May 2014 –July 2014, Vol. 4, No. 3; 1946-1964.

E- ISSN: 2249 –1929

Journal of Chemical, Biological and Physical Sciences

An International Peer Review E-3 Journal of Sciences
Available online atwww.jcbsc.org

Section A: Chemical Sciences

CODEN ( USA): JCBPAT Research Article

Schiff’s Base Ligands and Their Transition Metal

Complexes as Antimicrobial Agents
Pallavi Goel, Dinesh Kumar, Sulekh Chandra

1
Department of chemistry, SRM University, Modinagar, Ghaziabad, 201204, India
2
Department of Chemistry, Banasthali Vidyapith, Banasthali, Rajasthan-304022, India
3
Department of Chemistry, Zakir Hussain Delhi College, New Delhi-110002, India

Received: 08 July 2014; Revised: 17 July 2014; Accepted: 24 July 2014

Abstract: Schiff’s base ligands and their transition metal complexes comprise
miscellaneous therapeutically potent applications in the field of medicinal chemistry and
synthetic applications in the field of the organic and inorganic chemistry. This review
includes synthesis of Schiff’s base ligands and their transition metal complexes (Mn (II),
Cu(II), Ni(II) and Co(II) metal ions) and an appropriate balance between the broad
spectrum pharmacological profile. This study overview, collecting the most significant
strategies adopted in last few years to design promising antimicrobial transition metal
complexes of schiff’s bases which would be a help to the working scientists or
researchers in the biological field and is expected to hopefully produce analogues with
better biological profiles and with the minimal requirement to maintain the activity.

Keyword:Schiff’s baseligands, metal complexes, Biological activity, medicinal

chemistry

1946 J. Chem. Bio. Phy. Sci. Sec. A, May 2014 – July 2014; Vol.4, No.3; 1946-1964
Schiff’s … Pallavi et al.

INTRODUCTION

One of the great researchers named Hugo Schiff in the year 1864 invented Schiff’s bases. Schiff’s bases
are synthesized when condensation reaction take place between primary amine and carbonyl group
(aldehyde or ketone). Basically, a Schiff’s base (Figure 1) is a carbon-nitrogen double bond (-CH=N-,
azomethine or imine group) containing compound in which the carbonyl group (C=O) of an aldehyde or
ketone has been replaced by primary amine. The azomethine group of Schiff’s base play an important role
for showing excellent biological activities 1 .

Figure 1: Formation of Schiff’s base ligand Where R = alkyl group or aryl group

Although medicinal and biological chemistry was almost exclusively based on organic compound
Schiff’s base ligand and its transition metal complexes, during the past decades. Transition metal
complexes of Schiff’s base ligand had gain a growing interest in pharmacological field for the use as
antimicrobial agents and show good biological activities against pathogenic microorganisms 2-6 . It had
been observed with several experimental results that the metal complexes had more considerable
antimicrobial activity than their parent ligands 7-9 .
The currently available antimicrobial drugs provide the emerging microbial resistance which not only
drives the search for novel prokaryotic targets but also new molecules which inhibit the activity of drugs.
It may also represent an interesting task toward designing new antimicrobial drugs. Metal complexes of
Schiff’s base ligands also showed good anticancer activity10-11 . Many of the anticancer drugs are
multipurpose ligands12 , some of which demonstrate increased anticancer activity when used in the form of
their metal complexes13 . It had been suggested that certain forms of cancer are caused by virus.The
interaction between the metal ion and the ligand with cancer-associated viruses might signify an
important way for designing new anticancer agents 14, 15 .
There is also a possibility of inorganic metal complexes which provides the platforms for the
development of selective and potent pharmaceutical agents16-17 . A lot of research has been suggested as
per literature survey for the utilization of transition metal complexes of Schiff’s base ligands as drugs to
cure numerous diseases like carcinomas 18 , infection control, diabetes, anti-inflammatory19, lymphomas,
and neurological disorders. Transition metals show evidence of different oxidation states and can work
together with a number of negatively charged molecules. This activity of metal ions had been responsible

1947 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
Schiff’s … Pallavi et al.

for the development of metal based drugs which possess potential medicinal and pharmacological
applications20 .
Schiff’s bases containing heterocyclic scaffolds had been known to possess a broad range of biological
and medicinal activities for a long time 21 . In recent years, they are gaining significant interest in the area
of drug research22-24 and development related to their broad bioactivities such as antibacterial, antifungal25
anti-inflammatory, antioxidant26 , antiviral and anticancer activities 27 . The chemistry involved in the
formation of Schiff’s base complexes had been very well developed on account of the extensive diversity
of feasible structure for the ligands and their complexes, depending upon the presence of donor atoms. A
lot of Schiff’s bases and their transition metal complexes had been far and wide synthesized due to their
pharmaceutical and industrial applications 28 .
Recently, a number of researchers are expressing keen interest and are working in the field of
functionalizing metal complexes with biomolecules and nanomaterials for therapeutic applications. The
different routes have been used for attachment of metal complexes to different types of biomolecules and
nanomaterials. The nano-functionalized metal complexes of Schiff’s base ligands have been acted
towards targeted delivery and are used to demonstrate the broad range of opportunities and challenges of
this promising approach29-30 .
Manganese and its compounds are widely used in analytical chemistry, metallurgical processes, paint and
pigments industry and alloy industry, particularly in stainless steels. Schiff base complexes of manganese
(II) have an excellent catalytic property31 . After viewing the number of applications, it is highly
demandable and advantageous to synthesize and characterize Mn(II) complexes of Schiff’s base ligands,
which contain donor atoms (N, O, S). The transition metal complexes Mn(II), Co(II), Ni(II) and Zn(II) of
3-methoxysalicylaldehyde-2-aminobenzhydrazone had been exhibited higher antimicrobial activity than
the free Schiff’s base ligand32 .

Metal complexes of Mn(II) with a Schiff’s base ligand, which was derived from 3-Ethoxy
Salicylaldehyde and 2-(2-amino-phenyl)1-H-Benzimidazol(2-[(Z)-{(2-(1H-benzimidazole-2yl)phenyl]
imino} methyl]-6-ethoxy phenol) were synthesized. The synthesizedcomplexes were characterized by
elemental analysis, magnetic moment measurements, conductivity measurements, IR, UV-VIS, 1H
NMR, mass spectra and ESR spectral studies. Antimicrobial activity of the ligand and its Mn(II)
complexes were studied against two gram negative bacteria: E.Coli, P.flourescenceand two gram
positive bacteria: B.subitilis, S.aureus. The resulting data showed that the metal complexes were more
active than the free Schiff’s base ligand33 .
Complexes of Mn(II) had been synthesized with macrocyclic Schiff’s base ligand 2,3,9,10-tetraketo-
1,4,8,11-tetraazacycoletradecane(Figure 2). The ligand was derived by the condensation of
diethyloxalate and 1,3-diamino propane and characterized by elemental analysis, mass, IR and 1H-NMR
spectral studies. The structures of the complexes were confirmed by elemental analysis, molar
conductance, magnetic susceptibility measurements, IR, electronic and electron paramagnetic resonance
spectral studies. The molar conductance measurements of Mn(II) complexes in DMF correspond to non-
electrolyte nature. On the basis of spectral studies an octahedral geometry had been assigned. In vitro the
ligand and its metal complexes were evaluated against some fungi species i.e., F.odum, A.niger and
R.bataticola34 .

1948 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
Schiff’s … Pallavi et al.

O O
NH HN

Cl Mn Cl

NH HN
O O

Figure 2: Mn(II) complex of 2,3,9,10-tetraketo-1,4,8,11-tetraazacycoletradecane

Mn(II) complex of 5-aminosalicylicacid (Figure 3) had been synthesized and characterized by elemental
analyses, magnetic measurements, 1 H NMR, FT-IR, electronic and thermal studies. On the basis of the
above studies, the geometry of the metal complexes has been suggested. The synthesized ligand and its
Mn(II) complexes had been examined in vitro against C.albicans and A.fumigatus fungi and P.aeruginosa,
B.subtilis, E.coli, and S.aureus bacteria in order to check their antimicrobial activity. The experimental
results signify that the metal complexes had more activity than the free ligand 5- aminosalicylicacid35.

O
OH2
O O

Mn NH 2
H2 N
O O
.xH2O
OH2
O

Figure 3: Mn(II) complex of 5-aminosalicylicacid

Complexes of Mn(II) with curcumin ligand (Figure 4) had been synthesized and examined by elemental
analysis, molar conductance, magnetic susceptibility, 1 H-NMR, Infra-red, Raman, UV-Visible, EPR
spectroscopy, thermal analysis and X-ray diffraction analysis. The synthesized and its complexes were
screened for their antibacterial activitiy against E.coli, P.aeruginosa,S.aureus and B.subtilis bacteria and
fungicidal activity against C.albicans and A.flavus 36 .
Tetradentate macrocyclic ligand [1,2,5,6tetraoxo-3,4,7,8tetraaza-(1,2,3,4,5,6,7,8)tetrabenzene] (Figure 5)
and its transition metal complex of Mn(II) had been synthesized and analyzed by different spectral studies
like elemental analysis, molar conductance, NMR, mass, FT-IR, electronic and EPR. The spectral studies
FT-IR, electronic and EPR confirmed octahedral geometry for the metal complex. The LD 50 values of the
ligand and its metal complex had been screened. The antimicrobial activities also examined against

1949 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
Schiff’s … Pallavi et al.

different bacteria and plant fungi. The result was showing that macrocyclic ligand was potentially more
active towards tested microbial species than metal complex37 .

CH3
O

HO OH

CH3 O O

H 2O Mn OH2

O O CH 3

HO OH

O
H3 C

Figure 4: Mn (II) complex of curcumin

O O

N X HN
H

X H
NH N

O O

Figure 5: Mn(II) complex of 1,2,5,6tetraoxo-3,4,7,8tetraaza-(1,2,3,4,5,6,7,8)tetrabenzene

Transition metal complexes of Mn(II) with 2-acetyl thiophene thiosemicarbazone having general
composition [MnL2 X2 ] (Figure 6) had been synthesized. The ligand and its metal complexes had also
been characterized by elemental analysis, molar conductance, magnetic susceptibility, NMR, mass, IR,
UV, and EPR. The spectral studies of the ligand and complex confirms the bidentate nature of the ligand
and forms hexacoordinated Mn(II) complexes with octahedral geometry. The thermal studies shows that
Mn(II) complexes were more stable as compared to parent ligand. The mycological activities of the
complex had been examined against the plant pathogenic fungi i.e. R.bataticola, Fusariumodum, and
M.phaseolina38 .

1950 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
Schiff’s … Pallavi et al.

CH3
C
S X
N S NH2
HN
M
NH
H2N S X N
S
C
H3C

Figure 6: Mn(II) complex of 2-acetyl thiophene thiosemicarbazone

Cobalt has corrosion resistant property and because of this property, it is used in electroplating to protect
objects and give them an attractive finish. It is also widely used in alloy industries 39 . Cobalt compounds
had been used as dyeing material to color porcelain, glass, pottery, tile and enamel. Cobalt complex with
corrinoid ligands is also important biologically as cobalmins which is an essential part of vitamin B 12 40 .
The human body contains 5 mg of cobalamines. The deficiency of cobalmins causes the disease malicious
anaemia. Naturally occurring cobalt complexes involve the corrin ring system i.e.vitamin B12 41 . After
knowing all important applications, there is need to synthesis the Co complexes of Schiff’s base ligand
which may be used as biological agents.
Co(II) complexes with 1-phenyl-2,3-dimethyl-4(2-iminomethylbenzylidene)-pyrozol-5-(α-imino)-indole-
3-propionic acid (Figure 7) of general composition ML2 had been synthesized. The synthesized complex
was characterized by different spectral studies like elemental analysis, molar conductance, magnetic
susceptibility data, 1 H-NMR, IR, UV-Visible, FAB-Mass and EPR. The antimicrobial activities of
Schiff’s base ligand and its metal complex were also examined against the different agents of
microorganisms. The experimental results show that the metal complexes were more active than the free
ligand42 .
O R

Ph

Me O N N Me
N

Me N Co
N Me

N
Me N N O Me

Ph

R O

Figure 7: Co(II) complex of 1-phenyl-2,3-dimethyl-4(2-iminomethylbenzylidene)-

pyrozol-5-(α-imino)-indole-3-propionic acid

1951 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
Schiff’s … Pallavi et al.

Transition metal complex of Co(II) with benzil bis(carbohydarzone) (Figure 8) was synthesized and
studied structurally and pharmaceutically. The synthesized complex was characterized and analyzed by
different spectral studies like elemental analysis like elemental analyses, molar conductance, and
magnetic susceptibility, NMR, IR, UV-Visible, ESI mass and EPR. The biological activities of the
complex was examined against A.niger,A.brassicae and F.oxysporum fungi, which concluded that metal
free ligand had better growth inhibition power and this efficiency was positively affected by the Co(II)
complex43 .

C C
N X N

NH Co NH

C X C
HN O O NH

NH 2 NH 2

Figure 8: Co(II) complex of benzil bis(carbohydarzone), Where X = Cl- and NO3 -

Co(II) complexes of 1,10-phenanthroline (1,10-Phen) and 2-(1-(2-phenyl-hydrazono)-propan-2-

ylidene)hydrazine-carbothioamide had been synthesized. To study the synthesized complexes, different
analytical techniques were used like elemental analyses, 1 H-NMR, FT-IR, solid reflectance, molar
conductance and magnetic moment. The disc diffusion method were utilized to check the antimicro bial
activities of metal complexes against different types of bacteria like E.coli, B.subtillis, P.aeuroginosa and
S.aureus and different fungi like C.albicans, P.italicum, G.candidum and A.flavus. The results confirmed
the good antimicrobial activities of Co(II) complexes as compared to free ligand 44 .
Co(II) complexes with Schiff’s base ligand (Figure 9) were synthesized. The ligand had been prepared by
the condensation of 1,4-phenylenediamine with 5,7-dihydroxy-6-formyl-2-methylbenzopyran-4-one or 6-
formyl-7-hydroxy-5-methoxy-2-methylbenzo-pyran-4-one.The newly synthesized Co(II) complexes were
analyzed by different tools such as elemental analysis, magnetic susceptibility, molar conductance, UV -
VIS, FT-IR, , ESR and thermal analysis. Both the Co(II) complexes of the two Schiff base ligands had
been checked for antibacterial activities by using disk diffusion method against S.capitis and E.coli
whereas to check the antifungal activity A.flavus and C.albicans were utilized. The Result confirmed
better antibacterial activities of the newly synthesized complexes 45 .
Two novel Schiff’s base metal complexes of Co(II) (Figure 10) had been synthesized from 2-[(5-bromo-
2-hydroxybenzylidene)amino]pyridin-3-ol,{5-chloro-2-[(2-hydroxynaphthylidene)amino]phenyl}-phenyl
-methanone. All the synthesized compounds were characterized by various elemental and spectral
analysis i.e., FT-IR, FAB-mass, molar conductivity, electronic spectra, ESR, thermal, magnetic
susceptibility, cyclic voltammetry, electrical conductivity and XRD analyses and also tested against some
bacteria and fungi. The Schiff’s base ligand and their Co(II) complexes displayed a good activity against
the Gram-positive bacteria; S.aureusand Gram-negative bacteria; E.coliand fungi A.niger and C.albicans.

1952 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
Schiff’s … Pallavi et al.

The results showed that the metal complexes displayed better antimicrobial activity as compared to the
free ligand46 .

X
H
H C
C
N N

O
O Co
Co
O
O

N N
C
C H
H
X

Figure 9: Co(II) complexes of 1,4-phenylenediamine with 6-formyl-7-hydroxy-5-

methoxy-2-methylbenzo-pyran-4-one Where X = -OH

Br
H N

C N

O O
Co

OH2 OH2
OH2

Figure 10: Co(II) complexes of 2-[(5-bromo-2-hydroxybenzylidene)amino]pyridin-3-ol

The coordination complexes of Co(II) with the Schiff’s base ligands derived from isatin with 3-chloro-4-
floroaniline and 2-pyridinecarboxaldehyde with 4-aminoantipyrine (Figure 11)had been prepared. The
prepared compounds had been characterized by elemental analysis, molar conductance, electronic spectra,
FT-IR, FAB mass and magnetic susceptibility measurements. Both Schiff’s base ligands behaved as
bidentate and tridentate and coordinated through oxygen and nitrogen donor atoms. Schiff’s base ligands
and their metal complexes of Co(II) exhibited good activity against the bacteria species; S.aureus,
E.coliand S.fecalisand fungi A.niger, T.polysporum, C.albicans and A.flavus. The results indicated that
the metal complexes had higher antimicrobial properties as compared to the free Schiff’s base ligands47 .
Schiff’s base ligand 1-ethyl-1, 2, 3, 5, tetrahydroimidazo-quinazolin-5-one semicarbazone and its Co(II)
metal complexes (Figure 12) had been synthesized. The ligand and metal complexes were formulated on
the basis of elemental analysis, mass, IR, UV-visible, molar conductivity and magnetic susceptibility
measurements. In the light of above studies it is proposed that the ligand behaved a bidentate ligand and
coordination takes place through nitrogen of azomethine group and carbonyl oxygen of semicarbazone
1953 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
Schiff’s … Pallavi et al.

moiety. Thecomplexes were proposed octahedral geometry. Synthesized ligand and metal complexes
hadbeen screened for antimicrobial activity 48 .

H
Cl
H3C H
N

F N
N C
C N
N Cl.H2O
Co O H3C Co
O Cl2 N O
C Cl
N F

N
Cl
H

Figure 11: Co(II) complexes of isatin with 3-chloro-4-floroaniline and 2-

pyridinecarboxaldehyde with 4-aminoantipyrine

H
NH2
N C

N C N O
N C2H 5
N X Co X
N
C2H 5 N
O N C N

C N
H 2N
H

Figure 12: Co(II) complexes of 1-ethyl, 1,2,3,5, tetrahydroimidazo-quinazolin 5-one semicarbazone

Three azo group-containing Schiff base ligands, namely 1-{3-[(3-hydroxypropylimino) methyl]-4-

hydroxyphenylazo}-4-nitrobenzene, 1-{3-[(3-hydroxypropylimino)methyl]-4-hydroxyphenylazo}-2-
chloro-4-nitrobenzene and 1-{3-[(3-hydroxypropylimino) methyl]-4-hydroxyphenylazo}-4-chloro-3-
nitrobenzene were prepared. The ligands were characterized by elemental analysis, FT-IR spectroscopy,
UV-Vis, 13 C-NMR, 1 H-NMR spectroscopy and thermogravimetric analysis. The synthesized metal
complexes of Co(II) were synthesized and characterized by the physicochemical methods elemental
analysis, FTIR spectroscopy, UV-Vis spectroscopy, magnetic moment measurements, and
thermogravimetric analysis (TGA) and DSC. Schiff’s base ligands and their Co(II) complex were
evaluated for their biological inhibition against tested microorganisms49 .
A large number of Ni(II) complexes of biological nature, for example amino acids (glycine, α- alanine, β-
alanine, L-valine, serine, histidine etc), amino acid derivatives (peptides proteins and enzymes),
carbohydrates had already been reported. Nickel is one of the most toxic transition metals showing the
toxicity even in low doses to both ainimals and plants 50 . Issues of nasal and lung cancers have been
reported from the nickel refining industry. Nickel is found to exist in both the crystalline and amorphous

1954 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
Schiff’s … Pallavi et al.

state, out of which crystalline nickel compounds are carcinogenic while amorphous ones are weak or non-
carcinogenic51 . Considering such a large number of applications of Ni(II) complexes in biological
systems, it is highly demandable to prepare and analyze the nickel(II) complexes with Schiff’s base
ligands.
Ni (II) complexes were synthesized by the condensation of metal salts with semicarbazone /
thiosemicarbazone derived from p-dimethylaminobanzaldehyde. The general composition of the complex
was [NiL2 ]X2 ,where X = Cl- , NO3 - The metal complexes were characterized by elemental analysis,
magnetic susceptibility, molar conductance, IR and AAS studies. The Schiff bases and their metal
complexes were tested for their antibacterial and antioxidant activities52 .
A novel transition metal complexes of Ni(II) had been synthesized with three different Schiff’s base
ligands (Figure 13).. The ligands were prepared by condensation reaction of 3-amino-1H-1,2,4-triazole
with pyrrol-2-carboxaldehyde, 4-bromo-thiophene-2-carboxaldehyde, and 5-iodo-2-hydroxy
benzaldehyde. To confirm the structure of all the complexes different techniques like analytical, physical
and spectral methods were adopted. All the newly synthesized complexes were in vitro studied for
antimicrobial activities. The antibacterial activities were checked against four different Gram-negative
i.e., E.coli, S.sonnei, P.aeruginosa and S.typhi and two Gram-positive i.e., B.subtilis and S.aureus
bacterial species. The agar-well diffusion method is employed to check antifungal activity against fungal
species i.e., T.longifusus, C.albicans, A.flavus, M.canis, F.solani and C.glabrata. All the newly
synthesized complexes showed good antibacterial activity against one or more bacterial species. The
analyzed data revealed that the Ni(II) metal complexes showed higher activity than the parent ligands due
to complexation53 .

Figure 13: Ni(II) complexes of 3-amino-1H-1,2,4-triazole with pyrrol-2-carboxaldehyde

(1), 4-bromo-thiophene-2-carboxaldehyde (2), and 5-iodo-2-hydroxy benzaldehyde (3)
where M = Ni (II)
1955 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
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Ni(II) complex with novel ligand N,N′-bis(4-chlorobenzylidene)benzene-1,2-diamine (Figure 14) having

general formula [NiL(ox)]Cl2 (where ox = C2 O4 2 − ) had been synthesized. The ligand and its metal
complexes were analyzed by micro-analytical data, magnetic moment, molar conductance, 1 H-NMR, UV-
Visible, FT-IR, 13 C-NMR and EPR spectroscopic studies. The ligand and metal complex were tested for
their antimicrobial activity and their MIC values suggested that the complex had better activity as
compared to novel ligand and standard antibacterial (ciprofloxacin) and antifungal drugs (fluconazole) 54 .

N O
O

Ni
Cl 2

N
O
O

Figure 14: Ni(II) complex of N,N′-bis(4-chlorobenzylidene)benzene-1,2-diamine

A new Ni(II) complex had been synthesized with 3,4,8,9 tetraoxo-2,5,7,10 tetraaza-1,6dithio-
(3,4,8,9)dipyridinedodecane (Figure 15), having general composition [Ni(L)]X2 [where X = NO3 −, Cl−,
SO4 2−, CH3 COO−]. The ligand was hexadentate in nature. The newly synthesized complexes of
macrocyclic ligand were characterized by elemental method, molar conductance, electronic, EPR spectral,
mass, NMR, FT-IR, molecular modeling and thermal studies. The antimicrobial inhibition and MIC
values of the ligand and its metal complex had been screened against different species of bacteria and
fungi. As per the experimental results, the metal complexes showed better antibacterial and antifungal as
compared to parent ligand55 .

O O
C
C N N C
H H

N Ni N X2

H H
C N N C
C
O O

Figure 15: Ni(II) complex of 3,4,8,9 tetraoxo-2,5,7,10 tetraaza-1,6dithio-(3,4,8,9)dipyridinedodecane

1956 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
Schiff’s … Pallavi et al.

Schiff’s base ligand, 4-hydroxy-3-(1-(arylimino)ethyl)chromen-2-oneand its Ni(II) complexes (Figure

16) were synthesized by condensation. The ligand and the complexes were characterized by IR, 1 H-NMR,
13
C-NMR and mass spectral analysis. In vitro biological screening effects of the synthesized compounds
were tested by Agar cup method against the bacterial species S.aureus, E.coli, S.typhi and B.subtilis. The
poison food method had been employed to check antifungal activities against the fungal species A.niger,
P.chrysogenum, F.moneliforme and A.flavus. The experimental studies indicated that the Ni(II)
complexes exhibit higher antimicrobial activity than the free ligand56 .

O H 2O Ar CH3

N
O
O Ni
O
O
N

H3C H 2O
Ar O

Figure 16: Ni(II) complex of 4-hydroxy-3-(1-(arylimino)ethyl)chromen-2-one

Copper with chelating ligands forms coordination compounds. Copper(II) exists as [Cu(H2 O)6]2+ in
aqueous solution. Cu(II) complex exhibits the fastest water exchange rate for any transition metal aqua
complex. In recent years, a lot of research had been carried out to study the applications of copper
containing coordination complexes in various fields like medicinal, bioinorganic chemistry, catalyst,
analytical chemistry and many other industries 57-58 . Copper metal complexes with three different ligands
i.e.,4-phenyl-2,6-di(thiazole-2-yl)pyridine,4-(anthracen-9-yl)-2,6-di(thiazole-2-yl)pyridine,4-(benzofuran-
-2-yl)-2,6-di(thiazole-2-yl) had been prepared and analyzed. On the basis of elemental analysis and
spectral studies, the metal complexes had general composition [Cu(L)Cl2 ]. The synthesized metal
complexes also screened for their biological activity. The metal complexes displayed good activity
against tested microorganism59 . A number of water soluble copper(II) metal complexes of the general
composition [Cu(L)Cl] and [Cu(L’)Cl2 ] had been synthesized, where L is 2-(2-(1H-benzimidazol-2-
yl)ethyliminomethyl)phenol and 2-(2-(1H-benzimidazol-2-yl)-ethyliminomethyl)-4-methylphenol and L’
is(2-pyridin-2-yl-ethyl)pyridin-2-ylmethyleneamine,2-(1H-benzimidazol-2-yl)ethylpyridin-2-ylmethylene
amine,2-(1H-benzimidazol-2-yl)ethyl(1H-imidazol-2-lmethylene)amine and 2-(1H-benz imidazol-2-
yl)ethyl-(4,4a-dihydroquinolin-2-ylmethylene)amine. All the synthesized complexes with ligands were
characterized by different analytical and spectral techniques like elemental analysis, electronic absorption,
mass, IR and EPR. All the complexes were found to have incredible cytotoxic properties against the
HBL-100 human breast cancer cell line with potency more than that of the widely used drug cisplatin and
hence they had the potential to act as promising anticancer drugs. Interestingly, they were nontoxic to
normal cell lymphocytes isolated from human blood samples, revealing that they were selective in killing
only the cancer cells60 .

1957 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
Schiff’s … Pallavi et al.

Schiff’s base ligands were synthesized by the condensation reaction between 4,6-diacetylresorcinol with
3-hydrazino-5,6-diphenyl-1,2,4-triazine and isatin monohydrazone, respectively. The structures of the
ligands were elucidated by elemental analyses, IR, 1 H-NMR, electronic and mass spectra. Metal complex
of copper(II) (Figure 17) with Schiff’s base ligands were also synthesized. The mixed metal complex was
derived by reaction between synthesized ligands and Cu(II) ion in the presence of a secondary ligand [8-
hydroxyquinoline, 1,10-phenanthroline or benzoylacetone]. The newly synthesized mixed metal
complexes had been characterized by various analytical and spectroscopic techniques such as elemental
analysis, thermal analysis, molar conductivity, magnetic moment susceptibility, mass, IR, electronic and
ESR. The ligands and metal complexes exhibited significant antimicrobial property61 .

CH3
H
Ph N N COCH 3
N 1.5 H2O
OH 2
Cu
N
O
Ph N OH
O O

CH 3

Figure 17: Cu(II) complex of 4,6-diacetylresorcinol with 3-hydrazino-5,6-diphenyl-

1,2,4-triazine and isatin monohydrazone

Schiff’s base ligand was synthesized by the condensation of 4-aminoantipyrine with furfural and amino
acid. Cu(II) metal complex (Figure 18) of synthesized Schiff’s base ligand was also synthesized.
Structural features of ligand and metal complex were obtained from the analytical and spectral
techniques. The in vitro antibacterial and antifungal assay suggested that Cu(II) complex was good
antimicrobial agents against tested pathogens 62 .

Figure 18: Cu(II) complex of 4-aminoantipyrine with furfural and amino acid

1958 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
Schiff’s … Pallavi et al.

Schiff base ligands, derived from the condensation of 2-aminobenzenthiol with monoacetyl ferrocene in
the molar ratio 1:1 or in the molar ratio 1:2 for diacetyl ferocine had been derived. The chelation of the
ligands to metal ions took place through the sulphur atom of the thiol group and the nitrogen atoms of the
azomethine group. The chemical structures of ligands were identified by elemental analysis, IR, UV-
visible spectra, and 1 H-NMR spectra. Complexes were analysed by elemental analyses, IR, electronic
spectra, 1H-NMR as well as the magnetic susceptibility and conductivity measurement. The metal
complexes displayed different geometrical arrangements such as octahedral and square pyramidal
coordination. Schiff’s base ligands and their metal complexes were tested against two pathogenic bacteria
and fungi to study their biological activity. All the complexes exhibit antibacterial and antifungal
activities against tested organisms 63 .
Schiff’s base ligand containing 4-methoxy or 4-ethoxy thiosemicarbazone moieties and their transition
metal complexes with Cu(II) (Figure 19) were synthesized and characterized using 1 H-NMR, 13C-NMR,
HMQC, Mass, IR and UV-visible spectroscopy, elemental analysis, and magnetic susceptibility
measurements. The antimicrobial activity was also examined. Synthesized ligand and its metal complexes
exhibited good inhibition against certain bacteria and yeasts. Some of them were comparatively higher or
equipotent to the standard antibiotic and antifungal drugs. Some compounds showed moderate
antibacterial and antifungal activity 64 .

O H O
H H
H3C H H N N H H CH3
N N N N
O N N O
Cu
S S
N N

O H O

Figure 19: Cu(II) complex of 4-methoxy thiosemicarbazone

Cu(II) complexes (Figure 20) had been synthesized with a Schiff’s base ligand (1,4,5,7,10,11,12,15
octaaza,5,11,16,18-tetraphenyl, 3,4,12,13-tetramethyl cyclooctadecane) (L) derived from Schiff base
(obtained by the condensation of 4-aminoantipyrine and dibenzoylmethane) and ethylenediamine. The
chemical structure of the ligand was investigated by using various techniques i.e., elemental analysis, IR,
1
H-NMR, Mass and molecular modeling where as the coordination mode and geometry of the complexes
were confirmed by elemental analysis, molar conductivity, magnetic susceptibility, IR, electronic and
EPR spectral studies. On the basis of studies, the general composition of the complex was [Cu(L)Cl2 ].
The complex was non-electrolyte in nature. The ligand and its metal complex had shown antifungal
activity with their LD50 values determined by probit analysis against two economically important fungal
plant pathogens i.e. M.phaseolina and F.solani65.

1959 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
Schiff’s … Pallavi et al.

H2
C CH2 C C

H3C N Cl N CH3

Cu

H3C Cl CH3
N N N N

(CH2)2

Figure 20: Cu(II) complex of 1,4,5,7,10,11,12,15 octaaza,5,11,16,18-tetraphenyl,

3,4,12,13-tetramethyl cyclooctadecane

Tetraaza macrocyclic Cu(II) complexes (Figure 21) of composition [CuLX2 ] (where L = N4 donor
macrocyclic ligands) and (X = Cl−, NO3 −) had been synthesized and characterized by elemental analysis,
magnetic moments, IR, EPR, mass, electronic spectra and thermal studies. The biological activity of all
the complexes against gram-positive and gram-negative bacteria was compared with the activity of
existing standard antibacterial drugs like Linezolid and Cefaclor. Metal complexes were found to be most
potent against both gram-positive as well as gram-negative bacteria due to the presence of thio group in
the parent ligands66 .
O

HN NH
N Cl N

Cu

N Cl N
NH HN

Figure 21: Cu(II) complex of Tetraaza macrocyclic ligand

Cu(II) complex of Schiff’s base ligand had been synthesized, which was derived from o- hydroxy
benzaldehyde and 2-amino pyridine. The ligand and the complex were characterized by elemental
analysis, molar conductance, magnetic susceptibility, electronic spectra, IR and ESR spectroscopy. On the
basis of electronic spectral analysis and magnetic susceptibility values, geometry of complex was
proposed to be octahedral. The molar conductivity data of complex suggested non-electrolytic nature. The
ligand and metal complexes had been screened for microbiological activity67.

1960 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.
Schiff’s … Pallavi et al.

C
N
N

O Cu
O

N
N
C

Figure 22: Cu(II) complex of o- hydroxy benzaldehyde with 2-amino pyridine

According to the literature survey and researchers, it may be concluded that there is a great diversity to
synthesize novel transition metal complexes based on the choice of ligands. In view of its med icinal use
much concern is focused on Schiff base ligands due to the presence of donor atoms. So there is broad
scope for undertaking a well-organized study of coordination complexes of transition metals with variety
of Schiff’s base ligands.
CONCLUSION

The paper concludes that the Schiff’s base ligands and their transition metal complexes contribute diverse
therapeutically potent applications along with less economical, harmless and environmental friendly. It
reflects with careful investigation that a new strategy or new route can be developed to synthesize
medicinally potent new drug molecules. Also these heterocycles plays important and great potentials in
the field of the organic chemistry, inorganic chemistry as well as medicinal chemistry. These are
considered as magic moieties which not only possess almost all types of biological activities but also have
wide diversity in the biological profile which is the base to explore these Schiff’s base ligands and their
transition metal complexes to their multiple potentials against several activities.

ACKNOWLEDGMENTS

Author is thankful to Dr. (Prof) Manoj Kumar Pandey, Director and Dr S. Viswanathan, Administrative
Officer, SRM University, Modinagar for providing facilities and my Supervisor as well as co-supervisor
who always encourages, guide me throughout this work.

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Corresponding author: Pallavi Goel; 1 Department of chemistry, SRM University,

Modinagar, Ghaziabad, 201204, India

1964 J. Chem. Bio. Phy. Sci. Sec. A, May 2014-July 2014; Vol.4, No.3; 1946-1964.