International Journal of Organic Chemistry, 2011, 1, 71-77
doi:10.4236/ijoc.2011.13012 Published Online September 2011 (http://www.SciRP.org/journal/ijoc)
Copyright © 2011 SciRes. IJOC
Synthesis, Characterization and Antibacterial Activity of
Biologically Important Vanillin Related
Hydrazone Derivatives
Thiyagarajan Govindasami1, Anjana Pandey2, Nithya Palanivelu3, Ashutosh Pandey1*
1Department of Chemistry, Motilal Nehru National Institute of Technology, Allahabad, India
2Department of Biotechnology, University of Allahabad, Allahabad, India
3Department of Chemistry, BharathiarUniversity, Coimbatore, India
E-mail: *apandey70@yahoo.com
Received June 3, 2011; revised July 27, 2011; accepted August 5, 2011
Abstract
Hydrazone derivatives of vanillin are found to possess anti-bacterial activities. Based on higher bio-activity
of hydrazones, new hydrazone derivatives were synthesized from Piperdine-4-carboxylicacid methyl ester
(1). The compounds 1-pyrimidine-2-yl piperidine-4-carboxylicacid(4-hydroxy-3-methoxy benzylidine)-hy-
drazide (10), 1-pyrimidine-2-yl piperidine-4-carboxylicacid (3,4-dimethoxy benzylidine) hydrazide (11),
1-pyrimidine-2-yl piperidine-4-carboxylicacid(4-butoxy-3-methoxy benzylidine)-hydrazide (12), 1-pyrimi-
dine-2-yl piperidine-4-carboxylicacid(3-methoxy-4(2-methoxy ethoxy) benzylidine)-hydrazide (13) were
synthesized, purified and characterized by 1HNMR, 13CNMR, LCMS, FT-IR and HPLC techniques. The
synthesized hydrazone derivatives were further checked for anti-bacterial activities by paper disc diffusion
method against Pseudomonas aeruginosa and Staphylococcus aureus bacterial strains.
Keywords: Antibiotics, Fractional Crystallization, Hydrazones, Coupling Reaction
1. Introduction
Earlier, by Quantitative Structure Activity Relationship
(QSAR) studies, most of the rifamycin derivatives were
found to be biologically active compared to other com-
pounds [1]. For example, the hydrazones obtained from
3-formyl rifamycin and N-amino-N-methyl piperazine
derivatives were found to be biologically active and
tested for oral treatment of infections in animals [2]. Re-
cently, a lot of biologically important hydrazone deriva-
tives with a number of functional groups have been syn-
thesized from aromatic and aliphatic compounds [3].
Hydrazone derivatives are molecules containing highly
reactive azomethine group (CO-NH-N=CH) and thus
useful in new drug development [4]. Also, these are
found to possess anti-microbial [5-7], anti-mycobacterial
[8], anti-convulsant [9], analgesic [10], anti-inflamma-
tory [11,12], anti-platelet [13], anti-tubercular [14-16]
and anti-tumoral [17-19] activities. Diflunisal hydrazones
were also prepared as possible dual acting antimicrobial
and anti-tuberculosis agents with anti-inflammatory
properties [20]. Moreover, hydrazones has been recently
established as a good precursor for one-pot synthesis of
C-4 functionalized 1,2,3,4-tetrahydro quinolones con-
taining a quaternary stereo center [21]. Due to the growth
of population and changes in climatic conditions several
new diseases are likely to affect the human beings. So,
there is a continuous need for the synthesis of new bio-
logically active organic compounds by using a fast and
efficient approach which may act as potential antimicro-
bial agents. Based on the higher bio-reactivity of hydra-
zones, we have synthesized novel hydrazones (10-13)
from Piperdine-4-carboxylic acid methyl ester (1) cou-
pled with 2-chloro pyrimidine (2) along with other vanil-
lin derivatives (6-9). The anti-bacterial studies were ef-
fectively done for newly synthesized hydrazones by
standard disc diffusion method [22] with different con-
centrations.
2. Results and Discussion
2.1 Synthesis
Earlier studies on pyrimidine shows, that heterocyclic
G.THIYAGARAJAN ET AL.
72
compounds containing pyrimidine moiety shows various
biological activities. Therefore, we were tempted to syn-
thesize vanillin related hydrazones with a pyrimidine
moiety. A series of vanillin related hydrazones are syn-
thesized and their purity is checked by thin layer chroma-
tography (TLC) and HPLC techniques. All the synthe-
sized hydrazones structures are characterized by 1HNMR
along with 13CNMR; LC-MS and FT-IR spectral tech-
niques. There are three different types of coupling reac-
tions taking place in syntheses of the hydrazone deriva-
tives. In step-1, compound 1 is coupled with 2 to form 3
by “chloro-amine” coupling. In step-2 the product 3 was
reacted with 4 to form 5 by “ester-amine” condensation.
In step-3, vanillin derivatives (6-9) react with 5 to form
hydrazone derivatives (10-13) by “aldehyde-amine” cou-
pling. From the 1H NMR spectra, the structures of the
synthesized compounds (10-13) were confirmed on the
basis of the fact that the aldehydic proton (which was
visible at δ 10.55) in the starting compound 6 disap-
peared, and a new singlet due to the azomethine (CH=N)
group appeared at δ values between 8.06 - 8.11 ppm in
all the compounds. The CONH protons appearing as
singlets resonated at δ values between 11.20 and 11.25
ppm. Furthermore, the protons of CONH and CH=N
exhibited two separate signals in 1HNMR spectra in be-
tween 11.20 - 11.25 ppm and 8.06 - 8.11 ppm respec-
tively due to the nitrogen inversion, which is shown in
Figure 1.
The three -CH protons of the pyrimidine (pm) were
centered at δ value 8.35 ppm as doublets by integrating
in two proton and at δ value 6.60 ppm as triplets by inte-
grating in one proton.
In the 13CNMR spectra of 6 the carbon signal due to
(-CHO), was observed at δ 188.97 ppm. However in
products 10-13 this signal was found to be absent and a
new signal at δ values between 150.04 and 151.04 ppm
arose due to the presence of CH=N in compounds
(10-13).
The carbon signal of C=O group appeared at δ values
between 175.8 and 176.2 ppm. The molecular mass of
the synthesized compounds were recorded by LC-MS
techniques, which was registered in positive ion (+M)
mode. The FT-IR spectra of compounds (10-13) showed
absorption bands at 1652 - 1655 cm1 due to the presence
of C=O functional group, while the bands observed at
1582 - 1586 cm1 corresponded with C=N linkage and
3280 - 3413 cm1 observed due to the -NH group. The
absorption peak at 2845 - 2867 cm1 was due to the CH
linkage and the band appearing at 3845.4 cm1 in the IR
spectrum of the compound (10) represented OH group.
The synthetic conditions and melting points of the newly
synthesized compounds are summarized in Table 1.
Figure 1. Nitrogen inversion of compound 10.
Table 1. Reaction data of newly synthesized compounds
Compound Condition Purification method HPLC purity LCMS (+M)
3 Acetonitrile, 85˚C, Reflux, 6 h Column, 10% Ethyl acetate:Hexane 98.7 222.3
5 Methanol, 90˚C, Reflux, 5 h Crystallization, Methonol, 10 mL 99.6 222.6
10 Ethanol, 70˚C, Reflux, 8 h FC, Ethyl acetate:diethyl ether (5:10) mL 99.8 355.8
11 Ethanol, 70˚C, Reflux, 8 h FC,Dichloro methane:Hexane (3:8) mL 99.6 370.2
12 Ethanol, 70˚C, Reflux, 8 h FC, Dichloro methane:di ethyl ether (2:5) mL96.8 412.8
13 Ethanol, 70˚C, Reflux, 8 h FC, Ethyl acetate:Diethyl ether (5:6:4) mL97.8 414.8
FC—fractional crystallization.
Copyright © 2011 SciRes. IJOC
73
G.THIYAGARAJAN ET AL.
2.2. Antibacterial Activity
The anti-bacterial results showed that some of the com-
pounds were active against both Gram-positive S. aureus
and Gram-negative P. aeruginosa bacteria. Among the
tested solutions (10-13), the compounds (12) and (13)
showed good antibacterial activity against the test organ-
isms and 11 had moderate effective against S. aureus and
less effective against P. aeruginosa. The compound 10
had no anti-bacterial activity against P. aeruginosa and
lowest activity against S. aureus. It was observed that
maximum antibacterial activity was shown by com-
pounds containing the butoxy, methoxy and methyl-
ethoxy group with highly reactive azomethine (-NH-N=
CH-) group. On the other hand, compared to the standard
antibacterial drugs namely, Ciprofloxacin and Cefaclor
our synthesized hydrazones were having moderate ac-
tiveity against test organisms. The obtained results of
antibacterial activity have been summarized in Table 2.
3. Experimental
All synthetic manipulations were conducted in the dry
and nitrogen atmosphere. Solvents for synthesis were
reagent grade and dried by standard procedures [23]. The
starting materials are such as (1), (2), Hydrazine hydrate
(4), Vanillin (6) and Veratraldehyde (7) were obtained
from Sigma-Aldrich chemicals and acetone, methanol,
ethanol, acetonitrile and dichloromethane, which were
obtained from SRL Chemical Limited, India. The inter-
mediate vanillin derivatives such as 4-butoxy-3-methoxy
benzaldehyde (8) and 3-methoxy-4-(2-methoxy-ethoxy)
benzaldehyde (9) were prepared by typical procedures
[24,25]. Melting points of as synthesized compounds
were determined with open capillary tube on a Gallenk-
amp melting point apparatus. The 1H and 13CNMR were
recorded on a Bruker Avance-III, 300 MHz and 400
MHz. Liquid chromatography mass spectra (LCMS)
were run on “LCMS—Agilent Technologies-1200 Se-
ries” and purity was checked by “HPLC—Agilent Tech-
nogies-1200 Series”. IR spectra were recorded by “FT-
IR Nicolet 6700” spectrometer. All compounds were
routinely checked by TLC on silica gel G plates using
petroleum ether/ethyl acetate (7:3; 6:4; 5:5 by V/V) as
solvent system and the developed plates were visualized
by UV light, iodine vapour and KMnO4 solution. The
detailed scheme of synthesis has been shown in Scheme
1. The anti-bacterial studies performed in Center for Bio-
technology, University of Allahabad, India.
N
OO
H
NN
Cl
K2CO3
N
NN
OO
NH2NH2H2O (4)
O
OR
O
H
N
NN
OH
NNO
OR
N
NN
OH
NNH2
+
Step-1 Step-2
1235
10,11,12,13
6, 7,8, 9
R = -H;
-C H3;
-C H2-CH2-CH2-CH3;
-C H2CH2-O -C H 3
Step-3
1 - Piperdine-4-carboxylic acid methyl ester
2 - 2-Chloro pyrimidine
3 - 1-pyrimidine-2-yl-piperdine-4-carboxylic acid
methyl ester
4 - Hydrazine hydrate
5 - 1-Pyrimidin-2-yl-piperidine-4-carboxylic acid
hydrazide
6 - Vanillin
7 - Veratradehyde
8 - 4-Butoxy-3-methoxy-benzaldehyde
9 - 3-Methoxy-4-(2-methoxy-ethoxy) benzaldehyde
10 - 1-Pyrimidin-2-yl-piperidine-4-carboxylic acid
(4-hydroxy-3-methoxy benzylidene) - hydrazide
11 - 1-Pyrimidin-2-yl-piperidine-4-carboxylicacid
(3,4-dimethoxy benzylidene) hydrazide
12 - 1-Pyrimidin-2-yl-piperidine-4-carboxylic acid
(4-butoxy-3-methoxy - benzylidene)-hydrazide
13 - 1-Pyrimidin-2-yl-piperidine-4-carboxylic acid
[3-methoxy-4-(2-methoxy-ethoxy)-benzylidene]
hydrazide
Scheme 1. Synthetic sche me of novel hy drazone derivatives.
Copyright © 2011 SciRes. IJOC
G.THIYAGARAJAN ET AL.
74
Table 2 .Antibacterial activity of novel hydrazones (µ·gmL–1)
Staphylococcus aureus (G+) Pseudomonas aeruginosa (G–)
Compound
(µg·mL–1) 50 100 150 200 250 50 100 150 200 250
10 – + + ++ ++
+
11 + + ++ +++ +++
– + ++ ++
12 – + + ++ +++ + ++ +++ +++ +++
13 + ++ +++ +++ +++ ++ ++ +++ +++ ++++
DMSO – – – – – –
Ciprofloxacin ++ +++ ++++ ++++ ++++++++ +++ ++++ ++++ +++++
Cefoclor +++ +++ ++++ ++++ +++++
() No measurable activity; ( + )1 - 2 mm; (++ ) 3 - 5 mm; (+++) 6 – 8 mm; (++++) 9 - 12 mm; (+++++ )13 – 17 mm
3.1 Synthesis of 1-Pyrimidine-2-yl
piperdine-4-carboxylicacid Methyl Ester (3)
Methyl nipocotate [Piperdine-4-carboxylic acid methyl
ester (1) (1.3 mL, 8.7 mmol, 1.0 eq.)] and potassium car-
bonate (1.2 g, 8.7 mmol, 1.0 eq.) was added to a stirred
solution of 2-Chloro pyrimidine (2) (1.0 g, 8.7 mmol, 1.0
eq) in dry acetonitrile (10 mL) under nitrogen atmos-
phere and refluxed at 85oC in a sealed tube for 10 hrs
followed by cooling to room temperature. The solvent
was evaporated under high vacuum and the crude prod-
uct was extracted with ethyl acetate (3 × 50 mL). The or-
ganic layer was washed with water and brine, dried with
sodium sulfate, filtered and concentrated under reduced
pressure. The so obtained product was purified by col-
umn chromatography using 10% ethyl acetate in petro-
leum ether as eluant [Silica gel; Rf: 0.3 (Pet Ether:EA;
7:3)] to get the product (1-pyrimidine-2-yl-piperdine-
4-carboxylic acid (3)) as yellow liquid. 1.8 g, Yield: 93%.
1HNMR: (CDCl3, 300 MHz), δ 8.30 (d, 2H, J = 2.6 Hz,
pm-N-CH), 6.47 (t, J = 6.00 Hz, 1H, Pm-CH), 4.67 and
3.08 (m, 4H, Py-NCH2), 3.70 (s, 3H, -CH3), 2.61 (m, 1H,
Py-CH), 2.0 - 1.70 (m, 4H, -PyCH2); 13CNMR: (CDCl3,
300MHz), δ 175.2 (1C, C=O), 161.5 (1C, Pm-N-C-N),
157.6 (2C, Pm-N-CH), 109.6 (1C, Pm-CH), 51.7 (1C,
O-CH3), 43.1 (2C, Py-N-CH2), 41.4 (1C, Py-CH), 27.8
(2C, Py-CH2); LCMS: 221.3 (Calculated mass for M+,
222.3); HPLC purity: 98.7%.
3.2. Synthesis of 1-Pyrimidin-2-yl
piperidine-4-carboxylic Acid Hydrazide (5)
To a dry RB flask the product (3) (1.0 g; 4.5 mmol; 1eq)
was added to dry methanol (10 ml) containing Hydrazine
hydrate (4) (1.3 ml; 27 mmol; 8eq.) under nitrogen at-
mosphere and refluxed to 95˚C in sealed tube for 7 hrs.
The reaction mixture cooled to room temperature, con-
centrate under reduced pressure. The crude was purified
by crystallization, washed with petroleum ether and fil-
tered. White solid, 0.96 g Yield: 96%. 1HNMR: (CDCl3,
300 MHz), δ 9.02 (s, 1H, -NH), 8.34 (d, 2H, J = 2.4 Hz,
Pm-N-CH), 6.60 (t, J = 7.20 Hz, 1H, Pm-CH), 4.66 and
2.90 (m, 4H, Py-N-CH2), 4.16 (d, 2H, J = 2.8, NH2), 2.38
(m, 1H,Py-CH), 1.68 - 1.50 (m, 4H, Py-CH2); 13CNMR:
(CDCl3, 300 MHz), δ 174.02 (1C, C=O), 161.5 (1C,
Pm-N-C-N), 158.3 (2C, Pm-N-CH), 110.2 (1C, Pm-CH),
43.3 (2C, Py-N-CH2), 39.9 (1C, Py-CH), 28.3 (2C, Py-
CH2); LC-MS: 221.16 (Calculated mass for M+, 222.6);
HPLC purity: 99.6%.
3.3. General Procedure for Synthesis of (10-13)
Vanillin derivatives (6-9) (1.5eq.) were added to com-
pound (5) (1eq.) separately in dry ethanol/acetic acid (5:1
mL) under nitrogen atmosphere and the reaction mixtures
were refluxed at 85oC in sealed tube for 8 hrs. These were
slowly brought to room temperature and concentrated
under reduced pressure. The crude products purified by
fractional crystallization method by using ethyl acetate or
dichloromethane along with petroleum ether or diethyl
ether were filtered and dried under vacuum to give the
corresponding products (10-13) as white solids.
3.3.1. 1-Pyrim i di n-2 -yl-piperidin e-4 -car boxylicacid
(4-hydroxy-3-methoxy benzylidene)-
Hydrazide (10)
Yield: 93.9%. 1HNMR: (DMSO-d6, 300 MHz), δ 11.20
(s, 1H, -NH), 9.77 (s, 1H, -OH), 8.35 (m, 2H, Pm-N-CH),
8.06 (s, 1H, N=CH), 7.24, 7.05 and 6.80 (3H, Ar-CH),
6.60 (m, 1H, Pm-CH), 4.70 and 2.96 (m, 4H, Py-N-CH2),
3.80 (s, 3H, -CH3), 1.81 - 1.55 (m, 4H, Py-CH2); 13CNMR:
(DMSO-d6, 400MHz) δ 170.2 (1C, C=O), 161.1 (1C,
N-C-N), 157.9 (2C, Pm-N-CH), 151.4 (1C, N=CH),
146.7, 142.9, 125.7, 121.86, 115.3 and 108.8 (Ar-C),
109.8 (1C, Pm-CH), 55.5 (1C, O-CH3), 42.8 (2C,
Py-N-CH2), 40.12 (1C, Py-CH), 27.8 (2C, Py-CH2);
LC-MS: 354.4 (Calculated mass for M+, 355.8); FT-IR
(cm–1, KBr): 3845.4 (OH), 3413.4 (-NH), 2854.7 (-CH),
1662 (C=O), 1583.1 (C=N); HPLC purity: 99.8%; mp:
233.1˚C - 234.4˚C.
Copyright © 2011 SciRes. IJOC
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G.THIYAGARAJAN ET AL.
3.3.2. 1-Pyrim i di n-2 -yl-piperidin e-4 -car boxylicacid
(3,4-dimethoxy benzylidene) Hydrazide (11)
Yield: 96%. 1HNMR: (DMSO-d6, 300 MHz), δ 11.29 (m,
1H, -NH), 8.35 (d, J = 3.00 Hz, 2H, Pm-N-CH), 8.11 (s,
1H, N=CH), 7.27, 7.16 and 7.00 (3H, Ar-CH), 6.60 (m,
1H, Pm-CH), 4.70 and 2.96 (m, 4H, Py-N-CH2), 3.80 (s,
6H, O-CH3), 1.80 - 1.55 (m, 4H, Py-CH2);13CNMR:
(DM-SO-d6, 300 MHz), δ 176.2 (1C, C=O), 161.6 (1C,
N-C-N), 158.4 (2C, Pm-N-CH), 151.0 (1C, N=CH),
150.8, 149.4, 127.5, 122.0 and 112.1 (Ar-C), 108.9 (1C,
Pm-CH), 108.7 (Ar-C), 56.0 (2C, O-CH3), 43.4 (2C, Py-N-
CH2), 38.57 (1C, Py-CH), 28.3 (2C,Py-CH2); LC-MS:
369.5 (Calculated mass for M+, 370.2); FT-IR (cm–1, KBr):
3211.7 (NH), 2845.0 (-CH), 1652 (C=O), 1582 (C=N);
HPLC purity: 99. 6%; mp: 220.6˚C - 221.8˚C.
3.3.3. 1-Pyrim i di n-2 -yl-piperidin e-4 -car boxylicacid
(4-Butoxy-3-methoxy) Benzylidene Hydrazide
(12)
Yield: 96.1%. 1HNMR:(DMSO-d6, 300 MHz), δ 11.27
(m, 1H, -NH), 8.34 (d, J = 4.50 Hz, 2H, Pm-N-CH), 8.11
(s, 1H, N=CH), 7.25, 7.12 and 6.97 (3H,Ar-CH), 6.58 (m,
1H, Pm-CH), 4.68 and 2.93 (m, 4H, Py-CH2), 3.97 (m, 2H,
-OCH2), 3.77 (m, 3H, -OCH3), 1.71 (m, 4H, -CH2- CH2),
1.40 (m, 4H, Py-CH2), 0.92 (m, 3H, -CH3). 13CNMR:
((DMSO-d6, 300MHz), 176.0 (1C, C=O), 161.6 (1C,
N-C-N), 158.4 (2C, Pm-N-CH), 150.4 (1C, N=CH), 150.2,
149.61, 127.4, 122.0, 113.1 and 112.1 (Ar-CH), 110.2 (1C,
Pm-CH), 68.3 (1C, O-CH2), 55.9 (1C, O-CH3), 43.4 (2C,
Py-N-CH2), 41.5 (1C, Py-CH), 31.21 (1C, CH2), 28.3 (2C,
Py-CH2), 19.1 (1C, CH2), 14.1 ((1C, -CH3); LC-MS:
411.41 (Calculated mass for M+, 412.8); IR(cm–1, KBr):
3208.2 (NH), 2867.8 (-CH), 1655 (C=O), 1583.9 (C=N);
HPLC purity: 96.8%. mp: 213.8˚C - 215.1˚C.
3.3.4. 1-Pyrim i di n-2 -yl-piperidin e-4 -car boxylicacid
[3-methoxy-4-(2-methoxy ethoxy)-benzylidene
Hydrazide (13)
Yield: 78.1%. 1HNMR: (DMSO-d6, 300MHz), δ 11.25
(m, 1H, -NH), 8.35 (d, J = 2.8Hz, 2H, Pm-N-CH), 7.90
(s, 1H, N=CH), 7.27, 7.13 and 6.99 (3H, Ar-CH), 6.60
(m, 1H, Pm-CH), 4.70 and 2.95 (m, 4H, Py-N-CH2), 4.10
(m, 2H, -O-CH2), 3.65 (m, 2H, -CH2), 3.31 (d, J=7.8 Hz,
6H, -O-CH3), 1.81 - 1.52 (m, 4H, Py-CH2); 13CNMR:
(CDCl3, 400 MHz), δ 176.7 (1C, C=O), 161.5 (1C,
N-C-N), 157.7 (2C, Pm-N-CH), 150.3 (1C, N=CH),
149.84, 143.1, 127.0, 121.4 and 112.8 (Ar-C), 109.6 (1C,
Pm-CH), 108.7 (Ar-C), 70.8, 68.3 (CH2-O-CH2), 59.29
(1C, O-CH3), 55.8 (1C,O-CH3), 43.4 (2C, Py-N-CH2),
39.0 (1C, Py-CH), 27.6 (2C, Py-CH2); LC-MS: 413.5
(Calculated mass for +M, 414.8); FT-IR (cm–1, KBr):
3173.4 (NH), 2854.7 (-CH), 1659 (C=O), 1586.7 (C=N);
HPLC purity: 97.8%; mp: 188.1˚C - 189.1˚C.
3.4. Anti-Bacterial Assay
All the synthesized hydrazones were tested for their
anti-bacterial activity against a set of bacterial strains,
namely, Staphylococcus aureus, and Pseudomonas aeru-
ginosa by paper disc diffusion method with different
concentrations of the solutions prepared in Dimethyl
sulfoxide (DMSO). The reason of choosing DMSO for
antibacterial studies was that it has no effect on the
above mentioned bacterial strains. Nutrient agar was
used as the culture medium for the growth of bacterial
colony that was prepared by using peptone (3.0 g), NaCl
(3.0 g), Yeast (1.5 g), Agar (6.0 g) in 300 mL of distilled
water with pH at 7.0 The as prepared medium is auto-
claved at 15 pa for 20 minutes and kept at 85ºC for 30
minutes to sterilize the media. This media was then
poured into petridishes slowly in laminar flow environ-
ment, allowed to solidify and kept at 30˚C for 24 hrs.
The bacterial strains were inoculated by spreading in
peptidases and its temperature is maintained at 30˚C for
24 hr. Using paper disc (8 mm) in nutrient agar culture
medium, different concentrations (50, 100, 150, 200, 250
µg/mL) of the newly synthesized hydrazones (10-13)
were loaded through bacteria free micro pipettes. The
anti-bacterial activity was determined by measuring the
zone of inhibition in millimeters and compared with
standard drug Ciprofloxacin and Cefaclor.
4. Conclusions
We have developed the simple and crucial synthetic
technique of vanillin related hydrazone derivatives and
the reactions occurred very fast, under mild condition
using reasonable reagents and solvents, yield is also
higher. The anti-bacterial activity of synthesized novel
hydrazones were effectively screened against Gram posi-
tive S. aureus and Gram-negative P. aeruginosa bacterial
strains. Most of these compounds show moderate anti-
bacterial activity comparable with to marketable com-
pounds. The zone of inhibition of tested compounds
shows, the vanillin coupled hydrazone derivatives en-
compass potent bio-activities against bacterial strains.
Due to the strong bio-activity of our synthesized hydra-
zones can be further allowed to attempt other bio-acti-
vities against a number of diseases and this work will be
precious for further studies in terms of toxicity effect and
Quantity Structural Activity Relationship (QSAR) to
improve their biological and pharmacological properties.
5. Acknowledgements
We are appreciative to Dr. A. Thamaraichelvan and Dr.
M.Ganesan, Department of Chemistry, Thiagarajar Col-
Copyright © 2011 SciRes. IJOC
G.THIYAGARAJAN ET AL.
76
lege, Madurai, India for giving constant support to this
research work. Funding support from the DST project
SR/ME/S-3/0016/2008 is also acknowledged.
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