Synthesis and biological activity of bi/tricyclic azasugars fused thiazolidin-4-one and thiazinan-4-one by microwave-assisted tandem Staudinger/aza-Wittig/cyclization

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 8, 2012, Pages 2712-2716

  Li, Xiaoliu ^a,b   Qin, Zhanbin ^a   Yang, Tianyu ^a   Zhang, Hongzhi ^a   Wei, Sinan ^a   Li, Chunxiao ^a   Chen, Hua ^a   Meng, Ming ^a  

^a HEBEI UNIVERSITY   (China)

^b PEKING UNIVERSITY   (China)

Author keywords

Bi triazasugars; Biological activity; Microwave assisted; Staudinger aza Wittig cyclization; Thiazolidin 4 one

Indexed keywords

BICYCLIC AZASUGAR DERIVATIVE; BICYCLO COMPOUND; IMINOSUGAR; THIAZINAN 4 ONE; THIAZOLE DERIVATIVE; THIAZOLIDIN 4 ONE; THIOL DERIVATIVE; TRICYCLIC AZASUGAR DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; MICROWAVE IRRADIATION; MOUSE; NONHUMAN; ONE POT SYNTHESIS; REACTION ANALYSIS; STAUDINGER REACTION; STEREOCHEMISTRY; STEREOSPECIFICITY; STRUCTURE ANALYSIS; WITTIG REACTION;

ADJUVANTS, IMMUNOLOGIC; AZA COMPOUNDS; CARBOHYDRATES; CYCLIZATION; DRUG DISCOVERY; KILLER CELLS, NATURAL; MICROWAVES; STEREOISOMERISM; THIAZINES; THIAZOLIDINEDIONES;

EID: 84862824193     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.02.103     Document Type: Article

References (52)

1. P. Compain, and O.R. Martin Iminosugars: From Synthesis to Therapeutic Applications 2007 John Wiley & Sons Ltd Chichester, England
2. N. Asano B.O. Fraser-Reid, K. Tatsuta, J. Thiem, Glycoscience: Chemistry and Chemical Biology 2008 Springer Berlin 1887 1911
3. X.S. Ye, F. Sun, M. Liu, Q. Li, Y.H. Wang, G.S. Zhang, L.H. Zhang, and X.L. Zhang J. Med. Chem. 48 2005 3688
4. V.P. Vyavahare, C. Chakraborty, B. Maity, S. Chattopadhyay, V.G. Puranik, and D.D. Dhavale J. Med. Chem. 50 2007 5519
5. I. Pastuszak, J. Molyneux Russell, L.F. James, and A.D. Elbein Biochemistry 1990 1886 29
6. R.J. Nash, L.E. Fellows, J.V. Dring, C.H. Stirton, D. Carter, M.P. Hegarty, and E.A. Bell Phytochemistry 27 1988 1403
7. A.D. Elbein, J.E. Tropea, M. Mitchell, and G.P. Kaushal J. Bio. Chem. 265 1990 15599
8. T. Aoyagi, H. Suda, K. Uotani, F. Kojima, T. Aoyama, K. Horiguchi, M. Hamada, and T. Takeuchi J. Antibiot. 45 1992 1404
9. V.H. Lillelund, H.H. Jensen, X. Liang, and M. Bols Chem. Rev. 102 2002 515
10. T.D. Heightman, and A.T. Vasella Angew. Chem., Int. Ed. 38 1999 750
11. P. Ermert, A. Vasella, M. Weber, K. Rupitz, and S.G. Withers Carbohydr. Res. 250 1993 113
12. F. Dolhem, F.A. Tahli, C. Livre, and G. Demailly Eur. J. Org. Chem. 2005 5019
13. W. Zou, M. Bhasin, K. Vembaiyan, and D.T. Williams Carbohydr. Res. 344 2009 1024
14. J. Pabba, B.P. Rempel, S.G. Withers, and A. Vasella Helv. Chim. Acta 89 2006 635
15. L. Cipolla, M.R. Fernandes, M. Gregori, C. Airoldi, and F. Nicotra Carbohydr. Res. 342 2007 1813
16. G. Pandey, S.G. Dumbre, M. Islam Khan, and M. Shabab J. Org. Chem. 71 2006 8481
17. P.D. Pérez, M. Isabel García-Moreno, C.O. Mellet, and J.M. García-Fernández Eur. J. Org. Chem. 2005 2903
18. M. Benltifa, M. Isabel García-Moreno, C.O. Mellet, J.M. García-Fernández, and A. Wadouachi Bioorg. Med. Chem. Lett. 18 2008 2805
19. M.A. Moncayo, C.O. Mellet, J.M. García-Fernández, and M. Isabel García-Moreno J. Org. Chem. 74 2009 3595
20. L.D.S. Yadav, and C. Awasthi Carbohydr. Res. 345 2010 318
21. G. Pandey, S.G. Dumbre, M. Islam Khan, M. Shabab, and V.G. Puranik Tetrahedron Lett. 47 2006 7923
22. K. Jayakanthan, and Y.D. Vankar Tetrahedron Lett. 47 2006 8667
23. G. Enderlin, C. Taillefumier, C. Didierjean, and Y. Chapleur J. Org Chem. 74 2009 8388
24. R. Ben-Othman, M. Othman, K. Ciamala, M. Knorr, C. Strohmann, and B. Decroix Tetrahedron 65 2009 4846
25. M. Terinek, and A. Vasella Helv. Chim. Acta 88 2005 10
26. M. Terinek, and A. Vasella Tetrahedron: Asymmetry 16 2005 449
27. J. Pabba, N. Mohal, and A. Vasellam Helv. Chim. Acta 89 2006 1373
28. E. Dubost, D.L. Nouën, and J. Streith Eur. J. Org. Chem. 2006 610
29. M. Terinek, and A. Vasella Helv. Chim. Acta 87 2004 3035
30. M. Terinek, and A. Vasella Helv. Chim. Acta 87 2004 719
31. N. Mohal, B. Bernet, and A. Vasella Helv. Chim. Acta 88 2005 3232
32. B. Shanmugasundaram, and A. Vasella Helv. Chim. Acta 88 2005 2593
33. T. Flessner, and C.H. Wong Tetrahedron Lett. 41 2000 7805
34. B.G. Davis, R.J. Nash, A.A. Watson, C. Smith, and G.W.J. Fleet Tetrahedron 55 1999 4501
35. H. Chen, H.-H. Zhang, J.-N. Feng, X.-L. Li, L.-L. Jiao, Z.-B. Qin, Q.-M. Yin, P.-Z. Zhang, and J.-C. Zhang Eur. J. Org. Chem. 2009 6100
36. X.-L. Li, Q.-M. Yin, L.-L. Jiao, Z.-B. Qin, J.-N. Feng, H. Chen, J.-C. Zhang, and M. Meng Carbohydr. Res. 346 2011 401
37. Y.Y. Yang, W.G. Shou, Z.B. Chen, D. Hong, and Y.G. Wang J. Org. Chem. 73 2008 3928
38. S. Hirota, R. Kato, M. Suzuki, Y. Soneta, T. Otani, and T. Saito Eur. J. Org. Chem. 2008 2075
39. A. Verma, and S.K. Saraf Eur. J. Med. Chem. 43 2008 897
40. P. Compain, V. Chagnault, and O.R. Martin Tetrahedron: Asymmetry 20 2009 672
41. V.H. Jadhav, O.P. Bande, V.G. Puranik, and D.D. Dhavale Tetrahedron 66 2010 2830
42. D. Best, C. Wang, A.C. Weymouth-Wilson, R.A. Clarkson, F.X. Wilson, R.J. Nash, S. Miyauchi, A. Kato, and G.W.J. Fleet Tetrahedron: Asymmetry 21 2009 311
43. L.H. Choudhury, and T. Parvin Tetrahedron 67 2011 8213
44. H. Chen, Q.-M. Yin, C.-X. Li, E.-K. Wang, F. Gao, X.-B. Zhang, Z. Yin, S.-N. Wei, X.-L. Li, M. Meng, P.-Z. Zhang, N. Li, and J.-C. Zhang ACS Med. Chem. Lett. 2 2011 845
45. Chen, H.; Gao, F.; Yin, Q.-M.; Li, C.-X.; Li, N.; Meng, M.; Li, X.-L. Chin. J. Org. Chem. doi: 10.6023/cjoc1111291.
46. Y. Suhara, A. Kittaka, K. Ono, M. Kurihara, T. Fujishima, A. Yoshida, and H. Takayama Bioorg. Med. Chem. Lett. 12 2002 3533
47. M. Isabel García-Moreno, C.O. Mellet, and J.M. García-Fernández Eur. J. Org. Chem. 2004 1803
48. M.S.M. Timmer, M.D.P. Risseeuw, M. Verdoes, D.V. Filippov, J.R. Plaisier, G.A. van der Marel, H.S. Overkleeft, and J.H. van Boom Tetrahedron: Asymmetry 16 2005 177
49. J.-X. Xu Prog. Chem. 19 2007 700 (in Chinese)
50. C.O. Kappe Angew. Chem., Int. Ed. 43 2004 6250 6284
51. T. Srivastava, W. Haq, and S.B. Katti Tetrahedron 58 2002 7619
52. D. Marek, R. Uzan, D. Beaupere, G. Nowogrocki, and G. Laplace Tetrahedron Lett. 37 1996 49