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2000
Volume 21, Issue 8
  • ISSN: 1573-4072
  • E-ISSN: 1875-6646

Abstract

Introduction/Background

Age-related Alzheimer's disease is a common neurodegenerative disease. The number of Alzheimer's patients worldwide is expected to reach approximately 150 million by 2050. Breast cancer is one of the most common cancers in females, and its prevalence rises each year. Annually, worldwide, almost 500,000 women pass away due to breast cancer. Current treatments for Alzheimer’s disease and cancer aim to stop or slow the progression of the disease. Developing more effective methods of treatment has become a global effort. Many scientists from around the world are busy in finding effective treatment solutions for Alzheimer’s disease and cancer. The metal-ligand chemistry shows a variety of applications, including physiological and pharmacological activities.

Methods

The green and efficient synthesis of coordination complexes of novel azo-Schiff base ligand 4-[(E)-(5-chloro-2-hydroxy-3-{(E)-(3-nitrophenyl)diazenyl}benzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one was performed by grinding technique. Further, metal salts were introduced to this azo-Schiff base ligand, and metal complexes were synthesized. These synthesized products were characterized by 1H-NMR spectra, mass spectra, FTIR spectra, electronic spectra, elemental analysis, thermal analysis, X-ray powder diffraction, molar conductivity, ., and their anti-Alzheimer’s, anticancer, and antimicrobial activities were assessed by MTT assay and disc diffusion method, respectively.

Results and Discussions

The structures of the azo-Schiff base ligand and its metal complexes were confirmed by using various spectroscopic techniques. In the biological activity study, many complexes showed higher inhibition than the standard reference drug.

Conclusion

The synthesized metal complexes exhibited higher biological activities than the azo-Schiff base ligand. All metal complexes, except for some, served as anti-Alzheimer’s and anticancer agents.

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2025-02-26
2025-12-15

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References

  1. ZemedeY.B. Ananda KumarS. Synthesis, characterization, corrosion inhibition and biological evaluation of schiff bases.Int. J. Chemtech Res.20157172797286
     [Google Scholar]
  2. JarrahpourA. KhaliliD. De ClercqE. SalmiC. BrunelJ.M. Synthesis, antibacterial, antifungal and antiviral activity evaluation of some new bis-schiff bases of isatin and their derivatives.Molecules20071281720173010.3390/12081720 17960083
     [Google Scholar]
  3. KalaA.L.A. KumaraK. HarohallyN.V. LokanathN.K. Synthesis, characterization and hydrogen bonding attributes of halogen bonded o-hydroxy schiff bases: Crystal structure, hirshfeld surface analysis and dft studies.J. Mol. Struct.2020120212723810.1016/j.molstruc.2019.127238
     [Google Scholar]
  4. RajarajeswariC. LoganathanR. PalaniandavarM. SureshE. RiyasdeenA. AkbarshaM.A. Copper(II) complexes with 2NO and 3N donor ligands: Synthesis, structures and chemical nuclease and anticancer activities.Dalton Trans.201342238347836310.1039/c3dt32992e 23612925
     [Google Scholar]
  5. AbbasG. IrfanA. AhmedI. Al-ZeidaneenF.K. MuthuS. FuhrO. ThomasR. Synthesis and investigation of anti-covid19 ability of ferrocene schiff base derivatives by quantum chemical and molecular docking.J. Mol. Struct.2022125313224210.1016/j.molstruc.2021.132242 34975177
     [Google Scholar]
  6. SertY. GümüşM. GökceH. Kaniİ. Kocaİ. Molecular docking, hirshfeld surface, structural, spectroscopic, electronic, nlo and thermodynamic analyses on novel hybrid compounds containing pyrazole and coumarin cores.J. Mol. Struct.2018117185086610.1016/j.molstruc.2018.06.069
     [Google Scholar]
  7. AlexeevY.E. KharisovB.I. GarcíaT.C.H. GarnovskiiA.D. Coordination motifs in modern supramolecular chemistry.Coord. Chem. Rev.20102547-879483110.1016/j.ccr.2009.12.003
     [Google Scholar]
  8. GangulyA. GhoshS. KarS. GuchhaitN. Selective fluorescence sensing of cu(ii) and zn(ii) using a simple schiff base ligand: Naked eye detection and elucidation of photoinduced electron transfer (PET) mechanism.Spectrochim. Acta A Mol. Biomol. Spectrosc.2015143728010.1016/j.saa.2015.02.013 25721777
     [Google Scholar]
  9. MohanramI. MeshramJ. Synthesis and biological activities of 4-aminoantipyrine derivatives derived from betti-type reaction.ISRN Org. Chem.201420141710.1155/2014/639392 24955256
     [Google Scholar]
  10. FaddaA.A. ElattarK.M. Design and synthesis of some enaminonitrile derivatives of antipyrine as potential novel anti-inflammatory and analgesic agents.J. Biosci. Med. (Irvine)201531111412310.4236/jbm.2015.311015
     [Google Scholar]
  11. Al-HamdaniA.A.S. BalkhiA.M. FalahA. ShakerS.A. New azo-schiff base derived with ni(ii), co(ii), cu(ii), pd(ii) and pt(ii) complexes: Preparation, spectroscopic investigation, structural studies and biological activity.J. Chil. Chem. Soc.20156012774278510.4067/S0717‑97072015000100003
     [Google Scholar]
  12. ShindeA.H. PatilC.J. Synthesis and characterization of azo schiff bases and their β-lactam derivatives.Asian J. Chem.20203261520152410.14233/ajchem.2020.22657
     [Google Scholar]
  13. KargarH. Adabi ArdakaniA. MunawarK.S. AshfaqM. TahirM.N. Nickel(II), copper(II) and zinc(II) complexes containing symmetrical tetradentate schiff base ligand derived from 3,5-diiodosalicylaldehyde: Synthesis, characterization, crystal structure and antimicrobial activity.J. Indian Chem. Soc.20211892493250310.1007/s13738‑021‑02207‑x
     [Google Scholar]
  14. AnupamaB. PadmajaM. KumariC.G. Synthesis, characterization, biological activity and dna binding studies of metal complexes with 4‐aminoantipyrine schiff base ligand.J. Chem.20129138940010.1155/2012/291850
     [Google Scholar]
  15. SakhareK. SarwadeK. BharateY. SakhareM. Anticancer acitivity of Schiff base ligand(E)-4-((5-chloro-2 hydroxybenzylidene) amino)-1, 5-dimethyl-2-phenyl-1H-pyrazol-3(2H)- one and its Co(II), Cu(II) and Zn(II) metal complexes.J. Serb. Chem. Soc.202489216517510.2298/JSC230803092S
     [Google Scholar]
  16. SinghK. KumarY. PuriP. SharmaC. AnejaK.R. Antimicrobial, spectral and thermal studies of divalent cobalt, nickel, copper and zinc complexes with triazole Schiff bases.Arab. J. Chem.201710S978S98710.1016/j.arabjc.2012.12.038
     [Google Scholar]
  17. Abd El-WahebZ.H. MashalyM.M. FaheimA.A. Synthesis and characterization of cobalt(ii), cerium(iii), and dioxouranium(vi) complexes of 2,3-dimethyl-1-phenyl4-salicylidene-3-pyrazolin-5-one mixed ligand complexes, pyrolytic products, and biological activities.Chem. Pap.20055912536
     [Google Scholar]
  18. BharateY.N. SakhareK.B. SurvaseS.A. SakhareM.A. Synthesis, characterization and antibacterial screening of co[ii], ni[ii], cu[ii] acetate and vo[ii] oxysulphate complexes of schiff base ligand.202311034552
     [Google Scholar]
  19. DeviJ. YadavM. KumarD. NaikL.S. JindalD.K. Some divalent metal(ii) complexes of salicylaldehyde‐derived schiff bases: Synthesis, spectroscopic characterization, antimicrobial and in vitro anticancer studies.Appl. Organomet. Chem.2019332e469310.1002/aoc.4693
     [Google Scholar]
  20. JainR. MishraA. Microwave synthesis and spectral, thermal and antimicrobial activities of some novel transition metal complexes with tridentate schiff base ligands.J. Serb. Chem. Soc.20127781013102910.2298/JSC111001023J
     [Google Scholar]
  21. AnithaC. SumathiS. TharmarajP. SheelaC.D. Spectral, nlo, fluorescence, and biological activity of knoevenagel condensate of β-diketone ligands and their metal(ii) complexes.Int. J. Inorg. Chem.201120111810.1155/2011/493942
     [Google Scholar]
  22. Al ZoubiW. Al-HamdaniA.A.S. KaseemM. Synthesis and antioxidant activities of Schiff bases and their complexes: A review.Appl. Organomet. Chem.2016301081081710.1002/aoc.3506
     [Google Scholar]
  23. MohamedG.G. OmarM.M. IbrahimA.A. Biological activity studies on metal complexes of novel tridentate Schiff base ligand. Spectroscopic and thermal characterization.Eur. J. Med. Chem.200944124801481210.1016/j.ejmech.2009.07.028 19758728
     [Google Scholar]
  24. YousifE. MajeedA. Al-SammarraeK. SalihN. SalimonJ. AbdullahB. Metal complexes of schiff base: Preparation, characterization and antibacterial activity.Arab. J. Chem.201710S1639S164410.1016/j.arabjc.2013.06.006
     [Google Scholar]
  25. SawantR. WadekarJ. UkirdeR. BarkadeG. Synthesis, molecular docking and anticancer activity of novel 1,3-thiazolidin-4-ones.Ulum-i Daruyi202027334535210.34172/PS.2020.95
     [Google Scholar]
  26. AliI. WaniW.A. SaleemK. Empirical formulae to molecular structures of metal complexes by molar conductance.Synth. React. Inorg. Met.-Org. Nano-Met. Chem.20134391162117010.1080/15533174.2012.756898
     [Google Scholar]
  27. SasikumarG. BalajiT.N. Ibrahim SheriffA.K. Synthesis, characterization, dna binding and antimicrobial activity of tridentate Schiff base ligand and its cobalt(II) complexes.World J. Pharm. Res.20187856457410.20959/wjpr20188‑11221
     [Google Scholar]
  28. Gopal RaoS. IsmailM.B. DeivanayagamE. SrinivasaluK.R. BellirajS.K. ManoharC. Synthesis, characterization and antimicrobial activities of copper, nickel, cobalt, chromium complexes derived from (z)-4-fluoro-n-(2,7-dimethylhept-6-enylidene) benzenamine.J. Braz. Chem. Soc.20162811210.21577/0103‑5053.20160224
     [Google Scholar]
  29. MohamedG.G. OmarM.M. AhmedY.M. Metal complexes of tridentate schiff base: Synthesis, characterization, biological activity and molecular docking studies with covid‐19 protein receptor.Z. Anorg. Allg. Chem.202164723-242201221810.1002/zaac.202100245 34908618
     [Google Scholar]
  30. GopichandK. MahipalV. Nageswara RaoN. Majeed GanaiA. Venkateswar RaoP. Co(II), Ni(II), Cu(II), and Zn(II) complexes with benzothiazole schiff base ligand: Preparation, spectral characterization, dna binding, and in vitro cytotoxic activities.Results Chem.2023510086810.1016/j.rechem.2023.100868
     [Google Scholar]
  31. SilvaS. MartoJ. GonçalvesL. AlmeidaA.J. ValeN. Formulation, characterization and evaluation against sh-sy5y cells of new tacrine and tacrine-map loaded with lipid nanoparticles.Nanomaterials (Basel)20201010208910.3390/nano10102089 33096919
     [Google Scholar]
  32. OkkayU. Ferah OkkayI. In vitro Neuroprotective effects of allicin on alzheimer’s disease model of neuroblastoma cell line.J. Surg. Med.20226220921210.28982/josam.1068336
     [Google Scholar]
  33. RoucoL. AlvariñoR. AlfonsoA. Fernández-FariñaS. González-NoyaA.M. Martínez-CalvoM. PedridoR. Rodríguez-SilvaL. ManeiroM. Understanding the factors that influence the antioxidant activity of manganosalen complexes with neuroprotective effects.Antioxidants202413326510.3390/antiox13030265 38539799
     [Google Scholar]
  34. Abu BakarA.F. BahronH. KassimK. Synthesis, characterization and neurotoxicity screening of schiff base ligands and their complexes.Adv. Mat. Res.2012554-55693894310.4028/www.scientific.net/AMR.554‑556.938
     [Google Scholar]
  35. JayalkshmiR. JayakkumarV. DhivyaP. RajavelR. Synthesis and characterization of 4-amino antipyrine based schiff base complexes: Antimicrobial, cytotoxicity and dna cleavage studies2017681910.17577/IJERTV6IS080005
     [Google Scholar]
  36. Abdel-RahmanL.H. Abu-DiefA.M. El-KhatibR.M. Abdel-FatahS.M. Synthesis and characterization of azo schiff bases and their β-lactam derivatives.Bioorg. Chem.20166914015210.1016/j.bioorg.2016.10.009 27816797
     [Google Scholar]
  37. KalluruS. DammuL.K. NaraS.K. NimmagaddaV.V.J. Synthesis and characterization of schiff base, 3-hydroxy-4-(3-hydroxy benzylidene amino) benzoic acid and their ni(ii) and zn(ii) metal complexes.Int. J. Adv. Sci. Res.2023141353910.55218/JASR.202314105
     [Google Scholar]
  38. BashaM.T. AlghanmiR.M. ShehataM.R. Abdel-RahmanL.H. Synthesis, structural characterization, dft calculations, biological investigation, molecular docking and dna binding of co(ii), ni(ii) and cu(ii) nanosized schiff base complexes bearing pyrimidine moiety.J. Mol. Struct.2019118329831210.1016/j.molstruc.2019.02.001
     [Google Scholar]
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Anti-Alzheimer’s, Anticancer, and Antimicrobial Activities of Transition Metal Complexes of 4-[(E)-(5-chloro-2-hydroxy-3-{(E)-(3-nitrophenyl) diazenyl}benzylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one
Curr. Bioact. Compd. 21, E15734072349875 (2025); https://doi.org/10.2174/0115734072349875250224092826
/content/journals/cbc/10.2174/0115734072349875250224092826
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  • Article Type:     Research Article
Keyword(s): 4-Aminoantipyrine; Alzheimer’s disease; grinding technique; inhibition spectra; MCF-7; SHSY-5Y

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