Synthesis, Characterization and Antimicrobial Activity of N-2-(4-Chlorophenyl)acetyl Derivatives of (S)-Amino Acids

Article abstract of DOI:10.14233/ajchem.2020.22416

This paper reports the synthesis, characterization and antibacterial activity of N-2-(4-chlorophenyl)acetyl derivatives of various (S)-amino acids such as (S)-alanine, (S)-phenylalanine, (S)-leucine, (S)-methionine, (S)-proline and (S)-tryptophane. These

Full text of DOI:10.14233/ajchem.2020.22416

Asian Journal of Chemistry; Vol. 32, No. 2 (2020), 381-384
A
SIAN
J
OURNAL OF HEMISTRY
C
https://doi.org/10.14233/ajchem.2020.22416
Synthesis, Characterization and Antimicrobial Activity of
N-2-(4-Chlorophenyl)acetyl Derivatives of (S)-Amino Acids
1
1,*,
2
G. VENKATESHAPPA , P. RAGHAVENDRA KUMAR
and KRISHNA
1Department of Studies and Research in Chemistry, University College of Science, Tumkur University, Tumkur-572103, India
2Department of Biotechnology, University College of Science, Tumkur University, Tumkur-572103, India
*Corresponding author: Tel/Fax: +91 816 2260220; E-mail: raghukp1@gmail.com
Received: 26 August 2019;
Accepted: 25 October 2019;
Published online: 30 December 2019;
AJC-19730
This paper reports the synthesis, characterization and antibacterial activity of N-2-(4-chlorophenyl)acetyl derivatives of various (S)-amino
acids such as (S)-alanine, (S)-phenylalanine, (S)-leucine, (S)-methionine, (S)-proline and (S)-tryptophane. These compounds have been
1
successfully synthesized and their structures were confirmed by H NMR and 13C NMR and FT-IR spectroscopy. The antimicrobial
activity of these six (S)-amino acids derivatives have been evaluated by the agar well diffusion method against pathogens both Gram-
positive (S. aureus) and Gram-negative (K. aerogenes, E. coli and P. desmolyticumas) bacteria and fungi (A. flavus and C. albicans). All
these compounds have shown mild to moderate antimicrobial activity.
Keywords: Amino acid, N-2-(4-Chlorophenyl)acetyl chloride, Antibacterial activity, Antifungal activity.
been proved as potentially biologically active [15]. Therefore,
herein we report the synthesis, characterization and antimicro-
bial activity studies of N-2-(4-chlorophenyl)acetyl derivatives
of (S)-alanine (4-CPA), (S)-phenylalanine (4-CPPA), (S)-leucine
(4-CPL), (S)-methionine (4-CPM), (S)-proline (4-CPP) and
(S)-tryptophane (4-CPT).
INTRODUCTION
Amino acids are the monomers of proteins which are the
main building blocks of all living organisms. Some of the larger
and smaller molecules of peptides play vital roles as enzymes,
hormones and sometimes involves in the detoxification process.
Some of the naturally occurring peptides were shown good
biological activity [1]. The activity of these natural peptides is
limited due to average biostability, bioavailability and many
microbes were gained resistant over many naturally occurring
antimicrobial agents.
To overcome these problems, our interest has been directed
towards the synthesis of stable and more active derivatives of
α-amino acids. These compounds may play an important role
in the pharmaceutical field on account of their peptidomimetics,
high stability, easy laboratory synthesis and low toxicity. It
has been reported that based upon the type of groups attached
to the α-amino acids, the biological activities such as antimicro-
bial and anticancer activities would also vary [2]. Purinylamino
acid derivatives have been shown activity 10 to 25 times more
against M. tuberculosis than emblematic tuberculosis drugs
[3-5]. Likewise coumarinyl [6,7], pyrazolyl [8,9], thiophenyl
[10,11], sulphonamide [12-14] amino acid derivatives have
EXPERIMENTAL
Chemicals, reagents and solvents were purchased from
Spectrochem Ind. Pvt. Ltd. and SD fine chemicals Ind. Pvt.
Ltd. and all were used without further purification. 4-Chloro-
phenyl acetyl chloride was prepared by the reported method
[16]. Melting points were measured in an open capillary tube
closed at one end and all reported uncorrected. FT-IR spectra
were recorded with PerkinElmer Frontier-ATR spectrometer.
1H NMR and 13C NMR spectra were recorded at 400 and 100
MHz on Agilent 400 MR DD2 NMR spectrometer with tetra-
methylsilane (TMS) as an internal standard expressed on δ ppm
scale. Thin layer chromatography (TCL) was performed and
visualized under UV light, iodine vapour and/or KMnO4 spray.
For TLC, silica gel coated aluminum plates (Merck, 60F254)
were used. Bacterial strains Klebsiella aerogenes (NCIM-
2098), Escherichia coli (NCIM-5051), Staphylococcus aureus
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382 Venkateshappa et al.
Asian J. Chem.
(NCIM-5022) and Pseudomonas desmolyticum (NCIM-2028)
and fungal strains Aspergillus flavus (NCIM544) and Candida
albicans (NCIM-3100) were purchased from National Chemical
Laboratory (NCL), Pune, India. These strains were maintained
on nutrient agar slant at 4 °C. Standard antibiotics ciprooxacin
and fluconazole were purchased from Hi Media, Mumbai, India.
Synthesis of N-2-(4-chlorophenyl) acetyl derivatives
amino acids: The corresponding (S)-Amino acid (1.0 mmol)
was dissolved in minimum volume of water under stirring in a
1-neck round bottom flask surrounded by cooling bath (ice-
NaCl) maintaining the temperature of -4 to 0 °C. To this solu-
tion, an aqueous solution of NaOH (10 mL, 4.0 mmol) was
added and stirred for 4-5 min. Then, the resulting solution
was added (4-chlorophenyl) acetyl chloride drop-wise during
3 min under continuous stirring maintaining the temperature
below 0 °C. The stirring was continued further for 30 min and
then the reaction mixture was poured into ice cold water. This
mixture was acidified with dil. HCl forming a white precipitate
of N-(4-chlorophenyl) acetyl derivative of present α-amino
acid. The solid obtained was filtered and dried.
(S)-2-[2-(4-Chlorophenyl)acetamido]propanoic acid
(4-CPA): White solid; Yield: 70 %; m.p.: 136 °C; 1H NMR
(CDCl3, δ ppm): 1.220-1.238 (d, J = 7.2 Hz, CH3, 3H), 3.420
(s, Ar-CH2, 2H), 4.123-4.160 (m, CH, 1H), 7.230-7.251 (d,
o/m-Ar-H, 4H), 7.301-7.323 (d, o/m-Ar-H, 4H), 8.375-8.393
(d, J = 7.20, NH, 1H), 12.485 (s, COOH, 1H); 13C{1H} NMR
(DMSO-d6, δ ppm): 17.65 (CH3), 41.44 (Ar-CH2), 48.01 (CH),
128.49 (ArC, o to Cl), 131.30 (ArC, m to Cl), 131.47 (ArC, p
to Cl), 135.72 (ArC-Cl), 169.94 (CONH), 174.52 (COOH);
FT-IR (ATR, νmax, cm-1): 3332 (N-H, amide), 1705 (C=O, acid),
1622 (C=O, amide), 1554 (N-H, ben), 1490 (C-N, amide).
(S)-2-[2-(4-Chlorophenyl)acetamido]-3-phenylpro-
panoic acid (4-CPPA): White solid; Yield: 82 %; m.p.: 155
°C;1H NMR (CDCl3, δ ppm): 2.790-3.061 (dq, Ph-CH2, 2H),
3.328-3.476 (q, Cl-Ar-CH2, 2H), 4.361-4.417 (m, CH,1H),
7.087-7.260 (m, Ar-H, 9H), 8.369-8.349 (d, J = 8 Hz, NH,
1H), 12.5 (s, COOH, 1H); 13C{1H} NMR (DMSO-d6, δ ppm):
37.24 (Ph-CH2), 41.6 (Cl-Ar-CH2), 54.0 (CH), 126.77-138.03
(Ar-C), 170.0 (CO, amide), 173.43 (COOH); FT-IR (νmax, cm-1,
ATR): 3321 (N-H, amide), 1706 (C=O, acid), 1615 (C=O,
amide), 1555 (N-H, ben, amide), 1215 (NH-CO-C, ben).
(S)-2-[2-(4-Chlorophenyl)acetamido]-3-(ethylsulfanyl)
propanoic acid (4-CPM): Pale yellow viscous liquid; Yield:
80 %; 1H NMR (CDCl3, δ ppm): 1.914-2.032 (m, S-CH3 and
S-CH2, 5H), 2.404-2.455 (m, CH2, 2H), 3.561 (s,Ar-CH2, 2H),
4.622-4.671 (q, CH, 1H), 6.586-6.605 (d, J = 8 Hz, NH, 1H),
7.144-7.300 (m,Ar-H, 4H); 13C{1H} NMR (DMSO-d6, δ ppm):
15.07 (S-CH3), 30.1 (S-CH2), 31.278 (CH2), 41.61 (Ar-CH2),
51.53 (CH), 128.48 (o-ArC), 131.27 (m-ArC), 131.70 (p-ArC),
135.72 (C1), 170.38 (CO, amide), 173.69 (COOH). FT-IR
(νmax, cm-1,ATR): 3334 (N-H), 3254-2201 (ArC-H), 1740 (acid
C=O) 1704 (C=O, amide), 1614 (COO, asym. str.), 1601
(ArC=C), 1555 (N-H ben), 1492 (C-H, ben), 1415 (C-N), 1355
(COO symm str.), 1245 (C-N), 1093 (C-O), 803 (S-C), 763
(C-H, out of plane ben), 644 (N-H, out of plane ben).
2H), 3.411 (s, Ar-CH2, 2H), 4.443-4.495 (q, CH, 1H), 6.934-
7.508 (m, Ar-H, 9H), 8.345 (d, J = 8 Hz, NH, 1H), 10.829 (s
Indo-NH, 1H), 12.634 (s, COOH, 1H); 13C{1H} NMR (DMSO-
d6, δ ppm): 27.59 (Indo-CH2), 41.53 (Ar-CH2), 53.49 (C4),
110.25-136.54 (C-aromatic), 170.07 (NHCO), 173.76 (COOH);
FT-IR (νmax, cm-1,ATR): 3401 (COOH), 3310 (NH, ring), 1709
(C=O, acid), 1615 (C=O, amide), 1558 (N-H, ben),1250 (C-N).
(S)-2-[2-(4-Chlorophenyl)acetamido]-4-methylpenta-
noic acid (4-CPL): White solid; Yield: 85 %; m.p.: 148 °C;
1H NMR (CDCl3, δ ppm): 0. 878-0.887 (d, J = 3.6 Hz, CH3,
3H), 0. 893-0.902 (d, J = 3.6 Hz, CH3, 3H), 1.485-1.666 (m,
CH and CH2, 3H), 3.554 (s, Ar-CH2, 2H), 4.557 (bs, CH, 1H),
5.792-5.808 (d, J = 6.4 Hz, NH, 1H), 7.180-7.200 (d, J =
7.62 Hz, Ar-H, o to Cl, 2H); 7.302-7.322 (d, Ar-H, m to Cl,
2H); 13C NMR (CDCl3, δ ppm): 26.46 (CH3), 27.98 (CH3, 3H),
29.52 (CH), 46.29 (Ar-CH2), 55.52 (chiral CH), 128.49 (ArC,
o to Cl), 131.30 (ArC, m to Cl), 131.47 (ArC, p to Cl), 135.72
(ArC-Cl), 169.94 (CONH), 174.52 (COOH); FT-IR (νmax, cm-1,
ATR):3328 (N-H, amide), 2967 (ArC-H), 1706 (C=O, acid),
1614 (C=O, amide), 1557 (N-H, ben), 1245 (NH-CO, bend).
(S)-1-[(4-Chlorophenyl)acetyl]pyrrolidine-2-carboxylic
acid (4-CPP): Pale yellow low melting solid; Yield: 78 %;
m.p.: liquid at room temperature; 1H NMR (CDCl3, δ ppm):
1.967-2. 113 (m, pyr-CH2), 3.427-3.601 (m, pyr-CH2) 2H),
3.601 (s, Ar-CH2, 2H), 4.378-4.408 (t, CH, 1H), 7.124-7.253
(m, Ar-H, 4H), 9.4 (s, COOH, 1H); 13C{1H} NMR (DMSO-
d6, δ ppm): 22.77 (pyr-CH2), 29.38 (pyr-CH2), 31.51 (Ar-CH2),
47.26 (CH2), 59.23 (CH), 128.27-131.86 (ArC), 168.72 (CO,
amide), 174.05 (COOH); FT-IR (ATR, νmax, cm-1): 2979 (ArC-
H), 1732 (C=O, acid), 1625 (C=O, amide), 1245 (N-C, ben).
Antimicrobial activity: The antibacterial and antifungal
activities have been studied for the N-2-(4-chlorophenyl)acetyl
derivatives of six (S)-amino acids. The bacterial strains used
were K. aerogenes, E. coli and P. desmolyticum as Gram-negative
and S. aureus as Gram-positive bacteria and fungal strains A.
flavus and C. albicans.
Nutrient agar media and potato dextrose broth were used
to culture the bacteria and fungi, respectively. Nutrient agar
plates were prepared and swabbed using sterile L-shaped glass
rod with 100 µL of 24 h mature broth culture of individual
bacterial strains. The wells were crated of 6 mm into the each of
the petri plate using sterile cork borer. The solutions of each
compound (4-CPA, 4-CPPA, 4-CPM, 4-CPT, 4-CPL and 4-CPP)
were prepared in two concentrations of 10 and 20 µg/µL made
in DMSO and evaluated their antibacterial activity. Similarly
a standard antibiotic ‘ciprofloxacin’solution used as a positive
control of concentration 0.1 µg/µL. These solutions were added
into the wells by sterile micropipette. The plates were incubated
at 37 °C for 48 h. After the incubation period, the zone of inhi-
bition of each well was measured and the values were noted.
These measurements were made in triplicate for each compound
and the average values are reported in Table-1.
For antifungal activity sporulated culture of fungi strains
of potato dextrose agar (PDA) slant was incubated at 25 °C
for 48-96 h and then were transferred into 10 mL of sterile,
1 % saline solution. From each fungal spore 100 µL suspension
was spread on each PDA petri plate using L-shaped glass rod.
After spreading on PDA plates using sterile cork borer, made
(S)-2-[2-(4-Chlorophenyl)acetamido]-3-(7aH-indol-2-
yl)propanoic acid (4-CPT): White solid; Yield: 90 %; m.p.:
174 °C; 1H NMR (CDCl3, δ ppm): 2.977- 3.179 (m, Indo-CH2,

Vol. 32, No. 2 (2020)
Synthesis and Antimicrobial Activity of N-2-(4-Chlorophenyl)acetyl Derivatives of (S)-Amino Acids 383
TABLE-1
ANTIMICROBIAL ACTIVITIES OF N-2-(4-CHLOROPHENYL)ACETYL DERIVATIVES OF (S)-AMINO ACIDS
Compound
Ciprofloxacin
Fluconazole
Conc. (µg/µL)
K. aerogenes
12.33 0.03
–
E. coli
S. aureus
14.00 0.00
–
P. desmolyticum
15.60 0.03
–
A. flavus
–
C. albicans
–
0.1
4.0
10
20
10
20
10
20
10
20
10
20
10
20
13.67 0.03
–
10.27 0.03
1.00 0.00
1.67 0.03
0.55 0.00
2.27 0.03
1.00 0.00
2.50 0.06
1.37 0.03
2.17 0.03
1.50 0.06
2.00 0.00
0.75 0.06
1.32 0.00
11.50 0.06
1.50 0.06
2.33 0.03
1.60 0.03
2.33 0.03
1.57 0.03
3.67 0.03
0.00 0.00
1.00 0.00
1.00 0.00
2.33 0.33
1.20 0.00
1.50 0.03
4.00 0.00
6.40 0.17
2.86 0.00
4.43 0.07
3.21 0.00
4.83 0.23
1.12 0.00
1.66 0.09
3.00 0.00
4.86 0.00
1.80 0.10
2.82. 0.21
4.30 0.06
6.88 0.03
2.47 0.06
3.80 0.00
3.08 0.00
4.67 0.17
1.20 0.06
1.78 0.06
2.50 0.00
4.06 0.17
2.30 0.42
3.40 0.32
4.10 0.06
6.56 0.12
2.32 0.07
3.63 0.07
2.86 0.00
4.50 0.07
1.00 0.06
1.49 0.00
3.30 0.20
5.41 0.17
2.00 0.00
3.20 0.26
3.85 0.00
6.16 0.00
2.23 0.00
3.45 0.03
2.90 0.17
4.40 0.17
1.36 0.00
2.02 0.17
2.80 0.00
4.27 0.07
1.90 0.00
3.10 0.00
4-CPA
4-CPPA
4-CPM
4-CPT
4-CPL
4-CPP
(Mean SE)
O
O
Ice, NaCl
SOCl2
wells of 6 mm on each plate. The PDA plates were incubation
at 25 °C for 48-96 h. The solutions (10 and 20 µg/µL) of 4-CPA,
4-CPPA, 4-CPM, 4-CPT, 4-CPL and 4-CPP made in DMSO.
50 µL of each of these test solutions transferred into 6 mm wells
made above on PDA media plates. Similarly 4 µg/µL solution
of standard antifungal drug ‘fluconazole’ solution made in
DMSO and used as a positive control. The zone of inhibition
of each well was measured and the values were noted. Tripli-
cates were maintained for each compound and the average
values are reported in Table-1.
OH
Cl
Cl
Cl
-4 to 25 °C
(4-chlorophenyl)acetic acid
(4-chlorophenyl)acetyl chloride
1. Amino acid, H O
2
2. NaOH
3. Conc. HCl
OH
N
NH
O
and
O
O
R
O
Cl
Cl
HO
N-2-(4-chlorophenyl) acetyl derivatives of amino acids
RESULTS AND DISCUSSION
Amino acid
S
R = CH3;
= Ch2Ph;
( )-Alanine,CPA
(S)-Proline,
CPP
HO
R
S
( )-Phenyl alanine,CPPA
Synthesis of N-2-(4-chlorophenyl) acetyl derivatives of
amino acids contains two steps. The first step involves prepa-
ration of 4-chlorophenyl acetyl chloride. Thionyl chloride (3
mL, 41 mmol) was taken in a round bottom flask and cooled
in a cooling bath (NaCl) and then was added 4-chlorophenyl
acetic acid (500 mg, 2.93 mmol) slowly and dropwise maint-
aining the temperature in the range of 0 to -4 °C under stirring.
Then the reaction mixture was brought to room temperature
and continued stirring for further 3 h. The excess thionyl
chloride was distilled off that resulted 4-chlorophenyl acetyl
chloride in 80 % yield. The second step was the acetylation of
amino acids to the corresponding N-2-(4-chlorophenyl)acetyl
derivatives. These N-2-(4-chloro phenyl)acetamides of six amino
acids were synthesized at 0-4 °C. The reaction mixture was
acidified with dil. HCl to the corresponding products in good
yields (70-85 %) (Scheme-I). Both of these reactions were
carried out in fuming hood.
Characterization: All the six N-2-(4-chlorophenyl)acetyl
derivatives of (S)-amino acids (4-CPA, 4-CPPA, 4-CPM, 4-CPT,
4-CPL and 4-CPP) were completely characterized by 1H NMR,
13C NMR and FT-IR spectroscopy.
In the IR spectra of all the compounds, the vibrational
stretching band for C=O (acid) was appeared at 1709-1706
cm-1 except for 4-CPP in which this band was observed at 1732
cm-1. The stretching band for C=O (amide) bond was appeared
at lower wavenumber region 1625-1615 cm-1. These observa-
tions indicated the formation amide linkage in all the compounds.
The N-H bending band was appeared at 1558-1554 cm-1.
S
= CH2SCH2CH3; ( )-Methionine,CPM
O
NH
2
S
= CH2CH(CH3)2; ( )-Luecine,CPL
=
(S)-Tryptophen,
CPT
N
H
Scheme-I: Synthesis of N-2-(4-chlorophenyl)acetyl derivatives of (S)-amino
acids
In the proton NMR spectrum of 4-CPA the methyl protons
were appeared as a doublet at δ 1.220-1.238 ppm. In all the
compounds the chiral CH (H4) proton was appeared as a multi-
plet in the range of 4.123-4.495 ppm [17-19]. The C-C6H4CH2
(H1) protons were appeared as a singlet at 3.420 ppm, respec-
tively. In all the compounds, the ortho (H7,7’) and meta (H8,8’)
protons of 4-chlorophenyl ring were observed as two doublets
or multiplets in the range of δ 7.144-7.322 ppm. In 4-CPA,
4-CPM and 4-CPT the COOH proton was appeared at about
δ 12.5 ppm as a broad or very broad singlet whereas the CONH
(amide) proton was observed at δ 8.37 ppm in 4-CPA and
4-CPP and in 4-CPT the signal was appeared at 10.89 ppm. In
4-CPM and 4-CPL the NH proton was appeared at 6.586 and
5.792 ppm, respectively. In proton NMR spectrum of 4-CPPA
the Cl-C6H4CH2 (δ 2.466-2.848 and 3.016-3.061 ppm) and
PhCH2 (δ 4.361-4.417 ppm) protons were appeared as double
of a doublet due to their diastereotopic nature.
The products have been confirmed by their 13C NMR spectra.
The signals for CONH carbon (except in 4-CPP and 4-CPL)
was appeared in the range of δ 169-171 ppm whereas the

384 Venkateshappa et al.
Asian J. Chem.
COOH carbon was deshielded and observed in the range of
δ 171-175 ppm as shown by other amino acid derivatives [17-
19]. In 4-CPL the CONH and COOH carbons were found
highly deshielded as they have been appeared at δ ~175 and
~179 ppm, respectively.
CONFLICT OF INTEREST
The authors declare that there is no conflict of interests
regarding the publication of this article.
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ACKNOWLEDGEMENTS
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Authors are thankful to UGC for providing financial support
under the project MRP(S)-1043/11-12/KABA019/UGC-SWRO.