Please do not adjust margins
Page 9 of 11
New Journal of Chemistry
Journal Name
ARTICLE
1
2
3
4
5
6
7
8
9
To sum up, three transition compounds (1 , 2 and 3) based on
a new 4-acylpyrazolone derivative, 2-hydroxy-N'-((5 hydroxy-3-
methyl-1-(4-nitrophenyl)-4,5-dihydro-1H-pyrazol-4-yl)(phenyl)-
methylene)benzohydrazide (H2L), were prepared by using
different metal ions and anions for tuning the structure as well
as DNA binding properties. Crystal structure analysis shows that
DOI: 10.1039/C9NJ05948B
Stepanenko, V. V. Ivanov, J. Biomol. Struct.
Dyn, 2018, 36(15), 3902.
10 H. Wu, J. Yuan, Y. Bai, G. Pan, H. Wang, J. Kong, X. Fan, H.
Liu, Dalton Trans. 2012, 41, 8829.
11 F. Dimiza, C. P. Raptopoulou, V. Psycharis, A.
Papadopoulos, G. L. Psomas, Dalton Trans. 2010, 39, 4517.
12 H. Wu, G. Pan, Y. Bai, H. Wang, J. Kong, F. Shi, Y. Zhang, X.
Wang, Res. Chem. Intermed, 2015, 41, 3375.
13 H. Wu, C. Wang, F. Wang, H. Peng, H. Zhang, Y. Bai, J. Chin.
Chem. Soc, 2015, 62, 1028.
9
1
is a mononuclear compound with planar quadrilateral
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
configuration and its coplanarity is strong. Howerer, 2 is a
dinuclear five-coordinated Cu(II) compound with two copper
coordination units plane bridged by salicylhydrazide hydroxyl
groups of the ligand by replacing chloride anion in 1 with acetate.
3 is a quite different dinuclear compound with two Mn(III)
coordination sphere bridged by methoxyl which was resulted by
further replacing Cu(II) with Mn(III). DNA binding studies
performed on the pyrazolone ligand and its three complexes by
electron absorption titration and EB-DNA competition
experiments indicate they all bind DNA in an intercalation mode
and their binding affinity follows 1 > 2 > 3 > H2L. The results of
this experiment indicate that steric hindrance of compound
played pivotal roles in DNA binding. Furthermore, the structural
optimization of H2L, 1, 2 and 3 by DFT was performed, and TD-
DFT calculations were performed on this basis to gain a better
understanding of the electronic transitions in the UV-Vis spectra.
14 M. Aleksi
555.
ć, V. Kapetanović, Acta. Chim. Slov, 2014, 61,
15 H. Wu, Z. Yang, F. Wang, H. Peng, H. Zhang, C. Wang, K.
Wang. J. Photochem. Photobiol. B, 2015,148, 252.
16 X. W. Liang, J. Zang, M. Y. Zhu, Q. W. Gao, B. H. Wang, W.
F. Xu, Y. J. Zhang, ACS Med. Chem. Lett, 2016, 7 (10), 950.
17 H. Neha, N. Afsana, S. P. Shweta, K. G. Sankar, P. Dulal,
ACS Omega, 2018, 3 (2), 1955.
18 M.C. Taylor, J.H. Trevor, P.H. Chasity, D. Alexander, Org.
Biomol. Chem. 2019, 17, 8348.
19 A. M. R. Ibrahim, Molecules, 2018, 23, 2092.
20 P. Jessica, M. Fabio, P. Riccardo, P. Claudio, Inorg. Chem.
2016, 55 (22), 11770.
21 P. Riccardo, P. Claudio, M. Fabio, W. S. Brian, H. W. Allan,
B. Laura, C. Massimiliano, J. Med. Chem. 2014, 57 (11),
4532.
22 G. Mariappan, B. P. Saha, L. Sutharson, Saudi Pharm. J,
2011, 19, 115.
23 X. M. Peng, G. X. Cai, C. H. Zhou, et al, Curr. Top. Med.
Chem. 2013, 13, 1963.
24 J. S. Casas, M. S. Garcia-Tasende, Coord. Chem. Rev. 2007,
251, 1561-1589.
25 a) I. A. Patel, B. T. Thaker, P. B. Thaker, Indian J. Chem.
1998, 37, 429; b) I. A. Patel, B. T. Thaker, Indian J. Chem.
1999, 38, 427.
26 B. M. Mohapatta, V. Chakravortty, K. C. Das, Polyhedron,
1989, 8, 1509.
27 L. Yang, D. R. Powell, R. P. Houser, Dalton Trans. 2007, 9,
955.
28 D. Majumdar, J. K. Biswas, M. Mondal, M. S. S. Babu, S.
Das, R. K. Metre, S. S. SreeKumar, K. Bankura, D. Mishra,
ChemistrySelect, 2018, 3, 2912.
29 S. Youngme, J. Phatchimkun, U. Sukangpanya, C.
Pakawatchai, N. Chaichit, P. Kongsaeree, J. Krzystek, B.
Murphy, Polyhedron, 2007, 26, 871.
30 Y. L. Xu , H. Zhang, K. S. Shen , S. S. Mao , X. K. Shi , H. L.
Wu, Appl Organometal Chem, 2017, 32(1), 3902.
31 Y. X. Sun, L. Wang, X.Y. Dong, Z. L. Ren, Nano-Met. Chem,
2013, 43, 599.
32 P. Cui, Z. Chen, D. L. Gao, B. Zhao, W. Shi, P. Cheng, Cryst.
Growth Des. 2010, 10, 4370.
33 L. Q. Chai, L. J. Tang, L. C. Chen, J. J. Huang, Polyhedron,
2017, 122, 228.
Conflicts of interest
There are no conflicts to declare.
Acknowledgements
This work was supported by the National Natural Science
Foundation of China (Grant 21661019). We thank Prof. Wang
Nong and Xie Ke-Feng in Lanzhou Jiaotong University for the
Gauss calculation using the National Supercomputing Center in
Shenzhen, P. R. China.
References
1
2
R. Olby, Nature, 1974, 248, 782.
K. M. Vyas, R.V. Devkar, A. Prajapati, R.N. Jadeja,
Chem.Biol. Interact, 2015, 240, 250.
3
H. L. Wu, H. P. Peng, Y. H. Zhang, F. Wang, H. Zhang, C. P.
Wang, Z. H. Yang, Appl. Organomet. Chem, 2015, 29 443;
b) H. Zhang, Y. Xu, H. Wu, O. A. Stephen, X. Fan, RSC Adv,
2016, 6, 83697; c) H. Wu, Y. Zhang, C. Chen, J. Zhang, Y.
Bai, F. Shi, X. Wang, New J. Chem. 2014, 38, 3688.
34 R. N. Patel, Y. Singh, Y. P. Singh, R. J. Butcher, Polyhedron,
2016, 104, 116.
35 R. N. Patel, Y. Singh, Y. P. Singh, R. J. Butcher, J. Coord.
Chem, 2016, 15, 1.
4
5
6
7
8
C. Hemmert, M. Piti, M. Renz, H. Gornitzka, S. Soulet, B.
Meunier, J. Biol. Inorg. Chem, 2001, 6,14.
G. Zuber, J. C. Quada, S. M. Hecht, J. Am. Chem. Soc. 1998,
120, 9368.
36 M. Baldini, M. Belicchi-Ferrari, F. Bisceglie, P. P. Dall’Aglio,
G. Pelosi, S. Pinelli, P. Tarasconi, Inorg. Chem. 2004, 43
7170.
,
M. Aleksi
555.
ć, V. Kapetanović, Acta. Chim. Slov, 2014, 61,
37 A. Dimitrakopoulou, C. Dendrinou-Samara, A. A. Pantazaki,
M. Alexiou, E. Nordlander, D. P. Kessissoglou, J. Inorg.
Biochem. 2008, 102, 618.
38 H. L. Wu, F. Wang, F. R. Shi, Z. H. Yang, H. Zhang, H. P.
Peng, Transit. Metal. Chem. 2015, 40, 555.
M. J. Niu, Z. Li, H. H. Li, X. Li, J. M. Dou, S. N. Wang, RSC
Adv. 2015, , 37085.
5
M. Manoj, L. Michael, N. Stephen, A. Reem, W. B. David, Y.
Liu, B. Christian, W. W. David, J. Am. Chem. Soc. 2007,
129(17), 5688.
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 9
Please do not adjust margins