Abstract
Four new complexes of copper(II) and zinc(II), [Cu2L4] (1), [Cu2L2(N(CN)2)2]n (2), [Zn(HL)2I2] (3) and [Zn(HL)2(NCS)2] (4), where L is 5-bromo-2-((cyclopropylimino)methyl)phenolate, HL is the zwitterionic form of 5-bromo-2-((cyclopropylimino)methyl)phenol, were synthesized and characterized by elemental analysis and IR and UV-Vis spectroscopy. Structures of the complexes were further confirmed by single crystal X-ray structure determination. Complex 1 is a phenolate bridged dinuclear copper(II) compound, with the Cu atom in square pyramidal coordination. Complex 2 is a phenolate and dicyanamide bridged polynuclear copper(II) compound, with the Cu atom in square pyramidal coordination. Complexes 3 and 4 are mononuclear zinc(II) compounds, with the Zn atoms in tetrahedral coordination. The compounds were assayed for their antimicrobial activities. Complexes 1 and 2 have the most activities on B. subtilis, with MIC values of 1.2 μg/mL.
REFERENCES
N. Kordestani, H. Amiri Rudbari, A. R. Fernandes, L. R. Raposo, A. Luz, P. V. Baptista, G. Bruno, R. Scopelliti, Z. Fateminia, N. Micale, N. Tumanov, J. Wouters, A. Abbasi Kajani, and A.-K. Bordbar. Copper(II) complexes with tridentate halogen-substituted Schiff base ligands: Synthesis, crystal structures and investigating the effect of halogenation, leaving groups and ligand flexibility on antiproliferative activities. Dalton Trans., 2021, 50(11), 3990-4007. https://doi.org/10.1039/d0dt03962d
Y. Yuan, X.-K. Lu, G.-Q. Zhou, and X.-Y. Qiu. Syntheses, characterization, crystal structures and antimicrobial activity of Schiff base copper(II) complexes derived from 2-bromo-6-((2-(isopropylamino)ethylimino)methyl)phenol. Acta Chim. Slov., 2021, 68(4), 1008-1015. https://doi.org/10.17344/acsi.2021.7070
S. Han and Y. Wang. Synthesis, Characterization and crystal structures of Schiff base copper complexes with urease inhibitory activity. Acta Chim. Slov., 2021, 68(4), 961-969. https://doi.org/10.17344/acsi.2021.6965
T. K. Ghosh, S. Jana, S. Jana, and A. Ghosh. Tetra- and poly-nuclear Cd(II) complexes of an N3O4 Schiff base ligand: Crystal structures, electrical conductivity and photoswitching properties. New J. Chem., 2020, 44(34), 14733-14743. https://doi.org/10.1039/d0nj03325a
S. U. Parsekar, K. Paliwal, P. Haldar, P. K. S. Antharjanam, and M. Kumar. Synthesis, characterization, crystal structure, DNA and HSA interactions, and anticancer activity of a mononuclear Cu(II) complex with a Schiff base ligand containing a thiadiazoline moiety. ACS Omega, 2022, 7(3), 2881-2896. https://doi.org/10.1021/acsomega.1c05750
S. Mukherjee, S. Hansda, S. Nandi, T. Chakraborty, D. Samanta, K. Acharya, and D. Das. Azide-mediated unusual in situ transformation of Mannich base to Schiff–Mannich base and isolation of their Cu(II) complexes: Crystal structure, theoretical inspection and anticancer activities. Dalton Trans., 2021, 50(38), 13374-13386. https://doi.org/10.1039/d1dt01740c
M. Liu, H. Yang, D. Li, Q. Yao, H. Wang, Z. Zhang, and J. Dou. Zn and Cu complexes of o-van-gly Schiff base: Syntheses, crystal structures, fluorescence sensing and anticancer properties. Inorg. Chim. Acta, 2021, 522, 120384. https://doi.org/10.1016/j.ica.2021.120384
S. Esmaielzadeh and E. Zarenezhad. Copper(II) Schiff base complexes with catalyst property: Experimental, theoretical, thermodynamic and biological studies. Acta Chim. Slov., 2018, 416-428. https://doi.org/10.17344/acsi.2018.4159
Q. Poladian, O. Şahin, T. Karakurt, B. İlhan-Ceylan, and Y. Kurt. A new zinc(II) complex with N2O2-tetradentate Schiff-base derived from pyridoxal-S-methylthiosemicarbazone: Synthesis, characterization, crystal structure, DFT, molecular docking and antioxidant activity studies. Polyhedron, 2021, 201, 115164. https://doi.org/10.1016/j.poly.2021.115164
A. G. Ertürk, V. Sekeroglu, E. Yildirim, G. Dindaroglu, and Z. A. Sekeroglu. Antipyrine derived-Schiff base copper complex: Synthesis, characterization, and in vitro evaluation. Inorg. Chim. Acta, 2022, 543, 121146. https://doi.org/10.1016/j.ica.2022.121146
S.-F. Yu, X.-Y. Qiu, and S.-J. Liu. Syntheses, crystal structures and antimicrobial property of Schiff base copper(II) complexes. Acta Chim. Slov., 2020, 67(4), 1301-1308. https://doi.org/10.17344/acsi.2020.6321
A. M. S. Hossain, J. M. Méndez-Arriaga, C. Xia, J. Xie, and S. Gómez-Ruiz. Metal complexes with ONS donor Schiff bases. A review. Polyhedron, 2022, 217, 115692. https://doi.org/10.1016/j.poly.2022.115692
G. Paraskevopoulos, S. Monteiro, R. Vosátka, M. Krátký, L. Navrátilová, F. Trejtnar, J. Stolaříková, and J. Vinšová. Corrigendum to “Novel salicylanilides from 4,5-dihalogenated salicylic acids: Synthesis, antimicrobial activity and cytotoxicity”. Bioorg. Med. Chem., 2017, 25(8), 2530. https://doi.org/10.1016/j.bmc.2017.02.053
M. Zhang, D.-M. Xian, H.-H. Li, J.-C. Zhang, and Z.-L. You. Synthesis and structures of halo-substituted aroylhydrazones with antimicrobial activity. Aust. J. Chem., 2012, 65(4), 343. https://doi.org/10.1071/ch11424
H.-F. Guo, Y. Pan, D.-Y. Ma, and P. Yan. Effect of electron-withdrawing groups of Schiff base and its palladium complex on antimicrobial and catalytic activities. Chin. J. Inorg. Chem., 2013, 29(7), 1447-1453.
N. P. Rai, V. K. Narayanaswamy, T. Govender, B. K. Manuprasad, S. Shashikanth, and P. N. Arunachalam. Design, synthesis, characterization, and antibacterial activity of {5-chloro-2-[(3-substitutedphenyl-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanones. Eur. J. Med. Chem., 2010, 45(6), 2677-2682. https://doi.org/10.1016/j.ejmech.2010.02.021
H. Kargar, M. Fallah-Mehrjardi, R. Behjatmanesh-Ardakani, H. A. Rudbari, A. A. Ardakani, S. Sedighi-Khavidak, K. S. Munawar, M. Ashfaq, and M. N. Tahir. Binuclear Zn(II) Schiff base complexes: Synthesis, spectral characterization, theoretical studies and antimicrobial investigations. Inorg. Chim. Acta, 2022, 530, 120677. https://doi.org/10.1016/j.ica.2021.120677
T. Vijayan, J. Kim, M. Azam, S. I. Al-Resayes, A. Stalin, B. S. Kannan, A. Jayamani, A. Ayyakannu, and S. Nallathambi. Influence of co-ligand on the biological properties of Schiff base metal complexes: Synthesis, characterization, cytotoxicity, and antimicrobial studies. Appl. Organomet. Chem., 2022, 36(3). https://doi.org/10.1002/aoc.6542
J.-L. Hou, H.-Y. Wu, C.-B. Sun, Y. Bi, and W. Chen. Synthesis and X-ray crystal structures of trinuclear nickel(II) complexes derived from Schiff bases and acetate ligands with biological activity. Acta Chim. Slov., 2020, 67(3), 860-865. https://doi.org/10.17344/acsi.2020.5824
L.-W. Xue, X. Fu, G.-Q. Zhao, and Q.-B. Li. Zinc(II) complexes derived from Schiff bases: Syntheses, structures, and biological activity. Acta Chim. Slov., 2021, 68(1), 17-24. https://doi.org/10.17344/acsi.2020.5817
C.-L. Zhang, X.-Y. Qiu, and S.-J. Liu. Vanadium(V) complexes with bromo-substituted hydrazones: Synthesis, characterization, X-ray crystal structures and antimicrobial activity. Acta Chim. Slov., 2019, 66(3), 719-725. https://doi.org/10.17344/acsi.2019.5241
L.-Y. He, X.-Y. Qiu, J.-Y. Cheng, S.-J. Liu, and S.-M. Wu. Synthesis, characterization and crystal structures of vanadium(V) complexes derived from halido-substituted tridentate hydrazone compounds with antimicrobial activity. Polyhedron, 2018, 156, 105-110. https://doi.org/10.1016/j.poly.2018.09.017
S. M. Wu, X. Y. Qiu, J. C. Wang, S. J. Liu, and L. Y. He. Synthesis, characterization, and crystal structures of oxidovanadium(V) complexes derived from 2-chloro-N-(3,5-dichloro-2-hydroxybenzylidene)benzohydrazide with antimicrobial activity. Russ. J. Coord. Chem., 2019, 45(5), 378-384. https://doi.org/10.1134/s1070328419040109
P. Vianello, O. A. Botrugno, A. Cappa, G. Ciossani, P. Dessanti, A. Mai, A. Mattevi, G. Meroni, S. Minucci, F. Thaler, M. Tortorici, P. Trifiró, S. Valente, M. Villa, M. Varasi, and C. Mercurio. Synthesis, biological activity and mechanistic insights of 1-substituted cyclopropylamine derivatives: A novel class of irreversible inhibitors of histone demethylase KDM1A. Eur. J. Med. Chem., 2014, 86, 352-363. https://doi.org/10.1016/j.ejmech.2014.08.068
Z.-L. You, X. Han, P. Zhou, and L. Zhang. Syntheses and structures of 2-bromo-4-chloro-6-(cyclopropyliminomethyl)phenol and its zinc(II) complex. J. Coord. Chem., 2008, 61(13), 2046-2052. https://doi.org/10.1080/00958970701861623
Z.-L. You and J.-Y. Chi. Syntheses and structures of 2,4-dichloro-6-(cyclopropyliminomethyl)phenol and its copper(II) complex. J. Coord. Chem., 2006, 59(17), 1999-2004. https://doi.org/10.1080/00958970600717827
Bruker, SMART (Version 5.625) and SAINT (Version 6.01). Madison, Wisconsin, USA: Bruker AXS, 2007.
G. M. Sheldrick. SADABS. Program for Empirical Absorption Correction of Area Detector. Göttingen, Germany: University of Göttingen, 1996.
G. M. Sheldrick. SHELXTL V5.1 Software Reference Manual. Madison, Wisconsin, USA: Bruker AXS, 1997.
J. Meletiadis, J. F. G. M. Meis, J. W. Mouton, J. P. Donnelly, and P. E. Verweij. Comparison of NCCLS and 3-(4,5-dimethyl-2-thiazyl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) methods of in vitro susceptibility testing of filamentous fungi and development of a new simplified method. J. Clin. Microbiol., 2000, 38(8), 2949-2954. https://doi.org/10.1128/jcm.38.8.2949-2954.2000
W. J. Geary. The use of conductivity measurements in organic solvents for the characterisation of coordination compounds. Coord. Chem. Rev., 1971, 7(1), 81-122. https://doi.org/10.1016/s0010-8545(00)80009-0
S. Manna, E. Zangrando, H. Puschmann, and S. C. Manna. Tetranuclear Schiff base copper(II) complexes: Syntheses, crystal structure, DNA/protein binding and catecholase-like activity. Polyhedron, 2019, 162, 285-292. https://doi.org/10.1016/j.poly.2019.01.057
P. Chakraborty, S. Majumder, A. Jana, and S. Mohanta. Syntheses, structures, catecholase activity, spectroscopy and electrochemistry of a series of manganese(III) complexes: Role of auxiliary anionic ligand on catecholase activity. Inorg. Chim. Acta, 2014, 410, 65-75. https://doi.org/10.1016/j.ica.2013.10.013
P. Talukder, S. Shit, A. Sasmal, S. R. Batten, B. Moubaraki, K. S. Murray, and S. Mitra. An antiferromagnetically coupled hexanuclear copper(II) Schiff base complex containing phenoxo and dicyanamido bridges: Structural aspects and magnetic properties. Polyhedron, 2011, 30(11), 1767-1773. https://doi.org/10.1016/j.poly.2011.03.049
K. Bhar, S. Chattopadhyay, S. Khan, R. K. Kumar, T. K. Maji, J. Ribas, and B. K. Ghosh. Syntheses, structures and magnetic properties of 1,5 dicyanamide bridged coordination polymers of copper(II) and nickel(II) containing a tetradentate N-donor Schiff base. Inorg. Chim. Acta, 2011, 370(1), 492-498. https://doi.org/10.1016/j.ica.2011.02.055
A. Ray, G. Pilet, C. J. Gómez-García, and S. Mitra. Designing dicyanamide bridged 1D molecular architecture from a mononuclear copper(II) Schiff base precursor: Syntheses, structural variations and magnetic study. Polyhedron, 2009, 28(3), 511-520. https://doi.org/10.1016/j.poly.2008.11.054
H. Grove, M. Julve, F. Lloret, P. E. Kruger, K. W. Törnroos, and J. Sletten. Syntheses, crystal structures and magnetic properties of copper(II) polynuclear and dinuclear compounds with 2,3-bis(2-pyridyl)pyrazine (dpp) and pseudohalide as ligands. Inorg. Chim. Acta, 2001, 325(1/2), 115-124. https://doi.org/10.1016/s0020-1693(01)00642-9
S. S. Massoud and F. A. Mautner. Synthesis and structure determination of two new dinuclear end-to-end doubly bridged azido- and thiocyanato-copper(II) complexes derived from diethyldiethylenetriamine. Inorg. Chim. Acta, 2005, 358(12), 3334-3340. https://doi.org/10.1016/j.ica.2005.05.007
M. F. Iskander, T. E. Khalil, R. Werner, W. Haase, I. Svoboda, and H. Fuess. Synthesis, reactivity and magnetochemical studies on copper(II) complexes derived from N-salicylidenearoylhydrazines. X-ray structure of [mononitratoOO(–1)(N-salicylidenatobenzoylhydrazine)ONO(–1)]copper(II) monohydrate. Polyhedron, 2000, 19(8), 949-958. https://doi.org/10.1016/s0277-5387(00)00340-5
S. Chandra and A. K. Sharma. Biological and spectral studies of transition metal complexes with a quinquedentate Schiff base, 2,6-diacetylpyridine bis(thiocarbohydrazone). J. Coord. Chem., 2009, 62(22), 3688-3700. https://doi.org/10.1080/00958970903121305
J. Jiang, P. Liang, H. Yu, and Z. You. Synthesis, crystal structures and urease inhibition of mononuclear copper(II) and nickel(II) complexes with Schiff base ligands. Acta Chim. Slov., 2022, 69(3), 629-637. https://doi.org/10.17344/acsi.2022.7513
H. Kargar, R. Behjatmanesh-Ardakani, V. Torabi, M. Kashani, Z. Chavoshpour-Natanzi, Z. Kazemi, V. Mirkhani, A. Sahraei, M. N. Tahir, M. Ashfaq, and K. S. Munawar. Synthesis, characterization, crystal structures, DFT, TD-DFT, molecular docking and DNA binding studies of novel copper(II) and zinc(II) complexes bearing halogenated bidentate N,O-donor Schiff base ligands. Polyhedron, 2021, 195, 114988. https://doi.org/10.1016/j.poly.2020.114988
H. Kargar, R. Behjatmanesh-Ardakani, V. Torabi, A. Sarvian, Z. Kazemi, Z. Chavoshpour-Natanzi, V. Mirkhani, A. Sahraei, M. Nawaz Tahir, and M. Ashfaq. Novel copper(II) and zinc(II) complexes of halogenated bidentate N,O-donor Schiff base ligands: Synthesis, characterization, crystal structures, DNA binding, molecular docking, DFT and TD-DFT computational studies. Inorg. Chim. Acta, 2021, 514, 120004. https://doi.org/10.1016/j.ica.2020.120004
S. Slassi, A. El-Ghayoury, M. Aarjane, K. Yamni, and A. Amine. New copper(II) and zinc(II) complexes based on azo Schiff base ligand: Synthesis, crystal structure, photoisomerization study and antibacterial activity. Appl. Organomet. Chem., 2020, 34(4). https://doi.org/10.1002/aoc.5503
D.-L. Peng and N. Sun. Syntheses, characterization and crystal structures of Schiff base zinc(II) complexes with antibacterial activity. Acta Chim. Slov., 2018, 65(4), 895-901. https://doi.org/10.17344/acsi.2018.4543
S. Shit, M. Nandy, D. Saha, L. Zhang, W. Schmitt, C. Rizzoli, and T. N. G. Row. Synthesis, crystal structure and fluorescence properties of two dinuclear zinc(II) complexes incorporating tridentate (NNO) Schiff bases. J. Coord. Chem., 2016, 69(16), 2403-2414. https://doi.org/10.1080/00958972.2016.1197390
Funding
This work was financially supported by Ningbo Public Welfare Funds (Project Nos. 202002N3056 and 2021S142).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare that they have no conflicts of interests.
Additional information
Text © The Author(s), 2023, published in Zhurnal Strukturnoi Khimii, 2023, Vol. 64, No. 3, 106829.https://doi.org/10.26902/JSC_id106829
Rights and permissions
About this article
Cite this article
Li, M., Qiu, XY., Zheng, ZX. et al. Syntheses and Crystal Structures of Copper(II) and Zinc(II) Complexes Derived from 5-Bromo-2-((Cyclopropylimino)Methyl)Phenol with Antibacterial Activity. J Struct Chem 64, 347–364 (2023). https://doi.org/10.1134/S0022476623030022
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S0022476623030022