Synthesis, characterization, and antimicrobial activities of new N-(2-hydroxy-1-naphthalidene)-amino acid (L-tyrosine, L-arginine, and L-lysine) schiff bases and their manganese(III) complexes

Article abstract of DOI:10.1080/15533174.2013.776604

A new series of manganese(III) complexes Na[Mn(L¹) ₂].3H₂O, Na₃[MnL²(CH ₃COO)₄].2H₂O, Na[Mn(L³) ₂].2H₂O and amino acid Schiff bases (H₂L ¹); [N-(2-hydroxy-1-naphthylidene)tyrosine], (H₂L ²); [N-(2-hydroxy-1-naphthylidene)arginine], (H₂L ³); [N-(2-hydroxy-1-naphthylidene)lysine] have been prepared from 2-hydroxy-1-naphthaldehyde and a-amino acids (L-tyrosine, L-arginine, and L-lysine). The structures of the compounds were identified using elemental analyses, IR, UV-VIS, ¹H-NMR spectra, magnetic susceptibility measurements, and thermogravimetric analyses (TGA). All of these substances have been also examined for antibacterial activity against the pathogenic strains S. aureus, Sh. dys. typ 7, L. monocytogenes 4b, E. coli, S. typhi H, S. epidermis, Br. abortus, M. luteus, B. cereus, P. putida, and antifungal activity against C. albicans. Copyright Taylor & Francis Group, LLC.

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Synthesis, Characterization, and Antimicrobial
Activities of New N-(2-hydroxy-1-naphthalidene)-amino
Acid (L-Tyrosine, L-Arginine, and L-Lysine) Schiff Bases
and Their Manganese(III) Complexes
İffet Şakıyan a , Resül Özdemir a & Hatice Öğütcü b
a Department of Chemistry , Ankara University , Ankara , Turkey
b Department of Biology , Ahi Devran University , Kırşehir , Turkey
Accepted author version posted online: 06 Sep 2013.Published online: 06 Nov 2013.
To cite this article: İffet Şakıyan , Resül Özdemir & Hatice Öğütcü (2014) Synthesis, Characterization, and Antimicrobial
Activities of New N-(2-hydroxy-1-naphthalidene)-amino Acid (L-Tyrosine, L-Arginine, and L-Lysine) Schiff Bases and Their
Manganese(III) Complexes, Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 44:3, 417-423,
DOI: 10.1080/15533174.2013.776604
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Synthesis and Reactivity in Inorganic, Metal-Organic, and Nano-Metal Chemistry, 44:417–423, 2014
Copyright ꢀ Taylor & Francis Group, LLC
C
ISSN: 1553-3174 print / 1553-3182 online
DOI: 10.1080/15533174.2013.776604
Synthesis, Characterization, and Antimicrobial Activities
of New N-(2-hydroxy-1-naphthalidene)-amino Acid
(L-Tyrosine, L-Arginine, and L-Lysine) Schiff Bases
and Their Manganese(III) Complexes
1
1
2
˙
¨
¨
Iffet S¸akıyan, Resu¨l Ozdemir, and Hatice Og˘u¨tcu¨
1Department of Chemistry, Ankara University, Ankara, Turkey
2Department of Biology, Ahi Devran University, Kırs¸ehir, Turkey
3-dione; [MnL2(LH)2]ClO4, [MnL2(N3)] 0.5CH3OH (L =
(2-hydroxybenzyl-2-furylmethyl)imine), [Mn(A9)(L)(H2O)2]·
H2O (H2A9 = 4,4ꢁ-(p-tolyl methylene) bis(3-methyl-1-phenyl-
4,5-dihydro-1H-pyrazol-5-ol), and (HL = 1-cyclopropyl-6-flu-
oro-4-oxo-7-(piperazin-1-yl)-1,4-dihydroquinoline-3-carboxy-
lic acid) have antimicrobial activities against some bacteria and
fungi.[11–13] On the other hand, 2-hydroxy-1-naphthaldehyde
Schiff bases have also antimicrobial activities against some
bacteria and fungi.[14–18] Furthermore, amino acids are used
also as transporter for drug molecules in medicine.[19]
A new series of manganese(III) complexes Na[Mn(L1)2].3H2O,
Na3[MnL2(CH3COO)4].2H2O, Na[Mn(L3)2].2H2O and amino acid
Schiff bases (H2L1); [N-(2-hydroxy-1-naphthylidene)tyrosine],
(H2L2); [N-(2-hydroxy-1-naphthylidene)arginine], (H2L3); [N-(2-
hydroxy-1-naphthylidene)lysine] have been prepared from 2-
hydroxy-1-naphthaldehyde and a-amino acids (L-tyrosine, L-
arginine, and L-lysine). The structures of the compounds were
1
identified using elemental analyses, IR, UV-VIS, H-NMR spec-
tra, magnetic susceptibility measurements, and thermogravimetric
analyses (TGA). All of these substances have been also examined
for antibacterial activity against the pathogenic strains S. aureus,
Sh. dys. typ 7, L. monocytogenes 4b, E. coli, S. typhi H, S. epidermis,
Br. abortus, M. luteus, B. cereus, P. putida, and antifungal activity
against C. albicans.
Therefore, in this work we synthesized new series
amino acid Schiff bases with 2-hydroxy-1-naphthaldehyde:
(H2L1); [N-(2-hydroxy-1-naphthylidene)tyrosine], (H2L2); [N-
(2-hydroxy-1-naphthylidene)arginine], (H2L3); [N-(2-hydroxy-
1-naphthylidene) lysine], and their manganese(III) com-
plexes Na[Mn(L1)2].3H2O, Na3[MnL2(CH3COO)4].2H2O, and
Na[Mn(L3)2].2H2O. Their structures were determined using
Keywords 2-hydroxy-1-naphthaldehyde, antimicrobial activity,
arginine, lysine, manganese(III) complexes, Schiff base,
tyrosine
1
elemental analyses, IR, UV-vis, H-NMR spectra, magnetic
susceptibility measurements, and thermogravimetric analyses
(TGA) (Figures 1–3). The Schiff bases and manganese(III)
complexes have been also examined for antibacterial activity
against S. aureus, Sh. dys. typ 7, L. monocytogenes 4b, E.
coli, S.typhi H, S.epidermis, Br. abortus, M. luteus, B.cereus,
P. putida, and antifungal activity against C. albicans. These
results are compared with nine antibiotics Kanamycin, Sul-
phamethoxazol, Ampicillin, Chloroamphenicol, Ciprofloxacin,
Amoxycillin, Nystatin, Oflaxin, and Sulbactam.
INTRODUCTION
Metal-based drugs are used in medicine for treatment of
cancer, diabete, ulcer, anti-inflammatory, neurological and car-
diovascular diseases.[1–3] Some of Schiff bases and transition
metal complexes have also been used as drug for fungicidal,
bactericidal, antiviral, and antitubercular activity.[4–10]
In literature, it is determined that some manganese(III) com-
plexes, [Mn(C34H24N8O6)OAc] (OAc)2, [Mn(C34H24N8O6)
NO3](NO3)2, [Mn(C34H24N8O6)Cl]Cl2 of Schiff base ligands
from 1,4-dicarbonyl-phenyl-dihydrazide and chromene-2,
EXPERIMENTAL
Received 20 January 2013; accepted 10 February 2013.
The author expresses sincere thanks to Prof. Dr. Orhan Atakol for
TGA-DTA measurements and TUBITAK (The Scientific and Technical
Research Council of Turkey) for providing spectroscopy laboratory
facilities.
Address correspondence to Iffet S¸akıyan, Department of Chemistry,
Ankara University, 06100 Ankara, Turkey. E-mail: sakiyan@science.
ankara.edu.tr
Chemical and Physical Measurements
Manganese(III) acetate was prepared by the method of Gun-
duz et al.[20] The amino acids L-tyrosine (Tyr), L-arginine (Arg),
L-lysine (Lys)), 2-hydroxy-1-naphthaldehyde, methanol, and n-
heptane were purchased from Fluka, Sigma, Aldrich, Merck,
and Riedel de Haen, respectively.
˙
417

˙
I. S¸AKIYAN ET AL.
418
FIG. 1. Structures of Schiff bases.
C, H, and N were carried out using Leco 932 elemental an-
1
alyzer. H-NMR spectra of the Schiff bases were obtained on
FIG. 3. Suggested structures of manganese(III) complex of arginine Schiff
base.
a Bruker GmbH DPX-400 400 MHz High Performance Dig-
ital FT-NMR spectrometer (SiMe4 as standard) at TUBITAK
(The Scientific and Technical Research Council of Turkey).
Infrared spectra of the complexes and Schiff bases were ob-
tained from 4000 to 400 cm−1 in KBr pellets using a Mattson
FT-IR 1020 spectrophotometer. TGA of the complexes were
carried out under a N2 atmosphere using a Shimadzu DTG-
60H (ambient 750◦C) (flowing rate of N2 = 100 mL min−1
and the heating rate at 10◦C min−1 in 3 bar). Electronic spec-
tra of the Schiff bases and the complexes were recorded on an
Unicam UV2–100 UV/Visible spectrophotometer at Gazi Uni-
versity. Magnetic moments of the complexes were measured
at room temperature using a model MKI, Sherwood Scientific
(Cambridge, England) Magnetic Susceptibility Balance at Gazi
University. HgCo(SCN)4 was used as a standard.
General Procedure for The Preparation of Schiff Bases:
(H2L1); [N-(2-hydroxy-1-naphthylidene)tyrosine], (H2L2);
[N-(2-hydroxy-1-naphthylidene) arginine], (H2L3);
[N-(2-hydroxy-1-naphthylidene)lysine]
A solution of 2-hydroxy-1-naphthaldehyde (5 mmol, 0.61 g)
in methanol (50 mL) was added to amino acid (5 mmol) (L-
tyrosine, L-arginine, L-lysine) in methanol solution (50 mL).
The mixture was boiled under reflux for 3 h at 100◦C, then the
solvent was removed by rotary evaporation and the residue left
to stand at room temperature for at least 3 h. The resulting yellow
crystals were recrystallized from methanol/n-heptane (3:1).
General Procedure for The Preparation of Mn(III)
Complexes: Na[Mn(L1)2].3H2O;
Na3[MnL2(CH3COO)4].2H2O; Na[Mn(L3)2].2H2O
The complexes were prepared out by the template method.[21]
The amino acids (10 mmol) (L-tyrosine, L-arginine, L-
lysine) were dissolved in methanol (50 mL) containing NaOH
(20 mmol, 0.8 g) in a flask and stirred at room temperature
(20◦C) for 10 min. A solution of 2-hydroxy-1-naphthaldehyde
(10 mmol, 2.44 g) in methanol (50 mL) was then added. After
2 min, solid Mn(CH3COO)3.2H2O (5 mmol, 1.34 g) was added
and the mixture stirred magnetically for 3 h at room tempera-
ture. The dark brown solution was then evaporated to one-fifth
of its initial volume and left to stand overnight at room tempera-
ture. After one day, a dark red-brown microcrystalline solid was
FIG. 2. Suggested structures of manganese(III) complexes of lysine and tyro-
sine Schiff bases.

NEW N-(2-HYDROXY-1-NAPHTHALIDENE)-AMINO ACIDS LIGANDS
419
obtained, which was filtered and dried under vacuum. The solid
was recrystallized from a methanol/n-heptane (3:1) mixture.
Detection of Antimicrobial Activity
Antibacterial and antifungal activities of the ligands and
their complexes were tested in vitro against bacteria Staphy-
lococcus aureus (RSKK-07035), Shigella dysenteria type 7
(NCTC 9363), Listeia monocytogenes 4b (ATCC 19115), Es-
cherichia coli (ATCC 1230), Salmonella typhi H (NCTC
901.8394), Staphylocoocus epidermis sp., Brucella abortus
(RSKK-03026), Micrococcus luteus sp., Bacillus cereus sp.,
Pseudomonas putida sp., and fungus Candida albicans (Y-
1200-NIH) by the well-diffusion method. The test organisms
were grown on Mueller Hinton medium in Petri plates.[22] The
ligands and complexes were dissolved in dimethylformamide
(DMF) at a concentration of 0.25 μg/mL. DMF was used as
solvent and also for control. It was found to have no antimi-
crobial activity against any of the tested organisms. 1% (v/v)
of a 24-h broth culture containing 106 CFU/mL was placed
in sterile Petri dishes. Mueller-Hinton Agar (15 mL) kept at
45◦C was then poured into the Petri dishes and allowed to so-
lidity. Then 6-mm diameter wells were punched carefully by
using a sterile cork borer and were entirely filled with the test
solutions. The plates were incubated for 24 h at 37◦C. On com-
pletion of the incubation period, the mean value obtained for
the two holes was used to the calculate the zone of growth in-
hibition of each sample. Bacterial and fungal subcultures were
also tested for resistance to nine antibiotics Kanamycin, Sul-
phamethoxazol, Ampicillin, Chloroamphenicol, Ciprofloxacin,
Amoxycillin, Nystatin, Oflaxin, and Sulbactam.
SCH. 1. General procedure for synthesis of Schiff bases H2L1, H2L2, H2L3.
SCH. 2. General procedure for synthesis of manganese(III) complexes.
ganese (III) complexes were also synthesized by the method
shown in Scheme 2.
All the Schiff bases are yellow crystalline solids and stable
in atmospheric oxygen. The complexes are reddish-brown mi-
crocrystalline solids, but not stable in air. Manganese(III) com-
plexes and Schiff bases are easily soluble in methanol, DMF, and
DMSO. The general characteristic properties of all of the Schiff
bases and manganese(III) complexes are shown in Table 1.
IR Spectra
The important IR spectral bands for the synthesized lig-
ands and the complexes are given in Table 2. In the IR spec-
tra of the Schiff bases, the most characteristic bands appear at
1615–1641 cm−1 as an overlap which is attributable to v(C O)
and v(C N) stretching of the keto and imine form. It is de-
termined that the amino acid Schiff bases have keto and imine
tautomeric forms like in the literature.[23,24] These bands are
shifted to 1613–1633 cm−1 in the complexes, which means that
the imino nitrogen and phenolic oxygen of the ligands are co-
ordinated to the Mn(III) ion. Comparison of the IR spectra of
the metal complexes with those of the free ligands revealed that
all complexes have a broad band in the range 3333–3658 cm−1
assignable to v(OH) of water molecules associated with the
complexes.[25]
RESULTS AND DISCUSSION
Synthesis of Schiff Bases and Their Manganese(III)
Complexes
The Schiff bases, H2L1, H2L2 and H2L3 were prepared by
condensation of 2-hydroxy-1-naphthaldehyde with L-tyrosine,
L-arginine, and L-lysine, respectively, Scheme 1. Their man-
TABLE 1
Physical properties, analytical data, and formula weights (F.W) of the Schiff bases and manganese(III) complexes
Analysis found (calcd.)a (%)
Yield Mp, μeff
Compounds (empirical formula)
F.W.
Color
%
Dec◦C Bm
C
H
N
H2L1 (Tyr) (C20H17O4N)
H2L2 (Arg) (C17H20O3N4.H2O)
H2L3 (Lys) (C17H20O3N2)
Na[Mn(L1)2].3H2O (Tyr)
335.35 Yellow
346.38 Yellow
300.35 Yellow
20
70
80
219
250
150
—
—
—
71.46 (71.63) 4.29 (5.11)
58.96 (58.95) 5.46 (6.40) 16.29 (16.17)
67.95 (67.98) 5.49 (6.71)
4.62 (4.18)
8.96 (9.33)
3.52 (3.51)
6.61 (7.75)
798.65 Reddish Brown 35
330 3.75 59.84 (60.16) 3.97 (4.54)
330 3.16 40.21 (41.52) 4.37 (4.71)
330 4.14 57.78 (57.47) 4.16 (5.67) 36.05 (7.88)
Na3[MnL2(CH3COO)4] .H2O (Arg) 722.46 Reddish brown 50
Na[Mn(L3)2].2H2O (Lys)
710.63 Reddish brown 45

˙
420
I. S¸AKIYAN ET AL.
TABLE 2
Significant IR bands of amino acid Schiff bases and manganese(III) complexes (cm−1
)
v(C O)
Compound
v(O H)
v(N H)
v(COOH)
v(C N)
vas(COO)
v(C C)
vs(COO)
H2L1 (Tyr)
3235
3327
3414
3658
3333
3350
—
3244
—
3438
3170
3269
1710
1695
1710
—
1656
—
1613
1627
1633
1615
1616
1641
1579
—
—
1598
1599
—
1546
1567
1544
1535
1536
1537
1453
—
—
1428
1427
1456
H2L2 (Arg)
H2L3 (Lys)
Na[Mn(L1)2].3H2O (Tyr)
Na3[MnL2(CH3COO)4] 2H2O (Arg)
Na[Mn(L3)2].2H2O (Lys)
TABLE 3
1H-NMR spectra of Shiff bases (δ values ppm), DMSO-d6
Schiff bases
-OH
-COOH
-HC N
-ArC-H
-CH
-C-HH
H2L1 (Tyr)
H2L2 (Arg)
H2L3 (Lys)
14.2(s,1H))
9.25(s,1H)
9.9(s,1H)
10.50(s,1H)
8.75(s,1H)
8.85(s,1H)
9.2(s,1H)
6.6–7.9 (m,6H)
6.2–8.1 (m,6H)
6.40–7.8 (m,6H)
4.7(t,1H)
4.3(t,1H)
4.50(t,1H)
3.1–3.2 (d,2H)
2.58–2.90 (m,6H)
2.90–3.2 (m,8H)
—
—
s = singlet, d = doublet, t = triplet, m = multiplet.
TABLE 4
Electronic data of amino acid Schiff bases and manganese(III) complexes
Schiff bases and Mn(III) complexes
Bands λmax (nm), ε in cm2mol−1
)
H2L1 (Tyr)
306 (5912)
306 (1244)
302 (5844)
307 (6428)
307 (6428)
307 (1244)
404 (4292)
404 (1268)
397 (4580)
351 (3436)
382 (3424)
404 (1268)
425 (4396)
424 (1356)
415 (4716)
406 (3744)
409 (3756)
424 (1356)
H2L2 (Arg)
H2L3 (Lys)
Na[Mn(L1)2].3H2O (Tyr)
Na3[MnL2(CH3COO)4].2H2O (Arg)
Na[Mn(L3)2].2H2O (Lys)
488 (200)
489 (199)
496 (260)
TABLE 5
Thermogravimetric analyses of manganese(III) complexesa
Complexes
Xh2Oc + 2CO2 (50–250◦C)b
17.82 (17.78) (3H2O+2CO2)
34.00 (33.32) (2 H2O+4CO2)
18.78 (17.45) (2H2O+2CO2)
Residue Mn2O3 and MnO2 (250–800◦C)b
Na[Mn(L1)2].3H2O (Tyr)
89.56 (89.11) (MnO2)
77.95 (78.8) (Mn2O3)
77.77 (77.78) (Mn2O3)
Na3[MnL2(CH3COO)4] .2H2O (Arg)
Na[Mn(L3)2].2H2O (Lys)
aCalculated values in parantheses.
bTemperature ranges.
cX = 3, 2, and 2, respectively.

421

˙
I. S¸AKIYAN ET AL.
422
range 400–800◦C, the complexes probably convert to a mixture
of MnO2 and Mn2O3.
1H-NMR Spectra of Schiff Bases
1
The assignments of H-NMR spectra of the ligands were
recorded in DMSO-d6 in Table 3. Characteristic 1H-NMR sig-
nals at 14.2 ppm and 9.25–10.50 ppm are attributed phenolic-
OH and carboxylic-COOH protons, respectively. The peaks at
9.2–8.75 ppm are assigned to the –CH N proton. The multisig-
nals within the 6.2–8.1 ppm range are assigned to aromatic-H
protons. The three signals are at 4.50 ppm and 2.58–3.2 ppm
–CH and –CH2 protons. All the complexes are paramagnetic,
Antimicrobial Activities
Amino acid Schiff bases and manganese(III) complexes were
assayed in vitro for their ability to inhibit the growth of repre-
sentative S.aureus, Sh.dys. typ 7, L. monocytogenes 4b, E. coli,
S. typhi H, S. epidermis, Br. abortus, M. luteus, B. cereus, P.
putida, and antifungal activity against C. albicans.
The susceptibilities of certain strains of bacteria and a fungus
to the amino acid Schiff bases and their complexes were evalu-
ated by measuring the size of the bacteriostatic and fungistatic
diameter. The antibacterial activity of these compounds was also
compared with nine commercial antibiotics: Kanamycin, Sul-
phamethoxazol, Ampicillin, Chloroamphenicol, Ciprofloxacin,
Amoxycillin, Nystatin, Oflaxin, and Sulbactam. The results are
given in Table 6 for the Schiff bases, the manganese complexes,
and the antibiotics. Some of the synthesized compounds were
as effective as the antibiotics mentioned.
1
therefore the H-NMR spectra of the complexes could not be
obtained.
UV Spectra of Amino Acid Schiff Bases and Complexes
The electronic spectra data of the ligands and their complexes
in DMF are listed in Table 4.
In the UV-vis spectra of Schiff bases two strong broad bands
exhibit at ∼300 and ∼400–420 nm. It follows from the literature
that these bands can be assigned to the phenol-imine and keto-
amine forms.[24,26] They may be attributed to n → π∗ and π →
π∗ type transition, respectively.
Although in the spectra of all complexes, the band at
∼300 nm exist, the other bands at ∼400 and 420 nm are shifted
to shoulder bands. This means that in the complex Schiff bases
exist only in the phenol-imine form and coordinated Mn(III) ion
with phenolic oxygen and imine nitrogen.[24] For manganese(III)
complexes a rather broad band appears at 488–496 nm in the
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range from ambient to 800◦C at a heating rate of 10◦C min−1
.
Data for thermogravimetric analysis (TGA) are listed in Ta-
ble 5. The decomposition temperature and the weight losses of
the complexes were calculated from data. Thermal analyses of
the three complexes are in agreement with elemental analyses
and indicate the presence of various levels of water molecules
per manganese atom, which are lost at ca. 50–250◦C.[29,30] It
means that all of the complexes have coordinated water in their
structures. The second weight loss occurs at ca. 400◦C due to
the loss of CO2 groups from the complexes. In the temperature

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