Jamonline / 2(3); 2012 / 251262 Research Article

Mangesh Gharpure et al

Journal of Atoms and Molecules

An International Online Journal
ISSN 2277 1247

SYNTHESIS AND BIOLOGICAL EVALUATION OF VANADIUM (IV) COMPLEXES OF 3 HYDROXY FLAVONES Mangesh Gharpure1*, Ratiram Chaudhari2, Harjeet Juneja1, Vishwas Ingle1
1

Department of Chemistry, Rashtrasant Tukadoji Maharaj Nagpur University, Nagpur-440033, India 2 Department of Chemistry, S. K. Porwal College Kamptee, Maharashtra, India Revised on: 10-06-2012 Accepted on: 18062012

Received on: 29-05-2012 Abstract:

Vanadium complexes of 3-Hydroxy flavones have been synthesized using 3-Hydroxy flavones and vanadyl acetylacetonate in the stiochiometric ratio 2:1. Their structures have been established on the basis of elemental, spectral analysis (UV, IR, 1H NMR), and mass spectrometry. The synthesized compounds were tested for antimicrobial activity by cup plate diffusion method. The results indicate the enhanced activity of metal complexes over the parent ligands. Key Words: Flavones, vanadium, antibacterial, antitubercular activity and microwave. Introduction: Flavonoids represent one of the largest groups of natural products. In addition to the various * Corresponding author Mangesh Gharpure, Email: mangesh.gharpure@gmail.com Tel: +91 9921256452 functions of flavonoids in plants, their widespread distribution in nature, their

structural variability, their relatively low toxicity, and their antioxidant activities have increased the interest in flavonoids as beneficial for human health. Several

therapeutically interesting biological activities of certain flavonoids have been reported including antibacterial[1], antiviral, antiinflammatory[2,3], antithrombotic[5], antiallergic[4], antimutagenic,

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Jamonline / 2(3); 2012 / 251262 antineoplastic[6], neuroprotective properties[7], and antioxidant properties[8-11], etc. The biological activity of flavones can be

Mangesh Gharpure et al oxovanadium (IV) ion[17-19] and as a result a series of oxovanadium (IV) complexes with various flavonoid ligands have been

modified upon formation of metal complexes. Many biologically active compounds used as drugs possess modified pharmacological and toxicological potentials when administered in the form of metal-based compounds. Many metallic elements play a crucial role in living systems. A characteristic of metals is that they easily lose electrons from the familiar elemental or metallic state to form positively charged ions, which tend to be soluble in biological fluids. It is in this cationic form that metals play their role in biology. Whereas metal ions are electron deficient, most biological molecules such as proteins and DNA are electron rich. The attraction of these opposing charges leads to a general tendency for metal ions to bind and interact with biological important molecules. trace Vanadium for is an

investigated as potential anti-diabetes drugs as well as for their antitumor and osteogenic activities[20,21]. To further explore the clinical significances of flavones, we have undertaken a task to synthesize and use them as a potential candidate for metal complexation with vanadium with the hope that these compounds would potentially smart down mechanism of bacterial resistance. The newly synthesized flavones (4a-l) and their vanadium metal complexes[22,23] (5a-l) were characterized by elemental, spectral analysis (IR, 1H NMR) and mass spectrometry. The synthesized ligand and vanadium metal chelates have been screened for in vitro antibacterial activity against Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Pseudomonas aeruginosa and antifungal

element

different

activity against Aspergillus niger and Candida albicans strains. Materials and Methods: Experimental All the chemicals and solvents were obtained from Merck (LR grade) and were used without further purification. Melting points were taken in an open capillary tube and are uncorrected. The microwave assisted

organisms, and is present in almost all mammalian tissue. The coordination

chemistry of vanadium has been receiving increasing interest since it was found to be beneficial in various biological systems. Moreover, the flavonoid chelated compounds are more effective free radical scavengers than flavonoids alone[12-14]. It was also observed that some flavonoids possess

insulin-mimetic activity based on their antihyperglycemic effect[15,16]. These properties are increased upon complexation with

syntheses of oxovanadium complexes were carried out in a 300W laboratory microwave reactor, bench mate model CEM - 908010.

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Jamonline / 2(3); 2012 / 251262 FT-IR spectra were recorded (KBr disk) on a Shimadzu 8101A FT-IR spectrophotometer.
1

Mangesh Gharpure et al ethanol (50 mL), NaOH (10%, 56 mL) and H2O2 (30%, 13 mL) was stirred vigorously for 30 minutes and kept for 4 hrs at ice cold condition. It was poured on to cold 5N, 80 mL HCl. The solid was filtered, washed with water, dried and crystallised from alcohol (yield 66%); mp 170 C; FT-IR (KBr): 3222 (Ar-OH), due to presence of phenolic OH group, 3033, 3075 (aromatic str.), 1611 (C=O pyrone ring) cm1;
1

H NMR were obtained from Bruker Avance 400MHz spectrophotometer using

II

tetramethylsilane as an internal standard in CDCl3. Mass spectra were recorded on water Micromass Q-T of Micro spectrometer equipped with an ESI source. All the elemental analyses were done using Perkin Elmer 2400 CHN analyzer. The reactions were monitored on pre-coated TLC plates (Silica gel 60 F254, Merck), using iodine vapor as visualizing agent. General procedure for the Preparation of 1-(2-hydroxyphenyl)-3-phenylprop-2-en-1one (3a). To the mixture of o-hydroxy acetophenone (13.6 gm, 0.1 mol), alcohol (50 mL) and benzaldehyde (12.72 gm, 0.12 mol), NaOH (40%, 19 mL) was slowly added with vigorous stirring (2-3 hrs), till orange solid mass was obtained and left it overnight at ambient temperature. Cold 5N, 42 mL HCl was poured on to it with constant stirring. The yellow solid was filtered, washed with water, dried and crystallised from alcohol (yield 82%). Similarly, other chalcones (3b-l) were prepared. General procedure for the preparation of 3-hydroxy-2-phenyl-4H-chromen-4-one (4a). The mixture of 1-(2-hydroxyphenyl)-3-

H NMR (400 MHz,

CDCl3): 7.02 (s, 1H, OH), 7.26-8.27 (m, 9H, Ar-H) ppm; MS-EI, m/z = (M)+ = 238. Anal. Calcd for C15H10O3: C, 75.62; H, 4.23%. Found: C, 75.71; H, 4.13%. Similarly, other flavones (4b-l) were synthesized using this method and spectral data of these compounds are given as follows. 3-hydroxy-2-(3,4-dimethoxyphenyl)-4Hchromen-4-one (4b): Yield 68%; mp 210 C; FT-IR (KBr): 3212 (Ar-OH), 1622 (C=O pyrone ring) cm1; 1H NMR (400 MHz, CDCl3): 3.95 (s, 3H, OCH3), 3.97 (s, 3H, OCH3), 7.02 (s, 1H, OH), 7.00-8.25 (m, 7H, Ar-H) ppm; MS-EI, m/z = (M)+ = 298. Anal. Calcd for C17H14O5: C, 68.45; H, 4.73%. Found: C, 68.53; H, 4.67 %. 6-chloro-3-hydroxy-2-(3,4dimethoxyphenyl)-4H-chromen-4-one (4c). Yield 67%; mp 262 C; FT-IR (KBr): 3226 (Ar-OH), 1618 (C=O pyrone ring) cm1; 1H NMR (400 MHz, CDCl3): 3.95 (s, 3H, OCH3), 3.97 (s, 3H, OCH3), 7.02 (s, 1H, OH), 7.00-8.25 (m, 6H, Ar-H) ppm; MS-EI, m/z =

phenylprop-2-en-1-one 3 (2.24 gm, 0.01 mol), All rights reserved 2011

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Jamonline / 2(3); 2012 / 251262 (M)+ = 332. Anal. Calcd for C17H13ClO5: C, 61.36; H, 3.94%. Found: C, 61.42; H, 3.99%. 2-(4-(dimethylamino)phenyl)-3-hydroxy4H-chromen-4-one (4d). Yield 62%; mp 196 C; FT-IR (KBr): 3227 (Ar-OH), 1621 (C=O pyrone ring) cm1; 1H NMR (400 MHz, CDCl3): 3.06 (s, 6H, N(CH3)2), 6.89 (s, 1H, OH), 6.87-8.24 (m, 8H, Ar-H) ppm; MS-EI, m/z = (M)+ = 281. Anal. Calcd for C17H15NO3: C, 72.58; H, 5.37; N, 4.98%. Found: C, 72.70; H, 5.25; N, 5.03%. 6-chloro-2-(4-(dimethylamino)phenyl)-3hydroxy-4H-chromen-4-one (4e). Yield 66%; mp 242 C; FT-IR (KBr): 3215 (Ar-OH), 1632 (C=O pyrone ring) cm1; 1H NMR (400 MHz, CDCl3): 3.06 (s, 6H, N(CH3)2), 6.89 (s, 1H, OH), 6.87-8.24 (m, 7H, Ar-H) ppm; MS-EI , m/z = (M) = 315. Anal. Calcd for C17H14ClNO3: C, 64.67; H, 4.47; N, 4.44%. Found: C, 64.71; H, 4.39; N, 4.48%. 2-(furan-2-yl)-3-hydroxy-4H-chromen-4one (4f). Yield 64%; mp 151 C; FT-IR (KBr): 3218 (Ar-OH), 1617 (C=O pyrone ring) cm1; 1H NMR (400 MHz, CDCl3): 11.22 (s, 1H, OH), 5.11-8.16 (m, 7H, Ar-H) ppm; MS-EI, m/z = (M)+ = 228. Anal. Calcd for C13H8O4: C, 68.42; H, 3.53%. Found: C, 68.47; H, 3.59%.
+

Mangesh Gharpure et al 6-chloro-2-(furan-2-yl)-3-hydroxy-4Hchromen-4-one (4g). Yield 64%; mp 212 C; FT-IR (KBr): 3229 (Ar-OH), 1615 (C=O pyrone ring) cm1; 1H NMR (400 MHz, CDCl3): 11.22 (s, 1H, OH), 5.11-8.16 (m, 6H, Ar-H) ppm; MS-EI, m/z = (M)+ = 262. Anal. Calcd for C13H7ClO4: C, 59.45; H, 2.69%. Found: C, 59.55; H, 2.63%. 6-chloro-3-hydroxy-2-phenyl-4H-chromen4-one (4h). Yield 68%; mp 169 C; FT-IR (KBr) : 3227 (Ar-OH), 1616 (C=O pyrone ring) cm1; 1H NMR (400 MHz, CDCl3): 7.02 (s, 1H, OH), 7.26-8.27 (m, 8H, Ar-H) ppm; MS-EI, m/z = (M)+ = 272. Anal. Calcd for C15H9ClO3: C, 66.07; H, 3.33%. Found: C, 66.19; H, 3.45%. 2-(4-chlorophenyl)-3-hydroxy-4Hchromen-4-one (4i). Yield 65%; mp 192 C; FT-IR (KBr): 3202 (Ar-OH), 1619 (C=O pyrone ring) cm1; 1H NMR (400 MHz, CDCl3): 7.02 (s, 1H, OH), 7.26-8.27 (m, 8H, Ar-H) ppm; MS-EI, m/z = (M)+ = 272. Anal. Calcd for C15H9ClO3: C, 66.07; H, 3.33%. Found: C, 66.14; H, 3.29%. 6-chloro-2-(4-chlorophenyl)-3-hydroxy-4Hchromen-4-one (4j). Yield 66%; mp 232 C; FT-IR (KBr): 3212 (Ar-OH), 1608 (C=O pyrone ring) cm1; 1H NMR (400 MHz, CDCl3): 7.02 (s, 1H, OH), 7.26-8.27 (m, 7H, Ar-H) ppm; MS-EI, m/z = (M)+ = 306. Anal. Calcd for C15H8Cl2O3: C, 58.66; H, 2.63%. Found: C, 58.72; H, 2.69%.

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Jamonline / 2(3); 2012 / 251262 6-chloro-2-(4-fluorophenyl)-3-hydroxy-4Hchromen-4-one (4k). Yield 65%; mp 215 C; FT-IR (KBr): 3221 (Ar-OH), 1613 (C=O pyrone ring) cm1; 1H NMR (400 MHz, CDCl3): 7.02 (s, 1H, OH), 7.26-8.27 (m, 7H, Ar-H) ppm; MS-EI, m/z = (M)+ = 290. Anal. Calcd for C15H8ClFO3: C, 61.98; H, 2.77%. Found: C, 61.92; H, 2.83%. 2-(4-fluorophenyl)-3-hydroxy-4Hchromen-4-one (4l). Yield 63%; mp 162 C; FT-IR (KBr): 3220 (Ar-OH), 1614 (C=O pyrone ring) cm1; 1H NMR (400 MHz, CDCl3): 7.02 (s, 1H, OH), 7.26-8.27 (m, 8H, Ar-H) ppm; MS-EI, m/z = (M)+ = 256. Anal. Calcd for C15H9FO3: C, 70.31; H, 3.54%. Found: C, 70.44; H, 3.51%. General procedure for preparation of Bis [3-hydroxy-2-phenyl-4H-chromen-4one]VO(IV) complex (5a). The complex was prepared by mixing the ethanolic DMF solution (7:3) of vanadyl acetyl acetonate (1 mmol) and 3-hydroxy-2phenyl-4H-chromen-4-one (2 mmol) in 1:2 ratio. The mixture was irradiated in Bis

Mangesh Gharpure et al Similarly, other oxovanadium complexes (5bl) were synthesized using this method and spectral data of some compounds are given as follows. Bis [3-hydroxy-2-(3,4-dimethoxyphenyl)-

4H-chromen-4-one]VO(IV) complex (5b). Black, Yield 86%; FT-IR (KBr): 1612 (C=O pyrone ring), 970 (V=O), 509 (VO) cm1;
1

H NMR (400 MHz, CDCl3): 4.05 (s, 3H,

OCH3), 4.07 (s, 3H, OCH3), 7.30-9.05 (m, 7H, Ar-H) ppm; MS-EI, m/z = (M)+ = 661. Anal. Calcd for C34H26O11V: C, 61.78; H, 3.39 %. Found: C, 61.63; H, 3.57%. [6-chloro-3-hydroxy-2-(3,4-

dimethoxyphenyl)-4H-chromen-4one]VO(IV) complex (5c). Brown, Yield 87%; FT-IR (KBr): 1598 (C=O pyrone ring), 970 (V=O), 509 (VO) cm1;
1

H NMR (400 MHz, CDCl3): 4.04 (s, 3H,

OCH3), 4.07 (s, 3H, OCH3), 7.28-9.09 (m, 6H, Ar-H) ppm; MS-EI, m/z = (M)+ = 332. Anal. Calcd for C34H11Cl2O11V: C, 56.01; H, 3.32%. Found: C, 56.22; H, 3.29%. Bis [2-(4-(dimethylamino)phenyl)-3-

microwave oven for 3 min the crystalline complex was separated and collected by filtration, washed with hot methanol and air dried. Black, (yield 84%); FT-IR (KBr): 1589 (C=O pyrone ring), 970 (V=O), 509 (VO)cm1; 1H NMR (400 MHz, CDCl3): 7.41-9.23 (m, 9H, Ar-H) ppm; MS-EI, m/z = (M)+ = 541. Anal. Calcd for C30H18O7V: C, 66.60; H, 3.35%. Found: C, 66.81; H, 3.23%. All rights reserved 2011

hydroxy-4H-chromen-4-one]VO(IV) complex (5d). Dark red, Yield 85%; FT-IR (KBr): 1621 (C=O pyrone ring),
1 1

970

(V=O),

509

(VO) cm ; H NMR (400 MHz, CDCl3): 3.09 (s, 6H, N(CH3)2), 7.01-8.84 (m, 8H, Ar-H) ppm; MS-EI, m/z = (M)+ = 627. Anal. Calcd for C34H28N2O7V: C, 65.13; H, 4.50; N, 4.46%. Found: C, 65.01; H, 4.58; N, 4.43%. www.jamonline.in 255

Jamonline / 2(3); 2012 / 251262 Bis[6-chloro-2-(4-(dimethylamino)phenyl)3-hydroxy-4H-chromen-4-one]VO(IV) complex (5e). Dark red, Yield 86%; FT-IR (KBr): 1632 (C=O pyrone ring),
1 1

Mangesh Gharpure et al 609. Anal. Calcd for C30H16Cl2O7V: C, 59.17; H, 2.65%. Found: C, 59.01; H, 2.72%. Bis [2-(4-chlorophenyl)-3-hydroxy-4Hcomplex (5i).

chromen-4-one]VO(IV)

970

(V=O),

509

Black, Yield 85%; FT-IR (KBr): 1619 (C=O pyrone ring), 970 (V=O), 509 (VO) cm
1

(VO) cm ; H NMR (400 MHz, CDCl3): 3.11 (s, 6H, N(CH3)2), 7.07-8.89 (m, 7H, Ar-H) ppm; MS-EI , m/z = (M)+ = 695. Anal. Calcd for C34H26Cl2N2O7V: C, 58.76; H, 3.77; N, 4.03%. Found: C, 58.61; H, 3.82; N, 4.01%.

; 1H NMR (400 MHz, CDCl3): 7.26-8.27

(m, 8H, Ar-H) ppm; MS-EI, m/z = (M)+ = 609. Anal. Calcd for C30H16Cl2O7V: C, 59.17; H, 2.65%. Found: C, 59.04; H, 2.79%. Bis [6-chloro-2-(4-chlorophenyl)-3-

Bis [2-(furan-2-yl)-3-hydroxy-4H-chromen4-one]VO(IV) complex (5f). Pale brown, Yield 82%; FT-IR (KBr): 1617 (C=O pyrone ring),
1 1

hydroxy-4H-chromen-4-one]VO(IV) complex (5j). Black, Yield 82%; FT-IR (KBr): 1608 (C=O pyrone ring), 970 (V=O), 509 (VO) cm
1

970

(V=O),

509

(VO) cm ; H NMR (400 MHz, CDCl3): 5.11-8.16 (m, 7H, Ar-H) ppm; MS-EI, m/z = (M)+ = 511. Anal. Calcd for C26H14O9V: C, 61.11; H, 2.76%. Found: C, 61.26; H, 2.69%. Bis [6-chloro-2-(furan-2-yl)-3-hydroxy-4Hchromen-4-one]VO(IV) complex (5g).

; 1H NMR (400 MHz, CDCl3): 7.26-8.27

(m, 7H, Ar-H) ppm; MS-EI, m/z = (M)+ = 677. Anal. Calcd for C30H14Cl4O7V: C, 53.22; H, 2.08%. Found: C, 53.32; H, 2.02%. Bis [6-chloro-2-(4-fluorophenyl)-3-

hydroxy-4H-chromen-4-one]VO(IV) complex (5k). Black, Yield 86%; FT-IR (KBr): 1613 (C=O pyrone ring), 970 (V=O), 509 (VO) cm
1

Black, Yield 83%; FT-IR (KBr): 1615 (C=O pyrone ring), 973 (V=O), 510 (VO) cm
1

; 1H NMR (400 MHz, CDCl3): 5.11-8.16

+

(m, 6H, Ar-H) ppm; MS-EI, m/z = (M) = 589. Anal. Calcd for C26H12Cl2O9V: C, 53.02; H, 2.05%. Found: C, 53.15; H, 2.13%. Bis [6-chloro-3-hydroxy-2-phenyl-4Hcomplex (5h).

; 1H NMR (400 MHz, CDCl3): 7.26-8.27

(m, 7H, Ar-H) ppm; MS-EI, m/z = (M)+ = 655. Anal. Calcd for C30H14Cl2F2O7V: C, 55.01; H, 2.15%. Found: C, 55.12; H, 2.03%. Bis [2-(4-fluorophenyl)-3-hydroxy-4Hcomplex (5l).

chromen-4-one]VO(IV)

Brown, Yield 85%; FT-IR (KBr): 1616 (C=O pyrone ring), 970 (V=O), 509 (VO) cm
1

chromen-4-one]VO(IV)

; 1H NMR (400 MHz, CDCl3): 7.26-8.27

+

Black, Yield 84%; FT-IR (KBr): 1614 (C=O pyrone ring), 970 (V=O), 509 (VO) cm
1

(m, 8H, Ar-H) ppm; MS-EI, m/z = (M) = All rights reserved 2011

; 1H NMR (400 MHz, CDCl3): 7.26-8.27 www.jamonline.in 256

Jamonline / 2(3); 2012 / 251262 (m, 8H, Ar-H) ppm; MS-EI, m/z = (M)+ = 577. Anal. Calcd for C30H16F2O7V: C, 62.45; H, 2.79%. Found: C, 62.49; H, 2.71%. Biological Activity Antibacterial activity The synthesized compounds were screened for their antibacterial activities against

Mangesh Gharpure et al Aeruginosa. The antifungal activity of the complex was moderate and that of ligand was weak. The higher activity of the metal complex may owe the effect of metal ions on chelation. The polarity of the metal ion will be reduced to a greater extent due to the overlap of the ligand orbital and partial sharing of the positive charge of the metal ion with donor groups. Thus, it enhances the penetration of the complex into lipid

pathogenic bacteria such as Escherichia coli, Staphylococcus aureus, Bacillus subtilis and Pseudomonas aeruginosa using the cup plate diffusion method. The test compounds were dissolved in dimethyl concentration of 100 sulphoxide at a g/mL using

membranes and blocking of the metal binding sites in the enzymes of microorganisms. Results and Discussion: Acetylation of phenols followed by Fries migration gave 2-hydroxy acetophenones, reaction of 2-hydroxy acetophenones with different aromatic aldehydes produced 1-(2hydroxyphenyl)-3-phenylprop-2-en-1-one,

Ciprofloxacin and Sulphacetamide as a standard drug. All the inoculated plates were incubated at 35 C and the results were evaluated after 24 h of incubation. Antifungal activity The synthesized compounds were also

which on cyclization in alkaline H2O2 yielded 2-aryl/heteryl-3-hydroxychromone (3hydroxy flavones) (Scheme 1). Complexes formation between oxovanadium (IV) cation and 2-aryl/heteryl-3-hydroxychromones

screened for their antifungal activity against Aspergillus niger and Candida albicans using the cup plate diffusion method. The test compounds were dissolved in dimethyl sulphoxide at a concentration of 100g/mL. The zone of inhibition was observed after 7 days at 25 C and it was compared with Gentamycin and Clotrimazole as standard drugs as shown in Table 1. On the basis of observed zone of inhibition, it was found that the VO(IV) complex is more active than their respective ligand. It was found that the complex exhibit good antibacterial activity against E. coli, S. aureus, B. subtilis and P. All rights reserved 2011
0

performed in ethanolic dimethyl formide show the formation with 1:2 of metal mononuclear to ligand

complexes

stoichiometry (Scheme 2). The complexes are stable at room temperature, non-hygroscopic, insoluble in water but slightly soluble in chloroform and soluble in DMF and DMSO.

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Mangesh Gharpure et al

Scheme 1: Synthesis of 2-Aryl/Heteryl-3-hydroxychromones

OH R 1 i) AcCl, CH3COONa ii) AlCl3 R 2 OH C CH3 O

R1 CHO

EtOH 40% NaOH

O R O 4a-l

R1 OH

30% H2O2 EtOH NaOH R O 3

R1

Scheme 2: Synthesis of oxovanadium complexes of 2-Aryl/Heteryl-3-hydroxychromones

O 2 R O 4a-l MW OH EtOH DMF R R1 O O O V O O R1 R 5a-l O O R1 + O O V O O O

Where,

R = i) H, ii) Cl R1 = i) C6H5 ii) 3,4-(OCH3)C6H4 iii) 4-Cl C6H4 iv) 4-N(CH3)2C6H4 v) C4H3O vi) 4-F C6H5

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Jamonline / 2(3); 2012 / 251262 FT-IR spectra: The characteristic MASS Spectra:

Mangesh Gharpure et al The mass spectral data

infrared spectral assignment of ligands (4a-l) and their oxovanadium complexes (5a-l) are reported in experimental section. In the FT-IR spectra of ligand (4a), the presence of phenolic OH and carbonyl group are confirmed by peaks at 3234 and 1669 cm-1 respectively. However, in the spectra of the complex (5a) there is complete disappearance of peak at 3234 cm
-1

of ligands (4a-l) and their oxovanadium metal complexes (5a-l) are provided in the

experimental section. In the mass spectrum of complex (5a) the peak at m/z 541 corresponds to the [VO(L)2]+ ion and ligand (4a) m/z 238, this result supporting a metal to ligand as stoichiometry of 1:2 for this complex. Conclusions The complexes of vanadyl ion with 3-hydroxy chromones have been obtained in solid state and characterized. It has been suggested that the antibacterial and antifungal activity of ligands increased upon chelation/coordination with the vanadium metal atom. The chelation process reduces the polarity of metal ion by coordinating with ligands, which increase the lipophilic nature of the metals. This lipophilic nature of the metal enhanced its penetration through the lipoid layer of cell membrane of the microorganism.

suggesting absence of

phenolic OH group indicates its coordination. The band assigned to the carbonyl group is shifted to a lower wavelength comparing with that of the free ligand, proving its

coordination. Supplementary bands around 973 and 510 cm-1 for complex is assigned to the (V=O) and (VO) respectively. As a conclusion, comparison of the spectra of ligands and metal complexes conform the coordination of ligand to metal ion,

bidentately through the 3-hydroxy 4-keto groups.

1

H NMR Spectra:

The 1H NMR spectral

Acknowledgement Authors are thankful to the Head, Department of Chemistry, RTM Nagpur University, for the laboratory facilities, the Head, Department of Pharmacy, RTM Nagpur University for IR and antimicrobial activities and the Director, SAIF, Punjab University, Chandigarh for NMR and Mass spectra.

data of ligands (4a-l) and their oxovanadium metal complexes (5a-l) are provided in the experimental part. The 1HNMR spectra of the ligand (4a), show signals between 5.11-8.16 due to aromatic ring which get shifted downfield and appears between 6.67-8.18 in the vanadium complex (5a). The enolic proton at 7.02 ppm in the ligand disappeared in the spectra of its metal complex indicating deprotonation and coordination of the oxygen with the metal ion. All rights reserved 2011

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Mangesh Gharpure et al

Table 1. Antimcrobial activity of some ligands and metal complexes Compd Zone of Inhibitionb (mm) (Activity Index) std Antibacterial Activity Antifungal Activity Gram-positive Gram-negative S. aureus B. subtilis E. coli P. aeruoginosa C. albicans A. niger 18 17 21 17 18 16 19 16 17 16 17 16 15 16 16 15 14 15 19 18 21 20 18 19 22 20 21 22 21 23 21 20 19 20 18 21 16 15 17 17 16 18 21 20 23 19 20 19 22 18 21 18 19 18 19 19 20 17 16 17 23 21 24 22 21 23 25 23 25 24 24 25 23 22 21 23 20 22 18 19 18 20 19 21 33 29 34 22 21 25 31 26 29 21 23 24

4a 4c 4e 4f 4g 4j 4k 5a 5c 5e 5f 5g 5j 5k Std1 Std2

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