Furan 2 carboxylic

Synthesis, Physico -Chemical and Antimicrobial

Properties of n(II),Fe(II),Co(II),Ni(II),Cu(II),Zn(II)

and Cd (II), Mixed Ligand Complexes of cephalexin

mono hydrate (antibiotics) and Furan-2-carboxylic

acid Taghreed . Hashim Al-Noor1 Faiza. H Ghanim2 Bassim Abd Shahoobi3

1,2&3Department of Chemistry .Ibn -Al-Haithem College of Education for pure science, University of

Baghdad, Baghdad, Iraq.

Abstract— A series of new mixed ligand complexes of Mn(II),Fe(II),Co(II),Ni(II),Cu(II),Zn(II) and Cd

(II) have been synthesized with cephalexin mono hydrate ( CephH) = ( C16H19N3O5S.H2O) and

Furan-2-carboxylic acid(FCA H) =( C5H4O3) .The mixed ligand complexes have been characterized by

repeated melting point determination, spectroscopic spectral measurements (FT-IR,

UV-Vis.),molar conductance, magnetic susceptibility measurements and determination the percentage

of the metal in the complexes by flame(AAS). The ligands and their metal complexes were

screened for their antimicrobial activity against four bacteria (gram + ve) and (gram -ve).The proposed

structure of the complexes using program, Chem office 3D (2006) . The general formula have been

given for the prepared mixed ligand complexesNa2[M(FCA)3(Ceph)], M(II) = Mn (II) , Fe

(II),Co(II) ,Ni(II),Cu (II), Zn(II) , and Cd(II).

Index Terms— Cephalexin antibiotics, Furan 2-carboxylic acid, drugs mixed ligand complexes, and

antibacterial activities.

I. INTRODUCTION

Bioactive donor site of ( N,S/O) atoms in organic ligand moieties were widely used in the

development of metal based drugs, analytical, industrial, medicinal, agricultural, biological and clinical

areas. [1-2].

Many drugs possess modified toxicological and pharmacological properties when they are in the form

of metal complexes. The most widely studied metal in this respect is copper(II) which has proved beneficial

in diseases such as tuberculosis, gastric ulcers, rheumatoid arthritis and cancers. [3].The coordination

chemistry of some beta-lactam antibiotics with transition and d10 metal ions has been reported [4-8].

Furan-2-carboxylic acid( C5H4O3) (FCAH) is a heterocyclic aromatic compound with five- membered ring

structure consisting of four CH2 groups, one oxygen atom and a carboxylic group. [9].Synthesis and

identification of type mixed ligand complexes of M+2 Ions using Furan-2-carboxylic acid as a primary

ligand and 1,10-phenanthroline (phen )as secondary ligand has been reported. [10].

Literature survey shows that no studies on the synthesis and characterization of mixed ligand

complexes of Furan-2-carboxylic acid and cephalexin (antibiotics) have been reported.

In this paper we present the synthesis and study of Mn(II),Fe(II),Co(II),Ni(II), Cu(II),Zn(II), and Cd(II)

complexes with cephalexin mono hydrate (antibiotics) as a primary ligand and Furan-2-carboxylic acid

as secondary ligand.

II. EXPERIMENTAL

A. Chemicals : All chemical reagents and solvents used were of analytical grade and were used without

further purification and were used as received MnCl2.2H2O, FeCl2.9H2O,CoCl2.6H2O,

Techscripts1

Transactions on Engineering and Sciences ISSN: 2347-1964 (Online) 2347-1875 (Print)Vol.3, Issue 2, February 2015

NiCl2.6H2O,CuCl2.H2O, CdCl2.H2O, and ZnCl2,KOH (supplied by either Merck or Fluka) ethanol, methanol

dimethylforamaide, and KBr, acetone , benzene, and chloroform from (B.D.H).Cephalexin powder DSM

(Spain) and Furan-2-carboxylic acid (merck).

B. Instrumentals: UV-Vis spectra were recorded on a (Shimadzu UV- 160A) Ultra Violet-Visible

Spectrophotometer. IR- spectra were taken on a (Shimadzu, FTI R- 8400S) Fourier Transform Infrared

Spectrophotometer (4000- 400) cm-1 with samples prepared as KBr discs. Metal contents of the complexes

were determined by atomic absorption(A.A)technique using a Shimadzu AA 620G atomic absorption

spectrophotometer. The Chloride contents of complexes were determined by potentiometric titration

method using (686-Titro processor-665. Dosimat Metrohn Swiss). Conductivities were measured for

10-3M of complexes in DMF at 25оC using (conductivity meter, Jewnwary, model 4070). Magnetic

measurements were recorded on a Bruker BM6 instrument at 298°K following the Farady’s method. In

addition melting points were obtained using (Stuart Melting Point Apparatus). The proposed molecular

structure of the complexes was drawing by using chem. office prog, 3DX (2006).

C. General synthesis of the mixed ligands metal complexes: A general method was used for the synthesis of the

metal complexes .A solution of Furan-2-carboxylic acid (0.336 gm, 3 m mol) in 50% (v/v) ethanol –water (10

ml) containing potassium hydroxide (0.168, 3mmol) and a solution of cephalexin mono hydrate (0.347

gm ,1 m mol) in 50% (v/v)ethanol–water (10 mL) containing potassium hydroxide (0.056,1mmol)were

added simultaneously to a solution of MCl2.nH2O (1 m mol) in 50% (v/v) ethanol –water, (10 mL) in the

stoichiometric ratio.[3FCA- : M: ceph-] ( Scheme 1).The above solution was stirred for 1-houre and allowed

to stand for overnight .the product formed was filtered off ,washed several times with hot 50% (v/v)

ethanol –water to remove any traces of the un reacted starting materials and dried in air ,and analyzed

employing standard method. [11]

III. RESULTS AND DISCUSSION

A. Characterization of Metal Complexes: Generally, the complexes were prepared by reacting the respective

metal chloride with the ligands using 1:1:3 mole ratios, [M: Ceph:3(FCA)], i.e. one mole of metal chloride :

one mole of cephalexin and three moles of FCAK . The synthesis of mixed ligand metal complexes may be

represented as follows (Schem1):

KOH+

+ +MCl2

K+

OO

-O

K+

OO

-O

OO

HO

M

O

O

O

O

O

O

+ 3H 2O3

1:1(H2O:C2H5OH)

3

1:1(H

2 O:C

2 H5 O

H)

M= Mn(II),Fe(II ),Co(II),Ni(II),Cu(II),Zn(II) and Cd (II )

potassium Furan-2-carboxylate.

3

Furan-2-carboxylic ac id .

O

O

O

NH2

O

H

NH

N

SH

C H3

OO

HO

NH2

O

H

NH

N

SH

C H3

OO

OK2

Figure 1: Scheme (1): Preparation of K2[M(Ceph)(FCA)3] complexes

The formula weights and melting points, are given in(Table I ).Based on the physicochemical

Techscripts2


characteristics. All the mixed ligand complexes are colored complexes. They are stable in air at room

temperature, non hygroscopic and appears as powders with high melting points indicating a strong

metal-ligand bond. The synthesized complexes are sparingly soluble in the common organic solvents

(benzene, chloroform) but they are completely soluble in water, ethanol, acetone and dimethyl form amide

(DMF) solvent.

The complexes were analyzed for their metal by atomic absorption measurements, and chloride

contents were determined by standard methods [11]. Table(1) for all complexes gave approximated values

for theoretical values.The molar conductance values of the metal complexes (measured in 10−3 M DMF) are

in the range of (93.5-180.5) Ω-1 cm2 mol-1, indicating the electrolytic nature with(2:1).[12]. The atomic

absorption measurements and chloride contents (Table-1) for all complexes gave approximated values for

theoretical values.

B. UV-Visible Spectra and Magnetic Susceptibility Measurements: The values of band positions (λ max nm)Cm-1

and molar absorptivity's (ε max L cm-1 mol-1) are listed in Table (2) together with the proposed

assignments transition and magnetic moment values .The electronic spectral studies of mixed ligand

complexes of Mn(II), Fe(II),Co(II), Ni(II),Cu(II), Zn(II), and Cd(II) were carried out in (10−3 M) DMF solution.

The corrected magnetic moment (µeff) in Bohr magneton units of the mixed ligand complexes are given

in Table 2.The electronic spectra of d10[Zn(II) and C d(II)]complexes do show the charge transfer ,and the

magnetic susceptibility shows that two complexes have diamagnetic moments., because d-d transitions are

not possible hence electronic spectra did not give any fruitful information.in fact this result is a good

agreement with previous work of octahedral geometry.[2,13]. The magnetic moment value for the Ni(II) d8

complex is 3.11 B.M correspond to two unpaired electrons as expected for six coordinated spin free Ni(II)

species suggest an octahedral geometry. [4, 5]

Fe(II)complex exhibits one (d-d) transition electronic spectral band at 26246 cm-1 , which is ascribed to

transitions(5T2g→5Eg). Observed value magnetic moment 4.64B.M for Fe (II) complex suggest distorted

octahedral geometry[12,13].The magnetic moment value for the Co (II) complex is 4.90 B .M. expected for

octahedral geometry [13-14] with high spin paramagnetic d7 system (t2g5eg2) and 3 unpaired electrons.

The magnetic moment values of Mn(II) lie in 5.30 BM indicating octahedral stereochemistry of the

complex [2].The Ni(II) complexes show two(d-d) transition bands (Table 2) in the region around 21929

and 26666 cm-1,which are ascribed to transitions 3A2g(F) →3T1g(F) (ν 2) and

3A2g(F) →3T1g(P) (ν 3), respectively .As the ν 1 band occurs at low energy, usually in the range not

accessible due to instrumental limitations ,it is not observed in the present cases.

C. FT-IR of Na2 [Mn(Ceph)(FCA)3](1),Na2[Fe(Ceph)(FCA)3](2),Na2[Co(Ceph)(FCA)3](3),Na2[Ni

(Ceph)(FCA)3](4),

Na2[Cu(Ceph)(FCA)3](5),Na2[Zn(Ceph)(FCA)3] (6) and Na2[Cd (Ceph)(FCA)3] (7) complexes: The IR

spectra of the free ligands were compared with those of the metal complexes in order to ascertain the

bonding mode of the drug to metal ion in the complexes. The coordination of metal with the ligands

causes shifts of bands of the ligands to slightly lower or higher frequencies with different intensities [16].

The relevant vibration bands of the free ligand and the complexes are in the region 400–4000 cm−1.The

assignment of the characteristic bands (FT-IR) spectra for the free ligand(Ceph) and (FCAH) are

summarized in table (3) and (4 ) respectively. The characteristic frequencies of the (1), (2), (3), (4), (5), (6)

and (7) metal complexes are given in Table(5). Interpretation of IR bands of the complex have been carried

out comparing with the spectrum of IR of cephalexin , FCA and related compound have been well

studied [ 13,17]

The IR spectra of the (FCA) and ( Ceph.) exhibited characteristic band due ʋ (C=O) at 1685 cm-1 and

1691 cm-1 [5,18] respectively. The band of ʋ (C=O) in the region 1560-1691 cm-1 in the metal complexes

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showing the shift to lower wave numbers confirms that, the carbonyl oxygen is coordinated to the metal

ion [7,10]. IR spectra of the free ligands (FCA)and (Ceph.) exhibited a broad band at 2590 cm-1 along with

shoulder at 3010 cm-1 assignable to ʋ (CH) of Phenyl group respectively. A strong band typical of (C=C)

stretching frequency, υ, are found in 1685 cm-1 in (FCA) and in 1789 cm-1 in ( Ceph) respectively. The

un altered position of a band due to furan ring ν (C-O-C) and υ(C-S)in all the metal complexes indicates

that, these groups are not involved in coordination. The new weak bands in the region of (501-579) cm-1

and (435-497) cm-1 in the spectra of the complexes are assigned to stretching frequencies of (M-N) and

(M-O) bonds respectively [10,18] which interns support the involvement of oxygen and nitrogen atoms in

coordination [17,19].The asymmetric carboxyl stretching νasym(COO−) was shifted to higher frequency in

the 1585 and 1589 cm−1 range and the symmetric carboxyl stretching νsym(COO−) was shifted to lower

frequency in the 1379 and 1384 cm−1 range, indicating the linkage between the metal ion and carboxylato

oxygen atom. The asymmetric and symmetric stretching vibration of the carboxylate group in the

complexes shows the separation value (∆ν) greater than 200 cm−1.

The large difference (∆ν) between the νasym (-COO −) and νsy(-COO−) values greater than ∼200 cm−1

indicates the monodentate binding nature of the carboxylato group[17,19]

The results showed that the deprotonated ligand (Furan-2-carboxylic acid (FCA H) to

(Furan-2-carboxylate ion (FCA -) by using (KOH) coordinated to metal ions as a monodendate ligand

through the oxygen atom of the carboxylate group (−COO−),and the retention of υ (C-O-C) band of the

(FCA -) ring at 1224 cm-1 oxygen atom of the ring cm-1 indicates that is not taking part in

coordination.[10]

D. Antibacterial Activities studies: The effectiveness of an antimicrobial agent in sensitivity is based on the

zones of inhibition. The synthesized metal complexes were screened for their antimicrobial activity by well

plate method in nutrient agar. The invitro antibacterial activity was carried against 4 hold cultures of

pathogenic bacteria like gram (+)and gram (-) at 37o C. In order to ensure that solvent had no effect on

bacteria, a control test was performed with DMSO and found inactive in culture medium. Antimicrobial

activity was evaluated by measuring the diameter of the inhibition zone (IZ) around the hole. Most of the

tested compounds showed remarkable biological activity against different types of gram positive and

gram negative bacteria. The diameter of the susceptibility zones were measured in mm and the results are

presented in Table (6) Scheme (2). Compounds were considered as active when the (IZ) was greater than 6

mm. The ligand (FCAH) was active against Bacillus only. ( Ceph) and the all M(II) complexes showed

antibacterial activity against all the four strains of microbes. The Ni(II) complex was significantly more

active against four strains of microbes and Zn(II) complex shows moderate activity as presented in Table

(6). Scheme (2).A possible explanation is that, in the chelated complex, the positive charge of the metal is

partially shared with the donor atoms in the ligand and there is -electron delocalization over the whole

chelating ring. This, in turn, increases the lipophilic character of the metal chelate and favor's its

permeation through the lipid layers of the membranes of the micro-organism. [20, 21]. Apart from this,

other factors such as solubility, conductivity and dipole moment influenced by the presence of the metal

ions may also be reasons for the increased activity.[ 21,22]

IV. CONCLUSION

In conclusion, the Mn (II),Fe(II) Co(II),Ni(II),Cu(II),Zn(II), and Cd(II) complexes of mixed cephalexin

mono hydrate (antibiotics) and (FCA) are reported. The resultant complexes are characterized by melting

point, conductivity measurement, UV-Vis and Infra-red spectroscopy. Investigation of antimicrobial

activities was carried out against the tested organisms. All the complexes are found to be in octahedral

geometry. Preliminary results indicate that newly synthesized mixed ligand complexes

Na2[M(Ceph)(FCA)3] exhibited promising antibacterial activities and they warrant more consideration as

prospective antimicrobials.

Techscripts4


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Table 1: The physical properties of the compounds

Cl% Metal%

Λm

Ω-1 cm2 mol-1

In DMF

M .p °c

(de) °c Color M . wt

Compounds

Chemical Formula

- - 7.22 208 off-white 347.39 Ceph,H = C16H17N3O4S

- - 1.06 132-136de off-white 112.08 C5H4O3 (FCAH)

Nil 7.48 (8.01) 161.2 195de light- brown 733.66

Na2[Mn(Ceph)(FCA)3]

Nil 7.59 (7.51) 95.3 113de Green 735.37 Na2[Fe(Ceph)(FCA)3]

Nil 7.98 (8.18) 180.5 65de red- brown 738.62 Na2[Co(Ceph) (FCA)3]

Nil 7.95 (7.05) 98.55 236 Green-deep 738.34 Na2[Ni( Ceph)(FCA)3]

Nil 8.55 (9.05) 103.2 115 Green 743.17 Na2[Cu( Ceph)(FCA)3]

Nil 8.78 (9.18) 109.3 255 light-

Yellow

745.01 Na2[Zn(Ceph)(FCA)3]

Nil 14.19 (15.28) 93.5 de128 Yellow 792.03 Na2[Cd(Ceph )(FCA)3]

Λm = Molar Conductivity, de =decomposition

Table 2: Electronic Spectral data, magnetic moment, of the mixed ligands complexes

Compounds λmax ύ cm-1

ε max

L.mol-1cm-1 Possible assignment

µeff

BM

Ceph = C16H17N3O4S 279 35842 1503 →*

C5H4O3 (FCA) 270 37037 980 →* (C=C)

Na2[Mn(Ceph)(FCA)3] 274

780

36496

12820

20612

ligand field

6A 1g → 4Eg, 4T1g (4P) 5.30

Na2[Fe(Ceph)(FCA)3]

280

345

753

35714

28985

13280

2198

15558

ligand field

CT

5T2g → 5E2g

4.64

Na2[Co(Ceph) (FCA)3]

286

345

607

668

34965

28985

16474

14970

2308

1557

119

120

ligand field

CT

4T1g(F)→ 4T2g(F)(ν3)

4T1g(F)→4A2g(F)(ν2)

4.90

Na2[Ni(Ceph ) (FCA)3] 273

815

36630

12269

1463

4

CT

3A2g(F) → 3T1g(F)(ν3) 3.11

Na2[Cu(Ceph )(FCA)3] 288

360

34722

27777

2351

1187

CT

CT 1.83

Na2[Zn(Ceph )(FCA)3] 272 36764 1411 CT 0.0

Na2[Cd(Ceph )(FCA)3] 285 35087 2229 CT 0.0

Techscripts6


Table 3: Data from the infrared Spectrum for the free ligand Ceph (cm-1)

Com. (N-H)

primary

amine

ν (N-H)

Secondary

amide

ν

(C=O)

for

COOH

ν

(C=O)

β-lacta

m

ν

asm

COO-

ν

smy

COO-

ν

(C=C)

arom.

ν

(C-C

)

alip.

ν

(C-N)

ν

(C-O)

ν

(C-S)

ν

(C-H)

arom.

CephH 3275 3219 3049 1759 1691vs 1595 1398 1577 1163 1280 1247 580 3010

Table 4: Data from the infrared spectrum for the free ligand Furan-2-carboxylic acid (cm-1)

∆

ν

(-COO-)

sym- asym

ν

(-COO-)

sym

ν

(-COO-)

asym

ν

(C-O-C)

Furan ring

ν

(C=O)

ν

(CH)

cyclic

ν

OH

Compound

97 1382m 1479m 1226 s 1685 2590 3142vs FCAH

Table 5. Data from the Infrared Spectra M(II)-Mixed ligand complexes of cephalexin mono hydrate and

Furan-2-carboxylic acid(cm-1).

ν

(O-H)

υ(N-H)

primary

amine

ν

(N-H)

Secondary

amide

υ(C=O)

β-lactam

& Furan

ν

(C-O-C)

Furan

ring

ν

asm

COO

υsmy

COO

∆

ν(-COO-)

sym-

asym

ν

(C-S)

ν

M-N

ν

M-O

Mn 3423

3277 3045

1691

1566 1229

1591

1454

1396

1355 195 582 526w

493w

Fe 3381s

3140 3045

1583s

1560 1228

1583

1477

1365

1371s

218

569 501w

435w

Co 3392s

3228 3064s

1595

1226

1560

1481s

1365s

195 584 564w 493w

Ni 3354s

3250 3066s 1593s 1226 1558s 1367s 119 580 555w 489w

Cu 3421s

3248 3061s

1610s

1560 1226 1581s 1361s 220 581 579 472w

Zn 3435s

3232s 3057s

1608s

1564s 1226w

1608s

1481

1392

1361s 216 567 536w 472w

Cd 3456s

3211s 3061s

1589s

1560s 1228w

1608

1481

1383

1361s

225

582 532w 497w

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Table 6 . The antibacterial activity (IZ mml) data of M (II)-Mixed Ligand Complexes of

cephalexin mono hydrate and Furan-2-carboxylic acid

Compound E-coli Pseudomonas Staphylococcus

aureus Bacillus

Control(DMSO) 5 5 - -

Furan-2-carboxylic acid 5 5 6 14

ceph 18 16 16 16

Na2[Mn(Ceph)(FCA)3] 16 17 16 15

Na2[Fe(Ceph)(FCA)3] 17 15 17 15

Na2[Co(Ceph) (FCA)3] 18 16 15 17

Na2[Ni(Ceph ) (FCA)3] 17 17 18 23

Na2[Cu(Ceph )(FCA)3] 19 15 22 18

Na2[Zn(Ceph )(FCA)3] 16 13 15 10

Na2[Cd(Ceph )(FCA)3] 17 16 16 12

Figure 2: Scheme (2): Chart of biological effects of the studied compounds

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Furan 2 carboxylic

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