Synthesis, characterization, density functional theory (DFT) calculation and antibacterial activities of five-coordinate complexes of some first-row transition metals containing a benzoyl thiourea derivative

Farzanfar, Javad; Abdolahe, Elahe; Eskandari, Amir; Rezvani, Ali Reza; Samareh Delarami, Hojat

doi:10.22034/ecc.2020.113346

Document Type : Original Research Article

Authors

¹ Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran 2Pharmaceutical Sciences Research Center, Shiraz University of Medical Sciences, Shiraz, Iran

² Department of Chemistry, University of Sistan and Baluchestan, Zahedan, Iran

³ Department of Chemistry, University of Zabol, Zabol, Iran

https://doi.org/10.22034/ecc.2020.113346

Abstract

Using elemental analysis, Fourier transform infrared (FTIR) and UV-visible spectroscopies, as well as conductivity measurements, synthesis of 5 first-row transition metal complexes, including [M(L^')(H₂O)₂] (M=Mn (C1), Fe (C2), Co (C3), Ni (C4), Cu (C5)) relevant to a benzoyl thiourea ligand, which was derived by condensing 2-chlorobenzoyl-isothiocyanate with 2,6-diaminopyridine, to produce 1,1'-(pyridine-2,6-diyl)bis(3-(2-chlorobenzoyl) thiourea) (L) was conducted. The structures proposed for the five complexes were confirmed through the application of conformational analysis and geometry optimization. These compounds were studied in vitro in terms of antibacterial properties against the standard gram-positive and gram-negative bacterial strains, and their superior antibacterial activities compared to those of the new thiourea derivative were proven through the experiments.

Graphical Abstract

Keywords

Main Subjects

Inorganic chemistry

References

[1] A.A. Isab, S. Nawaz, M. Saleem, M. Altaf, M. Monim-ul-Mehboob, S. Ahmad, H.S. Evans, Polyhedron, 2010, 29, 1251-1256.

[2] N. Dolan, D.P. Gavin, A. Eshwika, K. Kavanagh, J. McGinley, J.C. Stephens, Bioorg. Med. Chem. Lett., 2016, 26, 630-635.

[3] P.R. Chetana, B.S. Srinatha, M.N. Somashekar, R.S. Policegoudra, J. Mol. Struct., 2016, 1106, 352-365.

[4] P. Cui, X. Li, M. Zhu, B. Wang, J. Liu ,H. Chen, Bioorg. Med. Chem. Lett., 2017, 27, 2234-2237.

[5] A. Bielenica, J. Stefańska, K. Stępień, A. Napiórkowska, E. Augustynowicz-Kopeć, G. Sanna, S. Madeddu, S. Boi, G. Giliberti, M. Wrzosek, Eur. J. Med. Chem., 2015, 101, 111-125.

[6] I. Ullah, A. Shah, A. Badshah, N.A. Shah, R. Tabor, Colloids Surf. A, 2015, 464, 104-109.

[7] N.A. Mohamed, N.A.A. El-Ghany, M.M. Fahmy, Int. J. Biol. Macromol., 2016, 82, 589-598.

[8] A.F. Elhusseiny, A. Eldissouky, A.M. Al-Hamza ,H.H.A.M. Hassan, J. Mol. Struct., 2015, 1100, 530-545.

[9] S.S. Hassan, M.M. Shoukry, R.N. Shallan, R. van Eldik, J. Coord. Chem., 2017, 70, 1761-1775.

[10] L. Qiao, J. Huang, W. Hu, Y. Zhang, J. Guo, W. Cao, K. Miao, B. Qin, J. Song, J. Mol. Struct., 2017, 1139, 149-159.

[11] F. Bílek, T. Křížová, M. Lehocký, Colloid. Surface. B., 2011, 88, 440-447.

[12] H.M. Faidallah, K.A. Khan, A.M. Asiri, J. Fluorine. Chem., 2011, 132, 870-877.

[13] S. Karakuş, S. Rollas, Farmaco 2002, 57, 577-581.

[14] S.B. Tsogoeva, M.J. Hateley, D.A. Yalalov, K. Meindl, C. Weckbecker, K. Huthmacher, Bioorg. Med. Chem., 2005, 13, 5680-5685.

[15] M. Mushtaque, F. Avecilla, M.S. Khan, Z.B. Hafeez, M.M.A. Rezvi, A. Srivastava, J. Mol. Struct., 2017, 1141, 119-132.

[16] I.-J. Kang, L.-W. Wang, C.-C. Lee, Y.-C. Lee, Y.-S. Chao, T.-A. Hsu, J.-H. Chern, Bioorg. Med. Chem. Lett., 2009, 19, 1950-1955.

[17] T. Yeşilkaynak, H. Muslu, C. Özpınar, F.M. Emen, R.E. Demirdöğen, N. Külcü, J. Mol. Struct., 2017, 1142, 185-193.

[18] W. Hernández, E. Spodine, L. Beyer, U. Schröder, R. Richter, J. Ferreira, M. Pavani, Bioinorg. Chem. Appl., 2005, 3, 299-316.

[19] E. Rodriguez-Fernandez, J.L. Manzano, J.J. Benito, R. Hermosa, E. Monte, J.J. Criado, J. Inorg. Biochem., 2005, 99, 1558-1572.

[20] M.K. Rauf, A. Badshah, M. Gielen, M. Ebihara, D. de Vos, S. Ahmed, J. Inorg. Biochem., 2009, 103, 1135-1144.

[21] H.-J. Zhang, X. Qin, K. Liu, D.-D. Zhu, X.-M. Wang, H.-L. Zhu, Bioorg. Med. Chem., 2011, 19, 5708-5715.

[22] I.C. Mendes, M.A. Soares, R.G. dos Santos, C. Pinheiro, H. Beraldo, Eur. J. Med. Chem., 2009, 44, 1870-1877.

[23] J. Farzanfar, K. Ghasemi, A.R. Rezvani, H.S. Delarami, A. Ebrahimi, H. Hosseinpoor, A. Eskandari, H.A. Rudbari, G. Bruno, J. Inorg. Biochem., 2015, 147, 54-64.

[24] H. Arslan, N. Duran, G. Borekci, C. Koray Ozer, C. Akbay, Molecules, 2009, 14, 519-527.

[25] G. Li, D.-J. Che, Z.-F. Li, Y. Zhu ,D.-P. Zou, New. J. Chem., 2002, 26, 1629-1633.

[26] C.K. Ozer, H. Arslan, D. Vanderveer, G. Binzet, J. Coord. Chem., 2009, 62, 266-276.

[27] C. Lee, W. Yang, R.G. Parr, Phys. Rev. B, 1988, 37, 785.

[28] G. Micera, E. Garribba, Int. J. Quantum Chem., 2012, 112, 2486-2498.

[29] G. Micera, V.L. Pecoraro, E. Garribba, Inorg. Chem., 2009, 48, 5790-5796.

[30] S. Gorelsky, G. Micera, E. Garribba, Chem. Eur. J., 2010, 16, 8167-8180.

[31] I. Wiegand, K. Hilpert, R.E.W. Hancock, Nat. Protoc., 2008, 3, 163-175.

[32] U. El-Ayaan, J. Mol. Struct., 2011, 998, 11-19.

[33] L. Sacconi, Pure Appl. Chem., 1968, 17, 95-128.

[34] W.J. Geary, Coord. Chem. Rev., 1971, 7, 81-122.

[35] W. Yang, H. Liu, M. Li, F. Wang, W. Zhou, J. Fan, J. Inorg. Biochem., 2012, 116, 97-105.

Eurasian Chemical Communications

Synthesis, characterization, density functional theory (DFT) calculation and antibacterial activities of five-coordinate complexes of some first-row transition metals containing a benzoyl thiourea derivative

References

References

Volume 2, Issue 9
September 2020
Pages 961-971

Synthesis, characterization, density functional theory (DFT) calculation and antibacterial activities of five-coordinate complexes of some first-row transition metals containing a benzoyl thiourea derivative

References

References

Volume 2, Issue 9September 2020Pages 961-971

Volume 2, Issue 9
September 2020
Pages 961-971