Synthesis of triazole-linked amino acid-aryl C-glycoside hybrids via click chemistry as novel PTP1B inhibitors

Chinese Journal of Chemistry

Volumn 29, Issue 6, 2011, Pages 1227-1232

  Wang, Jia ^a   He, Xiaopeng ^a   Gao, Lixin ^b   Sheng, Li ^b   Shi, Xiaoxin ^a   Li, Jia ^b   Chen, Guorong ^a  

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

^b SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

C glycoside; click chemistry; inhibitors; PTP; triazolyl amino acid

Indexed keywords

EID: 79959685874     PISSN: 1001604X     EISSN: 16147065     Source Type: Journal    
DOI: 10.1002/cjoc.201190228     Document Type: Article

References (34)

1. Elchelby, 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.,;, Kennedy, B. P.,. Science, 1999, 283, 1544.
2. Klaman, L. D.,;, Boss, O.,;, Peroni, O. D.,;, Kim, J. K.,;, Martino, J. L.,;, Zabolotny, J. M.,;, Moghal, N.,;, Lubkin, M.,;, Kim, Y. B.,;, Sharpe, A. H.,;, Stricker-Krongrad, A.,;, Shulman, G. I.,;, Neel, B. G.,;, Kahn, B. B.,. Mol. Cell. Biol., 2000, 20, 5479.
3. Stuible, M.,;, Doody, K. M.,;, Tremblay, M. L.,. Cancer Metastasis Rev., 2008, 27, 215.
4. Zhang, S.,;, Zhang, Z.-Y.,. Drug Discovery Today, 2007, 12, 373.
5. Vintonyak, V. V.,;, Antonchick, A. P.,;, Rauh, D.,;, Waldmann, H.,. Curr. Opin. Chem. Biol., 2009, 13, 272.
6. Combs, A. P.,. J. Med. Chem., 2010, 53, 2333.
7. Wiesmann, C.,;, Barr, K. J.,;, Kung, J.,;, Zhu, J.,;, Erlanson, D. A.,;, Shen, W.,;, Fahr, B. J.,;, Zhong, M.,;, Taylor, L.,;, Randal, M.,;, McDowell, R. S.,;, Hansen, S. K.,. Nat. Struct. Mol. Biol., 2004, 11, 730.
8. Takahashi, N.,;, Qi, Y.,;, Patel, H. R.,;, Ahima, R. S.,. J. Hepatol., 2004, 41, 391.
9. Liu, S.,;, Zeng, L.-F.,;, Wu, L.,;, Yu, X.,;, Xue, T.,;, Gunawan, A. M.,;, Long, Y.-Q.,;, Zhang, Z.-Y.,. J. Am. Chem. Soc., 2008, 130, 17075.
10. Ernst, B.,;, Magnani, J. L.,. Nat. Rev. Drug Discov., 2009, 8, 661.
11. Kolb, H. C.,;, Finn, M. G.,;, Sharpless, K. B.,. Angew. Chem., Int. Ed., 2001, 40, 2004.
12. Rostovtsev, V. V.,;, Green, L. G.,;, Fokin, V. V.,;, Sharpless, K. B.,. Angew. Chem., Int. Ed., 2002, 41, 2596.
13. Zeng, J.,;, Lü, X.,;, Zeng, C.,;, Hu, L.,;, Zhong, R.,. Chin. J. Chem., 2009, 27, 953.
14. Qiu, W.,;, Xu, J.,;, Li, X.,;, Zhong, L.,;, Li, J.,;, Li, J.,;, Nan, F.,. Chin. J. Chem., 2009, 27, 825.
15. Li, L.,;, Tang, W.,;, Zhao, Z.,. Chin. J. Chem., 2009, 27, 1391.
16. Huang, W.,;, Chao, J.,;, Yan, Q.,;, Xiao, S.,. Chin. J. Chem., 2010, 28, 1795.
17. Fu, Y.,;, Liu, Y.,;, Fu, X.,;, Zou, L.,;, Li, H.,;, Li, M.,;, Chen, X.,;, Qin, J.,. Chin. J. Chem., 2010, 28, 2226.
18. Aragão-Leoneti, V.,;, Campo, V. L.,;, Gomes, A. S.,;, Field, R. A.,;, Carvalho, I.,. Tetrahedron, 2010, 66, 9475.
19. Amblard, F.,;, Cho, J. H.,;, Schinazi, R. F.,. Chem. Rev., 2009, 109, 4207.
20. Jewett, J. C.,;, Bertozzi, C. R.,. Chem. Soc. Rev., 2010, 39, 1272.
21. Dondoni, A.,;, Giovannini, P. P.,;, Massi, A.,. Org. Lett., 2004, 6, 2929.
22. Kuijpers, B. H. M.,;, Groothuys, S.,;, Keereweer, A. B. R.,;, Quaedflieg, P. J. L. M.,;, Blaauw, R. H.,;, van Delft, F. K.,;, Rutjes, F. P. J. T.,. Org. Lett., 2004, 6, 3123.
23. Deng, Q.,;, Zheng, R.-R.,;, Ding, N.-N.,;, He, X.-P.,;, Chen, G.-R.,. Bull. Korean Chem. Soc., 2010, 31, 1055.
24. Lin, L.,;, Shen, Q.,;, Chen, G.-R.,;, Xie, J.,. Bioorg. Med. Chem., 2008, 16, 9757.
25. Lin, L.,;, Shen, Q.,;, Chen, G.-R.,;, Xie, J.,. Bioorg. Med. Chem. Lett., 2008, 18, 6348.
26. Yang, J.-W.,;, Li, C.,;, He, X.-P.,;, Zhao, H.,;, Gao, L.-X.,;, Zhang, W.,;, Shi, X.-X.,;, Tang, Y.,;, Li, J.,;, Chen, G.-R.,. Bull. Korean Chem. Soc., 2010, 31, 3359.
27. Song, S.-X.,;, Zhang, H.-L.,;, Kim, C.-G.,;, Sheng, L.,;, He, X.-P.,;, Long, Y.-T.,;, Li, J.,;, Chen, G.-R.,. Tetrahedron, 2010, 66, 9974.
28. Praly, J. P.,;, He, L.,;, Qin, B. B.,;, Tanoh, M.,;, Chen, G.-R.,. Tetrahedron Lett., 2005, 46, 7081.
29. He, L.,;, Zhang, Y. Z.,;, Tanoh, M.,;, Chen, G. R.,;, Praly, J. P.,;, Chrysina, E. D.,;, Tiraidis, C.,;, Kosmopoulou, M.,;, Leonidas, D. D.,;, Oikonomakos, N. G.,. Eur. J. Org. Chem., 2007, 596.
30. Goddard-Borger, E. D.,;, Stick, R. V.,. Org. Lett., 2007, 9, 3797.
31. Caddick, S.,;, Fitzmaurice, R.,. Tetrahedron, 2009, 65, 3325.
32. Miller, N.,;, Willianms, G. M.,;, Brimble, M. A.,. Org. Lett., 2009, 11, 2409.
33. Zhang, W.,;, Hong, D.,;, Zhou, Y.-Y.,;, Zhang, Y.-N.,;, Shen, Q.,;, Li, J.-Y.,;, Hu, L.-H.,;, Li, J.,. Biochim. Biophys. Acta, 2006, 1760, 1505.
34. Shi, L.,;, Yu, H. P.,;, Zhou, Y. Y.,;, Du, J. Q.,;, Shen, Q.,;, Li, J. Y.,;, Li, J.,. Acta Pharmacol. Sin., 2008, 29, 278.