Synthesis and cellular characterization of novel isoxazolo- and thiazolohydrazinylidene-chroman-2,4-diones on cancer and non-cancer cell growth and death

Bioorganic and Medicinal Chemistry

Volumn 22, Issue 9, 2014, Pages 2655-2661

  Jashari, Ahmed ^a   Imeri, Faik ^b   Ballazhi, Lulzime ^a,b   Shabani, Agim ^a   Mikhova, Bozhana ^c   Dräger, Gerald ^d   Popovski, Emil ^e   Huwiler, Andrea ^b  

^a State University of Tetova   (Macedonia)

^b UNIVERSITY OF BERN   (Switzerland)

^c BULGARIAN ACADEMY OF SCIENCES   (Bulgaria)

^d LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^e SS CYRIL AND METHODIUS UNIVERSITY   (Macedonia)

Author keywords

Akt; Apoptosis; Cancer cells; Chromandiones; PARP 1

Indexed keywords

3 [2 (4,5 DIMETHYLTHIAZOL 2 YL)HYDRAZINYLIDENE]CHROMAN 2,4 DIONE; 3 [2 (4H 1,2,4 TRIAZOL 3 YL)HYDRAZINYLIDENE]CHROMAN 2,4 DIONE; 3 [2 (5 BROMOTHIAZOL 2 YL)HYDRAZINYLIDENE]CHROMAN 2,4 DIONE; 3 [2 (5 METHYLISOXAZOL 3 YL)HYDRAZINYLIDENE]CHROMAN 2,4 DIONE; 3 [2 (5 METHYLTHIAZOL 2 YL)HYDRAZINYLIDENE]CHROMAN 2,4 DIONE; 3 [2 (5 TERT BUTYLISOXAZOL 3 YL)HYDRAZINYLIDENE]CHROMAN 2,4 DIONE; 3 [2 (ISOXAZOL 3 YL)HYDRAZINYLIDENE]CHROMAN 2,4 DIONE; 3 [2 (THIAZOL 2 YL)HYDRAZINYLIDENE]CHROMAN 2,4 DIONE; 4 HYDROXYCOUMARIN; COUMARIN DERIVATIVE; ISOXAZOLOHYDRAZINYLIDENE CHROMAN 2,4 DIONE DERIVATIVE; NICOTINAMIDE ADENINE DINUCLEOTIDE ADENOSINE DIPHOSPHATE RIBOSYLTRANSFERASE; PROTEIN KINASE B; THIAZOLOHYDRAZINYLIDENE CHROMAN 2,4 DIONE DERIVATIVE; UNCLASSIFIED DRUG; 4 HYDROXYCOUMARIN DERIVATIVE; 4-HYDROXYCOUMARIN; ANTINEOPLASTIC AGENT; COUMARIN; ISOXAZOLE DERIVATIVE; THIAZOLE DERIVATIVE;

ANTIPROLIFERATIVE ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL; CELL VIABILITY; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; INFRARED SPECTROSCOPY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; CELL LINE; CELL PROLIFERATION; CHEMISTRY; DRUG EFFECTS; MCF 7 CELL LINE; METABOLISM; SYNTHESIS; TOXICITY; U937 CELL LINE;

4-HYDROXYCOUMARINS; ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE; CELL PROLIFERATION; COUMARINS; HUMANS; ISOXAZOLES; MCF-7 CELLS; POLY(ADP-RIBOSE) POLYMERASES; THIAZOLES; U937 CELLS;

EID: 84899434051     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2014.03.026     Document Type: Article

References (43)

1. H. Raistrick, C.E. Stickings, and R. Thomas Biochem. J. 55 1953 421
2. J.W. Hinman, E.L. Caron, and H. Hoeksema J. Am. Chem. Soc. 79 1957 3789
3. A. Lacy, and R. O'Kennedy Curr. Pharm. Des. 10 2004 3797
4. M.A. Musa, V.L. Badisa, L.M. Latinwo, C. Waryoba, and N. Ugochukwu Anticancer Res. 30 2010 4613
5. I. Manolov, and N.D. Danchev Eur. J. Med. Chem. Chim. Ther. 30 1995 531
6. H. Wallick, D.A. Haris, M.A. Reagan, M. Ruger, and H.B. Woodruff Antibiot. Ann. 1956 Medical Encyclopedia, Inc., NY, p909
7. V.S. Parmar, K.S. Bisht, R. Jain, S. Singh, S.K. Sharma, S. Gupta, S. Malhotra, O.D. Tyagi, A. Vardhan, H.N. Pati, D.V. Berghe, and A.J. Vlietinck Ind. J. Chem. Sec. B 35 1996 220
8. S. Kirkiacharian, D.T. Thuy, S. Sicsic, R. Bakhchinian, R. Kurkjian, and T. Tonnaire II Farmaco 57 2002 703
9. C.F. Huebner, and K.P. Link J. Biol. Chem. 138 1941 513
10. A.A. Emmanuel-Giota, K.C. Fylaktakidou, D.J. Hadjipavlou-Litina, K.E. Litinas, and D.N.J. Nicolaides Heterocycl. Chem. 38 2001 717
11. L. Zhang, G. Jiang, F. Yao, Y. He, G. Liang, Y. Zhang, B. Hu, Y. Wu, Y. Li, and H. Liu PLoS One 7 2012 e 37865
12. H. Wang, W. Zheng, F. Xie, and H. Song Youji Huaxue 31 5 2011 708
13. M.A. Musa, A. Zhou, and O.A. Sadik Med. Chem. 7 2011 112
14. V. Pengo, G. Denas, S.P. Jose, and M.F. Pengo Thromb. Res. 125 2010 S103
15. V. Bobek, and J. Kovařík Biomed. Pharmacother. 58 2004 213
16. J. Watanabe, H. Nishiyama, Y. Matsui, M. Ito, H. Kawanishi, T. Kamoto, and O. Ogawa Oncogene 25 2006 2500
17. L.R. Zacharski, W.G. Henderson, F.R. Rickles, W.B. Forman, C.J. Cornell Jr., R.J. Forcier, R.L. Edwards, E. Headley, S.H. Kim, J.F. O'Donnell, R. O'Dell, K. Tornyos, and H.C. Kwaan Cancer 53 1984 2046
18. M.A. Musa, J.S. Cooperwood, M.O. Khan, and T. Rahman Arch. Pharm. (Weinheim) 344 2011 102
19. M.A. Musa, V.L. Badisa, L.M. Latinwo, C. Waryoba, and N. Ugochukwu Anticancer Res. 30 2010 4613
20. M.A. Musa, M.O. Khan, and J.S. Cooperwood Lett. Drug Des. Discov. 6 2009 133
21. G. Kokotos, V. Theodorou, C. Tzougraki, D. Deforce, and E. Van den Eeckhout Bioorg. Med. Chem. Lett. 7 1997 2165
22. J. Cui, and S. Li Curr. Med. Chem. 21 2014 519
23. F. KarcI, and N. Ertan Dyes Pigm. 64 2005 243
24. M.R. Yazdanbakhsh, A. Ghanadzadeh, and E. Moradi J. Mol. Liq. 136 2007 165
25. B.F. Abdel-Wahab, G.E.A. Awad, and F.A. Badria Eur. J. Med. Chem. 46 2011 1505
26. M.A. Gouda, M.A. Berghot, E.A. Baz, and W.S. Hamama Med. Chem. Res. 21 2012 1062
27. A. Kathuria, S. Jalal, R. Tiwari, A.N. Shirazi, S. Gupta, S. Kumar, K. Parang, and S.K. Sharma Chem. Biol. Interface 1 2011 279
28. F. Döll, J. Pfeilschifter, and A. Huwiler Biochim. Biophys. Acta 1738 2005 72
29. A. Huwiler, S. Stabel, D. Fabbro, and J. Pfeilschifter Biochem. J. 305 1995 777
30. K. Tabakovic, I. Tabakovic, M. Trkovnik, and N. Trinajstic Liebigs Ann. Chem. 11 1983 1901
31. A. Jashari, E. Hey-Hawkins, B. Mikhova, G. Draeger, and E. Popovski Molecules 12 2007 2017
32. A. Jashari, E. Popovski, B. Mikhova, R.P. Nikolova, and B.L. Shivachev Acta Crystallogr. E69 2013 o258
33. J.M. Brown Cancer Res. 33 1973 1217
34. A.M. Gil-Bernabé, S. Lucotti, and R.J. Muschel Br. J. Haematol. 162 2013 433
35. J.Y. Chuang, Y.F. Huang, H.F. Lu, H.C. Ho, J.S. Yang, T.M. Li, N.W. Chang, and J.G. Chung In Vivo 21 2007 1003
36. A. Maresca, C. Temperini, H. Vu, N.B. Pham, S.A. Poulsen, A. Scozzafava, R.J. Quinn, and C.T. Supuran J. Am. Chem. Soc. 131 2009 3057
37. J.-Y. Winum, M. Rami, A. Scozzafava, J.-L. Montero, and C. Supuran Med. Res. Rev. 28 2007 445
38. S. Chen, M. Cho, K. Karlsberg, D. Zhou, and Y.C. Yuan J. Biol. Chem. 27 2004 48071
39. M.A. Musa, J.S. Cooperwood, and M.O.F. Khan Curr. Med. Chem. 15 2008 2664
40. Y. Jacquot, L. Bermont, H. Giorgi, B. Refouvelet, G. Adessi, E. Daubrosse, and A. Xicluna Eur. J. Med. Chem. 36 2001 127
41. S.J. Braunhut, D. McIntosh, E. Vorotnikova, T. Zhou, and K.A. Marx Assay Drug Dev. Technol. 3 2005 77
42. J.C. Mallory, G. Crudden, A. Oliva, C. Saunders, A. Stromberg, and R.J. Craven Mol. Pharmacol. 68 2005 1747
43. M.G. Dozmorov, R.E. Hurst, D.J. Culkin, B.P. Kropp, M.B. Frank, J. Osban, T.M. Penning, and H.-K. Lin Prostate 69 2009 1077