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IJPRD, 2014; Vol 6(10):December-2014 (036 - 043)
International Standard Serial Number 0974 – 9446
-------------------------------------------------------------------------------------------------------------------------------------------------SYNTHESIS, SPECTROPHOTOMETRIC DETERMINATION AND ANTIMICROBIAL ACTIVITY OF COPPER (II) &
CHROMIUM (III) WITH SALISAL-2-THIOCARBOXYHYDRAZIDE (STCH){(Z)-1-(2-HYDROXYBENZYLIDENE)
THIOCARBONOHYDRAZIDE }
Archana Borhade*1 and Dr. Shobha Borhade1
1*
Adminstrative Officer, Director of Higher Education, Pune. Department Chemistry, S.M.B.S.T.College,
Sangamner, Maharashtra, India-422605
ABSTRACT
Thiocarboxyhydrazide has an increasing interest in the field of coordination chemistry in the formation of metal complexes. The
present paper deals with synthesis and spectrophotometric
determination of STCH. The ligand (STCH) shows absorption
spectrum at 290 nm at pH 4 and for complexes of it such as
copper (II) 380 nm & Chromium (III) 400 nm at pH 3 & 4
respectively. Beer’s law obeys upto 3 ppm for Cu (II) and upto 4
ppm for Cr (III). Sendell sensitivity for Cu (II) & Cr (III) was
0.009872 µg/cm-2 & 0.01358 µg/cm-2 In jobs continuous
variation method complexes of Cu (II) & Cr (III) with STCH, shows
M:L ratio 1:2. The elemental analysis of STCH have been done
and antimicrobial activity of local strain of klebsiella pneumonia,
shows Nil activity but its complexes such as Cu (II) shows 0.60 cm,
Cr (III) 0.60 cm. X-ray diffraction shows Octahedral
structure.Degree of dissociation, dissociation constant & stability
constant for Cu (II) was 0.0632 x 1013 , 0.0982 x 1012 & 0.08763 x
1013 and for Cr (III) 0.0781 x 1013 , 0.0877 x 1012 & 0.07913 x 1013
respectively.The change in free energy of the complex was -74.34
KJ/mole & -53.76 KJ/mole. Effect of diverse ion have been
studied.
Correspondence Author
Archana Borhade
Adminstrative Officer, Director of
Higher Education, Pune. Department
Chemistry, S.M.B.S.T.College,
Sangamner, Maharashtra,
India-422605
Email: [email protected]
Keywords-Copper(II),Chromium(III),Salisal-2-thiocarboxyhydra
zide, Spectrophotometry, Antimi crobial activity.
INTRODUCTION
Hydrazines & its derivatives constitute an
important class of compounds that has found wide
utility in organic synthesis [1,2]. It have
traditionally been employed as reagents for the
derivatization and characterization of carbonyl
compounds, N-N linkage has been used as a key
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36
International Journal of Pharmaceutical Research & Development
structural motif in various bioactive agents.
Increasing number of N-N bond-containing
heterocycles and peptidomimetics have made their
way
into
commercial
applications
as
pharmaceutical and agricultural agents [3,4].
Recently, hydrazide-hydrazones have gained great
importance due to their diverse biological
properties including antibacterial, antifungal,
anticonvulsant, anti-inflammatory, antimalarial
,antituberculosis activities [5-17]. &
anti-tumor agents [18-21]. hydrazoneHydrazides
and hydrazones are important synthons for several
transformations and have gained importance due
to their diverse biological and clinical applications
[22]. Hydrazone linkage provides a suitable system
for pH-dependent releaseof anticancer drugs from
drug-conjugates [23]. Several studies have been
devoted to the anticancer activity of
aroylhydrazone derivatives [24,25]. Hydrazone
derivatives containing an azomethine (–
CONHN=CH–) group have been shown to exhibit
antiproliferative activities and act as cytotoxic
agents with the ability to prevent cell progression
in cancerous cells through different mechanisms
[26]. The hydrazones are used as hole transporting
agents in organic layer photoconductors, as
quantitative analytical reagents, especially in
colorimetric and fluorometric determination of
metal ions [27-29]. Furthermore, some hydrazones
have also been used as herbicides, insecticides,
nematocides, rodenticides, and plant growth
regulators as well as plasticizers and stabilizers for
polymers. The metal complexes of hydrazones
have potential applications as catalysts,
luminescent probes, and molecular sensors [3032]. Isonicotinoylhydrazones are antitubercular; 4hydroxybenzoic acid[(5-nitro-2-furyl)methylene]hydrazide (nifuroxazide) is an intestinal antiseptic;
4-fluorobenzoic acid[(5-nitro-2-furyl)methylene]hydrazide [33] and 2,3,4-pentanetrione-3-[4-[[(5nitro-2furyl)methylene]hydrazino]carbonyl]phenyl]hydrazone [34]. The chemical properties of
hydrazones have been intensively studied in
several research fields because of their high
physiological activity and chelating capability
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ISSN: 0974 – 9446
[35].Several hydrazide–hydrazone derivatives
exhibited broad spectrum of biological activities
such as antimicrobial (36,37), antitubercular (3840), antidepressant (41), anticonvulsant (42),
antitumoral (43,44), analgesic, and antiinflammatory (45)activities.
Thiocarbohydrazides are an important class
of compounds which possess applications in many
fields. The chemistry of thiocarbohydrazides has
gained increased interest in both synthetic organic
chemistry and biological fields and has
considerable value in many useful applications such
as the assessment process of the threedimensional ultrastructure examination techniques
of interphase nuclei and tissues, besides their
therapeutic importance. They are also described
for use as fogging agents and are considered as
safe, storable, and cool-burning pyrotechnic
compounds for dissemination of smoke, chemical
warfare
agents.
On
the
other
hand,
thiocarbohydrazides are used in performing a
highly selective heavy metal ion adsorbent and as
complexing agents for the solvent extraction
separation methods.
Thiocarbohydrazide
derivatives
have
attracted much attention in recent years due to
their applications in the synthesis of heterocyclic
compounds [3], synthesis of transition metal
complexes [46] and in pharmacological studies
[47]. Macro cycles synthesized in the reactions of
thiocarbohydrazide with polycarbonyl compounds
and their complexes with the salts of divalent
metals are effective fungistatic agents. The
cytotoxicity
of
carbohydrazones
and
thiocarbohydrazones of some ketones is
comparable with or even exceeds the cytotoxicity
of the well-known commercial compound
melphalan [48]. Coordination properties of Schiff
Base towards metal ions have extensively
investigated due to their biological activity and
variable bonding potentialities in forming
complexes. Schiff base containing the -RC=N- group
have gained importance because of physiological
and pharmacological activities associated with
them. They constitute an interesting class of
chelating agents capable of co-coordinating with
37
International Journal of Pharmaceutical Research & Development
ISSN: 0974 – 9446
Uv-visible spectrophotometer model UV SL 164
equipped with 1 cm quartz cell is used . An Elico pH
meter LI-610 is used for the measurements. Perkin
Elimer 221 IR spectrophotometer usinf KBr pellets
techniques is used for IR studies. X-RD was taken
on PW 3710 diffractometer using CuK2 radiation
has been taken on the instrument BRUKER AC 300F
Elemental analysis and antimicrobial activity was
done in laboratory approved by Central
Government for AGMARK.
one or more metal ions giving mononuclear as well
as polynuclear metal complexes [49].
Cu(II) Schiff base complex is an ant tubercular
agent [50]. Many biologically active nitrogen
heterocycles have been synthesized by Cu (II) Schiff
base complexes mediated atom transfer radical
cyclisation [51]. The earliest investigations of the
hydrazides have been made as complexing reagent
first by Albert and Fallab [52-56] various analytical
applications were reported there after. In the
present work, we have synthesized transition metal
complexes with Schiff base derived from Salisal-2thiocarboxyhydrazide
(STCH){(Z)-1-(2hydroxybenzylidene) thiocarbonohydrazide }
Synthesis and Characterisation of STCH
Synthesis of STCH
Salisal-2-thiocarboxyhydrazide (STCH) is
synthesized by refluxing equimolar quantity of 2hydroxybenzaldehyde with thiocarboxyhydrazide in
methanol medium for 6 hours.
MATERIALS AND METHODS
The chemicals used are of analytical reagent grade.
For the spectrophotometric determination an Elico
Reaction
H
H
O
H
H
OH
N
N
H
C
N
S
N
H
H
2-hydroxybenzaldehyde
thiocarbonohydrazide
H
N
N
C
S
C
H
OH
N
H
N
H
H
(Z)-1-(2-hydroxybenzylidene)thiocarbonohydrazide
The crude product is crystallized by alcohol and
water (1:1) . The colour is yellow. The recrystallized
product has melting point is 1390C & molecular
weight by formula is 139.0
Elemental Analysis , Absorption spectra,
Infrared spectra,X-RD spectra was done.The
reagent is soluble in dimethylformamide (DMF)
alcohol etc. but soluble in water. Elemental analysis
have been done on atomic absorption / emission
spectrophotometer, 201 make Chemito and
nitrogen by kjeldah’s method, sulphur by
gravimetric method while C,H and O by carbon
analysis, oxygen analyser.
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38
International Journal of Pharmaceutical Research & Development
To an aliquote of solution containing ().1
mg/ml) metal ions of Cu(II) & Cr(III) by adding 0.5
ml of reagent and 1 ml of buffer solution of
suitable pH. Absorbance is recorded against the
reagent blank IR spectra recorded on perkin-elmer
221 READ spectrophotometer using KBr pallet
techniques.
Antimicrobial Activity :-The research on
biological activity of different metal complexes
have been greatly stimulated in 3:1 DMF + water
solution, molten medium poured in the sterile
plated and allowed to solidify. The culture of
klebsiella pneumonia spread on it. The plates
incubated
at 370 C.
RESULTS AND DISCUSSION
The ligand salisal-2-thiocarboxyhydrazide (STCH) is
yellow colour .The recrystallized product has
melting point is 1390C & molecular weight by
formula is 139.0. Elemental analysis shows % of
each element in the reagent ( STCH ) as C= 45.71 %,
H= 04.76 %, N= 26.66 %, S= 15.23 %, O= 07.161 %.
The ligand salisal-2-thiocarboxyhydrazide (STCH)
represents aromatic –O-H bond stretched at 3590
cm-1 while OH deformation at 1410 cm-1 ,C=S
stretch at 1610 cm-1 , N-H deformation at 1560 cm1
which support the structure by C-H deformation
of benzene ring at 740 cm-1 , C-H stretching first at
740 cm-1 & second at 825 cm-1 .UV & Vis spectra
measurements in UV and visible region were
recorded on elicospectrophotometer model SL-159
and the pH on elico-pH meter model. Spectra
Table : 1 XRD of STCH
No 2θ
Observed d Calculated
d
1
11.38 7.7885
7.7817
2
15.35 5.7800
5.7591
3
16.13 5.5040
5.4775
4
21.54 4.1314
4.1165
5
22.79 3.9084
3.8062
6
26.76 3.3363
3.3427
7
26.87 3.3235
3.2700
8
30.57 2.9292
2.9073
9
31.76 2.8221
2.8131
10 45.50 1.9966
1.9868
ISSN: 0974 – 9446
recorded in the region at 240 nm to 620 nm . The
absorption spectra of STCH shows absorption
maxima at 290 nm at pH 4 with molar extinction
coefficient is 6.01x 104 dm3 mole-1 . UV spectrum of
reagent indicates maximum absorption in UV
region and not in visible. Absorption spectra for
complexes of copper (II) 380 nm & Chromium (III)
400 nm at pH 3 & 4 respectively. The effect of
reagent concentration is optimized at low
concentration. The result obtained at apparent
molar absorptivity for Cu (II) & Cr (III). Beer’s law
obeys upto 3 ppm for Cu (II) and upto 4 ppm for Cr
(III). Sendell sensitivity for Cu (II) & Cr (III) was
0.009872 µg/cm-2 & 0.01358 µg/cm-2 In jobs
continuous variation method complexes of Cu (II) &
Cr (III) with STCH, shows M:L ratio 1:2. X-ray
diffraction shows good pattern ligand shows as in
table from the comparision of hkl values .It shows
Octahedral structure. The radius ratio r-/r is found
to be in between the range 0.4945 to 0.7071 which
indicates the structure is octahedral .Antimicrobial
activity of local strain of klebsiella pneumonia,
shows Nil activity but its complexes such as Cu (II)
shows 0.60 cm, Cr (III) 0.60 cm..Degree of
dissociation, dissociation constant & stability
constant for Cu (II) was 0.0632 x 1013 , 0.0982 x
1012 & 0.08763 x 1013 and for Cr (III) 0.0781 x 1013 ,
0.0877 x 1012 & 0.07913 x 1013 respectively.The
change in free energy of the complex was -74.34
KJ/mole & -53.76 KJ/mole. Effect of diverse ion
have been studied.
Sin2 θ
hkl
0.00984
0.01788
0.19763
0.03499
0.03894
0.05304
0.05907
0.07015
0.07495
0.15023
100
110
110
220
220
211
210
211
220
322
a
7.850
7.850
7.850
7.850
7.850
7.850
7.850
7.850
7.850
7.850
b
7.850
7.850
7.850
7.850
7.850
7.850
7.850
7.850
7.850
7.850
c
1.367
1.329
1.320
1.341
1.346
1.352
1.299
1.351
1.119
1.190
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International Journal of Pharmaceutical Research & Development
Table : 2 Characteristic properties of STCH
λ max
290 nm
3590-3420 cm-1
1310-1410 cm-1
Ligand
1610 cm-1
IR Spectra
1560 cm-1
740 cm-1 & 740 cm-1 1 st
845 cm-1 2nd
ISSN: 0974 – 9446
Conc.
5.74 x 104 dm3 mole-1 .
Weak O-H variable intensity sharp peak
Deformation –O-H
C=S streching
N-H deformation
Benzene ring with 4 adjacent H atoms
C-N stretching
Table : 3 Spectral properties of Cu(II) & Cr(III) complexes of STCH
Sr.No. Characteristics
Cu(II)
1
λ max
380 nm
2
pH
3
3
STCH required for max
0.4 cc
absorption
4
Beer’s law obeys upto
3 ppm
5
Sandell’s sensitivity
0.009872 µg/cm-2
6
Composition by Jobs and mole 1:2
ratio
7
Antimicrobial activity for local
0.60 cm
strain klebsiella pneumonia
8
Degree of dissociation
0.0632 x 1013
9
Dissociation constant
0.0982 x 1012
10
Stability constant
0.08763 x 1013
11
Change in free energy
-74.34 KJ/mole
Cr(III)
400 nm
4
0.3 cc
4 ppm
0.01358 µg/cm-2
1:2
0.50 cm
0.0781 x 1013
0.0877 x 1012
0.07913 x 1013
-53.76 KJ/mole
Table : 4 Effect of Diverse ion in the determination of Cu(II) & Cr(III) complexes
Sr.No Metal ion
Source of ion
Cu (II)
1
Ti (II)
TiCl2
47.62
2
Cr (II)
K2Cr2O7
26.34
3
Fe (III)
Amm. Ferrous Sulphate
23.00
4
SCN
NH4 SCN
None
5
CH3COO
CH3COONa
02.10
6
Hg (II)
HgCl2
98.54
7
Co (II)
CoSO4
59.00
8
Mg (II)
MgCl2
70.35
9
Pb (II)
Pb(NO3)2
89.15
10
Sn (II)
SnCl2
69.30
11
Citrate
Citric acid
59.00
12
Sr (II)
Sr (NO3)2
20.00
13
Ba(II)
BaCl2 2H2O
54.98
14
Ce (III)
Ce(NO3)2 6H2O
15
U(VI)
UO2 (CH3 COO)2 2H2O
45.09
Cr(III)
50.68
-----46.21
10.56
None
76.93
62.15
52.55
94.31
82.75
15.38
14.32
68.32
32.91
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40
International Journal of Pharmaceutical Research & Development
16
17
18
19
20
21
22
23
Ni (II)
Acetate
Tartrate
EDTA
Thiocyanate
Sulphate
Chloride
Bicarbonate
ISSN: 0974 – 9446
(NH4)2SO4 NiSO4 6H2O
CH3 COONH4
COOK CHOH CHOH COONa 4H2O
[CH2 N(CH2 COOH) CH2 COONa] 2H2O
NH4SCN
Na2 SO4
KCL
NaHCO3
45.30
31.56
none
58.25
15.62
11.99
52.19
none
68.14
58.02
12.01
59.01
26.01
31.05
10.99
00.34
Structure of the Complex
H
H
H
N
N
N
S
HO
N
H
C
Cu
C
H
N
S
N
N
OH
N
N
H
H
H
REFERENCES
1. Rallas S. Gulerman N. Erdeniz H, Synthesis and
antimicrobial activity of some new hydrazones
of 4-fluorobenzoic acid hydrazide and 3-acetyl2,5- disubstituted-1,3,4-oxadiazolines, Farmaco
2002; 57, 171-174.
2. Gursoy A,Terzioglu N, Otuk G, Synthesis of
some
new
hydrazide-hydrazones,
thiosemicarbazides and thiazolidinones as
possible antimicrobials, Eur. J. Med. Chem.
1997; 32, 753-757.
3. Vicini P, Zani F, Cozzini P, Doytchinova I,
Hydrazones of 1,2-benzisothiazole hydrazides:
synthesis, antimicrobial activity and QSAR
investigations, Eur. J. Med. Chem. 2002; 37,
553-564.
4. Mamolo M.G, Falagiani V, Zampieri D, Vio L,
Banfo E, Synthesis and antimycobacterial
activity of [5-(pyridin-2-yl)-1,3,4-thiadiazol-2ylthio]acetic
acid
arylidene-hydrazide
derivatives. IIFARMACO 2001; 56, 587-592.
5. Rahman V.M,Mukhtar S, Ansari W H, Lemiere
G, Synthesis, stereochemistry and biological
6.
7.
8.
9.
activity of some novel long alkyl chain
substituted thiazolidin-4-ones and thiazan-4one from 10-undecenoic acid hydrazide, Eur. J.
Med. Chem. 2005; 40, 173-184.
Dimmock
J.R, Vashishtha S.C, Stables
J.P,Anticonvulsant properties of various
acetylhydrazones, oxamoylhydrazones and
semicarbazones derived from aromatic and
unsaturated carbonyl compounds. Eur. J. Med.
Chem. 2000; 35, 241-248.
Yapia R, La Mara
M.P, Massieu
G.H,
Modifications
of
brain
glutamate
decarboxylase activity bypyridoxal phosphateglutamylhydrazone. Biochem.Pharmacol.1967;
16, 1211-1218.
Sava G, Perissin L, Lassiani L, Zabucchi G,
Antiinflammatory
action
of
hydrosolubledimethyl-triazenes
on
the
carrageen induced edema in guinea pigs. Chem.
Biol. Interac., 1985;53, 37-43.
Xia Y.L, Chuan-Dong F, Zhao B.X, Zhao J, Shin
D.S, Miaom J.Y,Synthesis and structure activity
relationships of novel 1-arylmethyl-3-aryl-1H-
Available online on www.ijprd.com
41
International Journal of Pharmaceutical Research & Development
pyrazole-5-carbohydrazide
hydrazone
derivatives as potential agents A549 lung
cancer cells. Eur. J. Med. Chem. 2008; 43,
2347-2353.
10. Melnyk P, Leroux V, Serghergert C, Grellier P,
Design, synthesis and in vitro antimalarial
activity of an acylhydrazone library. Bioorg.
Med. Chem. Lett. 2006; 16, 31-35.
11. Ajani O.O, Obafemi C.A, Nwinyi O.C, Akinpelu
D.A, Microwave assisted synthesis and
antimicrobial activity of 2- quinoxalinone-3hydrazone derivatives, Bioorg. Med. Chem.
2010; 18, 214-221.
12. Zheng L.W, Wu L.L, Zhao B.X, Dong W.L, Miao
Y.J, Synthesis of novel substituted
pyrazole-5-carbohydrazidehydrazone
derivatives and discovery of a potent apoptosis
inducer in A549 lung cancer cells,
Bioorg. Med. Chem. 2009; 17, 1957-1962.
13. Bhagavan N.V, Medical Biochemistry; Elsevier
Science B.V, Amsterdam, The Netherlands,
2002; 17, 331-363. Molecules 2011, 16 27.
14. Saulnier M.G, Velaprthi U, Zimmermann K, In
Progress In Heterocyclic Synthesis; Gribble, G,
Ed, Elsevier Science B.V, Amsterdam, The
Netherlands, 2005; 16, 228-271.
15. Short
E.I,Studies on the inactivation of
isonicotinyl acid hydrazide in normal subjects
and tuberculous patients. Tubercle 1962; 43,
33-42.
16. Holdiness M.R, A review of blood dyecrasias
induced by the antituberculosis drugs.Tubercle
1987; 68, 301-309.
17. Faroumadi
A, Kiano
Z, Soltani F,
Antituberculosis agents VIII: Synthesis and in
vitro antimycobacterial activity of alkyl -[5-(5nitro-2-thienyl)-1,3,4thiadiazole-2ylthio]acetates.Farmaco 2003; 58, 1073-1076.
18. Bokharev V.V, Ghidaspov A.A, Peresedova E.V,
Reaction of potassium salts of 2- amino-4-
ISSN: 0974 – 9446
methoxy-6-dinitro-methyl-1,3,5-triazines with
N2O4. Chem. Heterocycl. Comp. 2006; 42,
1096-1106.
19. Fernando R.P, Maia P.I, Leite S.R, Deflon V.M,
Batista A.A, Sato D.N, Franzblau S.G,Leite C.Q,
Thiosemicarbazones,
semicarbazones,
dithiocarbazates and hydrazide/hydrazone:
Anti– Mycobacterium tuberculosis activity and
cytotoxicity, Eur. J. Med. Chem. 2010; 45, 18981905.
20. Brzozowski Z, Czewski F.S, Synthesis and
antitumor activity of novel 2- amino-4-(3,5,5trimethyl-2-pyrazolino)-1,3,5-triazine
derivatives, Eur. J. Med. Chem. 2002; 37, 709720.
21. Sherif A, Rostom F, Polysubstituted pyrazoles,
part 6. Synthesis of some 1-(4-chlorophenyl)-4hydroxy-1H-pyrazol-3-carbonyl
derivatives
linked to nitrogenous heterocyclic ring systems
as potential antitumor agents. Bioorg. Med.
Chem. 2010; 18, 2767-2776.
22. Narasimhan B, Kumar P, Sharma D, Acta.
Pharm. Sci.,2010; 52, 169-180.
23. Ulbrich K, Subr V, Adv. Drug Del. Rev.,2004; 56,
1023-1050.
24. Vogel S, Kaufmann D, Pojarová M, Müller C,
Faller P, Kuhne S, Bednarski P, Angerer E,
Bioorg. Med. Chem.,2008; 16, 6436-6447
25. Liu W Y, Li H.Y, Zhao B.X, Shin D.S, Lian S, Miao
J.Y, Carbohydr. Res.,2009 ;344, 1270-1275
26. Onnis V, Cocco M.T, Fadda R,Congiu C, Bioorg.
Med. Chem.,2009; 17, 6158–6165
27. El-Sherif
A.A,Synthesis,
spectroscopic
characterization and biological activity on
newly synthesized copper(II) and nickel(II)
complexes incorporating bidentate oxygennitrogen hydrazone ligands, Inorganica Chimica
Acta, 2009; 362, 14,4991–5000.
28. Al-Hazmi
G.A,El-Asmy
A.A,
Synthesis,
spectroscopy and thermal analysis of copper (II)
Available online on www.ijprd.com
42
International Journal of Pharmaceutical Research & Development
hydrazone complexes, Journal of Coordination
Chemistry, 62 (2)337–345, 2009.
29. Sang Y.L, Lin X.L,Synthesis and crystal
structures of two Schiff-base copper (II)
complexes with antibacterial activities, Journal
of Coordination Chemistry,2010, 63( 2) 315–
322, 2010.
30. Singh M, Raghav N, Biological activities of
hydrazones: a review, International Journal of
Pharmacy and Pharmaceutical Sciences,
2011,3(4),26–32, 2011.
31. Pouralimardan O, Chamayou A.C, Janiak C,
Hosseini-Monfared H, Hydrazone Schiff basemanganese(II) complexes: synthesis, crystal
structure
and
catalytic
reactivity,
InorganicaChimicaActa, 2007, 360(5),1599–
1608.
32. Basu C, Chowdhury S, Banerjee R, Stoeckli
Evans H, Mukherjee S, A novel blue
luminescent high-spin iron(III) complex with
interlayer O-H-Cl bridging: synthesis, structure
and spectroscopic studies, Polyhedron, 2007,
26(14), 3617–3624.
33. Rollas S, Gulerman N, Erdeniz H, Synthesis and
antimicrobial activity of some new
hydrazones of 4-fluorobenzoic acid
hydrazide and 3-acetyl-2,5-disubstituted-1,3,4oxadiazolines Farmaco 2002; 57, 171174.
34. Kucukguzel S G, Rollas S,Kucukguzel I, Kiraz M,
Synthesis and Antimycobacterial activity of
some coupling products from 4-aminobenzoic
acid hydrazones. Eur. J. Med. Chem. 1999;
34,1093-1100.
35. Lindoy L.F, Livingstone S.E, Coord. Chem.
Rev.,1967, 2,173.
36. Jayabharathi J, Thangamani A, Padmavathy M,
Krishnakumar S, Med. Chem. Res., 2007; 15,
431.
ISSN: 0974 – 9446
37. Vicini P, Zani F, Cozzini P,Doytchinova I, Eur. J.
Med. Chem.,2002; 37, 553.
38. Kaymakçıoglu B.K, Rollas S, Farmaco, 2002 ; 57,
595.
39. Koçyigit-Kaymakçıoglu
B.E,Oruç-Emre
S,
Unsalan S, Rollas Med. Chem. Res., 2009; 18,
277.
40. Swamy B.N, Suma T.K, Rao V.G, Reddy G.C, Eur.
J. Med. Chem., 2007; 42, 420.
41. Ergenc N, Gunay N.S, Eur. J. Med. Chem., 1998;
33,143.
42. Ragavendran J, Sriram D, Patel S, Reddy I,
Bharathwajan N, Stables J, Eur. J. Med. Chem.,
2007; 42, 146.
43. M. El-Hawash S.A, Abdel Wahab A.E, ElDewellawy M.A, Arch. Pharm. Chem. Life. Sci.,
2006; 339, 14.
44. Zhang H, Drewe J,Tseng B, Kasibhatla S, Cai S.X,
Bioorg.Med. Chem., 2004; 12, 3649.
45. Todeschini A.R, MirandA.S, Silva C.M, Parrini
S.C, Barreiro E.J, Eur. J. Med. Chem., 1998; 33,
189.
46. Mikhailov O.V, Kazymova M.A, Shumilova T.A,
Chmutova G.A, Solovieva S.E Transition
Met.chem, Template 2005; 30:,299-304.
47. Suni M.M, Nair V.A, Joshua C.P, Tetrahedron
2001; 57, 2003-2009.
48. Talaatt I, El-Emary, Ashraf M ,Mohamed E,
Mohamed Ramadan, ARKIVOC 2009; 1, 150-197
49. Narang K.K, Rao T.R, Shrestha S, Shrestha S,
Synth. React. Inorg. Met. Org. Chem., 2000;30
(5), 931-954.
50. Lippard S.J, Bioinorganic chemistry second
edition, university science books millvalley
1994; 505-508.
51. Clerk A.J, Jones K, Tetrahedron letters 1989; 30:
5485-5489.
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