PTPN11 protein tyrosine phosphatase by NSC-87877, NSC- 117199 and their analogs. U.S. Patent 20,080,176,309, July 24, 2008.
9. Marvel, C.S.; Hiers, G.S. Isatin. Org. Synth., 1925, 5, 71-74.
10. Sureyya, O.; Eiichi, A.; Dogu, N. Synthesis and anti-tyrosine kinase activity of 3-(substituted-benzylidene)-1,3-dihydro-indolin derivatives: investigation of their role against p60c-Src receptor tyrosine kinase with the application of receptor docking studies. Farmaco, 2005, 60(6-7), 497-506.
11. Sun, L.; Tran, N.; Tang, F.; App, H.; Hirth, P.; McMahon, G.; Tang, C. Synthesis and biological evaluations of 3-substituted indolin- 2-ones: a novel class of tyrosine kinase inhibitors that exhibit selectivity toward particular receptor tyrosine kinases. J. Med. Chem., 1998, 41(14), 2588-2603. (Pubitemid 28321908)
12. Wolfgang, F.; Barbara, M.; Tobias, M.B.; Laura, C.; Heidi, S.; Pierfausto, S. Regiospecific synthesis of mono-N-substituted indolopyrrolocarbazoles. Org. Lett., 2005, 7(21), 4573-4576.
13. Torsten, K.; Manuela, K.; Frank, W. Facile synthesis of various nitrosubstituted derivatives of semaxinib (SU5416). Synth. Commun., 2008, 38(17), 3017-3022.
14. Arnaiz, D.; Bryant, J.; Chou, Y.L.; Feldman, R.; Hrvatin, P.; Islam, I.; Kochanny, M.; Lee, W.; Polokoff, M.; Yu, H.; Yuan, S. Indolinone derivatives and their use in treating disease-states such as cancer. U.S. Patent, 2,005,090,541, April 28, 2005.
15. Stetinova, J.; Kovac, J.; Sura, J.; Dandarova, M. Stereochemistry and photoisomerization of furfurylideneoxoindoles. Chem. Commun., 1977, 42, 2201-2206.
16. Zhang, W.; Hong, D.; Zhou, Y.Y.; Zhang, Y.N.; Shen, Q.; Li, J.Y.; Hu, L.H.; Li, J. Ursolic acid and its derivative inhibit protein tyrosine phosphatase 1B, enhancing insulin receptor phosphorylation and stimulating glucose uptake. Biochim. Biophys. Acta, 2006, 1760(10), 1505-1512. (Pubitemid 44428024)
17. Shi, L.; Yu, H.P.; Zhou, Y.Y.; Du, J.Q.; Shen, Q.; Li, J.Y.; Li, J. Discovery of a novel competitive inhibitor of PTP1B by highthroughput screening. Acta Pharmacol. Sin., 2008, 29(2), 278-284. (Pubitemid 351178427)