Synthesis of (glycopyranosyl-triazolyl)-purines and their inhibitory activities against protein tyrosine phosphatase 1B (PTP1B)

Chemistry and Biodiversity

Volumn 8, Issue 11, 2011, Pages 2035-2044

  Luo, Lei ^a   He, Xiao Peng ^a,b   Shen, Qiang ^c   Li, Jing Ya ^c   Shi, Xiao Xin ^a   Xie, Juan ^b   Li, Jia ^c   Chen, Guo Rong ^a  

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

^b UNIVERSITÉ PARIS SACLAY   (France)

^c SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Inhibitors; Protein tyrosine phosphatase; Purines; Triazole

Indexed keywords

2 AMINO 6 CHLORO 9 [[1 (2,3,4,6 TETRA O ACETYL B D GLUCOPYRANOSYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] 9H PURINE; 2 AMINO 6 CHLOROPURINE; 6 CHLORO 9 (PROP 2 YN 1 YL) 9H PURIN 2 AMINE; 6 CHLORO 9 [[1 (2,3,4,6 TETRA O ACETYL B D GLUCOPYRANOSYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL] 2 [[[1 (2,3,4,6 TETRA O ACETYL B D GLUCOPYRANOSYL) 1H 1,2,3 TRIAZOL 4 YL]METHYL]AMINO] 9H PURINE; 6 CHLORO N 9 BIS[[1 [[3,4,5 TRIS(BENZYLOXY)TETRAHYDRO 6 METHOXY 2H PYRAN 2 YL]METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHYL] 9H PURIN 2 AMINE; 6 CHLORO N,9 (PROP 2 YN 1 YL) 9H PURIN 2 AMINE; 6 CHLORO N,9 BIS[[1 [[3,4,5 TRIS(BENZYLOXY)TETRAHYDRO 6 METHOXY 2H PYRAN 2 YL]METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHYL] 9H PURIN 2 AMINE; 6 METHOXY N,9 BIS[[1 [[3,4,5 TRIS(BENZYLOXY)TETRAHYDRO 6 METHOXY 2H PYRAN 2 YL]METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHYL] 9H PURIN 2 AMINE; 6 METHOXY N,9 BIS[[1 [[3,4,5 TRIS(BENZYLOXY)TETRAHYDRO 6 METHOXY 2H PYRAN 2YL]METHYL] 1H 1,2,3 TRIAZOL 4 YL]METHYL] 9H PURIN 2 AMINE; LEUKOCYTE ANTIGEN RELATED PROTEIN TYROSINE PHOSPHATASE; METHYL 6 [4 [(2 AMINO 6 CHLORO 9H PURIN 9 YL)METHYL] 1H 1,2,3 TRIAZOL 1 YL] 2,3,4 TRI O BENZYL 6 DEOXY A D GALACTOPYRANOSIDE; METHYL 6 [4 [(2 AMINO 6 CHLORO 9H PURIN 9 YL)METHYL] 1H 1,2,3 TRIAZOL 1 YL] 2,3,4 TRI O BENZYL 6 DEOXY A D GLUCOPYRANOSIDE; METHYL 6 [4 [(2 AMINO 6 METHOXY 9H PURIN 9 YL)METHYL] 1H 1,2,3 TRIAZOL 1 YL] 2,3,4 TRI O BENZYL 6 DEOXY A D GALACTOPYRANOSIDE; METHYL 6 [4 [(2 AMINO 6 METHOXY 9H PURIN 9 YL)METHYL] 1H 1,2,3 TRIAZOL 1 YL] 2,3,4 TRI O BENZYL 6 DEOXY A D GLUCOPYRANOSIDE; NON RECEPTOR PROTEIN TYROSINE PHOSPHATASE 2; PROTEIN TYROSINE PHOSPHATASE; PROTEIN TYROSINE PHOSPHATASE 1B; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; PROTEIN TYROSINE PHOSPHATASE SHP 1; PROTEIN TYROSINE PHOSPHATASE SHP 2; PURINE DERIVATIVE; UNCLASSIFIED DRUG;

ACETYLATION; ARTICLE; CHEMICAL MODIFICATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CYCLOADDITION; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; IC 50;

CATALYTIC DOMAIN; CLICK CHEMISTRY; CYCLIZATION; DRUG DESIGN; ENZYME INHIBITORS; GLYCOCONJUGATES; GLYCOSYLATION; HUMANS; MOLECULAR STRUCTURE; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; PURINES; STRUCTURE-ACTIVITY RELATIONSHIP; TRIAZOLES;

EID: 81255209198     PISSN: 16121872     EISSN: 16121880     Source Type: Journal    
DOI: 10.1002/cbdv.201000242     Document Type: Article

References (33)

1. E. Fischer, Ber. Dtsch. Chem. Ges. 1898, 31, 2550.
2. M. Legraverend, Tetrahedron 2008, 64, 8585.
3. H. Rosemeyer, Chem. Biodiversity 2004, 1, 361.
4. M. Legraverend, D. S. Grierson, Bioorg. Med. Chem. 2006, 14, 3987.
5. A. P. Schmidt, D. R. Lara, D. O. Souza, Pharmacol. Ther. 2007, 116, 401.
6. G. Chiosis, B. Lucas, H. Huezo, D. Solit, A. Basso, N. Rosen, Curr. Cancer Drug Targets 2003, 3, 371.
7. W.C. Shakespeare 3rd, C.A. Metcalf, Y. Wang, R. Sundaramoorthi, T. Keemam, M. Weigele, R.S. Bohacek, D.C. Dalgarno, T.K. Sawyer, Curr. Opin. Drug Discov. Dev. 2003, 6, 729.
8. Z. Wang, B. J. Canagarajah, J. C. Boehm, S. Kassisà, M. H. Cobb, P. R. Young, S. Abdel-Meguid, J. L. Adams, E. J. Goldsmith, Structure 1998, 6, 1117.
9. J. Zablocki, R. Kalla, T. Perry, V. Palle, V. Varkhedkar, D. Xiao, A. Piscopio, T. Maa, A. Gimbel, J. Hao, N. Chu, K. Leung, D. Zeng, Bioorg. Med. Chem. Lett. 2005, 15, 609.
10. S. Pal, W. J. Choi, S. A. Choe, C. L. Heller, Z.-G. Gao, M. Chinn, K. A. Jacobson, X. Hou, S. K. Lee, H. O. Kim, L. S. Jeong, Bioorg. Med. Chem. 2009, 17, 3733.
11. F. Marcelo, F. V. M. Silva, M. Goulart, J. Justino, P. Sinaý, Y. Blériot, A. P. Rauter, Bioorg. Med. Chem. 2009, 17, 5106.
12. J. Romanowska, A. Szymańska-Michalak, J. Boryski, J. Stawiński, A. Kraszewski, R. Loddo, G. Sanna, G. Gollu, B. Secci, P. La Colla, Bioorg. Med. Chem. 2009, 17, 3489.
13. H. C. Kolb, M. G. Finn, K. B. Sharpless, Angew. Chem., Int. Ed. 2001, 40, 2004.
14. F. Amblard, J. H. Cho, R. F. Schinazi, Chem. Rev. 2009, 109, 4207.
15. D. E. Moller, Nature 2001, 414, 821.
16. J. Montalibet, B. P. Kennedy, Drug Discov. Today: Ther. Strat. 2005, 2, 129.
17. S. G. Julien, N. Dubé, M. Read, J. Penney, M. Paquet, Y. Han, B. P. Kennedy, W. J. Muller, M. L. Tremblay, Nat. Genet. 2007, 39, 338.
18. L. Bialy, H. Waldmann, Angew. Chem., Int. Ed. 2005, 44, 3814.
19. S. Lee, Q. Wang, Med. Res. Rev. 2007, 27, 553.
20. S. Zhang, Z.-Y. Zhang, Drug Discov. Today 2007, 12, 373.
21. V. V. Vintonyak, A. P. Antonchick, D. Rauh, H. Waldmann, Curr. Opin. Chem. Biol. 2009, 13, 272.
22. C. Wiesmann, K. J. Barr, J. Kung, J. Zhu, D. A. Erlanson, W. Shen, B. J. Fahr, M. Zhong, L. Taylor, M. Randal, R. S. McDowell, S. K. Hansen, Nat. Struct. Mol. Biol. 2004, 11, 730.
23. S. Liu, L.-F. Zeng, L. Wu, X. Yu, T. Xue, A. M. Gunawan, Y.-Q. Long, Z.-Y. Zhang, J. Am. Chem. Soc. 2008, 130, 17075.
24. C. Liljebris, J. Martinsson, L. Tedenborg, M. Williams, E. Barker, J. E. S. Duffy, A. Nygren, S. James, Bioorg. Med. Chem. 2002, 10, 3197.
25. K. R. Guertin, L. Setti, L. Qi, R. M. Dunsdon, B. W. Dymock, P. S. Jones, H. Overton, M. Taylor, G. Williams, J. A. Sergi, K. Wang, Y. Peng, M. Renzetti, R. Boyce, F. Falcioni, R. Garippa, A. R. Oliver, Bioorg. Med. Chem. Lett. 2003, 13, 2895.
26. L. Lin, Q. Shen, G.-R. Chen, J. Xie, Bioorg. Med. Chem. 2008, 16, 9757.
27. L. Lin, Q. Shen, G.-R. Chen, J. Xie, Bioorg. Med. Chem. Lett. 2008, 18, 6348.
28. W. R. Kobertz, C. R. Bertozzi, M. D. Bednarski, J. Org. Chem. 1996, 61, 1894.
29. X.-T. Zhou, C. Forestier, R. D. Goff, C. Li, L. Teyton, A. Bendelac, P. B. Savage, Org. Lett. 2002, 4, 1267.
30. S. Deng, U. Gangadharmath, C.-W. T. Chang, J. Org. Chem. 2006, 71, 5179.
31. W. E. Lindsell, C. Murray, P. N. Preston, T. A. J. Woodman, Tetrahedron 2000, 56, 1233.
32. W. Zhang, D. Hong, Y. Zhou, Y. Zhang, Q. Shen, J.-Y. Li, L.-H. Hu, J. Li, Biochim. Biophys. Acta-Gen. Subj. 2006, 1760, 1505.
33. L. Shi, H.-P. Yu, Y.-Y. Zhou, J.-Q. Du, Q. Shen, J.-Y. Li, J. Li, Acta Pharmacol. Sin. 2008, 29, 278.