Synthesis, crystal structures and biological activities of 2-acetylpyridine N(4)-cyclohexylthiosemicarbazone and its manganese(II) and nickel(II) complexes

Inorganic Chemistry Communications

Volumn 13, Issue 12, 2010, Pages 1572-1575

  Li, Ming Xue ^a   Zhang, Dong ^a   Zhang, Li Zhi ^a   Niu, Jing Yang ^a   Ji, Bian Sheng ^a  

^a HENAN UNIVERSITY   (China)

Author keywords

Complex; Crystal structure; Cytotoxic activity; Thiosemicarbazone

Indexed keywords

EID: 78649330408     PISSN: 13877003     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.inoche.2010.08.032     Document Type: Article

References (42)

1. J.E. Karp, F.J. Giles, I. Gojo, L. Morris, J. Greer, B. Johnson, M. Thein, M. Sznol, and J. Low Leuk. Res. 32 2008 71
2. D.X. West, A.E. Liberta, S.B. Padhye, R.C. Chikate, P.B. Sonawane, A.S. Kumbhar, and R.G. Xerande Coord. Chem. Rev. 123 1993 49
3. A. Murugkar, S. Padhye, S. Guha-Roy, and U. Wagh Inorg. Chem. Commun. 2 1999 545
4. M.D. Hall, N.K. Salam, J.L. Hellawell, H.M. Fales, C.B. Kensler, J.A. Ludwig, G. Szakács, D.E. Hibbs, and M.M. Gottesman J. Med. Chem. 52 2009 3191
5. S. Padhye, Z. Afrasiabi, E. Sinn, J. Fok, K. Mehta, and N. Rath Inorg. Chem. 44 2005 1154
6. C.R. Kowol, R. Trondl, P. Heffeter, V.B. Arion, M.A. Jakupec, A. Roller, M. Galanski, W. Berger, and B.K. Keppler J. Med. Chem. 52 2009 5032
7. S.K. Jain, B.S. Garg, and Y.K. Bhoon Spectrochim. Acta A 42 1986 959
8. M.E. Hossain, M.N. Alam, J. Begum, M.A. Ali, M. Nazimudhin, F.E. Smith, and R.C. Hynes Inorg. Chim. Acta 249 1996 207
9. H. Beraldo, and D. Gambino Mini Rev. Med. Chem. 4 2004 159
10. Z. Afrasiabi, E. Sinn, J. Chen, Y. Ma, and S. Padhye Toxicol. Appl. Pharmacol. 197 2004 40
11. D. Kovala-Demertzi, A. Domopoulou, M.A. Demertzis, G. Valle, and A. Papageorgiou J. Inorg. Biochem. 68 1997 147
12. A.G. Quiroga, and C.N. Ranninger Coord. Chem. Rev. 248 2004 119
13. S. Singh, N. Bharti, and P.P. Mohapatra Chem. Rev. 109 2009 1900
14. M.X. Li, C.L. Chen, C.S. Ling, J. Zhou, B.S. Ji, Y.J. Wu, and J.Y. Niu Bioorg. Med. Chem. Lett. 19 2009 2704
15. M.X. Li, Y. Bai, B.G. Zhang, C.Y. Duan, J. Xu, and Q.J. Meng Inorg. Chem. 44 2005 5459
16. M.X. Li, Q.Z. Sun, Y. Bai, C.Y. Duan, B.G. Zhang, and Q.J. Meng Dalton Trans. 2006 2572
17. M.X. Li, J. Zhou, C.L. Chen, and J.P. Wang Z. Naturforsch. 63b 2008 280
18. D. Zhang, Q. Li, M.X. Li, D.Y. Chen, and J.Y. Niu J. Coord. Chem. 63 2010 1063
19. D.Y. Chen, C.L. Chen, M.X. Li, J.Y. Niu, X.F. Zhu, and H.M. Guo J. Coord. Chem. 63 2010 1546
20. M.X. Li, C.L. Chen, D. Zhang, J.Y. Niu, and B.S. Ji Eur. J. Med. Chem. 45 2010 3169
21. M. Joseph, V. Suni, C.R. Nayar, M.R.P. Kurup, and H.-K. Fun J. Mol. Struct. 705 2004 63
22. +].
23. +].
24. 3, triclinic, space group P-1, a = 5.889(1) Å, b = 10.236(1) Å, c = 12.383(1) Å, α = 94.628(2)° β = 90.468(2)° γ = 90.987(2)° V = 743.86(13) Å 3, Z = 2, ρcalcd = 1.234 Mg•m-3, 2595 reflections collected, 2099 unique (Rint = 0.0454), R1 = 0.0608 [I > 2σ (I)], and wR2 = 0.1850 (all data). The data were collected on a Bruker APEX-II CCD diffractometer (MoKa, λ = 0.71073 Å) at 296(2) K. All structures were solved by the direct method and refined by the full-matrix least-squares on F2 using the SHELXL-97 [19,20]. All of the non-hydrogen atoms were refined anisotropically.
25. G.M. Sheldrick SHELXS 97, Program for Crystal Structure Solution 1997 University of Göttingen Göttingen
26. G.M. Sheldrick SHELXL 97, Program for Crystal Structure Refinement 1997 University of Göttingen Göttingen
27. J. Garcia-Tojal, M.K. Urtiaga, R. Cortes, L. Lezama, M.I. Arriortua, and T. Rojo J. Chem. Soc., Dalton Trans. 1994 2234
28. A. Sreekanth, and M.R.P. Kurup Polyhedron 23 2004 969
29. D.X. West, G.A. Bain, R.J. Butcher, J.P. Jasinski, Y. Li, and R.Y. Pordniakiv Polyhedron 15 1996 665
30. Crystal data for complex 1: C28H38MnN8S2 (605.72), Crystal dimensions 0.22 × 0.19 × 0.18 mm3, triclinic, space group P-1, a = 10.515(4) Å, b = 12.533(2) Å, c = 13.177(2) Å, α = 115.923(2)° β = 98.045(3)° γ = 99.434(3)° V = 1496.2(6) Å 3, Z = 2, ρcalcd = 1.344 Mg·m-3, 5238 reflections collected, 4283 unique (Rint = 0.0177), R1 = 0.0375 [I > 2σ (I)], and wR2 = 0.1084 (all data). The data were collected on a Bruker APEX-II CCD diffractometer (MoKa, λ = 0.71073 Å) at 296(2) K. All structures were solved by the direct method and refined by the full-matrix least-squares on F2 using the SHELXL-97. All of the non-hydrogen atoms were refined anisotropically.
31. Crystal data for complex 2: C28H38NiN8S2 (609.49), Crystal dimensions 0.30 × 0.27 × 0.22 mm3, monoclinic, space group P21/c, a = 11.697(1) Å, b = 20.844(1) Å, c = 12.129(1) Å, β = 92.946(1)° V = 2953.3(3) Å 3, Z = 4, ρcalcd = 1.371 Mg·m-3, 5140 reflections collected, 4179 unique (Rint = 0.0417), R1 = 0.0737 [I > 2σ (I)], and wR2 = 0.2411 (all data). The data were collected on a Bruker APEX-II CCD diffractometer (MoKa, λ = 0.71073 Å) at 296(2) K. All structures were solved by the direct method and refined by the full-matrix least-squares on F2 using the SHELXL-97. All of the non-hydrogen atoms were refined anisotropically.
32. K.V. Katti, P.R. Singh, and C.L. Barnes J. Chem. Soc., Dalton Trans. 1993 2153
33. F.A. Beckford, G. Leblanc, J. Thessing, M. Shaloski, B.J. Frost, L. Li, and N.P. Seeram Inorg. Chem. Commun. 12 2009 1094
34. T.S. Lobana, P. Kumari, and R.J. Butcher Inorg. Chem. Commun. 11 2008 11
35. M. Joseph, M. Kuriakose, M.R.P. Kurup, E. Suresh, A. Kishore, and S.G. Bhat Polyhedron 25 2006 61
36. A. Mishra, N.K. Kaushik, A.K. Verma, and R. Gupta Eur. J. Med. Chem. 43 2008 2189
37. M. Joseph, M. Kuriakose, M.R.P. Kurup, E. Suresh, A. Kishore, and S.G. Bhat Polyhedron 25 2006 61
38. The minimal inhibitory concentrations (MIC, μg/mL) were estimated by the disk diffusion method. The final concentration of all cultures in Mueller-Hinon agar (MHA) for bacteria was adjusted to 106 CFU/mL and used for inoculation in the MIC test. Serial dilutions of the test compounds (dissolved in DMSO) were prepared at concentrations of 0-2000 μg/mL. Each plate was inoculated with 0.1 mL of the prepared bacterial cultures. Similarly, each plate carried a blank disc, with solvent DMSO only in the center to serve as negative control. The inoculated plates were then incubated at 37 °C for 18-20 h. The minimal inhibitory concentration (MIC) was detected as the lowest concentration of drug in plate for which no visible growth took place by macroscopic evaluation. All determinations were performed in triplicate and confirmed by three separate experiments.
39. J.G. Tojal, A.G. Orad, J.L. Serra, J.L. Pizarro, L. Lezama, M.I. Arriortua, and T. Rojo J. Inorg. Biochem. 75 1999 45
40. -1 MTT in PBS) was added and cells were incubated for a further 4 h. 200 μL of DMSO were added to each culture to dissolve the MTT crystals. The MTT-formazan product dissolved in DMSO was estimated by measuring absorbance at 570 nm with a micro plate reader. Then the inhibitory percentage of each compound at various concentrations was calculated, and the IC50 value was determined.
41. H.G. Petering, and G.J. Van Giessen Biochem. Copper, Proc. Symp. 1966 197
42. H. Beraldo, and D. Gambino Mini-Rev. Med. Chem. 4 2004 31