Synthesis and Antimicrobial Activity Studies of Cyclobutane Ring Containing Schiff Base and their Metal Complexes

Abstract

In this study, thiosemicarbazone derivative Schiff base containing cyclobutane group and their Cu(II), Ni(II) ve Zn(II) complexes were synthesised and characterized. Purification of the synthesised compounds were carried out with crystallography and column cromatography techniques. In the characterization of the Schiff base and their complexes, IR, ¹H NMR, ¹³ C NMR spectral techniques and elemental analysis were used. All the complexes were found to be mononuclear and ML₂ form. Besides, antimicrobial activities of the Schiff base and its transition metal complexes have been tested different microorganisms.

Keywords

• Schiff Bases,Cyclobutane,Metal Complexes,Antimicrobial Activty

Siklobütan Halkası İçeren Schiff Bazı ve Metal Komplekslerinin Sentezi ve Antimikrobiyal Aktivite Çalışmaları

Öz

Bu çalışmada yapısında siklobütan grubu bulunan tiyosemikarbazon türevi Schiff bazı ve bunun nikel, bakır ve çinko kompleksleri sentezlenmiştir. Sentezlenen bileşiklerin saflaştırılması kristallendirme ve kolon kromatografisi ile yapılmıştır. Karakterizasyon işlemlerinde ise IR, ¹H NMR, ¹³C NMR ve elementel analiz gibi enstrümental analiz yöntemleri kullanılmıştır. Sentezlenen komplekslerin mononükleer olduğu ve ML₂ yapısında olduğu bulunmuştur. Ayrıca, sentezlenen bileşiklerin farklı mikroorganizmalara karşı antimikrobiyal etkileri araştırılmıştır.

Anahtar Kelimeler

• Schiff Bazı,Siklobütan,Metal Kompleksleri,Antimikrobiyal Aktivite

Kaynakça

1. H. Schiff, mitteilungen aus dem universities laboratorium in pisa: Finencue reihe organischerbasen. Justus Liebigs Ann. Chem. 131 (1864) 118.
2. S. Yamada, Advancement in stereochemical aspects of Schiff base metal complexes. Coord. Chem. Rev. 190e192 (1999) 537.
3. S. Roy, S. Halder, M.G.B. Drew, P.P. Ray, S. Chattopadhyay. Unprecedented photosensitivity of heterotrimetallic copper(ii)/sodium/mercury(ii) coordination polymer based thin film semiconductor device. New J. Chem. 42(2018) 15295.
4. A. Biswas, M.G.B. Drew, J. Ribas, C. Diaz, A. Ghosh. Synthesis, Crystal Structures and Magnetic Properties of a Phenoxo-Bridged Dinuclear Cu-II Complex and a Dicyanamide Bridged Novel Molecular Rectangle Based on It. Eur. J. Inorg. Chem. (2011)2405.
5. O.A.M. Ali, S.M.E. Medani, M.R.A. Serea, A.r.S.S. Sayed, Spectrochim. Acta, PartA 136 (2015) 651.
6. P.G. Cozzi, Metal-Salen Schiff base complexes in catalysis: practical aspects. Chem. Soc. Rev. 33 (2004) 410.
7. K.C. Gupta, A.K. Sutar, Catalytic activities of Schiff base transition metal complexes. Coord. Chem. Rev. 252 (2008) 1420.
8. J.P. Costes, S. Shova, W. Wernsdorfer. Structural and Magnetic Study of a Trinuclear Mn-II-Gd-III-Mn-II Complex. J. Chem. Soc., Dalton Trans. (2008)1843.

9. M. Orio, O. Jarjayes, H. Kanso, C. Philouze, F. Neese, F. Thomas, X-Ray Structures of Copper(II) and Nickel(II) Radical Salen Complexes: The Preference of Galactose Oxidase for Copper(II). Angew. Chem.Int. Ed. 49 (2010) 4989.
10. K.C. Gupta, A.K. Sutar, C.-C. Lin, Polymer-supported Schiff base complexes in oxidation reactions. Coord. Chem. Rev. 253 (2009) 1926.
11. D. Zhang, H. Wang, Y. Chen, Z.-H. Ni, L. Tian, J. Jiang, Hydrogen-Bond Directed Cyanide-Bridged Molecular Magnets Derived from Polycyanidemetalates and Schiff Base Manganese(III) Compounds: Synthesis, Structures, and Magnetic Properties. Inorg. Chem. 48 (2009)11215.
12. J. Lewinski, J. Zachara, I. Justyniak, M. Dranka, Hydrogen-bond supramolecular structure of group Schiff base complexes. Coord. Chem. Rev. 249 (2005)1185.
13. S. Mandal, G. Rosair, J. Ribas, D. Bandyopadhyay, Synthesis, crystal structure and magnetic characterization of a new phenoxo-bridged binuclear manganese(III) Schiff base complex exhibiting single-molecule-magnet behavior. Inorg. Chim. Acta 362 (2009)2200.
14. S. Thakurta, P. Roy, G. Rosair, C.J.G. García, E. Garribba, S. Mitra, .Ferromagnetic exchange coupling in a new bis(mu-chloro)-bridged copper(II) Schiff base complex: Synthesis, structure, magnetic properties and catalytic oxidation of cycloalkanes. Polyhedron28 (2009) 695.
15. S. Saha, S. Pal, C.J.G. García, J.M. Clemente-Juan, K. Harms, H.P. Nayek, Design of end-on cyanato bridged trinuclear Cu(II) Schiff base complex with salen type Schiff base ligand: synthesis, structural investigation and DFT study. Polyhedron 74 (2014) 1.
16. G. Bhargavi, M.V. Rajasekharan, J.-P. Costes, J.-P. Tuchagues, Antiferromagnetic interactions through phenoxo bridges and lattice water: Synthesis, structure, and magnetic properties of new Mn(III) Schiff base complexes in combination with thiocyanate ligand. Polyhedron 28(2009) 1253.
17. K. Ghosh, M.G.B. Drew, S. Chattopadhyay, Synthesis and structure of a cobalt(III) complex containing pendant Schiff base ligand: Exploration of its catechol oxidase and phenoxazinone synthase like activity. Inorg. Chim. Acta 482 (2018) 23.
18. N. Sarkar, K. Harms, S. Chattopadhyay, Methylene spacer regulated variation in conformation of tetradentate N2O2 donor Schiff bases trapped in manganese(III) complexes. Polyhedron 141 (2018) 198.
19. C.-T. Yang, M. Vetrichelvan, X. Yang, B. Moubaraki, K.S. Murray, J.J. Vittal, Syntheses, structural properties and catecholase activity of copper(II) complexes with reduced Schiff base N-(2-hydroxybenzyl)-amino acids. Dalton Trans. (2004) 113.
20. T. Basak, A. Bhattacharyya, M. Das, K. Harms, A. Bauza, A. Frontera,S. Chattopadhyay, Chemistry 2 (2017) 6286.
21. S. Bosch, P. Comba, L.R. Gahan, G. Schenk, Dinuclear Zinc(II) Complexes with Hydrogen Bond Donors as Structural and Functional Phosphatase Models. Inorg. Chem. 53 (2014) 9036.
22. R. Sanyal, X. Zhang, P. Kundu, T. Chattopadhyay, C. Zhao, F.A. Mautner, D. Das, Mechanistic Implications in the Phosphatase Activity of Mannich-Based Dinuclear Zinc Complexes with Theoretical Modeling. Inorg. Chem. 54 (2015) 2315.
23. A.A. Jarrahpour, M. Motamedifar, K. Pakshir, N. Hadi, M. Zarei, Synthesis of novel azo Schiff bases and their antibacterial and antifungal activities. Molecules 9(2004) 815.
24. A.M. Mahindra, J.M. Fisher, M. Rabinovitz, Bathocuproıne Sulfonate - A Tıssue Culture-Compatıble Indıcator Of Copper-Medıated Toxıcıty. Nature 303 (1983) 64.
25. T.L. Yang, X.S. Tai, W.W. Qin, W.S. Liu, M.Y. Tan, Determination of trace terbium(III) with N,N ',N ''-tri(3-indolemethanal)triaminotriethylamine based on a new fluorescence enhancement system. Anal. Sci. 20 (2004) 493.
26. D. Dey, G. Kaur, A. Ranjani, L. Gayathri, P. Chakraborty, J. Adhikary, J. Pasan,D. Dhanasekaran, A.R. Choudhury, M.A. Akbarsha, N. Kole, B. Biswas, Eur. J.Inorg. Chem. (2014) 3350.
27. A.P. Vieira, C.A. Wegermann, A.M.D.C. Ferreira, New J. Chem. 42 (2018)13169.
28. S.V. More, D.V. Dongarkhadekar, R.N. Chavan, W.N. Jadhav, S.R. Bhusare, R.P. Pawar, Synthesis and characterization of Pd(II), Pt(II), Cu(I), Ag(I) and Cu(II) complexes with N,O-hybrid pyrazole ligand, J. Indian Chem. Soc. 79 (2002) 768.
29. A.K. Bhendkar, K. Vijay, A.W. Rant, Synthesis, spectroscopic characterization and biological evaluation studies of Schiff's base derived from naphthofuran-2-carbohydrazide with 8-formyl-7-hydroxy-4-methyl coumarin and its metal complexes. Acta Cienc. Indica - Chem. 30 (2004) 29.
30. S. Shu, X. Cai, J. Li, Y. Feng, A. Dai, J. Wang, D. Yang, Ming-Wei Wang, H. Liu, Synthesis and enzyme inhibitory activities of some new pyrazole-based heterocyclic compounds Bioorg. Med. Chem. 24 (2016) 2852.
31. N. Raghav, M. Singh, Mıxıng Of States And The Determınatıon Of Lıgand-Fıeld Parameters For Hıgh-Spın Octahedral Complexes Of Nıckel(Iı) - Electronıc-Spectrum And Structure Of Bıs(1,7-Dıaza-4-Thıaheptane)Nıckel(Iı) Perchlorate Bioorg. Chem. 75 (2017) 38.
32. S. Shit, J. Chakraborty, B. Samanta, A.M.Z. Slawin, V. Gramlich, S. Mitra, Conversion of some 2(3H)-furanones bearing a pyrazolyl group into other heterocyclic systems with a study of their antiviral activityStruct. Chem. 20 (2009) 633.
33. S. Basu, I. Pal, R.J. Butcher, G. Rosair, S. Bhattacharya, Electronıc Propertıes And Stereochemıstry Of Mono-Nuclear Complexes Of Copper(Iı) Ion. J. Chem. Sci. 117 (2005) 167.
34. M.A. Telpoukhovskaia, C. Orvig, Dıspersıon Correctıons + Crystal Structure Refınements, Chem. Soc. Rev. 42 (2013) 1836.
35. A. Sarkar, S. Pal, Regioselective reaction: Synthesis, characterization and pharmacological studies of some new Mannich bases derived from 1,2,4-triazoles Polyhedron 26 (2007) 1205.
36. M. Aslam, I. Anis, N. Afza, A. Hussain, L. Iqbal, J. Iqbal, Z. Ilyas, S. Iqbal, A.H. Chaudhry, M. Niaz, Discovery and investigation of antiproliferative and apoptosis-inducing properties of new heterocyclic podophyllotoxin analogues accessible by a one-step multicomponent synthesisInt. J. Curr. Pharmaceut. Res. 4 (2012) 42.
37. M. Aslam, I. Anis, N. Afza, M.T. Hussain, L. Iqbal, A. Hussain, S. Iqbal, T.H. Bokhari, M. Khalid, Metal Complexes of Schiff Base Derived from Salicylaldehyde-a Review. Med. Chem. Drug Dis. 3 (2012) 80.
38. I. Yilmaz and A. Cukurovali, Synthesis and Antimicrobial Studies of Thiazole Containing Schiff Base and their Metal Complexes. Afyon Kocatepe University Journal of Science and Engineering. 19, 3 (2019) .