The Bivalent Cu, Ni and Zn Complexes of Unsymmetrical ONO Tridentate Schiff Base Ligands Derived from 2-Aminobenzoic Acid: Antimicrobial and Molluscicidal Activity

Bivalent Cu(II), Ni(II) and Zn(II) complexes were synthesized using the prepared tridentate Schiff base ligands derived from 2-aminobenzoic acid as the primary amine condensed with different substituted aldehydes (salicylic acid, 0-vaniline, 2-carboxybenzaldehyde, 1-(3formyl-4-hydroxyphenylazo)-4-methylbenzene and 1-(3formyl-4-hydroxyphenylazo benzene). The ligands and their corresponding complexes have been characterized using analytical, spectroscopic, conductivity and magnetic moment measurements. The analytical data showed the stoichiometry of the metals to ligands was (1:1). The conductivity data showed that all the complexes were non-electrolytes. The geometry of Cu(II) complexes were suggested to be distorted square planer. Ni(II) complexes are square-planar and Zn(II) complexes were tetrahedral. The antimicrobial investigation showed that the metal complexes had remarkable enhancement of activity with zinc complexes and were having highest susceptibility. The complex [ZnSL4.H2O] showed MIC value of 12.5 μg/ disc against Candida albicans and the complex [ZnSL5.H2O] indicated MIC value of 50 μg/disc against Streptococcus pneumonia. The molluscicidal activity tests against the land snail Eobania vermiculata showed that complexes were more toxic with LC 50 of 0.4 mg/L, while the LC 50 of the ligands was at 0.5 mg/L.

[1]  P. He,et al.  Molluscicidal activity and mechanism of toxicity of a novel salicylanilide ester derivative against Biomphalaria species , 2017, Parasites & Vectors.

[2]  Reza Bohloli Khiavi Methods for in vitro evaluating antimicrobial activity: A review , 2017 .

[3]  S. Swathy,et al.  Synthesis, spectroscopic investigation and antimicrobial activities of some transition metal complexes of a [(2-hydroxyacetophenone)-3-isatin]-bishydrazone , 2016 .

[4]  S. Zabin,et al.  Oxo/dioxo-vanadium(V) complexes with Schiff base ligands derived from 4-amino-5-mercapto-3-phenyl-1,2,4-triazole , 2016 .

[5]  Yu-hua Fan,et al.  Synthesis, crystal structures and biological evaluation of three ternary copper(II) complexes with fluorinated anthranilic acid derivatives , 2016, Transition Metal Chemistry.

[6]  Md. Rabiul Hasan,et al.  Nickel complexes of Schiff bases derived from mono/diketone with anthranilic acid: Synthesis, characterization and microbial evaluation , 2016 .

[7]  P. A. Ajibade,et al.  Synthesis, Characterization, Anticancer, and Antioxidant Studies of Ru(III) Complexes of Monobasic Tridentate Schiff Bases , 2016, Bioinorganic chemistry and applications.

[8]  Lin Ma,et al.  Metal complexes of anthranilic acid derivatives: A new class of non-competitive α-glucosidase inhibitors , 2016 .

[9]  A. Asadi,et al.  Structural, spectroscopic, electrochemical and antibacterial studies of some new nickel(II) Schiff base complexes , 2016 .

[10]  M. Balouiri,et al.  Methods for in vitro evaluating antimicrobial activity: A review☆ , 2015, Journal of pharmaceutical analysis.

[11]  P. A. Ajibade,et al.  Transition metal complexes of symmetrical and asymmetrical Schiff bases as antibacterial, antifungal, antioxidant, and anticancer agents: progress and prospects , 2015 .

[12]  V. McKee,et al.  A new Salen-type azo-azomethine ligand and its Ni(II), Cu(II) and Zn(II) complexes: Synthesis, spectral characterization, crystal structure and photoluminescence studies. , 2015, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[13]  A. Morsali,et al.  Sonochemical synthesis of two new copper(II) complexes with azo ligands derived from anthranilic acid and β-naphtol. , 2015, Ultrasonics sonochemistry.

[14]  S. Salehzadeh,et al.  Probing the effect of arm length and inter- and intramolecular interactions in the formation of Cu(II) complexes of Schiff base ligands derived from some unsymmetrical tripodal amines , 2015 .

[15]  V. Sudarsan,et al.  Synthesis, characterization, photoluminescence and computational studies of mono- and diorgano-gallium complexes containing azo linked salicylaldimine Schiff bases , 2015 .

[16]  Sheng Lin,et al.  Metal complexes as potential modulators of inflammatory and autoimmune responses , 2014, Chemical science.

[17]  H. Zengin,et al.  A novel azo-azomethine based fluorescent dye and its Co(II) and Cu(II) metal chelates , 2014 .

[18]  Hamid Khanmohammadi,et al.  Solvatochromism, spectral properties and antimicrobial activities of new azo–azomethine dyes with N2S2O2 donor set of atoms , 2014 .

[19]  S. G. Shankarwar,et al.  Synthesis, spectral, thermal, potentiometric and antimicrobial studies of transition metal complexes of tridentate ligand , 2014 .

[20]  A. Taeb,et al.  Synthesis, characterization, and electrochemical study of some novel, azo-containing Schiff bases and their Ni(II) complexes , 2013 .

[21]  H. Khanmohammadi,et al.  Azo-azomethine dyes with N, O, S donor set of atoms and their Ni(II) complexes: Synthesis, characterization and spectral properties , 2013 .

[22]  M. S. Iqbal,et al.  Anti-inflammatory and selective COX-2 inhibitory activities of metal complexes of Schiff bases derived from aldoses , 2013, Medicinal Chemistry Research.

[23]  A. El-Sherif,et al.  Synthesis, characterization, biological activity and equilibrium studies of metal(II) ion complexes with tridentate hydrazone ligand derived from hydralazine. , 2012, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[24]  H. Khanmohammadi,et al.  Thermally stable water insoluble azo-azomethine dyes: synthesis, characterization and solvatochromic properties. , 2012, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[25]  M. Ebqa’ai,et al.  Synthesis, characterization, biological activities, and luminescent properties of lanthanide complexes with N,N′-bis(2-hydroxy-1-naphthylidene)-1,6-hexadiimine , 2012 .

[26]  M. Nair,et al.  Synthesis, characterization, antifungal, antibacterial and DNA cleavage studies of some heterocyclic Schiff base metal complexes , 2012 .

[27]  M. M. Abd El Aziz,et al.  Mono and binuclear Ag(I), Cu(II), Zn(II) and Hg(II) complexes of a new azo-azomethine as ligand: synthesis, potentiometric, spectral and thermal studies. , 2011, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[28]  L. Modolo,et al.  Schiff bases: A short review of their antimicrobial activities , 2011 .

[29]  Samir Alghool,et al.  Synthesis, spectroscopic thermal and biological activity studies on azo-containing Schiff base dye and its Cobalt(II), Chromium(III) and Strontium(II) complexes , 2010 .

[30]  M. Rahimi‐Nasrabadi,et al.  Reaction Between Anthranilic Acids, Salicylaldehydes and Isocyanides in Water: An Efficient Synthesis of 2-{[2-(Alkylimino)-1-benzofuran-3-yliden]amino}benzoic Acids. , 2010 .

[31]  R. Zayed,et al.  Molluscicidal Activity of Some Solanum Species Extracts against the Snail Biomphalaria alexandrina , 2010, Journal of parasitology research.

[32]  Xiaoli Gao,et al.  Ternary oxovanadium(IV) complexes of ONO-donor Schiff base and polypyridyl derivatives as protein tyrosine phosphatase inhibitors: synthesis, characterization, and biological activities , 2009, JBIC Journal of Biological Inorganic Chemistry.

[33]  E. Erdem,et al.  Synthesis and characterization of azo-linked Schiff bases and their nickel(II), copper(II), and zinc(II) complexes , 2009 .

[34]  Teraze A. Youssef Reactions of chromium and molybdenum carbonyls with bis-(salicylaldehyde)-1,3-propylenediimine Schiff base , 2008 .

[35]  G. Mohamed,et al.  Synthesis, characterization and biological activity of some transition metals with Schiff base derived from 2-thiophene carboxaldehyde and aminobenzoic acid. , 2005, Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.

[36]  D. Fitzgerald,et al.  Parallel synthesis and in vitro activity of novel anthranilic hydroxamate-based inhibitors of the prostaglandin H2 synthase peroxidase activity. , 2005, Organic & biomolecular chemistry.

[37]  P. A. Vigato,et al.  The challenge of cyclic and acyclic schiff bases and related derivatives , 2004 .

[38]  Ashok Kumar,et al.  Newer N-substituted anthranilic acid derivatives as potent anti-inflammatory agents. , 2002, European journal of medicinal chemistry.

[39]  C. Lim,et al.  Tetrahedral vs Octahedral Zinc Complexes with Ligands of Biological Interest: A DFT/CDM Study , 2000 .

[40]  Y. Elerman,et al.  Keto–enol tautomerism, conformations and structure of N-(2-hydroxy-5-methylphenyl), 2-hydroxybenzaldehydeimine , 1999 .

[41]  F. Albert Cotton,et al.  Advanced Inorganic Chemistry , 1999 .

[42]  W. A. Bashir,et al.  Diazotised anthranilic acid as a reagent for the spectrophotometric determination of ethyl acetoacetate in aqueous solution , 1984 .