Abstract
The present manuscript describes the synthesis, spectral characterisation, DFT studies and biological activity of a series of 3d transition metal complexes of (E)-2-((2-(benzo[d]thiazole-2-yl)hydrazono)methyl)-5-(diethylamino)phenol (L1) in (1:1) and (1:2) ratio. Various spectral analysis revealed the presence of ONN binding domain in L1. The elemental composition was confirmed using mass spectrometry technique. The stability of the geometry was also confirmed with DFT based method using B3LYP/LanL2Dz level of theory. Absence of any imaginary frequency revealed the presence of geometry on global minima of potential energy surface. Job’s plot confirm the stoichiometric ratio of metal complexes. Electrochemical behaviour (cyclic voltammetry), magnetic moment and Conductance measurements were also investigated for the metal-complexes. Kinetic parameters for different stages of thermal decomposition of metal complexes were calculated by using Coats–Redfern and Broido method. Positive free-energy of decomposition describes the non-spontaneous nature of thermal decomposition. The negative ΔS value observed for metal complexes under consideration reveals the ordered arrangement of metal complexes than their reactants. The octahedral environment of Co2+, Ni2+, Cu2+ and Cd2+ complexes was elucidated with the help of spectroscopic data. The ligand (L1) and its metal complexes (M1–M8) exhibited excellent α-amylase and moderate anti-oxidant activities. Maximum α-amylase inhibition was exhibited by M7 with a percentage inhibition of 96.65% (IC50 = 0.070 µM) and the lowest by M1 (87.00%, IC50 = 0.086 µM).
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Lovic, D., Piperidou, A., Zografou, I., Grassos, H., Pittaras, A., Manolis, A.: The growing epidemic of diabetes mellitus. Curr. Vasc. Pharmacol. 18, 104–109 (2019). https://doi.org/10.2174/1570161117666190405165911
Pareja-Galeano, H., Garatachea, N., Lucia, A.: Exercise as a polypill for chronic diseases. Prog. Mol. Biol. Transl. Sci. 135, 497–526 (2015). https://doi.org/10.1016/bs.pmbts.2015.07.019
Mayfield, J.: Diagnosis and classification of diabetes mellitus: new criteria. Am. Fam. Phys. 58(6), 1355–1362 (1998)
Jean-Marie, E.: Diagnosis and classification of diabetes mellitus. Encycl. Endocr. Dis. 29, 105–109 (2018). https://doi.org/10.1016/B978-0-12-801238-3.65822-1
Proença, C., Ribeiro, D., Freitas, M., Fernandes, E.: Flavonoids as potential agents in the management of type 2 diabetes through the modulation of α-amylase and α-glucosidase activity: a review. Crit. Rev. Food Sci. Nutr. 62, 3137–3207 (2022). https://doi.org/10.1080/10408398.2020.1862755
Gao, H., Zhang, Q., Jean’ne, M.S.: Fused heterocycle-based energetic materials (2012–2019). J. Mater. Chem. A 8, 4193–4216 (2020)
Kajal, A., Bala, S., Kamboj, S., Sharma, N., Saini, V.: Schiff bases: a versatile pharmacophore. J. Catal. (2013). https://doi.org/10.1155/2013/893512
Ali, R., Siddiqui, N.: Biological aspects of emerging benzothiazoles: a short review. J. Chem. (2013). https://doi.org/10.1155/2013/345198
Rouf, A., Tanyeli, C.: Bioactive thiazole and benzothiazole derivatives. Eur. J. Med. Chem. 97, 911–927 (2015)
Gjorgjieva, M., Tomašič, T., Kikelj, D., Mašič, L.P.: Benzothiazole-based compounds in antibacterial drug discovery. Curr. Med. Chem. 25, 5218–5236 (2018)
Noolvi, M.N., Patel, H.M., Kaur, M.: Benzothiazoles: search for anticancer agents. Eur. J. Med. Chem. 54, 447–462 (2012). https://doi.org/10.1016/j.ejmech.2012.05.028
Zhao, S., Zhao, L., Zhang, X., Liu, C., Hao, C., Xie, H., Sun, B., Zhao, D., Cheng, M.: Design, synthesis, and structure-activity relationship studies of benzothiazole derivatives as antifungal agents. Eur. J. Med. Chem. 123, 514–522 (2016). https://doi.org/10.1016/j.ejmech.2016.07.067
Netalkar, P.P., Netalkar, S.P., Revankar, V.K.: Synthesis, crystal structures and characterization of late first row transition metal complexes derived from thiosemicarbazone hub: DNA binding/cleavage studies. Appl. Organomet. Chem. 29, 280–289 (2015). https://doi.org/10.1002/aoc.3286
Hornung, M.W., Kosian, P.A., Haselman, J.T., Korte, J.J., Challis, K., Macherla, C., Nevalainen, E., Degitz, S.J.: In vitro, ex vivo, and in vivo determination of thyroid hormone modulating activity of benzothiazoles. Toxicol. Sci. 146, 254–264 (2015)
Hutchinson, I., Jennings, S.A., Vishnuvajjala, B.R., Westwell, A.D., Stevens, M.F.G.: Antitumor benzothiazoles. 16. Synthesis and pharmaceutical properties of antitumor 2-(4-aminophenyl) benzothiazole amino acid prodrugs. J. Med. Chem. 45, 744–747 (2002)
Soni, B., Ranawat, M.S., Sharma, R., Bhandari, A., Sharma, S.: Synthesis and evaluation of some new benzothiazole derivatives as potential antimicrobial agents. Eur. J. Med. Chem. 45, 2938–2942 (2010)
Mariappan, G., Prabhat, P., Sutharson, L., Banerjee, J., Patangia, U., Nath, S.: Synthesis and antidiabetic evaluation of benzothiazole derivatives. J. Korean Chem. Soc. 56, 251–256 (2012)
Paramashivappa, R., Kumar, P.P., Rao, P.V.S., Rao, A.S.: Design, synthesis and biological evaluation of benzimidazole/benzothiazole and benzoxazole derivatives as cyclooxygenase inhibitors. Bioorg. Med. Chem. Lett. 13, 657–660 (2003)
Choudhary, S., Kini, S.G., Mubeen, M.: Antioxidant activity of novel coumarin substituted benzothiazole derivatives. Der Pharma Chem. 5, 213–222 (2013)
Taha, M., Ismail, N.H., Imran, S., Wadood, A., Rahim, F., Khan, K.M., Riaz, M.: Hybrid benzothiazole analogs as antiurease agent: synthesis and molecular docking studies. Bioorg. Chem. 66, 80–87 (2016). https://doi.org/10.1016/j.bioorg.2016.03.010
Fricker, S.P.: Metal based drugs: from serendipity to design. Dalton Trans. (2007). https://doi.org/10.1039/b705551j
Yao, Z.-J., Jin, G.-X.: Transition metal complexes based on carboranyl ligands containing N, P, and S donors: synthesis, reactivity and applications. Coord. Chem. Rev. 257, 2522–2535 (2013)
Garnovskii, A.D., Vasil’chenko, I.S.: Rational design of metal coordination compounds with azomethine ligands. Russ. Chem. Rev. 71, 943–968 (2002). https://doi.org/10.1070/rc2002v071n11abeh000759
Malik, M.A., Dar, O.A., Gull, P., Wani, M.Y., Hashmi, A.A.: Heterocyclic Schiff base transition metal complexes in antimicrobial and anticancer chemotherapy. Med. Chem. Commun. 9, 409–436 (2018). https://doi.org/10.1039/c7md00526a
Bonaccorso, C., Marzo, T., La Mendola, D.: Biological applications of thiocarbohydrazones and their metal complexes: a perspective review. Pharmaceuticals 13, 4 (2020)
Kulkarni, N.V., Revankar, V.K., Kirasur, B.N., Hugar, M.H.: Transition metal complexes of thiosemicarbazones with quinoxaline hub: an emphasis on antidiabetic property. Med. Chem. Res. 21, 663–671 (2012)
Vinusha, H.M., Kollur, S.P., Revanasiddappa, H.D., Ramu, R., Shirahatti, P.S., Prasad, M.N.N., Chandrashekar, S., Begum, M.: Preparation, spectral characterization and biological applications of Schiff base ligand and its transition metal complexes. Results Chem. 1, 100012 (2019)
Kurdekar, G.S., Sathisha, M.P., Budagumpi, S., Kulkarni, N.V., Revankar, V.K., Suresh, D.K.: 4-Aminoantipyrine-based Schiff-base transition metal complexes as potent anticonvulsant agents. Med. Chem. Res. 21, 2273–2279 (2012)
Pahonțu, E., Ilieș, D.-C., Shova, S., Oprean, C., Păunescu, V., Olaru, O.T., Rădulescu, F.Ș, Gulea, A., Roșu, T., Drăgănescu, D.: Synthesis, characterization, antimicrobial and antiproliferative activity evaluation of Cu(II), Co(II), Zn(II), Ni(II) and Pt(II) complexes with isoniazid-derived compound. Molecules 22, 650 (2017)
Sharfalddin, A.A., Hussien, M.A.: Bivalence metal complexes of antithyroid drug carbimazole; synthesis, characterization, computational simulation, and biological studies. J. Mol. Struct. 1228, 129725 (2021)
Saha, N., Mukherjee, N.: Synthesis, characterisation and coordinating properties of a new pyrazole-derived thiosemicarbazone, a potential antiviral agent: Co(III), Ni(II) and Cu(II) complexes of neutral and deprotonated 5(3)-methylpyrazole-3(5)-aldehydothiosemicarbazone. Polyhedron 3, 1135–1140 (1984)
Wu, A., Duan, L.: Transition metal complexes of N-(4,6-dimethoxypyrimidin-2-Ylcarbamothioyl)benzamide: design, synthesis and herbicidal activity. J. Chin. Chem. Soc. 56, 539–542 (2009)
Gayakwad, D.R., Sarda, S.R., Nawale, R.B., Munde, S.B., Bharad, J.V., Kendrekar, P.S.: Synthesis and biological activity of novel Schiff base ligand and its transition metal complexes. J. Curr. Pharma Res. 9, 3378–3385 (2019)
Abu-Dief, A.M., Mohamed, I.M.A.: A review on versatile applications of transition metal complexes incorporating Schiff bases. Beni-Suef Univ. J. Basic Appl. Sci. 4, 119–133 (2015)
Mandal, S., Modak, R., Goswami, S.: Synthesis and characterization of a copper(II) complex of a ONN donor Schiff base ligand derived from pyridoxal and 2-(pyrid-2-yl)ethylamine—a novel pyridoxal based fluorescent probe. J. Mol. Struct. 1037, 352–360 (2013)
Beigi, Z., Kianfar, A.H., Farrokhpour, H., Roushani, M., Azarian, M.H., Mahmood, W.A.K.: Synthesis, characterization and spectroscopic studies of nickel(II) complexes with some tridentate ONN donor Schiff bases and their electrocatalytic application for oxidation of methanol. J. Mol. Liq. 249, 117–125 (2018)
Al Zoubi, W.: Biological activities of Schiff bases and their complexes: a review of recent works. Int. J. Org. Chem. (2013). https://doi.org/10.4236/ijoc.2013.33A008
Abd El-Razek, S.E., El-Gamasy, S.M., Hassan, M., Abdel-Aziz, M.S., Nasr, S.M.: Transition metal complexes of a multidentate Schiff base ligand containing guanidine moiety: synthesis, characterization, anti-cancer effect, and anti-microbial activity. J. Mol. Struct. 1203, 127381 (2020)
Singh, K., Bala, I., Kataria, R.: Crystal structure, Hirshfeld surface and DFT based NBO, NLO, ECT and MEP of benzothiazole based hydrazone. Chem. Phys. 538, 110873 (2020). https://doi.org/10.1016/j.chemphys.2020.110873
Sakthi, M., Ramu, A.: Synthesis, structure, DNA/BSA binding and antibacterial studies of NNO tridentate Schiff base metal complexes. J. Mol. Struct. 1149, 727–735 (2017)
Aboafia, S.A., Elsayed, S.A., El-Sayed, A.K.A., El-Hendawy, A.M.: New transition metal complexes of 2,4-dihydroxybenzaldehyde benzoylhydrazone Schiff base (H2dhbh): synthesis, spectroscopic characterization, DNA binding/cleavage and antioxidant activity. J. Mol. Struct. 1158, 39–50 (2018)
Singh, K., Siwach, P.: Synthesis, spectroscopic, theoretical and biological evaluation of novel Schiff base complexes of divalent transition metals. Appl. Organomet. Chem. (2021). https://doi.org/10.1002/aoc.6553
Gülcan, M., Sönmez, M.: Synthesis and characterization of Cu(II), Ni(II), Co(II), Mn(II), and Cd(II) transition metal complexes of tridentate Schiff base derived from O-vanillin and N-aminopyrimidine-2-thione. Phosphorus Sulfur Silicon Relat. Elem. 186, 1962–1971 (2011)
Kumari, B., Singh, K., Sharma, A.: Synthesis, crystal structure and molecular docking studies of novel Schiff base ligand 9-(((3-ethyl-5-mercapto/thio-4H-1,2,4-triazole-4-yl)imino)methyl)-anthracene and its complexes with Ni(II), Cu(II), Zn(II) and Cd(II): comparative spectral, thermo-kinetics, radical scavenging and antimicrobial studies. Chem. Data Collect. 38, 100833 (2022)
Alaghaz, A.-N.M.A., Ammar, Y.A., Bayoumi, H.A., Aldhlmani, S.A.: Synthesis, spectral characterization, thermal analysis, molecular modeling and antimicrobial activity of new potentially N2O2 azo-dye Schiff base complexes. J. Mol. Struct. 1074, 359–375 (2014)
Anacona, J.R., Mago, K., Camus, J.: Antibacterial activity of transition metal complexes with a tridentate NNO amoxicillin derived Schiff base. Synthesis and characterization. Appl. Organomet. Chem. 32, e4374 (2018)
Durmus, S., Atahan, A., Zengin, M.: Synthesis, characterization and electrochemical behavior of some Ni(II), Cu(II), Co(II) and Cd(II) complexes of ONS type tridentate Schiff base ligand. Spectrochim. Acta A 84, 1–5 (2011)
Abou-Melha, K.S.: Transition metal complexes of isonicotinic acid (2-hydroxybenzylidene)hydrazide. Spectrochim. Acta A 70, 162–170 (2008). https://doi.org/10.1016/j.saa.2007.07.023
Jayendran, M., Sithambaresan, M., Begum, P.M.S., Kurup, M.R.P.: Cd(II) and Ni(II) complexes from a tridentate NNO Schiff base: crystal structures, spectral aspects and Hirshfeld surface analysis. Polyhedron 158, 386–397 (2019). https://doi.org/10.1016/j.poly.2018.11.020
Chang, J., Zhang, S.-Z., Wu, Y., Zhang, H.-J., Sun, Y.-X.: Three supramolecular trinuclear nickel(II) complexes based on Salamo-type chelating ligand: syntheses, crystal structures, solvent effect, Hirshfeld surface analysis and DFT calculation. Transit. Met. Chem. 45, 279–293 (2020)
Singh, K., Kumar, Y., Puri, P., Kumar, M., Sharma, C.: Cobalt, nickel, copper and zinc complexes with 1,3-diphenyl-1H-pyrazole-4-carboxaldehyde Schiff bases: antimicrobial, spectroscopic, thermal and fluorescence studies. Eur. J. Med. Chem. 52, 313–321 (2012)
Reddy, A.S., Mao, J., Krishna, L.S., Badavath, V.N., Maji, S.: Synthesis, spectral investigation, molecular docking and biological evaluation of Cu(II), Ni(II) and Mn(II) complexes of (E)-2-((2-butyl-4-chloro-1H-imidazol-5-yl) methylene)-N-methylhydrazinecarbothioamide (C10H16N5ClS) and its DFT studies. J. Mol. Struct. 1196, 338–347 (2019)
Abd El-halim, H.F., Omar, M.M., Mohamed, G.G.: Synthesis, structural, thermal studies and biological activity of a tridentate Schiff base ligand and their transition metal complexes. Spectrochim. Acta A 78, 36–44 (2011)
Venugopal, N., Krishnamurthy, G., Bhojyanaik, H.S., Giridhar, M.: Novel bioactive azo-azomethine based Cu(II), Co(II) and Ni(II) complexes, structural determination and biological activity. J. Mol. Struct. 1191, 85–94 (2019)
Deswal, Y., Asija, S., Dubey, A., Deswal, L., Kumar, D., Jindal, D.K., Devi, J.: Cobalt(II), nickel(II), copper(II) and zinc(II) complexes of thiadiazole based Schiff base ligands: synthesis, structural characterization, DFT, antidiabetic and molecular docking studies. J. Mol. Struct. 1253, 132266 (2021)
Ragole, V.D., Gayakwad, S.V., Wankhede, D.S.: Novel Schiff base (E)-2-((4-chloro-3-nitrophenylimino)(phenyl) methyl)-5-methoxyphenol and mixed ligand complexes of Mn(II), Fe(III), Co(II), Ni(II) and Cu(II): synthesis, structure elucidation and potency study as antibacterial, antimalarial, antiox. J. Iran. Chem. Soc. (2021). https://doi.org/10.1007/s13738-021-02431-5
Singh, H., Sindhu, J., Khurana, J.M., Sharma, C., Aneja, K.R.: Syntheses, biological evaluation and photophysical studies of novel 1,2,3-triazole linked azo dyes. RSC Adv. 4, 5915–5926 (2014). https://doi.org/10.1039/c3ra44314k
Yousef, T.A., El-Reash, G.M.A., Al-Zahab, M.A., Safaan, M.A.A.: Physicochemical investigations, biological studies of the Cr(III), Mn(II), Fe(III), Co(II), Ni(II), Cu(II), Zn(II), Cd(II), Hg(II) and UO2(VI) complexes of picolinic acid hydrazide derivative: a combined experimental and computational approach. J. Mol. Struct. 1197, 564–575 (2019)
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Indu Bala thanks Department of Chemistry, Kurukshetra University, Kurukshetra for providing research facilities and for the grant of University Research Fellowship.
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IB: Experimental, data curation, analysis, writing original draft. KS: Review and editing.
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Singh, K., Bala, I. Structural investigations, DFT, anti-oxidant and α-amylase inhibitory activity of metal complexes of benzothiazole based hydrazone. J Incl Phenom Macrocycl Chem 103, 301–316 (2023). https://doi.org/10.1007/s10847-023-01196-z
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DOI: https://doi.org/10.1007/s10847-023-01196-z