research article synthesis, characterization, and...

Hindawi Publishing CorporationInternational Journal of Inorganic ChemistryVolume 2013 Article ID 549805 6 pageshttpdxdoiorg1011552013549805

Research ArticleSynthesis Characterization and Biological Evaluation of Some3d-Metal Complexes of Schiff Base Derived from Xipamide Drug

Suman Malik1 Suparna Ghosh2 Bharti Jain3 Archana Singh1 and Mamta Bhattacharya1

1 Department of Chemistry Sadhu Vaswani College Bairagarh Bhopal 462030 India2Department of Chemistry Career College Bhopal 462023 India3 Department of Chemistry Sarojini Naidu Govt Girls Post Graduate (Autonomous) College Shivaji Nagar Bhopal 462003 India

Correspondence should be addressed to Suman Malik drsumanmalikgmailcom

Received 31 August 2012 Revised 25 October 2012 Accepted 7 November 2012

Academic Editor Alfonso Castineiras

Copyright copy 2013 Suman Malik et al This is an open access article distributed under the Creative Commons Attribution Licensewhich permits unrestricted use distribution and reproduction in any medium provided the original work is properly cited

The present paper deals with the synthesis and characterization of metal complexes of Schiff base derived from xipamide adiuretic drugThe bidentate ligand is derived from the inserted condensation of 5-aminosulfonyl-4-chloro-N-26-dimethyl phenyl-2-hydroxybenzamide (Xipamide) with salicylaldehyde in a 1 1 molar ratio Using this bidentate ligand complexes of Hg(II) Zn(II)and VO(IV) with general formulaML

2have been synthesizedThe synthesized complexes were characterized by several techniques

using molar conductance elemental analysis magnetic susceptibility FT-IR spectroscopy electronic spectra mass spectra andparticle size analysis The elemental analysis data suggest the stoichiometry to be 1 2 [M L] All the complexes are nonelectrolyticin nature as suggested bymolar conductancemeasurements Infrared spectral data indicate the coordination between the ligand andthe central metal ion through deprotonated phenolic oxygen and azomethine nitrogen atoms Spectral studies suggest tetrahedralgeometry for Hg(II) Zn(II) complexes and square pyramidal geometry for VO(IV) complex The pure drug synthesized ligandand metal complexes were screened for their antifungal activities against Aspergillus niger and Aspergillus flavus The ligand and itsHg(II) and VO(IV) complexes were screened for their diuretic activity too

1 Introduction

Coordination complexes are gaining importance in recentyears especially in the designing of long acting drugs inmetabolism The metal complexes from bidentate ligandshave often been studied recently because of their technicalapplications [1 2] and applications in enhancement of drugaction [3 4] Transition metals are essential for normalfunctioning of living organism and are therefore of greatinterest as potential drugs [5] The coordination chemistryof nitrogen donor ligands is an active area of research Agreat deal of attention in this area has been focused onthe complexes formed by 3d metals with bidentate ligandsusing both sulfur and nitrogen [6 7] The Schiff bases arean important class of ligands in coordination chemistry Thestudy of structural and binding features of various Schiff basecomplexes can play an important role in better understandingof the complex biological process Schiff bases derived fromsalicylaldehyde are well known for their interesting ligationalproperties and exclusive applications in different fields

[8ndash10] It is well known from the literature that Schiff basesderived from thiazide drugs have a strong ability to formmetal complexes [11] The interaction of these donor ligandsand metal ions gives complexes of different geometries andliterature survey reveals that these complexes are potentiallymore biologically active Thus in recent years Schiff basesand their metal complexes have attained much attractionbecause of their extensive biological activities [12 13]Keeping the above fact in our mind and in continuation ofour earlier work on transition metal complexes with Schiffbases [14 15] the ligand xipamide-salicylaldimine Schiff base(L) has been synthesized In the present paper the synthesisand characterization of the ligand and its complexes withHg(II) Zn(II) and VO(IV) are being reported

2 Experimental

All the chemicals used were of ARGR grade and purchasedfrom E-Merck (USA) Chemicals were used without any

2 International Journal of Inorganic Chemistry

Table 1 Analytical data and molar conductance values for ligand and metal complexes

S number Ligandcomplexes Elemental analysis () found (Calcd) Mpt (∘C) Color Molar conductanceΩminus1 cm2 molminus1C N S Cl M

1 L 5687 (5757) 584 (596) 691 (697) 750 (761) mdash 250 Peach mdash2 HgL2 4708 (4732) 497 (501) 548 (573) 634 (636) 1770 (1798) 241 Off-White 1323 ZnL2 5348 (5385) 564 (571) 638 (652) 701 (714) 651 (667) 218 White 1284 VOL2 5287 (5317) 579 (570) 667 (652) 709 (725) 527 (518) 242 Yellow 118

purification Xipamide drug was provided by Dishman Phar-maceuticals which was used as such for the synthesis ofligand

Elemental analyses were carried out on model 240PerkinElmer elemental analyzer at CDRI Lucknow Metalcontents were determined gravimetrically using standardmethods [16] Conductivity measurements were made inanhydrous DMF on a Systronics model 305 (India) Conduc-tivity Bridge Magnetic susceptibility measurements of thecomplexes in the solid state were determined by vibratingsample magnetometer at Centre for Advance TechnologyIndore at room temperature The electronic spectra of themetal complexes in DMF were recorded on a Perkin-ElmerUV WinLab Spectrophotometer at School of Studies inChemistry and Biochemistry Vikram University UjjainIndia The infrared spectra of the ligand and complexes wererecorded in KBr pellets using Perkin-Elmer FT-IR spec-trophotometer in the range 4000ndash400 cmminus1 at School of Stud-ies in Chemistry and Biochemistry Vikram UniversityUjjain India Particle size analysis was carried out at SICARTGujarat using laser diffraction particle size analyzer Theinstrument used was CILAS 1064LD model in the range of004ndash500120583mThemelting points of the ligand and complexeswere recorded in open capillaries on a capillary melting pointapparatus

The antifungal activities of both the ligands and theircomplexes were tested in vitro for growth inhibitory againstAspergillus niger and Aspergillus flavus by agar growth foodpoison technique [17] at different concentrations comparedwith Grisofulvin as appositive control

The diuretic activity of Hg(II) and VO(IV) complexeswere tested on white albino mice at Jawaharlal Nehru CancerHospital and Research Centre Bhopal India Mice were fedwith standard rodent pellet diet and acidified double-distilledwater The selected test compound ligand and standarddrug xipamide (XM) at a dose of 024mg suspended in05 gum acacia were administrated to animals of respectivegroup One group of animal was taken as control For themeasurement of weight of urine Whatman no 1 filter paperwas used The urine weight was recorded after two hours

21 Synthesis of the Ligand (Xipamide Salicylaldimine) Equi-molar (001M) solutions of pure drug (022 gm) and salicy-laldehyde (014mL) were separately dissolved in methanol-water mixture (1 1) and refluxed for four hours and keptfor a day Peach colour crystals of xipamide Schiff basewere formed in the reaction mixture and were filtered andwashed thoroughly with 50methanol-water mixture dried

Xipamide-salicylaldimine Schiff base

CH3

H3OH

OH

CC

COO

OH H

N NS

Cl

Figure 1 Structure of ligand

over vacuum and weighed Melting point of Schiff base wasrecorded The structure of the synthesized ligand is shown inFigure 1

22 Synthesis of Complexes For the synthesis of complexes0006M ligand solution was prepared in 50 acetone-watersolvent and refluxed for four hours with 0003M solutionof metal salts separately The refluxed solutions were keptfor some days Solid crystalline compounds appeared in thesolution whichwere filtered washedwith 50 acetone-watermixture dried and weighedMelting points of the complexeswere recorded

3 Results and Discussion

The analytical data of the complexes and their molar con-ductance values are given in Table 1 All these complexesare analyzed for 1 2 stoichiometry of the type ML

2 On the

basis of these characterizations it has been found that all thecomplexes are nonhygroscopic stable at room temperatureinsoluble in water but fairly soluble in DMSO The molarconductance values of these complexes are too low to accountfor their electrolytic behavior [18 19]

31 Spectral Studies of Ligand and Its Complexes

311 IR Spectra The characteristic vibrations and assign-ments of ligand and its complexes are described in Table 2The IR spectra of the complexes indicate that the ligandbehaves as bidentate and coordinates with metals via azome-thine nitrogen and phenolic ndashOH groups The shift of 119907C=Nto lower wave number by 30ndash40 cmminus1 in the complexesindicates that these groups are involved in complexation[20 21] The ligand shows strong band at 3386 cmminus1 dueto phenolic ndashOH group [22] This band is absent in all themetal complexes indicating the involvement of this group

International Journal of Inorganic Chemistry 3

Table 2 IR spectral data (cmminus1) of ligand and its complexes

S number Ligandcomplexes 119881NndashH 119907C=N 119881CndashO 119907C=O 119907MndashN 119907MndashO

1 C22H19N2O5ClS 3302 1639 1282 1671 mdash mdash2 C44H36N4O10Cl2S2Hg 3301 1598 1312 1669 514 6153 C44H36N4O10Cl2S2Zn 3300 1623 1288 1681 514 5804 C44H36N4O10Cl2S2VO 3300 1620 1281 1680 505 608

1172521

23053506475

1503679

2716411 980862

100

80

60

40

20

200 300 400 500 600 700 800 900

()

Figure 2 Mass spectrum of ZnL2

in complex formation [23] Moreover the shift of the 119907CndashOphenolic bands from 1282 cmminus1 in ligand to 1282ndash1312 cmminus1in the spectra of metal complexes supports the coordinationof the phenolic oxygen atom to the metal ion [24] The bandsfor 119907MndashO modes appeared in the range of 580 cmminus1ndash615 cmminus1in all the complexes [25] The presence of sharp band inthe region 503ndash514 cmminus1 in the spectra of all the complexesassigned to 119907MndashN mode [26] further support the involvementof azomethine nitrogen atom in coordination In additionto these bands VO(IV) complex exhibits the characteristicstretching frequency [27 28] for V=O at 952 cmminus1

312 Magnetic Susceptibility and Electronic Spectra Themagnetic moment obtained for the oxovanadium (IV) com-plex at room temperature is 177 BM and its electronicspectra displayed bands at 13986 17094 and 21740 cmminus1assigned for 2B

2rarr2E 2B

2rarr2B1 and 2B

2rarr2A1transi-

tions respectivelyThese values suggest the square pyramidalgeometry for VO(IV) complex [29] The Hg(II) and Zn(II)

complexes are found to be diamagnetic as expected for d10systems and may have tetrahedral geometry [30]

313 Mass Spectra The mass spectrum of [Zn(C22H18ClN2

O5S)2] as shown in Figure 2 shows a molecular ion peak at

119898119911 980 (I) due to [Zn(L)2] sdot+ which is in accordance with

the proposed formula of the complexThe other peaks at119898119911values 151 and 271 may be due to the fragments (C

9H11NO) sdot+

and [Zn(ClC6H4COH)SO

2NH] sdot+ The base peak at 119898119911 117

may be due to the zinc metal linked to the donor atoms of theligand Such type of fragmentation pattern has been reportedby many workers [31 32]

314 Particle Size Analysis To find out the maximum effi-ciency of the drugs and their metal complexes studies on theparticle size analysis are being considered very helpful [33]The bioavailability of low-solubility drug is often intrinsicallyrelated to the drug particle size Smaller particle size of thecomplexes is responsible for the enhanced solubility of thedrug [34] The results of the particle size analysis carried


CH3

CH3

SO2

SO2CH

CH

HC

3

OH

OH

C

CO

O

O

O

MH

H

N

NN

N

Cl

Cl

H3C

(a)

Structure of VOL2

CH3

CH3

SO2

SO2CH

CH

HC

3

OH

OH

C

CO

OO

O

O

VH

H

N

NN

N

Cl

Cl

H3C

(b)

Figure 3 Structure of metal complexes

Table 3 Particle sizemeasurement of pure drug ligand and itsmetalcomplexes

S number Sample code Particle size (120583m)1 XM 1122 L 9563 HgL2 6754 VOL2 645

out for the pure drug ligand and its Hg(II) and VO(IV)complexes have been recorded in Table 3These results revealthat after complexation the size of the ligand and complexesgot reduced to a considerable extent as compared to theirparent drug xipamide (XM) It is well known that smaller sizeleads to better absorption so it is concluded from our resultthat complexation enhanced the absorption and potency ofthe drug [35]

315 Antimicrobial Activity For antifungal activity the lig-and and itsmetal complexeswere screened againstAspergillusnigerand the findings are given in Table 4 These complexesshowed higher activity with 12ndash17mm inhibition than theligand which showed only 1148mm inhibition at the sameconcentration as that of the test drug However ligand

Table 4 Antimicrobial screening data of the ligand L and its metalcomplexes

S number Compoundcomplex

Antifungal zone of inhibition (in mm)A niger A flavous

1 L 1148 10382 HgL2 1576 16413 ZnL2 1345 14334 VOL2 1700 21225 Grisofulvin 1938 1822

and their complexes showed lower activity as compared tostandard drug griseofulvin with 1938mm inhibition at thesame concentration

Antifungal activity studies of ligand and its complexesagainst Aspergillus flavus showed that all the complexes with1147ndash2122mm inhibition showed higher activity than theligand which showed only 1038mm inhibition only VO(IV)complex showed higher activity than standard drug whichshowed 1822mm inhibition at the same concentration as thatof the test drug It is known that chelation tends to make theligand act as more powerful and potent antimicrobial agentthus inhibiting more of the microbes than the parent ligand[36]


Table 5 Diuretic screening data of the pure drug ligand and its metal complexes

Group Ligandcomplexes Average volume of urine (120583L) Final average (120583L)100 PM 300 PM 500 PM

I Control 11394 16722 11801 13306 plusmn 29656

II Xipamide 15566 20809 26691 21022 plusmn 55656

III L 17575 23548 28910 23344 plusmn 56702

IV HgL2 26554 28312 34312 29726 plusmn 406777

V VOL2 38666 37529 37857 38017 plusmn 5852

316 Diuretic Activity The diuretic activity of the Hg(II)and VO(IV) complexes was tested on white albino miceand recorded in Table 5 The selected test compound ligandand standard drug xipamide at a dose of 024mg suspendedin 05 gum acacia were administrated to animals of therespective group The result revealed that metal complexeshave more diuretic activity as compared to the respectiveligand and pure drug Thus it is revealed that complexationcan increase the pharmaceutical activity of the parent drug[37]

Statistical analyses were performed by using one-wayanalysis of variance ANOVA followed by GraphPad InStat 3Statistical significancewas accepted at the 5 level (119875 lt 005)TheVO(IV) complex is found to bemore significant with119875 lt0001 whereas Hg(II) complex is also found to be significantwith 119875 lt 005

4 Conclusion

The outcome of the above results confirms the stoichiometryof the complexes to be 1 2 [M L] as indicated by elemen-tal analysis and conductometric measurements IR spectrasuggest that the ligand behaves as bidentate and coordinatesto the central metal ion through azomethine nitrogen andphenolic ndashOH groupThis has been further confirmed on thebasis of NMR spectral studies Mass spectra further supportthe above stoichiometry on the basis of respective molecularmasses and fragmentation patterns Thus on the basis ofabove physicochemical and spectral studies the assignedstructures for the metal complexes are shown in Figures 3(a)and 3(b) The complexes are found to have higher biologicalactivities as compared to the respective ligand and the parentdrug that somehow justifies the purpose of the researchwork The present work will be further extended to thesynthesis of metal complexes using other biologically activemetals and evaluation of their biological activities

Acknowledgments

Theauthors gratefully acknowledge the financial support pro-vided by UGCThey are also indebted to CDRI Lucknow forproviding the facilities of elemental analysis SICART Gujratfor TGA and particle size studies IIT Chennai for massspectra and Vikram University Ujjain for recording IR andelectronic spectraThe authors are thankful to Dr N GaneshSenior Research in Charge and Scientist of Jawaharlal NehruCancer Hospital and Research Centre Bhopal India fordeveloping protocol and facilities for diuretic activity

References

[1] N Raman VMuthuraj S Ravichandran andA KulandaisamyldquoSynthesis characterisation and electrochemical behaviour ofCu(II) Co(II) Ni(II) and Zn(II) complexes derived from acety-lacetone and p-anisidine and their antimicrobial activityrdquo Jour-nal of Chemical Sciences vol 115 no 3 pp 161ndash167 2003

[2] C Briickner S J Rettig and D Dolphin ldquo2-Pyrrlythiones asmonoanionic bidentate N S- chelators synthesis andmolecularstructure of 2-pyrrlythionato complexes of Ni(II) Co(II) andHg(II)rdquo Inorganic Chemistry vol 39 pp 6100ndash6106 2000

[3] Y Prashanthi K Kiranmai Ira Kumar S Chityala and V KShivraj ldquoSpectroscopic characterization and biological activityof mixed ligand complexes of Ni(II) with 110-phenanthrolineand heterocyclic schiff basesrdquo Bioinorganic Chemistry andApplications vol 2012 Article ID 948534 8 pages 2012

[4] N Raman S J Raja J Joseph A Sakthivel and J D Raja ldquoDesi-gning synthesis spectral characterization of antimicrobial andDNA active tridentate Schiff base ligands and their complexesrdquoJournal of the Chilean Chemical Society vol 53 no 3 pp 1599ndash1604 2008

[5] E Malhotra N K Kaushik and H S Malhotra ldquoSynthesis andstudies of ionic chelates of hafnocene with guaninerdquo Indian Jou-rnal of Chemistry vol 45 no 2 pp 370ndash376 2006

[6] VMuresan L S Sbirna S Sbirna C I Lepadatu and NMure-san ldquoTransition metal complexes with a new thioamide of thedibenzofuran seriesrdquo Acta Chimica Slovenica vol 48 no 3 pp439ndash443 2001

[7] A Choudhary R Sharma M Nagar and M Mohsin ldquoTransi-tion metal complexes with N S donor ligands as syntheticantioxidants synthesis characterization and antioxidant activ-ityrdquo Journal of Enzyme Inhibition and Medicinal Chemistry vol26 no 3 pp 394ndash403 2011

[8] L Tatar D Ulku and O Atakol ldquoZinc(II) complexes of biden-tate Schiff base ligands containing methoxyphenyl and nitro-phenyl groupsrdquo Acta Crystallographica C vol 55 part 4 pp508ndash510 1999

[9] P Piotr H Adam P Krystaian B Bogemil and B Franz ldquoBio-logical properties of schiff bases and azo derivatives of phenolsrdquoCurrent Organic Chemistry vol 13 no 2 pp 124ndash148 2009

[10] F Shabani L A Saghatforoush and S Ghammamy ldquoSynthesischaracterization and anti-tumour activity of iron(III) Schiffbase complexes with unsymmetric tetradentate ligandsrdquo Bul-letin of the Chemical Society of Ethiopia vol 24 no 2 pp 193ndash199 2010

[11] C T Supuran ldquoComplexes with biologically active ligandsPart 1 Synthesis of coordination compounds of diazoxide withtransition- and main-group cationsrdquoMetal-Based Drugs vol 3no 1 pp 25ndash30 1996

[12] S Jain N K Jain and K S Pitre ldquoElectrochemical analysisof sparfloxacin in pharmaceutical formulation and biochemical


screening of its Co(II) complexrdquo Journal of Pharmaceutical andBiomedical Analysis vol 29 no 5 pp 795ndash801 2002

[13] S Chandra D Shukla and L K Gupta ldquoSynthesis andspectroscopic studies of Co(II) Ni(II) and Cu(II) complexeswithNdonor(N4)macrocyclic ligand(DSLF)rdquo Journal of IndianChemical Society vol 85 pp 800ndash806 2008

[14] S Malik S Ghosh and L Mitu ldquoComplexes of some 3d-metalswith a Schiff base derived from 5-acetamido-134-thiadiazole-2-sulphonamide and their biological activityrdquo Journal of theSerbian Chemical Society vol 76 no 10 pp 1387ndash1394 2011

[15] S Ghosh S Malik B Jain and M Gupta ldquoSynthesis spectraland pharmacological studies of some transition metal com-plexes derived from Schiff base of Acetazolamide drugrdquo Journalof Indian Chemical Society vol 89 pp 471ndash478 2012

[16] I Vogel Quantitative Inorganic Analysis Longman Green andCo London UK 1959

[17] V Kumar and R Dhakrey ldquoSynthesis and studies of somemetal chelates with phenylglyoxal-4- iminoantipyrine(PGIA)and 4-N-(m-phenoxybenzylidene) amino antipyrine [4-N-(MPB)AAP]rdquo Journal of Indian Council of Chemists vol 20 no1 pp 61ndash68 2003

[18] W J Geary ldquoThe use of conductivity measurements in organicsolvents for the characterisation of coordination compoundsrdquoCoordination Chemistry Reviews vol 7 pp 81ndash122 1971

[19] B K Kumar V Ravinder G B Swamy and S J SwamyldquoSynthesis and characterization of iron(III) cobalt(II) nickel(II) copper(II) ruthenium(II III) rhodium(III) and palla-dium(II) complexes with N-(2-carboxyphenyl)-and 2-amino-N-(2-carboxyphenyl)-benzamidesrdquo Indian Journal of ChemistryA vol 33 pp 136ndash142 1994

[20] N Bharti S S Sharma F Naqui and A Azam ldquoNew palla-dium(II) complexes of 5-nitrothiophene-2-carboxaldehyde thi-osemicarbazones synthesis spectral studies and In vitro anti-Amoebic activityrdquo Bioorganic ampMedicinal Chemistry vol 11 pp2923ndash2929 2003

[21] K Shankar R Roshni K Saravankumar P M Reddy andY Peng ldquoSynthesis of tetraaza macrocyclic PdII complexesantibacterial and catalytic studiesrdquo Journal of the Indian Chem-ical Society vol 86 no 2 pp 153ndash161 2009

[22] M L H Nair and L Sharma ldquoSynthesisspectral and thermalstudies of Cu(II) complexes of azodyes derived from 23-dimethyl-1-phenyl-4-amino-5-pyrazolonerdquo Journal of the Indi-an Chemical Society vol 86 no 2 pp 133ndash138 2009

[23] V Reddy N Patil and B R Patel ldquoSynthesis and characteri-zation of Co(II) Ni(II) and Cu(II) complexes with ON and Sdonar ligandsrdquo Journal of Indian Council of Chemists vol 23 no2 pp 1ndash3 2006

[24] VD Bhat andA Ray ldquoSynthesis characterization and electricalconductivity of polyesters polyamides and doped polymersrdquoSynthetic Metals vol 92 pp 115ndash120 1998

[25] D Prakash C Kumar S Prakash A K Gupta and K R RP Singh ldquoSynthesis spectral characterization and antimicrobialstudies of some new binuclear complexes of CuII andNiII Schiffbaserdquo Journal of Indian Chemical Society vol 86 no 12 pp1257ndash1261 2009

[26] N Raman S Esthar and C Thangaraja ldquoA new Mannich baseand its transition metal (II) complexesmdashsynthesis structuralcharacterization and electrochemical studyrdquo Journal of Chem-ical Sciences vol 116 no 4 pp 209ndash213 2004

[27] R Garg N Fahmi and R V Singh ldquoSpectral and biocidalstudies of manganese(II) dioxomolybdenum(VI) and oxo-vanadium(V) complexes with monobasic bidentate Schiff base

ligandsrdquo Journal of the Indian Chemical Society vol 86 pp 670ndash678 2009

[28] S Z Bootwala ldquoSynthesis and characterization of binuclearcomplexes of oxovanadium (IV) oxozirchonium(IV) dioxo-uranium(VI) and thorium(IV) with NN1015840-bis [(1E2E)-2-(hydroxyimino)-1-phenylethylidene] biphenyl-441015840-diaminerdquoAsian Journal of Chemistry vol 23 no 12 pp 5466ndash5470 2011

[29] M Revanasiddappa C Basavarajja T Suresh and S D AngadildquoSynthetic spectral and antimicrobial activity studies of firstrow transition metal complexes derived from lansoprazoledrugrdquo Journal of the Indian Chemical Society vol 86 pp 127ndash132 2009

[30] C A Barnes and E Bosch ldquoSynthesis and X-ray crystalstructure of a complex formed by reaction of 12-bis(21015840-pyridylethynyl)benzene and Mercury(II) Chloriderdquo Journal ofChemical Crystallographyy vol 36 no 9 pp 563ndash566 2006

[31] MMH Khalil E H Ismail G GMohamed EM Zayed andA Badr ldquoSynthesis and characterization of a novel Schiff basemetal complexes and their applications in determination of ironin different types of natural waterrdquo Open Journal of InorganicChemistry vol 2 pp 13ndash21 2012

[32] S Chandra S Parmar and Y Kumar ldquoSynthesis spectroscopicand antimicrobial studies on bivalent zinc and mercury com-plexes of 2-formylpyridine thiosemicarbazonerdquo BioinorganicChemistry and Applications vol 2009 Article ID 851316 6pages 2009

[33] T AllenParticle SizeMeasurement ChapmanampHall NewYorkNY USA 4th edition 1990

[34] R S Joseyphus and M S Nair ldquoAntibacterial and antifungalstudies on some Schiff base complexes of Zinc(II)rdquoMycobiologyvol 36 no 2 pp 93ndash98 2008

[35] K Dua M V Ramana U V Singh Sara et al ldquoInvestigationof enhancement of solubility of norfloxacin 120573-cyclodextrin inpresence of acidic solubilizing additivesrdquoCurrentDrugDeliveryvol 4 no 1 pp 21ndash25 2007

[36] MM Hania ldquoSynthesis and antibacterial activity of some tran-sitionmetal complexes of oxime semicarbazone and phenylhy-drazonerdquoE-Journal of Chemistry vol 6 supplement 1 pp S508ndashS514 2009

[37] S Biswas T Murugesan K Maiti L Ghosh M Pal and B PSaha ldquoStudy on the diuretic activity of Strychnos potatorumLinn seed extract in albino ratsrdquo Phytomedicine vol 8 no 6pp 469ndash471 2001

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Table 1 Analytical data and molar conductance values for ligand and metal complexes

S number Ligandcomplexes Elemental analysis () found (Calcd) Mpt (∘C) Color Molar conductanceΩminus1 cm2 molminus1C N S Cl M

1 L 5687 (5757) 584 (596) 691 (697) 750 (761) mdash 250 Peach mdash2 HgL2 4708 (4732) 497 (501) 548 (573) 634 (636) 1770 (1798) 241 Off-White 1323 ZnL2 5348 (5385) 564 (571) 638 (652) 701 (714) 651 (667) 218 White 1284 VOL2 5287 (5317) 579 (570) 667 (652) 709 (725) 527 (518) 242 Yellow 118

purification Xipamide drug was provided by Dishman Phar-maceuticals which was used as such for the synthesis ofligand

Elemental analyses were carried out on model 240PerkinElmer elemental analyzer at CDRI Lucknow Metalcontents were determined gravimetrically using standardmethods [16] Conductivity measurements were made inanhydrous DMF on a Systronics model 305 (India) Conduc-tivity Bridge Magnetic susceptibility measurements of thecomplexes in the solid state were determined by vibratingsample magnetometer at Centre for Advance TechnologyIndore at room temperature The electronic spectra of themetal complexes in DMF were recorded on a Perkin-ElmerUV WinLab Spectrophotometer at School of Studies inChemistry and Biochemistry Vikram University UjjainIndia The infrared spectra of the ligand and complexes wererecorded in KBr pellets using Perkin-Elmer FT-IR spec-trophotometer in the range 4000ndash400 cmminus1 at School of Stud-ies in Chemistry and Biochemistry Vikram UniversityUjjain India Particle size analysis was carried out at SICARTGujarat using laser diffraction particle size analyzer Theinstrument used was CILAS 1064LD model in the range of004ndash500120583mThemelting points of the ligand and complexeswere recorded in open capillaries on a capillary melting pointapparatus

The antifungal activities of both the ligands and theircomplexes were tested in vitro for growth inhibitory againstAspergillus niger and Aspergillus flavus by agar growth foodpoison technique [17] at different concentrations comparedwith Grisofulvin as appositive control

The diuretic activity of Hg(II) and VO(IV) complexeswere tested on white albino mice at Jawaharlal Nehru CancerHospital and Research Centre Bhopal India Mice were fedwith standard rodent pellet diet and acidified double-distilledwater The selected test compound ligand and standarddrug xipamide (XM) at a dose of 024mg suspended in05 gum acacia were administrated to animals of respectivegroup One group of animal was taken as control For themeasurement of weight of urine Whatman no 1 filter paperwas used The urine weight was recorded after two hours

21 Synthesis of the Ligand (Xipamide Salicylaldimine) Equi-molar (001M) solutions of pure drug (022 gm) and salicy-laldehyde (014mL) were separately dissolved in methanol-water mixture (1 1) and refluxed for four hours and keptfor a day Peach colour crystals of xipamide Schiff basewere formed in the reaction mixture and were filtered andwashed thoroughly with 50methanol-water mixture dried

Xipamide-salicylaldimine Schiff base

CH3

H3OH

OH

CC

COO

OH H

N NS

Cl

Figure 1 Structure of ligand

over vacuum and weighed Melting point of Schiff base wasrecorded The structure of the synthesized ligand is shown inFigure 1

22 Synthesis of Complexes For the synthesis of complexes0006M ligand solution was prepared in 50 acetone-watersolvent and refluxed for four hours with 0003M solutionof metal salts separately The refluxed solutions were keptfor some days Solid crystalline compounds appeared in thesolution whichwere filtered washedwith 50 acetone-watermixture dried and weighedMelting points of the complexeswere recorded

3 Results and Discussion

The analytical data of the complexes and their molar con-ductance values are given in Table 1 All these complexesare analyzed for 1 2 stoichiometry of the type ML

2 On the

basis of these characterizations it has been found that all thecomplexes are nonhygroscopic stable at room temperatureinsoluble in water but fairly soluble in DMSO The molarconductance values of these complexes are too low to accountfor their electrolytic behavior [18 19]

31 Spectral Studies of Ligand and Its Complexes

311 IR Spectra The characteristic vibrations and assign-ments of ligand and its complexes are described in Table 2The IR spectra of the complexes indicate that the ligandbehaves as bidentate and coordinates with metals via azome-thine nitrogen and phenolic ndashOH groups The shift of 119907C=Nto lower wave number by 30ndash40 cmminus1 in the complexesindicates that these groups are involved in complexation[20 21] The ligand shows strong band at 3386 cmminus1 dueto phenolic ndashOH group [22] This band is absent in all themetal complexes indicating the involvement of this group





1172521

23053506475

1503679

2716411 980862

100

80

60

40

20

200 300 400 500 600 700 800 900

()




2rarr2E 2B

2rarr2B1 and 2B

2rarr2A1transi-







9H11NO) sdot+






CH3

CH3

SO2

SO2CH

CH

HC

3

OH

OH

C

CO

O

O

O

MH

H

N

NN

N

Cl

Cl

H3C

(a)

Structure of VOL2

CH3

CH3

SO2

SO2CH

CH

HC

3

OH

OH

C

CO

OO

O

O

VH

H

N

NN

N

Cl

Cl

H3C

(b)















I Control 11394 16722 11801 13306 plusmn 29656


III L 17575 23548 28910 23344 plusmn 56702

IV HgL2 26554 28312 34312 29726 plusmn 406777

V VOL2 38666 37529 37857 38017 plusmn 5852



4 Conclusion


Acknowledgments


References


















































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of





1172521

23053506475

1503679

2716411 980862

100

80

60

40

20

200 300 400 500 600 700 800 900

()




2rarr2E 2B

2rarr2B1 and 2B

2rarr2A1transi-







9H11NO) sdot+






CH3

CH3

SO2

SO2CH

CH

HC

3

OH

OH

C

CO

O

O

O

MH

H

N

NN

N

Cl

Cl

H3C

(a)

Structure of VOL2

CH3

CH3

SO2

SO2CH

CH

HC

3

OH

OH

C

CO

OO

O

O

VH

H

N

NN

N

Cl

Cl

H3C

(b)















I Control 11394 16722 11801 13306 plusmn 29656


III L 17575 23548 28910 23344 plusmn 56702

IV HgL2 26554 28312 34312 29726 plusmn 406777

V VOL2 38666 37529 37857 38017 plusmn 5852



4 Conclusion


Acknowledgments


References


















































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of


CH3

CH3

SO2

SO2CH

CH

HC

3

OH

OH

C

CO

O

O

O

MH

H

N

NN

N

Cl

Cl

H3C

(a)

Structure of VOL2

CH3

CH3

SO2

SO2CH

CH

HC

3

OH

OH

C

CO

OO

O

O

VH

H

N

NN

N

Cl

Cl

H3C

(b)















I Control 11394 16722 11801 13306 plusmn 29656


III L 17575 23548 28910 23344 plusmn 56702

IV HgL2 26554 28312 34312 29726 plusmn 406777

V VOL2 38666 37529 37857 38017 plusmn 5852



4 Conclusion


Acknowledgments


References


















































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of




I Control 11394 16722 11801 13306 plusmn 29656


III L 17575 23548 28910 23344 plusmn 56702

IV HgL2 26554 28312 34312 29726 plusmn 406777

V VOL2 38666 37529 37857 38017 plusmn 5852



4 Conclusion


Acknowledgments


References


















































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of






































Journal of

Chemistry


Advances in

Physical Chemistry



Journal of

Volume 2014














Journal of

Spectroscopy



Journal of


Quantum Chemistry






CatalystsJournal of

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