Synthesis of Cinnamanilide Derivatives and Their Antioxidant and Antimicrobial Activity

Article abstract of DOI:10.1155/2015/208910

The amide derivatives of cinnamic acid were synthesized and their antimicrobial and antioxidant activities were investigated. The investigation of antimicrobial potentials of the compounds demonstrated a strong activity against 21 bacterial strains comprising Gram-positive and Gram-negative bacteria. Compounds 2a, 2b, and 3b showed strong antimicrobial activity against all microorganisms with the pMIC value ranging from 2.45 to 3.68. Compounds 2a, 3a, and 3b demonstrated strong antioxidant activity with % inhibition of the DPPH radical of 51% (±1.14), 41% (±1.01), and 50% (±1.23), respectively. These findings indicate that the amide derivatives of the cinnamic acid possess strong antibacterial and antioxidant activities.

Full text of DOI:10.1155/2015/208910

Hindawi Publishing Corporation
Journal of Chemistry
Volume 2015, Article ID 208910, 5 pages
http://dx.doi.org/10.1155/2015/208910
Research Article
Synthesis of Cinnamanilide Derivatives and Their Antioxidant
and Antimicrobial Activity
Satish Balasaheb Nimse,1 Dilipkumar Pal,2 Avijit Mazumder,3 and Rupa Mazumder3
1Institute for Applied Chemistry and Department of Chemistry, Hallym University, Chuncheon 24252, Republic of Korea
2Institute of Pharmaceutical Sciences, Guru Ghasidas Vishwavidyalaya, Bilaspur, Chhattisgarh 495009, India
3Department of Pharmaceutical Technology, Noida Institute of Engineering and Technology, Greater Noida 201306, India
Correspondence should be addressed to Satish Balasaheb Nimse; satish nimse@hallym.ac.kr
Received 12 October 2015; Revised 2 December 2015; Accepted 7 December 2015
Academic Editor: Artur M. S. Silva
Copyright © 2015 Satish Balasaheb Nimse et al. is is an open access article distributed under the Creative Commons Attribution
License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly
cited.
e amide derivatives of cinnamic acid were synthesized and their antimicrobial and antioxidant activities were investigated.
e investigation of antimicrobial potentials of the compounds demonstrated a strong activity against 21 bacterial strains
comprising Gram-positive and Gram-negative bacteria. Compounds 2a, 2b, and 3b showed strong antimicrobial activity against
all microorganisms with the pMIC value ranging from 2.45 to 3.68. Compounds 2a, 3a, and 3b demonstrated strong antioxidant
activity with % inhibition of the DPPH radical of 51% ( 1.14), 41% ( 1.01), and 50% ( 1.23), respectively. ese findings indicate
that the amide derivatives of the cinnamic acid possess strong antibacterial and antioxidant activities.
1. Introduction
known to possess toxic and carcinogenic side effects in animal
models [9]. erefore, the demand has increased because of
questions about the long-term safety and negative consumer
perception of the commonly used synthetic antioxidants
BHT and BHA. e discovery of compounds that can show
both antimicrobial and antioxidant activities with no toxic
effects on health is highly awaited.
Due to its common occurrence in plants and its low toxic-
ity [10, 11], cinnamic acid has been evaluated as an antioxidant
compound [12, 13]. Moreover, the cinnamic acid derivatives
are reported to possess better antimicrobial activity than
cinnamic acid itself [14, 15]. In the present paper the synthesis,
antimicrobial, and antioxidant activities of the amide deriva-
tives of cinnamic acid are presented.
Discovery of simple organic compounds with the antimicro-
bial and antioxidant activities is of growing concern in the
food industries for their preservative properties [1, 2]. Preser-
vation of industrial food containing polyunsaturated fatty
acids (eicosapentaenoic (20:5ꢀ-3) acid) has been a subject
of growing interest, because of their importance in human
nutrition. ꢀ-3-Polyunsaturated fatty acids have several health
benefits in cardiovascular disease, immune disorders, inflam-
mation, allergies, and diabetes [3]. erefore, the develop-
ment of the antimicrobial compounds that can act as food
preservatives by inhibiting the growth of bacteria or fungi,
including mold, is very important [4].
Apart from the bacterial deterioration, the radical asso-
ciated oxidation of fatty acids is one of the most important
reactions leading to a degeneration of food [5, 6].Several com-
pounds with the antioxidant activity have been used to slow
down the radical associated oxidative reactions. Antioxidants
are molecules that inhibit or quench free radical reactions and
delay or inhibit the cellular damage [7, 8]. The butylated hydro-
xyanisole (BHA), butylated hydroxytoluene (BHT), and ter-
tiary butylhydroquinone (TBHQ) have been used commonly
as food antioxidants. However, some of these molecules are
2. Materials and Methods
All chemicals, solvents, and biochemical reagents were of
analytical grade and purchased from commercial sources.
1,1-Diphenyl-2-picrylhydrazyl (DPPH) was purchased from
Aldrich Chemical Co. (Milwaukee, WI, USA). UV-Vis spec-
tra were obtained on a Perkin-Elmer 554 double beam spec-
trophotometer. e final products were characterized by 1H

2
Journal of Chemistry
R
2a = -H
R
2b = -2-OH
2c = -4-Cl
O
R
H2N
2d = -4-Br
NH
2e = -2-NO2
2f = -3-NO2
2g = -4-NO2
2
O
Cl
O
1
R
R
R
H
N
3a = -CH3
N
R
3b = -CH2CH3
R
3
Scheme 1: Synthesis of compounds 2a–2g and 3a-3b.
and 13C NMR (JEOL FX-90Q FT NMR, 300 MHz) and mass
spectrometry (JEOL JMS 600 Mass Spectrometer).
9.52, (s, 1H, -OH), 7.96 (d, 1H, ꢂ = 15.6 Hz, CH=CH), 7.38–
7.65 (m, 6H, Ar-H), 7.18 (d, 1H, ꢂ = 15.163Hz, CH=CH), 6.90–
6.96 (dt, 2H, Ar-H), 6.81 (t, 1H, Ar-H). C NMR (d6-DMSO,
300 MHz, 298 K): 164.6 (C=O), 148.3 (HO-Ar-C), 140.7 (Ar-
CH=CH), 135.5, 130.2, 129.5, 128.5, 128.3, 127.3, 125.1, 123.3,
122.5, 116.2 (Ar), 119.5 (CH=CH-C=O). JEOL JMS 600, EI+
mode: m/z = 239.2945 [M]+, 240.2946 [M + H]+.
2.1. General Procedure for the Synthesis of Compounds 2a–2g
and 3a-3b. Compounds 2a–2d and 3a-3b (Scheme 1) were
synthesized by slight modification of the typical procedure
adopted for various cinnamic acid derivatives [16, 17]. To
a stirred solution containing aniline derivatives or amine
derivatives (25 mmol), K CO (4.15 g, 30 mmol), and tetrahy-
(2c) N-(4-Chlorophenyl)cinnamamide. 76.65% yield, 1H
2
3
NMR (CDCl , 300 MHz, 298 K) ꢁ (ppm): 7.76 (d, 1H,
3
drofuran (30 mL), the cinnamoyl chloride (4.10 g, 20 mmol)
dissolved tetrahydrofuran (5 mL) was added dropwise at 0∘C.
e mixture was stirred at 0∘C for 30 min and then at RT for
3 hours. e solution was concentrated under vacuum and
then poured on ice cold water with stirring. e precipitated
product was washed with water and dried in an oven at 100∘C.
e final compounds were then obtained by crystallization
from ethanol.
ꢂ = 15.6 Hz, CH=CH), 7.62–7.60 (m, 4H, Ar-H), 7.52 (d, 2H,
Ar-H), 7.41–7.39 (m, 3H, Ar-H), 7.33 (br, 1H, -NH), 6.58 (d,
ꢂ = 15.6 Hz, 1H, CH=CH). 13C NMR (300 MHz, CDCl ):
3
164.0 (C=O), 142.9 (Ar-CH=CH), 136.6, 134.5 (Ar), 130.2
(Cl-Ar-C), 129.1, 129.04, 128.9, 121.2 (Ar-C), 120.04 (CH=CH-
C=O). JEOL JMS 600, EI+ mode: m/z = 257.7134 [M]+,
258.7136 [M + H]+.
(2d) N-(4-Bromophenyl)cinnamamide. 70.45% yield, 1H
For the synthesis of compounds 2e–2g, to a stirred solu-
tion of respective aniline derivatives (30 mmol) in diethyl
ether (30 mL), the cinnamoyl chloride (4.10 g, 20 mmol) dis-
solved in diethyl ether (5 mL) was added dropwise at 0∘C. e
mixture was stirred at 0∘C for 30 min and then at RT for 3
hours. Afer completion of reaction the solvent was concen-
trated and then added to 100 mL of dichloromethane. e
solution was washed 3 times with 1 N HCl and 2 times with
NMR (CDCl , 300 MHz, 298 K) ꢁ (ppm): 7.79 (d, 1H, ꢂ =
3
15.6 Hz, CH=CH), 7.57–7.54 (m, 4H, Ar-H), 7.49 (d, 2H, Ar-
H), 7.43–7.41 (m, 3H, Ar-H), 7.34 (br, 1H, -NH) 6.55 (d, 1H,
ꢂ = 15.6 Hz, CH=CH). 13C NMR (300 MHz, CDCl ): 164.1
3
(C=O), 141.0 (Ar-CH=CH), 138.0, 132.2, 130.1, 129.5, 129.3,
128.1 (Ar), 121.5 (Br-Ar-C), 119.7 (CH=CH-C=O). JEOL JMS
600, EI+ mode: m/z = 302.1662 [M]+, 303.1664 [M + H]+.
1 N NaHCO . e separated organic layer was dried over
3
(2e) N-(2-Nitrophenyl)cinnamamide. 70.34% yield. 1H NMR
Mg SO and solvent was evaporated completely to obtain a
2
4
(CDCl , 300 MHz, 298 K) ꢁ (ppm), 10.61 (br, 1H, -NH), 8.92
residue. e final compounds were obtained by crystalliza-
tion from ethanol.
3
(1H, d, ꢂ = 7.8 Hz, Ar-H), 8.22 (1H, d, ꢂ = 8.4 Hz, Ar-H), 7.75
(d, 1H, ꢂ = 15.6 Hz, CH=CH), 7.64–7.70 (t, 1H, Ar-H), 7.56–
7.59 (dd, 2H, Ar-H), 7.39–7.41 (m, 3H, Ar-H), 7.17–7.20 (t, 1H,
Ar-H), 6.58 (d, 1H, ꢂ = 15.6 Hz, CH=CH). 13C NMR (d6-
(2a) N-Phenylcinnamamide. 75.55% yield, 1H NMR (CDCl ,
3
300 MHz, 298 K) ꢁ (ppm): 9.74 (s, 1H, -NH), 7.57 (m, 10H,
Ar-H), 7.50 (d, 1H, ꢂ = 15.6 Hz, CH=CH), 6.72 (d, 1H,
DMSO, 300 MHz,): 164.9 (C=O), 144.2 (NO -Ar-C), 136.9
2
ꢂ = 15.6 Hz, CH=CH). 13C NMR (300 MHz, CDCl ): 163.66
(Ar-CH=CH), 136.4, 135.8, 134.8, 130.9, 129.5, 128.7, 126.3,
123.6, 122.8 (Ar), 121.6 (CH=CH-C=O). JEOL JMS 600, EI+
mode: m/z = 268.2617 [M]+.
3
(C=O), 140.32 (Ar-CH=CH), 139.16, 134.86, 129.42, 128.90,
128.11, 127.52, 122.31 (Ar), 121.62 (CH=CH-C=O). JEOL JMS
600, EI+ mode: m/z = 223.2089 [M]+, 224.2087 [M1+ H]+.
(2f ) N-(3-Nitrophenyl)cinnamamide. 72.95% yield, 1H NMR
(2b) N-(2-Hydroxyphenyl)cinnamamide. 50.76%, H NMR
(d6-DMSO, 300 MHz, 298 K) ꢁ (ppm): 10.03 (bs, 1H, -NH),
(d6-DMSO, 300 MHz, 298 K) ꢁ (ppm), 10.68 (br, 1H, -NH),
8.77 (1H, s, Ar-H), 8.02 (d, 1H, ꢂ = 7.8 Hz, Ar-H), 7.89 (d,

Journal of Chemistry
Microbial strain
3
Table 1: Antimicrobial activity of compounds 2a–2g and 3a-3b.
pMIC
2a
2.45
2b
3.68
2c
2.81
2d
2.58
2e
2.83
2f
3.13
2g
3a
3b
E. coli K99
∗
∗
∗
E. coli 306
E. coli K88
E. coli LT37
2.45
2.45
3.95
3.38
3.68
3.68
2.81
3.11
4.41
2.88
2.58
2.58
2.83
3.13
4.03
2.83
2.83
4.43
∗
∗
2.41
∗
∗
∗
4.03
3.61
3.85
3.54
E. coli 872
E. coli ROW 7/12
E. coli 3:37C
E. coli CD/99/1
Salmonella TyphiTy2
Shigella dysenteriae 1
Shigella dysenteriae 8
Shigella sonnei 1
Shigella boydii D13629
Shigella flexneri Type 6
Vibrio cholerae 1313
Vibrio cholerae 293
Vibrio cholerae 1315
Vibrio cholerae 85
2.75
2.75
2.75
2.75
3.95
3.68
3.68
3.68
3.38
3.68
2.78
3.68
2.78
3.08
3.08
3.68
3.38
3.38
3.38
2.81
3.11
2.81
3.11
2.51
2.51
2.51
2.58
2.58
2.58
2.58
3.13
2.83
2.83
2.83
2.83
3.13
2.53
3.13
∗
∗
2.83
∗
∗
2.53
∗
2.34
2.34
2.64
2.94
2.94
2.64
3.85
2.53
∗
∗
∗
∗
2.53
∗
∗
∗
2.53
2.53
2.83
3.13
3.83
2.53
3.13
2.53
2.53
3.13
2.83
∗
∗
∗
2.83
2.53
∗
∗
∗
∗
2.53
∗
2.71
∗
2.51
∗
2.53
∗
∗
∗
2.51
3.11
3.11
3.11
3.11
∗
2.53
2.53
2.53
3.13
4.03
2.53
2.53
2.83
2.83
2.53
2.71
∗
2.94
∗
2.45
2.45
3.05
3.95
∗
2.58
2.58
2.58
2.41
∗
2.34
∗
3.31
2.94
Staphylococcus aureus ML267
Bacillus pumilus 82
Bacillus subtilis ATCC 6633
∗
2.78
3.38
3.68
2.51
∗
∗
4.03
2.53
2.53
3.43
∗
2.94
2.75
3.95
∗
∗
∗
∗
∗
∗
3.01
3.24
3.71
∗
∗
∗
∗
No antimicrobial activity was observed in the concentration range of 5–800 ꢀg/mL.
1H, ꢂ = 7.8 Hz, Ar-H), 7.44–7.72 (m, 7H, Ar-H, CH=CH),
1.25 (m, 6H, CH ). 13C NMR (300 MHz, CDCl ): 165.7
(C=O), 142.3 (Ar-CH=CH), 135.5, 129.4, 128.7, 127.7 (Ar), 117.7
(CH=CH-C=O), 42.3 (CH -CH ), 13.2 (-CH ). JEOL JMS
3
3
6.82 (d, 1H, ꢂ = 15.6 Hz, CH=CH). 13C NMR (d6-DMSO,
300 MHz,): 164.6 (C=O), 148.5 (NO -Ar-C), 141.6 (Ar-
2
2
3
3
CH=CH), 140.9, 135.0, 130.4, 129.4, 128.3, 125.6, 122.1, 113.9
(Ar), 118.1 (CH=CH-C=O). JEOL JMS 600, EI+ mode: m/z =
268.2615 [M]+.
600, EI+ mode: m/z = 203.2913 [M]+, 204.2732 [M + H]+.
2.2. Antimicrobial Activity. e antimicrobial activity of the
synthesized compounds was tested in vitro against twenty-
one microorganisms. Stock solutions (1 mg/mL) of synthe-
sized compounds 2a–2g and 3a-3b were prepared by dissolv-
ing each compound in dimethyl sulfoxide. Calculated vol-
umes of stock solutions were dispensed in series of McCart-
ney bottles previously containing calculated volumes of ster-
ile cooled molten nutrient agar media (40–45∘C) to prepare
the volume of 30 mL each with dilutions of 5, 10, 25, 50, 100,
200, 400, and 800 ꢃg/mL. ese sterile nutrient agar media
solutions were poured into Petri plates and allowed to solidify.
ese plates were kept in the refrigerator at 4∘C for 24 h to
allow the uniform diffusion of the compounds throughout
the nutrient agar medium. Before spot inoculation, plates
were kept at 37∘C for 2 h. One loop full (loop diameter: 3 mm)
of an overnight grown peptone water culture of each microor-
ganism was inoculated, and the location of the inoculation
was marked by the checkerboard technique. e spot inocu-
lated plates were incubated at 37∘C for 24 h and the minimum
inhibitory concentration (MIC, mM) values were obtained.
(2g) N-(4-Nitrophenyl)cinnamamide. 68.23% yield, 1H NMR
(d6-DMSO, 300 MHz, 298 K) ꢁ (ppm): 10.90 (s, 1H, -NH),
8.22 (d, 2H, ꢂ = 8.7 Hz, Ar-H), 7.93 (d, 2H, ꢂ = 7.8 Hz, Ar-H),
7.69–7.43 (m, 6H, Ar-H, CH=CH), 6.85 (d, 1H, ꢂ = 15.0 Hz,
CH=CH). 13C NMR (d6-DMSO, 300 MHz,): 164.9 (C=O),
146.1 (NO -Ar-C), 142.8, 142.4 (Ar), 142.2 (Ar-CH=CH), 135.0,
2
129.5, 128.5, 125.7, 121.9 (Ar-C), 119.6 (CH=CH-C=O). JEOL
JMS 600, EI+ mode: m/z = 268.2615 [M]+, 269.2657 1[M + H]+.
(3a) N,N-Dimethylcinnamamide. 73.34% yield, H NMR
(CDCl , 300 MHz, 298 K) ꢁ (ppm): 7.66–7.71 (d, 1H, ꢂ =
3
15.6 Hz, CH=CH), 7.53 (d, 2H, ꢂ = 7.8 Hz, Ar-H), 7.35 (m,
3H, Ar-H), 6.68 (d, 1H, ꢂ = 15.0 Hz, CH=CH), 3.12 (s, 6H,
-CH ). 13C NMR (300 MHz, CDCl ): 167.0 (C=O), 142.9 (Ar-
3
3
CH=CH), 135.5, 129.8, 129.0, 128.0 (Ar), 117.3 (CH=CH-C=O),
37.0 (CH ). JEOL JMS 600, EI+ mode: m/z = 175.0993 [M]+,
3
176.1403 [M + H]+.
(3b) N,N-Diethylcinnamamide. 76.85% yield, 1H NMR
(CDCl , 300 MHz, 298 K) ꢁ (ppm): 7.73 (d, 1H, ꢂ = 15.9 Hz,
e calculated pMIC (−log MIC) values are presented in
3
10
CH=CH), 7.55 (m, 2H, ꢂ = 7.8 Hz, Ar-H), 7.39 (m, 3H, Ar-H),
Table 1. Experiments were done in triplicate, and the results
were presented as mean values of the three measurements.
6.85 (d, 1H, ꢂ = 15.0 Hz, CH=CH), 3.40–3.50 (m, 4H, CH ),
2

4
Journal of Chemistry
100
80
60
40
20
0
2.3. Antioxidant Activity. e antioxidant activity of the
synthesized compounds (2a–2g, 3a-3b) was evaluated using
the DPPH free radical scavenging assay [18]. e 200 ꢃL of
test sample solution (1 mg/mL) was added to 4 mL of 100 ꢃM
methanolic DPPH. e solution was allowed to incubate
for 20 minutes at 25∘C, and the absorbance was measured
at 517 nm. Ascorbic acid (1 mg/mL) was used as reference
standard. A blank was prepared without adding the standard
or test compound. e lower absorbance of the reaction mix-
ture indicates higher free radical scavenging activity. e
capability to scavenge the DPPH radical was calculated using
the following equation:
Ascorbic 2a 2b 2c 2d 2e
2f
2g 3a 3b
acid
Compounds
Figure 1: DPPH radical scavenging activity of compounds 2a–2g
and 3a-3b.
ꢄ
− ꢄ
control
sample
% inhibition =
× 100,
(1)
ꢄ
control
where ꢄ
is the absorbance of the DPPH alone and
is the absorbance of DPPH in the presence of com-
From the results of the microbiological studies, it is
evident that substituents on the amide nitrogen of cinna-
mamide derivatives 2a–2g and 3a-3b play a critical role in
their antimicrobial activities. Derivatives 2a–2g and 3a-3b
were obtained from primary amines (aniline derivatives) and
secondary amines, respectively. It is important to notice that
compound 2b, which contains o-hydroxyphenyl substituent
on the amide nitrogen, showed a significant increase in the
antimicrobial activity as compared to compound 2a, which
contains only phenyl group. Compound 2c containing p-
chlorophenyl substituent on the amide nitrogen showed
strong activity as compared to compound 2d, which contains
p-bromophenyl substitution on the amide nitrogen. Among
the compounds containing the nitrophenyl substituents on
the amide nitrogen, compound 2e showed strong activity as
compared to compounds 2f and 2g. e m-nitrophenyl sub-
stituent in compound 2e endows it with a strong antibacterial
activity as compared to the o-nitrophenyl and p-nitrophenyl
substituents in compounds 2f and 2g, respectively. It is also
important to notice that the aromatic substituents on the
amide nitrogen allow overall strong activity as compared to
the aliphatic substituents. e presence of bulky ethyl groups
on the amide nitrogen of compound 3b allows it to demon-
strate strong activity as compared to compound 3b contain-
ing methyl groups.
control
ꢄ
sample
pounds 2a–2g, 3a-3b. All determinations were performed in
triplicate (ꢅ = =). e results are presented in Figure 1.
3. Results and Discussions
3.1. e Synthesis. e amide derivatives of cinnamic acid 2a–
2g and 3a-3b were synthesized to study the effect of amide
nitrogen substituents on the antimicrobial activity. As shown
in Scheme 1, the reaction of cinnamoyl chloride with corre-
sponding aromatic or aliphatic amines gave compounds 2a–
2g and 3a-3b. All compounds were obtained in good yield,
purified by recrystallization, and characterized by 1H NMR,
13C NMR, and mass spectrometry.
3.2. Antimicrobial Activity. e pMIC (− log(MIC)) values
of compounds 2a–2g, 3a-3b are presented in Table 1. Except
compound 2d, all compounds showed a good antibacterial
activity against Gram-negative compared to Gram-positive
bacterial strains. Compound 2b showed strong antimicrobial
activity against all microorganisms with the pMIC values
ranging from 2.78 to 3.68. However, compound 2d demon-
strated little (pMIC = 2.58) or no antibacterial activity in the
tested concentration domain. Similarly, compound 3a also
showed very poor or no antimicrobial activity against the
tested microorganisms. erefore, compounds 2d and 3a
were considered as poor antimicrobial compounds. Com-
pounds 2c, 2e–2g showed the highest antimicrobial activity
against E. coli LT37 with the pMIC of 4.03–4.43. Moreover,
compounds 2e and 2f demonstrated strong activity against
Vibrio cholerae 85 and Staphylococcus aureus ML267, respec-
tively.
Compound 2a demonstrated strongest activity against
E. coli LT37, Salmonella Typhi Ty2, Vibrio cholerae 85, and
Bacillus subtilis ATCC 6633 with the pMIC value of 3.95.
Compound 2b showed strong activity against all microorgan-
isms except for Shigella dysenteriae 1, Shigella sonnei 1, and
Staphylococcus aureus ML267 with the lowest pMIC value of
2.78. Compound 2c did not show any antibacterial activity
against Shigella sonnei 1 and Bacillus pumilus 82. Compound
3b showed the strongest activity against E. coli LT37 and
Shigella boydii D13629 with the pMIC of 3.85.
3.3. Antioxidant Activity. DPPH radical scavenging is con-
sidered as a good in vitro model and is widely used to assess
antioxidant efficacy [19, 20]. e DPPH free radical scaveng-
ing assay was employed to evaluate the antioxidant activity of
the synthesized compounds. e DPPH radical scavenging
activity of compounds 2a–2g, 3a-3b (50 ꢃg/mL) was com-
pared with that of ascorbic acid at the same concentration.
As presented in Figure 1, the results of antioxidant screenings
were expressed as % of inhibition of the DPPH radical.
As depicted in Figure 1, most compounds showed moder-
ate-to-good antioxidant activity. Compounds 2a, 3a, and
3b showed strong activity as indicated by the % inhibition
of the DPPH radical, 51% ( 1.14), 41% ( 1.01), and 50%
( 1.23), respectively. Compounds 2b and 2g showed very low
activity with the % inhibition of 16% ( 1.12) and 14% ( 1.09),
respectively. Compounds 2c, 2d, 2e, and 2f showed moderate
activity with the % inhibition of 34% ( 1.96), 35% ( 0.98),

Journal of Chemistry
5
31% ( 0.97), and 30% ( 1.02), respectively. e results clearly
indicate the electron donating groups on the amide nitrogen
(3a-3b) play an important role in scavenging the free radicals.
Moreover, compound 2a, which contains phenyl group on
amide nitrogen, demonstrates almost similar radical scav-
enging activity to that of compounds 3a, 3b, which contain
dimethyl and diethyl substituents on amide nitrogen, respec-
tively.
However, the electron withdrawing substituents such as
p-chloro, p-bromo, and o-nitro, m-nitro, and p-nitro on
phenyl ring in compounds 2c, 2d, and 2e–2g, respectively,
significantly decrease radical scavenging activity. e results
obtained in this study are in line with other findings [21].
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Most of the amide derivatives of cinnamic acid mentioned in
this showed moderate-to-high antibacterial and antioxidant
activities. e investigation of antimicrobial potentials of the
compounds demonstrated a strong activity against 21 bac-
terial strains comprising Gram-positive and Gram-negative
bacteria. Compounds 2a, 2b, and 3b showed strong antimi-
crobial activity against all microorganisms with the pMIC
value ranging from 2.45 to 3.68. Compounds 2a, 3a, and
3b demonstrated strong antioxidant activity. ese findings
encourage the synthesis of new amide derivatives of cinnamic
acid. ese findings indicate that the amide derivatives of
the cinnamic acid afford strong antibacterial and antioxidant
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Conflict of Interests
[16] C. Sa´nchez-Moreno, “Review: methods used to evaluate the
free radical scavenging activity in foods and biological systems,”
Food Science and Technology International, vol. 8, no. 3, pp. 121–
137, 2002.
All authors declare that there is no conflict of interests.
Acknowledgment
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is research was supported by the Hallym University
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