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Transition metal complexes of s-triazine derivative: new class of anticonvulsant, anti-inflammatory, and neuroprotective agents

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Abstract

A new series of transition metal complexes of 2,4-bis(indolin-3-one-2-ylimino)-6-phenyl-1,3,5-triazine) (BIPTZ) have been synthesized. The structural features of BIPTZ and metal(II) complexes were investigated using elemental analyses, magnetic susceptibility, molar conductance, mass, IR, UV–Vis, 1H NMR, 13C NMR, CV, and ESR spectral studies. Electronic absorption spectra and magnetic susceptibility measurements of the complexes predict their geometry. The redox behavior of the copper(II) complexes has been studied by cyclic voltammetry. All the synthesized compounds may serve as potential photoactive materials as indicated from their characteristic fluorescence spectrum. The Schiff base and its metal complexes were screened for anticonvulsant and anti-inflammatory activities in vivo. The metal(II) complexes are potent agents in treating neurochemical and behavioral abnormalities seen in Parkinson’s diseased (PD) mice than free ligand.

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References

  • Akinchan NT, Drozdzewski PM, Holzer W (2002) Synthesis and spectroscopic studies of Zn(II) and Hg(II) complexes of isatin-3-thiosemicarbazone. J Mol Str 641:17–22

    Article  CAS  Google Scholar 

  • Baindur N, Chadha N, Brandt BM, Asgari D, Patch R (2005) 2-Hydroxy-4,6-diamino-(1,3,5)-triazines: a novel class of VGEF-R2(KDR) tyrosine kinase inhibitors. J Med Chem 48:1717–1724

    Article  CAS  PubMed  Google Scholar 

  • Bhusan subudhi B, Panda P, Sahoo S (2007) Synthesis and evaluation of antimicrobial activity of metal complexes of 4-(2′-hydroxy phenylimino)phenyl sulphonamide. J Pharm Sci autumn 3:245–248

    Google Scholar 

  • Cerchiaro G, Ferreira AM (2006) Oxindoles and copper complexes with oxindole-derivatives as potential pharmacological agents. J Braz Chem Soc 17:1473–1485

    Article  CAS  Google Scholar 

  • Chandra S, Jain D, Sharma A, Sharma P (2009) Coordination modes of a Schiff base pentadentate derivative of 4-aminoantipyrine with Co(II), Ni(II) and Cu(II) metal ions: synthesis, spectroscopic and antimicrobial studies. Molecules 14:174–190

    Article  CAS  PubMed  Google Scholar 

  • Chohan ZH, Humayun PA, Khan KM (2004) Metalloantibiotics: synthesis and antibacterial activity of Co(II), Cu(II) and Zn(II) complexes of Kefzol. J Enzym Inhib Med Chem 19:161–164

    Article  CAS  Google Scholar 

  • Chohan LS, Jain CP, Chauhan RS, Goswami AK (2010) Wound-healing activity of hydroxy triazines-a new class of bioactive compounds. J Pharm Sci 2(1):539–546

    Google Scholar 

  • Cueva Acuria, Faure R, Nuria A, Cabeza I, Sonia B, Pulido J, Miguel N, Carreterp M, Quirosoloxabal M (2003) Synthesis and characterization of several lumazine derivative complexes of Co(II), Ni(II), Cd(II), Pd(II) and Pt(II), X-ray structure of a mononuclear Cu(II) complex and a dinuclear Cd complex. Inorg Chim Acta 351:356–362

    Article  Google Scholar 

  • Dahl O (1969) Four- and five- coordinate nickel(II) complexes with trimethyl phosphine. Acta Chim Scandinavica 23:2342–2354

    Article  CAS  Google Scholar 

  • Davidson WM, Boyki WD (1978) Synthesis of s-triazines as potential antiviral agents. J Pharm Sci 65:737–739

    Article  Google Scholar 

  • Ellman GL (1959) Tissue sulfhydryl groups. Arch Biochem Biophys 82:70–77

    Article  CAS  PubMed  Google Scholar 

  • Emaraa AAA, Abou-Hussen AA (2006) Spectroscopic studies of bimetallic complexes derived from tridentate or tetradentate Schiff bases of some di- and tri-valent transition metals. Spectrochim Acta Part A 64:1010–1024

    Article  Google Scholar 

  • Fouda MFR, Abd-Elzaher MM, Shakdofa MME, Ayad MF (2008) Synthesis and characterization of transition metal complexes of N′-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)methylene)thiophene-2. Transit Met Chem 32:219–228

    Article  Google Scholar 

  • Geary (1971) The use of conductivity measurements in organic solvents for the characterization of coordination compounds. Coord Chem Rev 7:81–122

    Article  CAS  Google Scholar 

  • Gudasi KB, Patil SA, Vadavi RS, Shenoy RV (2006) Crystal structure of 2-(2-hydroxy-3-methoxyphenyl)-3-(2-hydroxy-3-methoxybenzylamino)-1,2-dihydroquinazolin-4(3H)-one and the synthesis, spectral and thermal investigation of its transition metal complexes. Transit Met Chem 31:586–592

    Article  CAS  Google Scholar 

  • Gupta LK, Chandra S (2006) Spectroscopic characterization and EPR spectral studies on transition metal complexes with a novel tetradentate, 12-membered macrocyclic ligand. Spectrochim Acta Part A 65:792–796

    Article  Google Scholar 

  • Hazell A, Mckenzie CJ, Nielsen LP (2000) Synthesis, structural characterization and electronic behavior of iron(II) and nickel(II) complexes of N, N-bis(2-pyridylmethyl)aniline. Polyhedron 19:1333–1338

    Article  CAS  Google Scholar 

  • Henke BR, Consler TG, Go N, Hale RL, Lambart M (2002) A new series of estrogen receptor modulators that display selectivity for estrogen receptor β. J Med Chem 45:5492–5505

    Article  CAS  PubMed  Google Scholar 

  • Hielman PW, Scozzie RD, Hielman RD, Wayner RJ (1980) Synthesis and anti-inflammatory evaluation of 3-methylthio-1,2,4-triazines, 3-alkoxy-1,2,4-triazines and 3-aryloxy-1,2,4-triazines. J Pharm Sci 69:282–285

    Article  Google Scholar 

  • Kannappan R, Mahalakshmy R, Rajendran TM, Venkatesan R, Sambasiva Rao P (2003) Magnetic, catalytic, EPR and electrochemical studies on binuclear copper(II) complexes from 3,4- disubstituted phenol. Proc Indian Acad (Chem Sci) 115:1–14

    Article  CAS  Google Scholar 

  • Kasumov VT, Koksal F (2004) Synthesis, spectral characterization and redox property of some transition metal complexes with salicylaldimines bearing 2,6-di-phenylphenol. Spectrochim Acta Part A 60:31–39

    Article  CAS  Google Scholar 

  • Katiyar SB, Srivastava K, Puri SK, Chauhan PMS (2005) Synthesis of 2-(3,5-substituted pyrazol-1-yl)-4,6-trisubstituted triazine derivatives as antimalarial agents. Bioorg Med Chem Lett 15:4957–4960

    Article  CAS  PubMed  Google Scholar 

  • Khalil SME (2003) Synthesis, spectral, magnetic studies on metal complexes of 5-methyl-3-(2-hydroxyphenyl)pyrazole. J Coord Chem 56:1013–1024

    Article  CAS  Google Scholar 

  • Klenke B, Stewart M, Barrett M, Brun R, Gilbert IH (2001) Synthesis and biological evaluation of s-triazine substituted polyamines as potential new anti-trypanosomal drugs. J Med Chem 44:3440–3452

    Article  CAS  PubMed  Google Scholar 

  • Kulkarni AD, Patil SA, Naik VH, Badami PS (2011) DNA cleavage and antimicrobial investigation of Co(II), Ni(II) and Cu(II) complexes with triazole Schiff bases: synthesis and spectral characterization. Med Chem Res 20:346–354

    Article  CAS  Google Scholar 

  • Majumder A, Rosair GM, Mallick A, Chattopadhyay N, Mitra S (2006) Synthesis, structures and fluorescence of Ni, Zn and Cd complexes with N, N, O-tridentate Schiff base N-2-pyridylmethylidene-2-hydroxy-phenylamine. Polyhedron 25:1753–1762

    Article  CAS  Google Scholar 

  • Murukan B, Sindhu kumar B, Mohanan K (2007) Synthesis, spectral, electrochemical and antimicrobial studies of Copper (II) complexes with isatin derived bishydrazone and different co-ligands. J Coord Chem 60:1607–1617

    Article  CAS  Google Scholar 

  • Mylari BL, Withbroe GJ, Beebe DA, Brackett NS, Cohn EL (2003) Design and synthesis of a novel family of triazine-based inhibitors of sorbitol dehydrogenase with oral activity: 1{4(3R,5S-dimethyl-4(4-methyl-(1,3,5)-triazin-2-yl)-piperazin-1-yl)-(1,3,5)triazin-2-yl}-(R)ethanol. J Bioorg Med Chem 11:4179–4188

    Article  CAS  Google Scholar 

  • Ohkawa H, Ohishi N, Yagi K (1979) Assay for lipid peroxides in animal tissues by thiobarbituric acid reaction. Anal Biochem 95:351–358

    Article  CAS  PubMed  Google Scholar 

  • Omar MM, Mohamed GG (2005) Potentiometric, spectroscopic and thermal studies on the metal chelates of 2-(thiazolylazo)-2-naphthalenol. Spectrochim Acta Part A 61:929–936

    Article  CAS  Google Scholar 

  • Poojary B, Lobo PL, Manjunatha K, Kumar V, Chullikana A (2012) Synthesis of some 7-arylidene-3-(4-metylthio)benzyl-7H-thiazole (2,3-c)(1,2,4) triazine-4,6-diones and their anticonvulsant and antimicrobial activity. J Chem Pharm Res 4(5):2522–2531

    Google Scholar 

  • Porter JR, Archibald SC, Brown JA, Childs A, Crotchety D, Head JC (2002) Discovery and evaluation of N-(triazin-1,3,5-yl)phenylalanine derivatives as VLA-4 integrin antagonists. Bioorg Med Chem Lett 12:1591–1594

    Article  CAS  PubMed  Google Scholar 

  • Ram Agarwal K, Singh L, Sharma D, Agarwal H (2006) Synthesis, biological, spectral and thermal investigations of Co(II), Ni(II) complexes of N-isonicotinamido-2,4′-dichlorobenzaldehyde. Bioinorg chem Appl. 1–9

  • Ray RK, Kauffman GB (1990) EPR spectra and covalency of bis(amidinourea/0-alkyl-1-amidiniurea)Cu(II) complexes Part II: properties of the CuN4 2− chromophore. Inorg Chim Acta 173:207–214

    Article  CAS  Google Scholar 

  • Sharaby CM (2007) Synthesis, spectroscopic, thermal and antimicrobial studies of some novel metal complexes of Schiff based derived from [N′-(4-methoxy-1,2,5-thiadiazol-3-yl)sulphanilamide] and 2-thiophene carboxaldehyde. Spectrochim Acta Part A 66:1271–1278

    Article  Google Scholar 

  • Singh K, Singh Barwa M, Tyagi P (2006) Synthesis, characterization and biological studies of Co(II), Ni(II), Cu and Zn complexes with bidentate schiff bases derived by heterocyclic ketone. Eur J Med Chem 41:147–153

    Article  PubMed  Google Scholar 

  • Solankee A, Thakor I (2006) Synthesis of pyrazolines, isoxazolines and aminopyrimidines as biological potent agents. Indian J Chem 45B:517–522

    CAS  Google Scholar 

  • Stefancich G, Artico M, Silvestre R (1991) Non-steroidal anti-inflammatory agents. Synthesis and anti-inflammatory activity of 5-methyl-10,11-dihydro-5H-pyrrolo(1,2-b)(1,2,5)benzotriazepine-11-acetic acid and its 10-aroyl derivatives. Phytopathology 55:135–141

    Google Scholar 

  • Sun CW, Wang HF, Zhu J, Yang DR (2011) Synthesis, insecticidal activities and molecular docking studies of 1,5-disubstituted-1,3,5-hexahydrotriazine-2-(N-nitro)imines. J Heterocycl Chem 48:829–835

    Article  CAS  Google Scholar 

  • Thakurta S, Butcher RJ, Pilet G, Mitra S (2009) Synthesis of octahedral Co(II) complexes with mono- and di-condensed Schiff base ligands: a template-directed approach for the isolation of a rare kind of mixed-ligand complex. J Mol Struct 929:112–119

    Article  CAS  Google Scholar 

  • Tharmaraj P, Kodimunthiri D, Sheela CD, Prakash P (2009) Bis-(3,5-dimethyl-pyrazolyl-1-methyl)-3-(phosphanyl-propyl)-amine complexes of Cu(II), Ni(II) & Co(II). J Coord Chem 62:1347–1355

    Article  CAS  Google Scholar 

  • Yamada Y, Sakurai H, Miyashita Y, Fujisawa K, Okamoto KI (2002) Crystal structures, electronic absorbance and reflectance spectral behaviors and electrochemical property of 5-coordinated chloro Cu(II) complexes with 5,6-disubstituted-1,10-phenanthroline. Polyhedron 21:2143–2147

    Article  CAS  Google Scholar 

  • Yang P, Yang Y, Zhang C, Yang XJ, Hub HM, Gao Y, Wu B (2009) Synthesis, structure and catalytic ethylene oligomerization of nickel(II), cobalt(II) complexes with symmetrical and unsymmetrical 2,9-diaryl-1,10-phelanthroline ligands. Inorg Chim Acta 362:89–96

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Department of Chemistry, C.R. Engineering College, Madurai, India

    R. Shanmugakala

  2. Department of Chemistry, Thiagarajar College, Madurai, India

    P. Tharmaraj

  3. Department of Chemistry, The American College, Madurai, India

    C. D. Sheela

  4. Department of Pharmacology, K.M. College of Pharmacy, Madurai, India

    N. Chidambaranathan

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  1. R. Shanmugakala
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  2. P. Tharmaraj
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  3. C. D. Sheela
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  4. N. Chidambaranathan
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Correspondence to P. Tharmaraj.

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Shanmugakala, R., Tharmaraj, P., Sheela, C.D. et al. Transition metal complexes of s-triazine derivative: new class of anticonvulsant, anti-inflammatory, and neuroprotective agents. Med Chem Res 23, 329–342 (2014). https://doi.org/10.1007/s00044-013-0634-0

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