Design and diversity-oriented synthesis of novel 1,4-thiazepan-3-ones fused with bioactive heterocyclic skeletons and evaluation of their antioxidant and cytotoxic activities

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 1, 2012, Pages 743-746

  Shi, Feng ^a   Zeng, Xiao Ning ^b   Cao, Xu Dong ^a   Zhang, Shu ^b   Jiang, Bo ^a   Zheng, Wei Fa ^a   Tu, Shu Jiang ^a  

^a JIANGSU NORMAL UNIVERSITY   (China)

^b THE FIRST AFFILIATED HOSPITAL OF NANJING MEDICAL UNIVERSITY   (China)

Author keywords

1,4 Thiazepine; Antioxidant activity; Cytotoxicity; Multicomponent reactions

Indexed keywords

ASCORBIC ACID; CARBAZOLE DERIVATIVE; HETEROCYCLIC COMPOUND; ISOXAZOLE; PYRAZOLE; SOLVENT; THIAZEPINE DERIVATIVE;

ANIMAL CELL; ANTIOXIDANT ACTIVITY; ARTICLE; CANCER CELL CULTURE; CARCINOMA CELL; CELL STRAIN HCT116; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYTOTOXICITY; DIVERSITY ORIENTED SYNTHESIS; DRUG DESIGN; DRUG SYNTHESIS; EMBEDDING; ENVIRONMENTAL EXPOSURE; GREEN CHEMISTRY; HUMAN; HUMAN CELL; IN VITRO STUDY; MICROWAVE RADIATION; MULTICOMPONENT REACTION; NONHUMAN; REACTION TIME;

ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; CARBAZOLES; CELL LINE, TUMOR; CHEMISTRY, PHARMACEUTICAL; DRUG DESIGN; DRUG SCREENING ASSAYS, ANTITUMOR; HCT116 CELLS; HUMANS; MICROWAVES; MODELS, CHEMICAL; PYRAZOLES; SOLVENTS; TEMPERATURE; THIAZEPINES;

EID: 84655176701     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.09.081     Document Type: Article

References (35)

1. B. Zaleska, D. Ciez, J. Grochowski, P. Serda, and W. Winnik Liebigs Ann. 2 1996 211
2. P.G. Sammers Chem. Rev. 76 1976 113
3. S.A. Matlin, and L. Chan Chem. Commun. 1980 798
4. A. Levai, J. Ott, and G. Snatzke Monatsh. Chem. 123 1992 919
5. J. Bohrisch, H. Faltz, M. Patzel, and J. Liebscher Tetrahedron 50 1994 10701
6. N.R. Monks, D.C. Blankey, S.J. East, R.I. Dowell, J.A. Caluete, N.J. Curtin, C.E. Arris, and D.R. Newell Eur. J. Cancer 11 2002 1543
7. J.B. LePez, N. DzXuong, C. Gosse, and C. Paolett Proc. Natl. Acad. Sci. U.S.A. 71 1974 5078
8. E.S. El-Tamany, F.A. El-Shahed, and B.H. Mohamed J. Serb. Chem. Soc. 64 1999 9
9. Z.H. Ismail, G.M. Aly, M.S. El-Degwi, H.I. Heiba, and M.M. Ghorab Egypt. J. Biotechnol. 13 2003 73
10. M.E.A. Zaki, H.A. Soliman, O.A. Hiekal, and A.E. Rashad Z. Naturforsch., C 61 2006 1
11. S.-J. Tu, X.-D. Cao, W.-J. Hao, X.-H. Zhang, S. Yan, S.-S. Wu, Z.-G. Han, and F. Shi Org. Biomol. Chem. 7 2009 557
12. S.L. Schreiber Science 287 2000 1964
13. S. Dandapani, and L.A. Marcaurelle Curr. Opin. Chem. Biol. 14 2010 362
14. S. Oh, H.J. Jang, S.K. Ko, Y. Ko, and S.B. Park J. Comb. Chem. 12 2010 548
15. H.F. Sore, D.T. Blackwell, S.J.F. MacDonald, and D.R. Spring Org. Lett. 12 2010 2806
16. A. Kumar, G. Gupta, and S. Srivastava J. Comb. Chem. 12 2010 458
17. V. Karapetyan, S. Mkrtchyan, J. Hefner, C. Fischer, and P. Langer J. Org. Chem. 75 2010 809
18. C.-H. Chen, M.-H. Chien, M.-L. Kuo, C.-T. Chou, J.-J. Lai, S.-F. Lin, S. Thummanagoti, and C.-M. Sun J. Comb. Chem. 11 2009 1038
19. B. Jiang, W.-J. Hao, X. Wang, F. Shi, and S.-J. Tu J. Comb. Chem. 11 2009 846
20. F. Shi, A.-X. Dai, X.-H. Zhang, B. Jiang, and S.-J. Tu ACS Comb. Sci. 13 2011 147
21. F. Shi, S. Zhang, S.-S. Wu, Y. Gao, and S.-J. Tu Mol. Divers. 15 2011 497
22. D.J. Ramon, and Y. Miguel Angew. Chem., Int. Ed. 44 2005 1602
23. L. Weber, K. Illgen, and M. Almstetter Synlett 1999 366
24. G. Li, H.X. Wei, S.H. Kim, and M.D. Carducci Angew. Chem., Int. Ed. 40 2001 4277
25. D.B. Ramachary, and S. Jain Org. Biomol. Chem. 9 2011 1277
26. Yu, J.; Shi, F.; Gong, L.-Z. Acc. Chem. Res. 2011, in press. doi:10.1021/ar2000343 and references cited therein.
27. B. Jiang, S.J. Tu, P. Kaur, W. Wever, and G. Li J. Am. Chem. Soc. 131 2009 11660
28. F. Shi, C. Li, M. Xia, K. Miao, Y. Zhao, S. Tu, W. Zheng, G. Zhang, and M. Ning Bioorg. Med. Chem. Lett. 19 2009 5565
29. P. Wei, X. Zhang, S. Tu, S. Yan, H. Ying, and P. Ouyang Bioorg. Med. Chem. Lett. 19 2009 828
30. B. Jiang, C. Li, F. Shi, S.-J. Tu, P. Kaur, W. Wever, and G. Li J. Org. Chem. 75 2010 2962
31. F. Shi, A.-X. Dai, S. Zhang, X.-H. Zhang, and S.-J. Tu Eur. J. Med. Chem. 46 2011 953
32. F. Shi, J. Ding, S. Zhang, W.-J. Hao, C. Cheng, and S. Tu Bioorg. Med. Chem. Lett. 21 2011 1554
33. The experimental procedures of synthesis and bioassay as well as the spectroscopic data of the synthesized compounds are available in the Supplementary data.
34. R.A. Anderson, C.L. Broadhurst, M.M. Polansky, W.F. Schmidt, A. Khan, V.P. Flanagan, N.W. Schoene, and D.J. Graves J. Agric. Food Chem. 52 2004 65
35. W. Zheng, Y. Zhao, M. Zhang, Z. Wei, K. Miao, and W. Sun Med. Mycol. 47 2009 814