Review Article on Metal Complexes derived from 2’-hydroxyacetophenone based Schiff Base

Introduction

Schiff base is a compound in which imine bond is present. Schiff base as ligand have been used to formed metal complexes because of its high stability in different conditions. 2’-hydroxyacetophenone based Schiff base metal complexes shows several important biological activities, therefore we reports various studies as following:

Antimicrobial and Antibacterial Studies

Ruthenium (III) complexes of 2-hydroxyacetophenone with ethylenediamine, propylenediamine, tetramethylenediimine, orthophenylenediimineteseted for antibacterial activities against Escherichianfeacalis and S.typhi¹. Co²⁺, Ni²⁺, Cu²⁺, and Zn²⁺ complex made with the acetylacetone and para-anisidine, had higher antibacterial activity than free ligand².Cu²⁺ complex of 2-hydroxyacetophenone N (4)-methyl-4-phenylthiosemicarbazone and different amine like cyclohexyl amine/morphine/hexamethyleneimine with co-ligand , 2,2’-bipyridyl and 1,10- phenanthroline have been studied for antibacterial activities against Escherichiancoli, Staphylococcus aureus³.

Antibacterial activity of 3d-transition metals M²⁺  and UO₂^(IV) complexes of 2-hydroxy-5-methylacetophenone and glycine have been tested against EscherichianColi,Shigellaflexneri, Salmonella Typhi,Proteus vulgaris,Bacillus coagulans, Pseudomonas aeruginosa, Staphylococcus aureus, Klebsiellapneumoniae, Salmonella typhimurium, Enterococcus faecalis,Staphylococcus epidermidis, Enterobacteraerogenes⁴.

Antimicrobial studies of Co²⁺ and Cu²⁺ ions complexes of tetradentated schiff base ligand made from o-phenylenediamine and 2-hydroxyacetophenone reveals that all the synthesized complexes have higher activities against bacillus cereus, staphylococcus aureus and Escherichian Coli as compared to free ligand, whereas Co²⁺ complexes show best results than Cu²⁺complex⁵. Mixed ligand complexes of different 3d-transition metal ions with bis(4-methoxybenzylidene)-ethylenediamine (4-methoxybenzaldehyde and ethylenediamine),N,N’-bis (2-hydroxyacetophenone)-ethylenediamine(2-hydoxyacetophenone and ethylenediamine), bis(4-methoxybenzylidene)o-phenylinediamine(4-methoxybenzaldehyde and o-phenylinediamine have been studied for biocidal studies against bacillus substlisand EscherichianColi ⁶. Trinuclear Schiff base complex of Cu²⁺and Pb²⁺ ions have been made by 2-hydroxyacetophenone and 1,3-propanediamine as Schiff base ligand⁷. Mixed Schiff base ligand complexes of Cu²⁺, Ni²⁺ and Mn²⁺ions derived from 4-choloroaniline-salicylaldehyde, benzaldehyde-2-aminophenol and 4-nitroaniline-2-hydroxyacetophenone characterized. Antibacterial activity of synthesized complexes and free ligand were evaluated by paper disc technique and found that free ligands show less activities as compared to their metal (II) complexes against staphylococcus aureus, Klebshellia, EscherichianColi, bacillus substilis.Because of Electron releasing group in the Co²⁺ mixed Schiff base complexes, it’s have higher antimicrobial activity than the other metal M²⁺ mixed ligand complexes⁸.Cyclic voltammogram studied suggested that almost all the synthesized mixed ligand complexes shows redox behavior in DMF using 0.1 M Tetrabuty lammoniumperchlorate as supporting electrolute.

Different transition metal complexes of 2-hydroxyacetophenone with N,N’-dimethylethyldiamine and 4-(2-aminoethyl)morpholine have been tested for Antibacterial studies against  Acinetobacterbaumannii, Methicillin-resistant-Staphylococcus aureus, Pneumonia  and Pseudomonas aeruginosa and formed compounds not show antimicrobial activities against Klebsiella pneumonia⁹.

3-(substituted phenyl)-4-amino-5-hydrazino-1,2,4-triazole and 2-hydroxyacetophenone Schiff base and their Zn²⁺ complex have been studied forantimicrobial and bactericidal activities¹⁰. Tetradentated unsymmetrical ligand and  Mn²⁺,Co²⁺,Ni²⁺,Cu²⁺,Cr²⁺complexes derived from ethylenediamine with o-hydroxyacetophenone and Fe³⁺ complexes were synthesized with ethylenediamine with 5-chloro-2-hydroxyacetophenone, characterized by different techniques.And found that all the complexes was semiconducting in nature and homogenous phase material. Almost all the formed complexes exhibited regular octahedral geometry except Ni²⁺ complexes which is having square planner geometry and Cu²⁺ Complexes is having distorted octahedral geometry. Antimicrobial activities of unsymmetricalligand and the complexes carried out aganistStaphalococcusaureus, Bacillus subtilis,Salmonella typhimurium, Escherichia. Observation reveals that all the complexes have higher activities with their parent ligand which is explained by chelation theory¹¹.

Complexes of Co²⁺, Cr³⁺ and Fe³⁺ ions shows good antibacterial activities against selected gram positive bacterial strains and Mn²⁺,Ni²⁺ and Fe³⁺ complexes were show good resistance against Escherichia coli¹².

Mixed ligand complex of Co²⁺ ion with 5-chloro-2-hydroxyacetophenone N(4) methylthiosemicarbazone and heterocyclic base have been studies for antibiological and antioxidant activity¹³.

 Different 3d-transition metal complexes of o-hydroxyacetophenone, 5-chloro-2-hydroxyacetophenone and ethylenediamine have been tested for antimicrobial activities against Gram +ve bacteria, Gram –ve bacteria¹⁴.

Antimicrobial activity of polymeric Schiff base and it’s Mn²⁺, Co²⁺, Ni²⁺, Cu²⁺ and Zn²⁺  complexes screened against EscherichianColi,Bacillus substlis,Staphalococcusaureus, Pseudomonas aeruginosa,Salmonella typhimurium and their antifungal activity also tested against Candida albicans,MicrosporumcanisandAspergillusniger. Antimicrobial activity results showed that polymer complex of Cu²⁺ ion have higheractivity in comparisons to other formed polymer metal complexes. Cu²⁺and Zn²⁺ metal polymer complexes showed significant antifungal activity while othercomplexes showed moderate antifungal activity. Cu²⁺ complex have more activities against selected bacterial strains and fungi explained byhigher stability constant of Cu²⁺ ion causes stronger interaction with donor atoms ofSchiff base ligand, which reduced the polarity and increase lipophilic nature of Cu²⁺ ions,which favor its greater penetration through bacterial cell wall to kill the microorganismeffectively³⁰.

Mixed ligand of 2-hydroxyacetophenone and glycine aminoacid with N-donor ligands and its Cu²⁺ complexes tested for antibacterial activities against Pseudomonas aeruginosa, Klebsiellapneumoniae, Bacillus subtilis, Streptococcus pneumoniae, and Staphylococcus

aureusand found that the free ligand doesnot show any activities against the selected microbes¹⁵. Different transition metal complexes of Schiff base (o-hydroxyacetophenone and L-cystein with ethylenediamine) have been studied for antimicrobial activities and larvicidal activities against C. quinquefasciatus¹⁶.Antimicrobial studies of Co²⁺ and Cu²⁺ions complexes of tetradentated ligand made by o-phenylenediamine and 2-hydroxyacetophenone reveals that all the synthesized complexes have higher activities against bacillus cereus, staphylococcus aureus and E. Coli as compared to free ligand whereas Co²⁺ ion complex show best results than Cu²⁺ion complex¹⁷.Cu²⁺ and Ni²⁺ ions Schiff base complex of 3,5-dichloro-2-hydroxyacetophenone and 4, 5-dichloro-o-phenylenediaminestudied for antimicrobial activity against BacillusSubtilisand Pseudomonas.

N,N-dimethylethylenediaminewith 2-acetylpyridine and 2-hydroxyacetophenone schiff base and its Complexes antibacterial activity potential have been checked against Methicillin-ResistantStaphylococcus Aureus, AcinetobactorBaumannii, Pseudomonas Aeruginosa and KlebsiellaPneumonia Screened by Disc Diffusion Assay. and found that Cu²⁺ and Ni²⁺ions metalSchiff base Co-ordinated complexes shows moderate inhibition against Methicillin- ResistantS.Aureus and weak antibacterial activity against A.Baumannii,P. Aeruginosa in the disc diffusion test and then further analyzed results from MIC value showed that both the complexes were activeagainst Methicillin-Resistant Staphylococcus Aureus and have resistant to AcinetobactorBaumannii, and Pseudomonas Aeruginosa. Zinc (II) Complexes have more resistance activitythan its ligand, which is explained by chelating theory²².

Antimicrobial activity of Cu²⁺, Ni²⁺ and Zn²⁺ions complexes 3-(2-aminophenyl) quinazolin-2-methyl-4(3H)-one and 2,4-dihydroxyacetophenone have been done against Methicillin resistant S. aureus²⁵.

Study of antibacterial activities of Fe³⁺, Ni²⁺, Cd²⁺ ions schiff base complexes making with o-hydroxyacetophenone and propane -1,2-diamine reveals that Cd²⁺ and Fe³⁺ions complexes against examined human pathogenic bacteria²⁶. 

Antifungal Studies

Antifungal activities against alternariatriticina and Puccina recondite have been done on Cu²⁺ and Ni²⁺ mixed schiff base complex derived from 7-formyl-8-hydroxyquinoline, 2-hydroxyacetophenone, ethylenediamine Schiff base ligand¹⁸. Co²⁺ Schiff base complex of 2-hydroxyacetophenone and it’s N-phenyl derivative have been formed to check it’s antifungal activity against alternaria alternate,Fursariumoxysporum and Myrotheciumroridum by spore germination inhibition method¹⁹.

Tetradentated unsymmetrical Schiff base derived from ethylenediamine with o-hydroxyacetophenone and it’s Mn²⁺,Co²⁺,Ni²⁺,Cu²⁺,Cr³⁺ and Fe³⁺ ions complexes weresynthesizedbyethylenediamine with 5-chloro-2-hydroxyacetophenone,studied for antifungal activity by using potato dextrose agar medium containing starch against Aspergillusoryzae and Fusarium species¹¹.

Transition metal complexes of o-hydroxyacetophenone,5-chloro-2-hydroxyacetophenone and ethylenediamine have been also studied for antifungal activities againstAspergillusoryzaeand  Fusariumspecies^14,20.

Cytotoxicity Studies

Different transition metal complexes ofN,N’-dimethylethyldiamine and 4-(2-aminoethyl)morpholine with 2-hydroxyacetophenone have been tested for cytotoxicity on MCF-7cells⁹.

Schiff base complexes of Copper²⁺, Manganese²⁺,Nickel²⁺and Zinc²⁺ions formed by N,N-dimethylethylenediamine with 2-acetylpyridine and 2-hydroxyacetophenone in the presence of Cl^– ,N^3- and SCN^– ions were characterized by different parameters. Cytotoxicity of prepared complexes were checked against human breast cancer cell MCF-7 which revealed that prepared complexes showed very weak cytotoxicity in comparison to available anticancer drugs²².

Cu²⁺ and Co²⁺ metal ions complexes of schiff bases formed by 1, 8-diminonaphthalene with4-chloroacetophenone, 2-hydroxy-3-methoxybenzaldehyde and characterized throughphysicochemical techniques. The magnetic susceptibility data reveals paramagnetic properties of Cu²⁺ is because of one unpaired electron, formed tetrahedral or square planar geometry. Co²⁺ shows paramagnetic property is because of three lone pair and formed tetrahedral geometry. Neurotoxicial screening results revealed that schiff base ligands and its complexes were non-toxic to the neuroblastoma SH-SYSY all lines. Almost All the formed compounds enhance the growth of these cells at concentration about 1mM ²³.

Cu²⁺ ,Mn²⁺, Ni²⁺ and Zn²⁺ ions complexes with 2-hydroxyacetophenone and 4-(2-aminoethy)morpholine studied for their cytotoxicity activities on MCF-7 breast cancer cell line and WRL68 normal liver cell line²⁴.

Oxidation and Reduction properties

Oxidation reaction of cyclooctene and tetraline have been catalyzed by ruthenium (III) Schiff base complex of ethylene1,2-diamine with 2-hydroxyacetophenone²⁷.

6-(3’-N-pyrrolpropoxy)-2-hydroxyacetophenone and ethylenediamineschiff base copper (II) complex have electro-oxidation properties against methanol, ethanol and benzyl alcohol, isopropylic alcohol³².

Schiff base has been derived by the 5’-(N-methyl-N-phenylamino-methyl)-2’-hydroxyacetophenone with ethylenediamine and 5’-chloromethyl-2’-hydroxyacetophenone with N-methylaniline,Refluxing with Ni(II)acetate tertrahydrate to form catalyst for the reduction of 1-iodooctane²⁸.

Electrochemical behavior of ferrocericCu(II) Complex was also explored which formed by 5-choloromethyl-2-hydroxyacetophenone, N-ferrocenemethylaniline with 1,2-diaminoethane Schiff base³⁴.

Thermodynamic Studies

Non-symmetric (N)₃O-tetradentate Schiff base complex of Cu²⁺ ion with 2-hydroxyacetophenone,1,2-diamino-2-methylpropane and pyrrolecarboxaldehyde were synthesized for the study of kinetic template effect and Result showed that due to kinetic template effect 3d-Cu (II) ion complex is formed and no other ions were prepared²⁹.                

Polymer metal (II) complexes of Mn²⁺,Co²⁺,Ni²⁺,Cu²⁺ and Zn²⁺ metal ions synthesized with polymeric Schiff base, with formaldehydeand monomeric Schiff base of 2’- hydroxyacetophenone and o-phenylenediamine.Thermo gravimetric studies of polymeric Schiff base ligand and their complexes reveal that complexes are more thermal stable thanligand. Cu (II) complex was most thermally stable than other formed metal (II) based complexes, which Zn (II) complex also have good thermal stability³⁰.

Antioxidant properties

Mixed ligand complex of Co²⁺ ion complexes with 5-chloro-2-hydroxyacetophenone N(4)methylthiosemicarbazone and heterocyclic base (Pyridine,2,2’-bipyridine, β-picoline,1,10-phenanthroline, α-picoline)¹³ and complexes of schiff base (o-hydroxyacetophenone and L-cystein with Ethylenediamine) have been studied for antioxidant activities¹⁶. Co²⁺ and Ni²⁺ ions schiff base complexes with tryptamine and 5-methoxy-2-hydroxyacetophenone, 5-methyl-2-hydroxyacetophenone and 2-hydroxyacetophenone were also formed to check their anti-oxidant properties³¹.

Formation of different complexes of 2’hydroxyacetophenone

Via Electrosynthesis

Electrosynthesis of Cu¹⁺ ion complex with 2’-hydroxy-5’-methyl-acetophenone and triphenylphosphine have been done in CH₃CN using Pt-Cu electrode³³

With Unsymmetric or mixed Schiff bases

Tetradentate Schiff base of 2-hydroxyacetophenone and ethylenediamine react with chromium and molybdenum carbonyls to form Schiff base complex³⁵.

Unsymmetrictetradentateschiff base derived from N-(2-hydroxyacetophenone)-1-amino-2-phenyleneimine as a half part with salicylaldehyde, 2-hydroxy-1-naphthaldehyde, 2-pyrrolecarboxaldehyde and 2 –pyridinecarboxaldehyde, and their Ni²⁺ and Cu²⁺ ions complexes were synthesized and characterized by different physiochemical technique³⁶.

Chromium, Molybdenum and Ruthenium complex of biodentate 2-hydroxyacetophenone propylimine and tetradentatebis-(2-hydroxyacetophenone)ethylenediimine have been formed³⁷.

Cu (II) complexes of mixed ligand have been synthesized with conjugated heterocyclic nitrogen base i.e. 1,10-phenanthroline, N-phenyl-o-hydroxyacetophenoimine and N-phenyl-2,4-dihydroxyacetophenonimine and characterized by different physicochemical methods. The data of magnetic moments and molar conductance of suggested its monomeric and ionic nature ³⁸.

Different ligand complex of Cu²⁺ ion with salicylaldehyde-2-hydroxyacetophenone and ethylenediamine have been synthesized³⁹.

Cu²⁺and Ni²⁺ ions complexes of mixed ligand of salicyldehyde, and 2-hydroxyacetophenone with ammonia, ethylenediamine, propylenendiamine have been formed⁴⁰.

 Mixed ligand complex of Cu²⁺and Ni²⁺ions of 2-hydroxypropiophenone with salicylaldehyde or 2-hydroxy-1-naphthaldehyde have been formed⁴¹.

Cu²⁺ ion mixed ligand complex of 2-hydroxyacetophenone and acetylacetone, with ammonia, methyl amine or ethyl amine, ethylenediamine, propylenediamine have been formed⁴².

 Cu (II) mixed Schiff base complex of salicylaldehyde, ethylenediamine and 2-hydroxyacetophenone have been synthesized in the presence of H₂S gas⁴³.

With optically active schiff base Ligand

2-Hydroxyacetophenone with different chiral diamines, 1,2-diaminocyclohexane, 1,2-diphenylethylenediamine and 2,2’-diamino-1,1’-binaphtalene in different reaction condition have been formed and Tetranuclear Cu²⁺ ion schiff base complex of 2-hydroxyacetophenone and 1,3-propanediamines with adduct sodium perchlorate where 2-hydroxyacetophenone act as guest and acetonitrile solvent molecule also formed⁴⁴.

With Different Amino Acids

Schiff base complexes of Cu(II) of different hydroxyketones (2-hydroxyacetophenone, 5-methyl-2-hydroxyacetophenone5-chloro-2-hydroxy-acetophenonewith tryptamine⁴⁵and Palladium (II) and platinum (II) complex of substituted o-hydroxyacetophenone with glycine have been fomed²¹.

Mixed ligand of 2-hydroxyacetophenone and glycine aminoacid with N-donor ligands (pyridine, piperidine, pyrrolidine, hydrazine, imidazole, benzimidazole, 8-hydroxyquinoline and nicotinamide) and its Cu²⁺ ion complexes have been formed¹⁵.

Co²⁺ and Ni²⁺ ions schiff base complexes with tryptamine and 5-methoxy-2-hydroxyacetophenone,5-methyl-2-hydroxyacetophenone and 2-hydroxyacetophenone were formed ³¹.

Mixed ligand complexes of Co²⁺,Cu²⁺,Ni²⁺,Zn²⁺ and Fe²⁺ions were formed by 2-hydroxyacetophenone and tyrosine as first ligand with 4-diamethylaminobenzaldehyde and  2,4-dinitrophenylhydrazine as second ligand⁴⁶.

Cu²⁺ ion complex of 2-hydroxyacetophenone N(4)-methyl-4-phenylthiosemicarbazone and different amine like cyclohexyl amine/morphine/hexamethyleneimine with co-ligand 2,2,’-bipyridyl and 1,10-phenanthroline³.

Different transition metal complexes of 2-hydroxyacetophenone with N, N’-dimethylethyldiamine and 4-(2-aminoethyl) morpholine⁹ and Copper,Manganese,Nickeland Zinc complexes with 2-hydroxyacetophenone and 4-(2-aminoethy) morpholine have been formed²⁴.

Cu(II)mixed ligand complex of 2-hydroxyacetophenone and acetylacetone, with ammonia, methyl amine or ethyl amine, ethylenediamine, propylenendiamine have been formed⁴².

Cu²⁺ion complex of 2-hydroxyacetophenone N (4)-methyl-4-phenylthiosemicarbazone and different amine like cyclohexyl amine/morphine/hexamethyleneimine with co-ligand 2,2,’-bipyridyl and 1,10-phenanthroline have been synthesized³.

With thiosemicarbazide

Schiff base of 4-phenylthiosemicarbazide and 2-hydroxyacetophenone have been formed ⁴⁷.

X-ray diffraction studies of 2-hydroxyacetophenone N-(4)-cyclohexyl thiosemicarba zone have been done⁴⁸.

Mixed ligand complex of Co²⁺ ion complexes with 5-chloro-2-hydroxyacetophenone N(4)methylthiosemicarbazone and heterocyclic base(Pyridine,2,2’-bipyridine, 1,10-phenanthroline, α-picoline, β-picoline) have been made¹³.

Dinuclear Cu (II) complex of 2-hydroxyacetophenone-N(4)-cyclohexylthiosemicarbazone and 2-hydroxyacetophenone-N(4)phenylthiosemicarbazone have been made⁴⁹.

Formation of schiff base complex of Cu²⁺ and Ni²⁺ by amine exchange reaction between Cu²⁺ –Ni²⁺ ions solution of 2-hydroxyacetophenoimine and ethylenediamine and propylenediamine have been done⁵⁰.

With o-hydroxyacetophenoneoxime

Different transition metal(II) ion complexes of o-hydroxyacetophenoneoxime Schiff base have been made⁵¹.Some trivalent lanthanides complexes with o-hydroxyacetophenoneoxime have been studied⁵².

With Adduct

Cu (II) complex of salicylaldehyde, 1,3-propanediamine and 2-hydroxyacetophenone, with adductsodiumperchlorate have been made⁵³.Copper (II)- Manganese (II) complex of 1,3-propanediamine and 2-hydroxyacetophenone Schiff base ligand with three different polyatomic anions adduct with three different polyatomic anions adduct azide, cyanate or thiocyante have been made⁵⁴. Tetranuclear adduct of Cu (II) of 2-hydroxyacetophenone and 1,3-propanediamines Schiff base complex sodium perchlorate where 2-hydroxyacetophenone act as guest too and acetonitrile solvent molecule also in it⁵⁵. Cu (II)-Ni(II) complex and Cu(II)-Zn (II) complex of salicylaldehyde,2-hydroxyacetophenone and 1,3-propanediamine have been made with different adduct⁵⁶.

Azidobriged Cu²⁺ ion complex of di-schiff base ligand made by 2-Hydroxyacetophenone and 1, 3-propanediamine have been studied⁵⁷.

With different Metal ions

Schiff base complexes of La³⁺,Pr³⁺ and Nd³⁺ were made by o-hydroxyacetophenone with the same ratio of 2-hydroxyethylamine and 2-hydroxy-n-propylamine in benzene⁵⁸. Some trivalent lanthanides complexes with o-hydroxyacetophenoneoxime have been studied⁵².

Mg²⁺, Ca²⁺,Sr²⁺, Ba²⁺ ions complex of mixed ligand of 5-chlorosalicylaldehyde , 2-hydroxyacetophenone and/or 2-hydroxypropiophenone have been made⁵⁹.

IR spectral data of stable Schiff base complexes of uranyl (VI) complexes made with 2-hydroxyacetophenone-1, 2-diaminoethane and 2-hydroxyacetophenone-2-aminophenol reveals that N,N-bis( o-hydroxyacetophenone)1,2-diaminoethane ligand is tetradentate and o-hydroxyacetophenone-2-aminophenol ligand is tridentate⁶⁰.

UO₂ (II) and Th (IV) Schiff base complex of o-hydroxyacetophenone and o-aminoacetophenone have been studied on testicular atrophy in albino rats⁶¹.

Bis(5’-bromo-2’-hydroxyacetophenone) oxovanadium(IV) complex have been studied for spermicidal activity against human sperm⁶².

Trinuclear Schiff base complex of Cu (II) and Pb (II) have been synthesized by 2-hydroxyacetophenone and 1,3-propanediamine as Schiff base ligand⁷.Tripalladium complex of Pd(II) with 2-hydroxyacetophenone, hydrazine hydrate and propylisothiocyanate have been formed⁶³.

Nitration and Bromination Reactions of Cu (II) complexes

Nitration of the Cu²⁺ion complexes of schiff base ligand of 2-hydroxyacetophenonimine with acetylacetone, benzoylacetone,ordibenzolmethane have been done⁶⁴. Bromination and nitration of Cu²⁺ ion schiff base complexes of salicylaldehyde, 2-hydroxy-1-naphthaldehyde with ethylenediamine have been done⁶⁵.

Heterometallic Complexes

Tetra nuclear heterometallic complex of Cu (II) –Cd(II) of Schiff base 1,3-propanediamine and 2-hydroxyacetophenone have been made⁶⁶. Heterometallic Copper(II)-mercury(II) complex of schiff base ligand of 1,3-propanediamine and 2-hydroxyacetophenone have been made and structure studies done on three formed complexes (1) [(CuL-CH₃).HgCl₂ ],(2)[CuL-CH₃ )₂.HgCl₂ and (3) [CuL-CH₂ -HgCl)₂ ]⁶⁷.

Copper (II)-Nickel(II) complexes have been made in the presence of polyatomic anions adduct dicyanamide or thiocyanate with 1,3-propanediamine and 2-hydroxyacetone ligand⁶⁸.

Trinuclear Cu(II)-Co(II) complex of salicylaldehyde, 2-hydroxyacetophenone and 1,3-propanediamine adduct with dicyannamide Bridge⁶⁹.

Homo and hetero binuclear Schiff base complex of Cu²⁺– Cu²⁺ ions and Cu²⁺-Ni²⁺ions made by 3,5-dicholoro-2-hydroxyacetophenone with o-phenylenediamine and also biological activity have been checked againstStaphylococcus aureus, Bacillus and Escherichia coli, Proteus⁷⁰. Heterobinuclear Cu (II)-Ni (II) complex of 4-chloro-o-phenylenediamine and 3,5-dichloro2-hydroxyacetophenone have been made and studied for antibacterial activities against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, Bacilli and for anticancer activities on human breast cancer cell⁷¹.

Discussion

Metal complexes containing 2-hydroxyacetophenone based Schiff base have various important biological activities but still there is need to find more properties and to form new complexes.

Acknowledgments

We are thankful to Dr. Kiran Dixit, Principal, Research Center, P.M.B. Gujarati Science College, Indore and Prof.  L.S.Alawa, Principal, S.R.S. Govt. College, Sardarpur-Rajgarh, Dhar, M.P.

Conflict of Interest

There is no conflict of Interest.

References

1. Thangadurai, T. D.; Natarajan, K. Indian J. Chem.,2002, 41 A, 741-745
2. Raman, N.; Muthuraj, V.;  Ravichandran, S.;Kulandaisamy, A.Proc. Indian Acad. Sci. (Chem. Sci.), 2003, 115(3), 161–167
   CrossRef
3. Seena, E. B.; Bessy Raj, B.N.; PrathapachandraKurup,M. R.; Suresh E. J. Chem. Crystallogr., 2006, 36 (3) 189-193
   CrossRef
4. Badwaik,V.B.; Deshmukh,R.D.;Aewar,A.S. J. Coord. Chem., 2009, 62(12), 2037–2047
   CrossRef
5. Hamil. A. M.; Khalifa, K.M.; AL-Houni, A.; El-ajaily, M.M. Rasayanj.chem., 2009, 2(2),261-266
6. Thakor, Y.J.; Patel, S.G.; Patel, K.N.  J. Chem. Pharm. Res. , 2010, 2(5),518-525
7. Biswas, S.; Ghosh, A. Indian J. Chem.,2011, 50 A, 1356-1362
8. Usharani, M.; Akila, E.; Rajavel, R.  J. Chem. Pharm. Res.,2012, 4(1), 726-731
9. Gwaram, N.S.; Ali, H.M.; Saharin, S.M., Abdulla, M.A., Hassandarvish, P.; Lin, T.K.; Ching, C.L.; Ooi, C.L.J. Appl. Pharm. Sci.,2012, 2 (12), 027-038
10. Singh, A.K.; Pandey, O.P.; Sengupta, S.K. SpectrochimActa A: Mol. Biomol. Spectrosc.,2012, 85(1), 1-6
11. Maldhure, A.K.; Aswar, A.S.Am. J. PharmTech Res., 2013, 3(6), 462-486
12. Thomas,V.T.; Madhu,N.T.; Radhakrishnan,P.K. Synth. React. Met-Org. Chem., 2002, 32, 1799-1809
    CrossRef
13. Gujarathi, J. R.; Pawar, N. S.; Bendrea, R. S.J. Chem. Pharm. Res.,2013, 5(7), 161-168
14. Maldhure, A.K.; Aswar, A.S. Am. J. PharmTech Res.,2013, 3(6), 462-486
15. Pramanik, H.A.R.; Das, D.; Paul, P.C.; Mondal, P.; Bhattacharjee, C.R.  J. Mol. Struct., 2014,1059,309-319
    CrossRef
16. Saranya, J.; Lakshmi, S.S. J. Chem. Pharm. Res.,2015, 7(4), 180-186
17. Abdel, K.M.; Minas, A.; Sakina, A.; Khalid; Salman, M.I.J.S.E.A.S., 2016,2(11),162-167
18. Patel, V.K.; VasanwaIa, A.M.; Jejurkar, C.R.Indian J. Chem.,1989,28A, 719-721
19. Hothi, H.S.; Makkar, A.; Sharma, J.R.; Manrao, M.R. Eur. J. Med. Chem.,2006, 41, 253–255.
    CrossRef
20. Maldhure , A.K.; Aswar, A.S. Am. J. Pharm.Tech. Res.,2013 , 3(6), 462-483.
21. Offiong, O.E.; Nfor, E.; Ayi, A.A. Transit. Met. Chem.,2000, 25, 369-373
    CrossRef
22. Gwaram, N.S.; Ali, H.M.; Saharin, S.M.; Abdulla, M.A.; Hassandarvish, P.; Lin, T.K.; Ching, C.L.; Ooi, C. L.J. App. Pharm. Sci.,2012, 2 (10),  027-038
    CrossRef
23. Bakar, A.F.A.; Bahron, H.; Kassim, K.  Adv. Mat. Res., 2012, 554-556, 938-943
    CrossRef
24. Gwaram, N.S.; Hassandarvish, P.J. Appl. Pharm. Sci.,2014, 4 (10), 075-080
    CrossRef
25. Siddappa, K.; Mane, S.B.; Manikprabhu, D.Bioinorg. Chem. Appl.,2014, 2014, 343540, 08
26. Uddin, M.N.; Chowdhury, D.A.; Rony, M.M.A.J.C.A.,2014, 1(2), 12-18
27. Ali, O.; Mostefa, K.; Djouhra, A., Anny, J.; Christian, A.Electrochimica. Acta., 2012, 75 (30), 366-370
    CrossRef
28. Ourari, A.; Ouennoughi, Y.; Aggoun, D.; Mubarak, M.S.; Pasciak, E.M.; Peters, D.G.Polyhedron.,2014,67, 59-64
    CrossRef
29. Costes, J.P.; Fellah, F.Z.C.; Dahan, F.; Duhayon, C.Polyhedron,.2013, 52, 1065-1072
    CrossRef
30. Rasool, R.; Hasnain, S.; Nishat, N.Des. Monomers. Polym., 2014, 17(3), 217-226
    CrossRef
31. Lomari, A.A.; Ibrahim, M.M.; Mohamed, M.E. Asian J. Chem.,2016, 28(11), 2505-2511
    CrossRef
32. Ourari, A.; Aggoun, D.; Ouahab, L.Inorg. Chem. Commun.,2013, doi: 10.1016/j.inoche.2013.04.002
    CrossRef
33. Yuan, Y.; Yao, J.; Lin, C.; Zhang, Y.; Gu, R. Synth. React. Inorg. Met.-Org. Nano-Met. Chem,2005, 35 (5), 385-390
    CrossRef
34. Ouennoughi,Y.; Karce, H. E.; Aggoun, D.; Lanez, T.; Ruiz-Rosas, R., Bouzerafa, B.; Ourari, A.; Morallon, E.J. Organomet. Chem., 2017, doi: 10.1016/j.jorganchem.2017.08.016
    CrossRef
35. Ramadan, R.M.; Hamza, M.S.A.; Alp, S.A.J. Coord. Chem.,1998, 43(1), 31-39
    CrossRef
36. Lashanizadegan, M.; Boghaei, D.M.Synth. React. Inorg. Met. Org. Chem., 2000, 30(1), 89-98
    CrossRef
37. Ali, S.A.; Soliman, A.A.; Aboaly, M.M.; Ramadan, R.M.J. Coord. Chem.,2002, 55(10), 1161-1170
    CrossRef
38. Thaker, B.T.; Surati, K.R.; Patel, P.; Parmar, S.D.J. Iran. Chem. Soc.,2006, 3(4), 371-377
    CrossRef
39. Balundgi, R.H.; Chakravorty, A. Inorg. Chem.,1973, 12 (5), 981-985
    CrossRef
40. Thaker, B.T.; Bhattacharya P.K.J. inorg, nucl. Chem.,1975, 37, 615-18
    CrossRef
41. Jani, B.; Bhattacharya, P.K. Indian J. Chem., 1977, 15A, 750-752
42. Doraswamy, U.; Bhattacharya, P.K.Indian J. Chem., 1977, 15A, 129-131
43. Jani, B.; Bhattacharya, P.K. Indian J. Chem., 1979, 18A, 80-81
44. Gao, W.T.; Zheng, Z.Molecules., 2002, 7, 511-516
    CrossRef
45. Zarza, P.M.; Medina, A.; Mederos, A.; Gili, P.; Nuzez, P. Transition. Met. Chem.,1990, 15, 152-155
    CrossRef
46. El-ajaily, M. M.; Maihub, A. A.; Mahanta, U. K.; Badhei, G.; Mohapatra, R. K.; Das, P. K.Rasayan. J. Chem.,2018, 11(1), 166-174.
47. Seena, E.B.; Manoj, E.; Kurup, M.R.P.ActaCryst., 2006., C62, 0486-0488.
48. Seena, E.B.; Raj, B.N.B.; Kurup, M.R.P.; Suresh, E.J. Chem. Crystallogr.,2006, 36(3), 189–193
    CrossRef
49. Seena, E.B.; Sithambaresan, M.; Vasudevan, S.; Kurup, M.R.P.J. Chem. Sci.,2020, 132, 149
    CrossRef
50. Thaker, B.T.; Bhattayacharya, P.K. Indian J. Chem.,1979 , 17A, 371-374
    CrossRef
51. Ingle, D.B.; Khanolkar, D.D.Indian J. Chem.,1976, 14 A 596-598
    CrossRef
52. Mohan, M.; Tandon, J.P.; Gupta, N.S. Inorganica. Chimica. Acta.,1986 , 111, 187-192
    CrossRef
53. Biswas, S.; Naiya, S.; Drew, M.G.B.; Estarellas, C.; Frontera, A.; Ghosh, A. Inorganica. Chimica. Acta.,2011, 366(1), 219-226
    CrossRef
54. Biswas, S.; Naiya, S.; Garc, C.J.G.; Ghosh, A. Dalton Trans.,2012, 41, 462
    CrossRef
55. Biswasa, S.; Naiyaa, S.; Drewc, M.G.B.; Ghosha, A. J. Indian Chem. Soc.,2012, 89, 1317-1322
56. Biswas, S.; Ghosh, A.Polyhedron., 2013, 65, 322-331
    CrossRef
57. Biswas, S.; Ghosh, A.J. Mol. Struct.,2012, 1019, 32-36
    CrossRef
58. Agarwal, S.K.; Tandon, J.P.Monatsh. Chem.,1975, 106, 261-270
    CrossRef
59. Prasad, R.N.; Agrawal, M.; Sharma, M.J.Serb.Chem.Soc.,2002, 67(4), 229–234
    CrossRef
60. Sonbati, A.Z.E.; Diab, M.A.; Asmy, A.A.E.Synth. React. Inorg. Met.-Org. Chem.,1989, 19(7), 731-740
    CrossRef
61. Gudasi, K.B.; Nadagouda,G.S.; Goudar, T.R. J. Indian Chem. Soc.,2006 , 83(4), 376-378
    CrossRef
62. D’Cruz, O.J.; Dong, Y.; Uckun, M. F. Biol. Reprod.,1999, 60, 435-444
    CrossRef
63. Yadav, P. N.; Demertzis, M.A.; Demertzi, D.K.; Castineiras, A.; West, D. X.  Inorganica. Chimica. Acta.,2002, 332, 204–209.
64. Doraswamy, U.; Bhattachary, P.K.Indian. J.Chem.,1977, 15 A, 828-82.
65. Mohankumar, V.B.; Kohli, R.K.; Bhattachary, P.K.Indian. J.Chem.,1977, 15A, 1025-1027.
66. Biswas, S.; Ghosh, A.polyhedron.,2011, 30, 676-681
    CrossRef
67. Biswas, S.; Saha, R.; Ghosh, A.Organometallics.,2012, 31, 3844-3850
    CrossRef
68. Biswas, S.; Diaz, C.; Ghosh, A.Polyhedron.,2013, 51(4) , 96-101
    CrossRef
69. Biswas, S.; García, C. J. G.; Juan, J. M. C.; Benmansour, S.; Ghosh, A.Inorg. Chem.,2014, 53, 2441−2449
    CrossRef
70. Bhoopathy, R.P.A.; Malathy, M.; Jayalakshmi, R.; Rajavel, R.Int. J. Pharm. Chem. Biol. Sci., 2016, 5(2), 11-22
    CrossRef
71. Parasuraman, B.; Rajendran, J.; Rangappan, R. Orient. J. Chem., 2017, 33 (3), DOI : http://dx.doi.org/10.13005/ojc/330321
    CrossRef

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