Synthesis and characterization of 2-pyrazoline derivatives and their in silico and in vitro studies on antimicrobial and anticancer activities

Article abstract of DOI:10.14233/ajchem.2019.22082

The new series of 1-(4,5-dihydro-5-phenyl-3-diphenylpyrazol-1-yl)butan-1-one derivatives were synthesized by cyclization method using biphenyl chalcone with n-butyric acid and hydrazine hydrate. The synthesized 1-(4,5-dihydro-5-phenyl-3-diphenylpyrazol-1-

Full text of DOI:10.14233/ajchem.2019.22082

Asian Journal of Chemistry; Vol. 31, No. 10 (2019), 2191-2196
A
SIAN
J
OURNAL OF HEMISTRY
C
https://doi.org/10.14233/ajchem.2019.22082
Synthesis and Characterization of 2-Pyrazoline Derivatives and their
in silico and in vitro Studies on Antimicrobial and Anticancer Activities
1
2
2
1
1,*,
S. RATHINAMANIVANNAN , K. MEGHA , RAJA CHINNAMANAYAKAR , ASHOK KUMAR and M.R. EZHILARASI
1
2
Department of Chemistry, Prist University, Thanjavur-613403, India
Department of Chemistry, Karpagam Academy of Higher Education, Coimbatore-641021, India
*
Corresponding author: E-mail: mrezhilarasi@gmail.com
Received: 15 March 2019; Accepted: 26 April 2019;
Published online: 30 August 2019;
AJC-19521
The new series of 1-(4,5-dihydro-5-phenyl-3-diphenylpyrazol-1-yl)butan-1-one derivatives were synthesized by cyclization method using
biphenyl chalcone with n-butyric acid and hydrazine hydrate. The synthesized 1-(4,5-dihydro-5-phenyl-3-diphenylpyrazol-1-yl)butan-1-
1
13
one derivatives chemical structures were confirmed from spectral data such as FT-IR, H and C NMR. 2-Pyrazoline derivatives were
docked with bacterial (1UAG) and breast cancer (1OQA) protein. Based on high binding affinity score, the best compound was subjected
to in vitro anticancer activity by MTT assay. Also, antimicrobial activity were studied for synthesized 2-pyrazoline derivatives.
Keywords: Biphenyl chalcone, Hydrazine hydrate, n-Butyric acid, Antimicrobial activity, Molecular docking studies.
that compound only was subjected to anticancer activity.Also,
antimicrobial activity were screened for 2-pyrazoline deriva-
tives.
INTRODUCTION
Cancer is a life-threatening disease and the number of
cancer-related deaths is increasing alarmingly. Based on the
literature review, more than 90 % of cancer patients die due to
the chronic tumor metastases. The large number of anticancer
drugs are currently available, but these drugs can eradicate
cancer cells without harming normal tissues. So, the develop-
ment of new chemotherapeutic scaffolds which selectively act
on the target without any side effects has become an important
objective of the medicinal fields [1]. In women community,
breast cancer is the most important disease across world [2].
The pyrazole compounds exhibited a various biological activity
such as anticancer [3-8], antibacterial [9] and fungi static activity
EXPERIMENTAL
The chemicals were purchased from Sigma-Aldrich.
Melting point were determine using MELT-Temp apparatus
and the values were uncorrected. The FT-IR spectrum was
recorded with the help of Shimadzu 8400s model and FT-IR
-1
spectrometer in the range of 4000-400 cm and KBr used as
internal reference. The Bruker 400 MHz and 100 MHz
1
13
spectrometer was used to record the H and C NMR values.
Procedure for the synthesis of biphenyl chalcone deriv-
atives (3a-e): 4-Acetyl biphenyl (0.1 mol) and substituted
aromatic aldehyde (0.1 mol) were taken in 250 mL Erlenmeyer
flask and to this approximately added nearly 30-35 mL of
ethanol containing 20 % NaOH solution. This reaction mixture
was stirred well for 3 h and then transferred the solution to 500
mL beaker containing pieces of ice cubes then kept in overnight
at room temperature. After that solid precipitate was filtered
and washed with water. This solid product was recrystallized
using ethanol. Finally, the purity of the compound was checked
by TLC [11].
[
10].
The current research work is mainly focused on the synth-
esis of 2-pyrazoline derivatives (5a-e) from biphenyl chalcone
react with hydrazine hydrate and n-butyric acid by cyclization
method. Before that biphenyl chalcone derivatives were synthe-
sized using various substituted aromatic aldehydes react with
4
-acetylbiphenyl in the presence of strong base by Claisen-
Schmidt condensation method.After that 2-pyrazoline compounds
were docked with bacterial (1UAG) and breast cancer (1OQA)
protein. Furthermore, based on high binding affinity score,
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2
192 Rathinamanivannan et al.
Asian J. Chem.
Synthesis of 1-(4,5-dihydro-5-phenyl-3-diphenylpyrazol-
Elemental analysis of C26
H
26
2
N O calcd. (found) %: C, 81.56
1
-yl)butan-1-one derivative (5a-e): Chalcone (0.1 mol) and
(81.64); H, 6.79 (6.85); N, 7.32 (7.32); O, 4.18 (4.18).
1-(4,5-Dihydro-3-diphenyl-5-(4-chlorophenyl pyrazole-
1-yl)butan-1-one) derivative (5c):Yield 59 %; m.p.: 194 ºC;
hydrazine hydrate (0.1 mol) with 30 mL of n-butyric acid were
taken in round bottom flask. This reaction mixture was refluxed
for 14-16 h. Then the completion of the reaction was monitored
using TLC. After completion of the reaction, this mixture was
poured in to crushed ice cube containing 250 mL beaker and
kept in overnight. Finally, the solid precipitate was filtered,
washed with water. Then this solid product was recrystallized
using ethanol. Finally, the purity of compound was checked
by TLC (Scheme-I).
-1
light brown; IR (KBr, νmax, cm ): 1402.25 (C=N), 1664.57
1
(C=O), 112.93 (C-N), 3165.19 (Ar-CH); H NMR (CDCl
400 MHz; δ ppm: 3.28 (1H, dd, H4a, J4a,4e = 18.2 Hz, J4a,5a
3
),
=
3.8 Hz); 3.93 (1H, dd, H4e, J4e,4a = 17.9 Hz, J4e,5a = 11 Hz);
5.63 (1H, dd, H5a, J5a,4a = 12.1 Hz, J5a,4e = 4.1 Hz); 2.79-2.85
(-CH
2
- of C-2′);1.61-1.83 (-CH
C NMR δ ppm: 171.93 (C=O), 151.18 (C=N), 37.61 (C-4),
9.03 (C-5), 18.99 (-CH -), 31.01 (-CH -), 13.90 (C-4′), 127.63-
30.31 (Ar-C); 141.06, 138.30, 138.01, 137.48 (Ipso carbon).
OCl calcd. (found) %: C, 74.45
74.52); H, 5.70 (5.75); N, 6.94 (6.95); O, 3.97 (3.97); Cl,
2
- of C-3′); 7.09-7.79 (Ar-H).
13
5
1
2
2
CHO
O
C
Elemental analysis of C25
(
H
23
N
2
+
H C
3
X
2
(1a-e)
EtOH 0 °C,
8
.79 (8.80).
-(4, 5-Dihydro-3-diphenyl-5-(4-nitrophenyl pyrazole-
-yl)butan-1-one) derivative (5d):Yield 67 %; m.p.: 208 ºC;
NaOH 3 h stirring
1
1
-1
O
C
light brown; IR (KBr, νmax, cm ): 1402.25 (C=N), 1656.85
1
(C=O), 1115.81 (C-N), 3165.19 (Ar-CH); H NMR (CDCl
3
),
=
C
H
CH
400 MHz; δ ppm: 3.31 (1H, dd, H4a, J4a,4e = 17.6 Hz, J4a,5a
X
(
3a-e)
4
5
.3 Hz); 3.79 (1H, dd, H4e, J4e,4a = 18.3 Hz, J4e,5a = 12.7 Hz);
.71 (1H, dd, H5a, J5a,4a = 12.9 Hz, J5a,4e = 4.4 Hz); 2.63-2.77
X = 1a = 3a = 5a = H
n-Butyric acid Hydrazine
X = 2b = 3b = 5b = 4-CH3
X = 2c = 3c = 5c = 4-Cl
X = 2d = 3d = 5d = 4-NO2
X = 2e = 3e = 5e = 4-OCH3
(4)
hydrate
(-CH - of C-2′); 1.58-1.71 (-CH - of C-3′); 7.13-7.89 (Ar-H).
2
2
13
C NMR δ ppm: 170.08 (C=O), 150.08 (C=N), 35.39 (C-4),
58.92 (C-5), 18.10 (-CH -), 29.03 (-CH -), 14.99 (C-4′), 128.03-
131.91 (Ar-C), 143.76, 139.94, 138.89, 137.35 (Ipso carbon).
Elemental analysis of C25 calcd. (found) %: C, 72.55
72.62); H, 5.56 (5.61); N, 10.15 (10.16); O, 11.60 (11.61).
1-(4,5-Dihydro-3-diphenyl-5-(4-methoxyphenyl pyra-
O
2
2
H C
N
3
N
H
23
N O
3 3
(
(
5a-e)
X
zole-1-yl)butan-1-one) derivative (5e):Yield 67 %; m.p.: 196
Scheme-I: Synthetic pathway for 2-pyrazoline derivatives (5a-e)
-1
ºC; light brown; IR (KBr, νmax, cm ): 1412.25 (C=N), 1664.57
1
(
4
C=O), 1246.02 (C-N), 3165.19 (Ar-CH); H NMR (CDCl
3
),
=
Spectral data
-(4,5-Dihydro-3-diphenyl-5-phenylpyrazole-1-yl)-
butan-1-one derivative (5a):Yield 64 %; m.p.: 172 ºC; Light
00 MHz; δ ppm: 3.28 (1H, dd, H4a, J4a,4e = 16.9 Hz, J4a,5a
1
3.7 Hz); 3.82 (1H, dd, H4e, J4e,4a = 17.7 Hz, J4e,5a = 12.3 Hz);
5.65 (1H, dd, H5a, J5a,4a = 12.4 Hz, J5a,4e = 4 Hz); 2.69-2.78 (-CH
of C-2′); 1.63-1.80 (-CH - of C-3′); 3.73 (-OCH ), 7.39-7.97
(Ar-H). C NMR δ ppm: 172.33 (C=O), 152. 99 (C=N), 36.01
(C-4), 57.19 (C-5), 19.07 (-CH -), 30.91 (-CH -), 13.95 (C-4′),
55.98 (OCH ), 126.03-132.92 (Ar-C), 144.01, 140.01, 140.09,
139.82 (Ipso carbon). Elemental analysis of C26 calcd.
2
-
-
1
brown; IR (KBr, νmax, cm ): 1405.85 (C=N), 1661.37 (C=O),
2
3
1
13
1
156.52 (C-N), 3085.55 (Ar-CH); H NMR (CDCl
δ ppm: 3.18 (1H, dd, H4a, J4a,4e = 17.6 Hz, J4a,5a = 3.2 Hz); 3.76
1H, dd, H4e, J4e,4a = 17 Hz, J4e,5a = 12.2 Hz; 5.60 (1H, dd, H5a,
3
), 400 MHz;
2
2
(
3
J
1
1
(
1
5a,4a = 11.2 Hz, J5a,4e = 3.2 Hz); 2.73-2.88 (-CH
2
- of C-2′),
- of C-3′); 7.23-7.82 (Ar-H). C NMR δ ppm:
71.58 (C=0), 153.35 (C=N), 36.22 (C-4), 60.14 (C-5), 18.47
-), 29.76 (-CH -), 14.06 (C-4′), 125.60-128.99 (Ar-C),
42.97,142.14, 140.18, 130.46 (Ipso carbon). Elemental analysis
O calcd. (found) %: C, 81.41 (81.49); H, 6.51
6.57); N, 7.59 (7.60); O, 4.34 (4.34).
-(4,5-Dihydro-3-diphenyl-5-(p-tolylpyrazole-1-yl)
butan-1-one) derivative (5b):Yield 67 %; m.p.: 188 ºC; light
H
26
N O
2 2
1
3
.66-1.77 (-CH
2
(found) %: C, 78.29 (78.36); H, 6.52 (6.58); N, 7.02 (7.03);
O, 8.03 (8.03).
Molecular docking studies:The docking studies have been
carried out using ADT version 1.5.6 and Auto dock version
4.2.5.1 docking program.
Preparation of protein: The bacterial protein and human
breast cancer protein were directly downloaded from PDB
(Protein Data Bank) with pdb id: 1UAG and 1OQA.
Ligand preparation: 2D structure of 2-pyrazoline deriv-
atives is drawn using Chemdraw ultra 8.0. After that Chem 3D
ultra 8.0 was used to convert the 2D structure into 3D structure.
The energy is minimized using semi empirical AM1 method.
All the structures are saved as pdb file format for input to
ADT. Finally, all the ligand structures are saved as Pdb format
to carry out docking study in Auto dock Vina.
-CH
2
2
of C25
H
24
N
2
(
1
-1
brown; IR (KBr, νmax, cm ): 1402.25 (C=N), 1664.57 (C=O),
112.93 (C-N), 3138.18 (Ar-CH); H NMR (CDCl ), 400 MHz;
δ ppm: 3.25 (1H, d, H4a, J4a,4e = 16 Hz, J4a,5a = 4 Hz); 3.88 (1H,
dd, H4e, J4e,4a = 18.1 Hz, J4e,5a = 12.7 Hz); 5.69 (1H, dd, H5a,
5a,4a = 12.3 Hz, J5a,4e = 3.6 Hz); 2.61-2.93 (-CH
1
1
3
J
1
1
(
1
2
- of C-2′), 1.53-
1
3
.69 (-CH
71.02 (C=O), 151.87 (C=N), 37.13 (C-4), 57.83 (C-5), 19.60
-), 32.08 (-CH -), 14.20 (C-4′), 23.40 (CH ), 127.73-
29.80 (Ar-C), 145.71, 144.52, 143.87, 143.21 (Ipso carbon).
2
- of C-3′), 7.32-7.91 (Ar-H). C NMR δ ppm:
-CH
2
2
3
Formation of grid: A grid box with a dimension of 40 ×
3
40 × 40 Å in 0.375 Å spacing and centered on 30.473, 47.997,

Vol. 31, No. 10 (2019)
Synthesis and Characterization of 2-Pyrazoline Derivatives 2193
Mean OD sample
9.563 has created around the binding site of protein usingADT.
Viability (%) =
×100
The center of the box was set at ligand center and grid energy
calculations were carried out.
Mean OD of control group
Docking protocol: The Auto dock calculation such as
default parameters had been used and 10 docked confirmations
were generated for each compound. The energy calculations
was done using genetic algorithms. The outputs were exported
to chimera 1.10 and discovery studio 4.5 for visual inspection
of the binding modes and interaction of the compounds with
amino acid residues in the active site [12].
Antimicrobial activity: 2-Pyrazoline compounds were
screened for antimicrobial activity by agar disk diffusion method.
In this studies, ciprofloxacin was used as a reference compound
and dimethyl sulfoxide as the solvent control of this activity.
Four different strains viz. Streptococcus, Staphylococcus aureus,
Escherichia coli and Pseudomonas aeruginosa were used.
RESULTS AND DISCUSSION
Biphenyl chalcone derivatives (3a-e) were synthesized
from 4-acetylbiphenyl reacts with aromatic substituted alde-
hydes in the presence of strong base by Claisen-Schmidt con-
densation method. Then biphenyl chalcone derivatives were
reacted with hydrazine hydrate and n-butyric acid by cyclization
method to yield 2-pyrazoline derivatives (Scheme-I). The
synthesized 2-pyrazolines chemical structure were elucidated
1
13
using FT-IR, H and C NMR spectral studies.
In the FT-IR spectrum of compound 5a, the C=N stretching
frequency of pyrazole moiety observed at 1405.85 cm and
-1
-1
the C=O stretching was observed at 1661.37 cm , while the
-1
C-N stretching observed at 1156.52 cm . The aromatic CH
Anticancer activity
-1
1
stretching was observed at 3085.55 cm . In H NMR spectrum
MTT assay: MDA-MB-231 Cell was initially procured
compound 5a exhibited the doublet of doublet at 3.18 ppm
from National Centre for Cell Sciences (NCCA), Pune, India
J4a,4e = 17.6 Hz and J4a,5a = 3.2 Hz is due to the presence of H-
and maintained Dulbecco′s modified eagle′s medium, DMEM
4a proton of pyrazole moiety. Also H-4e proton of pyrazole
moiety exhibited another doublet of doublet at 3.76 ppm J4e,5a
= 17 Hz and J4e,5a = 12.2 Hz. Doublet of doublet at 5.60 ppm
2
(
Sigma Aldrich, USA). The cell line was cultured in 25 cm
tissue culture flask with DMEM supplemented with 10 % FBS,
L-glutamine, sodium bicarbonate (Merck, Germany) and an anti-
biotic solution containing penicillin (100 U/mL). Streptomycin
J
5a,4a = 11.2 Hz & J5a,4e = 3.2 Hz which indicate the presence of
H-5a proton of pyrazole moiety. The multiplet present at 2.73-
2.88 ppm is due to the presence of -CH - of butane moiety.
(
100 µg/mL) and ampheotericin B (2.5 µg/mL) cultured cell
lines were kept at 37 ºC in a humidified 5 % CO incubator
NBS Eppendorf, Germany). The viability of cells was evaluated
2
2
The multiplet present at 1.66-1.77 ppm is due to the presence
of methyl group in butane moiety. The aromatic protons are
appeared at 7.23-7.82 ppm.
(
by direct observation of cells by inverted phase contrast micro-
scope and followed by MTT assay method.
13
13
In C NMR spectrum, compound 5a shows the C NMR
13
Cells seeding in 96 well plate: Two-day old confluent
at 171.58 ppm which is attributed to C=O. The C NMR at
153.35 ppm is due to the presence of C-3 carbon of pyrazole
moiety and at 36.22 ppm is due to the presence of C-4 carbon
of pyrazole moiety. Similarly, at 60.14 ppm is due to the presence
of C-5 carbon of pyrazole moiety and at 14.06 ppm is due to
monolayer of cells try ionized and the cells were suspended in
4
1
0 % growth medium, 100 µL cell suspension (5 × 10 cells/
well) was seeded in 96 well tissue culture plate and incubated
at 37 ºC in a humidified 5 % CO incubator.
2
13
Preparation of compound stock: 1 mg of a sample was
weighed and dissolved in 1 mL DMEM using a cyclomixer.
The sample solution was filtered through 0.22 µm Millipore
syringe filter to ensure the sterility.
the presence of methyl group of butane moiety. However, C
resonance at 18.47 ppm is due to the presence of C-3′ carbon
2
of -CH - group of butane moiety and at 29.76 ppm is due to
2
the presence of C-2′ carbon of -CH -group of butane moiety.
Anticancer evaluation: After 24 h the growth medium
was removed, freshly prepared each compounds in 5 % DMEM
was five times serially diluted by two-fold dilution (100, 50,
The aromatic carbons are appeared at 125.60-128.99 ppm.
in silicoActivity: The synthesized 2-pyrazoline derivatives
were docked with bacterial protein (PDB id: 1UAG) and breast
cancer protein (PDB id: 1OQA). The docking studies which
are reported in terms of the docking score, which means the
lower score, the better and interactions. In ligand, 2-pyrazoline
derivatives (5a-e) were individually, docked with bacterial
proteins. Docking results are shown in Table-1. Thus, it can be
seen that 2-pyrazoline derivatives exhibit good docking score
compared to the standard drug (ciprofloxacin). Based on the
docking score, compound 5c exhibit high binding affinity score
compared with other compound of this series. Compound 5c
exhibit two H-bond interaction with the amino residue is SER
A: 415 and PHE A: 422. Also, this compound exhibited two
hydrophobic interaction with the amino residue is ALA A:
414 and LEUA: 416. Other compounds results are also shown
in Table-1.
2
5, 12.5, 6.25 µg/mL) in 500 µL of 5 % DMEM and ach concen-
tration of 100 µL were added in triplicates to the respective
wells and incubated at 37 ºC in a humidified 5 % CO
Non-treated control cells were also maintained.
2
incubator.
Anticancer assay by MTT method: 15 mg of MTT
(
Sigma, M-5655) was reconstituted in 3 mL PBS until completely
dissolved and sterilized by filter sterilization.After 24 h of the
incubation period, the sample content in wells was removed
and 30 µL of reconstituted MTT solution was added to all test
and cell control wells, the plate was gently shaken well and
incubated at 37 ºC in a humidified 5 % CO
After the incubation period, the supernatant was removed and
00 µL of MTT solubilisation solution (DMSO, Sigma-Aldrich)
2
incubator for 4 h.
1
was added and the wells were mixed gently in order to solubilize
the formazan crystals. The absorbance values were measured
by using a microplate reader at a wavelength of 540 nm [13].
The % of growth inhibition was calculated using the formula:
2-Pyrazoline derivatives were docked with breast cancer
protein 1OQA: The synthesized 2-pyrazoline compounds
were docked with breast cancer protein. The binding affinity

2
194 Rathinamanivannan et al.
TABLE-1
Asian J. Chem.
TABLE 2
2
-PYRAZOLINE COMPOUNDS WERE DOCKED
2-PYRAZOLINEDERIVATIVES WERE DOCKED
WITH BREAST CANCER PROTEIN
WITH BACTERIAL PROTEIN 1UAG
Binding
affinity score
kcal/mol)
Binding affinity
score (kcal/mol) interaction
H-Bond
H-Bond
interaction
Hydrophobic
interaction
Compd.
Hydrophobic interaction
Compound
(
5a
-6.8
-7.1
-7.1
HIS A: 69 PRO A: 59, PRO A: 103,
ILE A: 102
SER A:415
PHE A:422
SER A:415
PHE A:422
SER A:415
PHE A:422
SER A:415
PHE A:422
SER A:415
PHE A:422
ASN A:178,
ASN A:271,
GLU A:327
ALA A:414
LEU A:416
ALA A:414
LEU A:416
ALA A:414
LEU A:416
ALA A:414
LEU A:416
ALA A:414
LEU A:416
5a
-8.4
5b
-
PRO A: 18, CYS A: 15,
VAL A: 38
PRO A: 18, VAL A: 38,
CYS A: 15
CYS A: 15
CYS A: 15
5b
-8.4
-8.5
-8.3
-8.3
5c
-
5c
5d
5e
-7.2
-7.0
-
-
5d
the other compound of this series. Compound 5d does not exhibit
any H-bond interaction with amino residue of protein 1OQA.
Also, this compound exhibit only one hydrophobic interaction
with the amino residue is CYS A: 15 (Fig. 1). The 2D and 3D
image of the synthesized 2-pyrazoline derivatives (5a-e) are
shown in Table-3.
5e
Ciprofloxacin
-7.7
ALA A:328
score, hydrogen bond interaction and hydrophobic interaction
results are shown in Table-2. From this result, compound 5d
have high binding affinity score (-7.2 kcal/mol) compared with
MTT assay for 1-(4,5-dihydro-3-diphenyl-5-(4-nitro-
phenylpyrazole-1-yl)butan-1-one (5d): Based on high binding
Interactions
van der Waals
π−π stacked
π−π T-shaped
π-Alkyl
Fig. 1. 2D and 3D image for compound 5d docked with breast cancer protein 1OQA
TABLE-3
2D AND 3D IMAGE FOR THE SYNTHESIZED COMPOUNDS (5a-e)
Compound
2D image
3D image
5a
Interactions
van der Waals
π-Cation
Conventional hydrogen bond
π-Alkyl

Vol. 31, No. 10 (2019)
Synthesis and Characterization of 2-Pyrazoline Derivatives 2195
5
b
Interactions
van der Waals
Alkyl
Conventional hydrogen bond
π-Cation
π-Alkyl
5
c
Interactions
van der Waals
Conventional hydrogen bond
π-Cation
Alkyl
π-Alkyl
5
d
Interactions
van der Waals
π-Cation
Conventional hydrogen bond
π-Alkyl
5
e
Interactions
van der Waals
π-Cation
π-Alkyl
Conventional hydrogen bond

2
196 Rathinamanivannan et al.
Asian J. Chem.
Ciprofloxacin
Interactions
van der Waals
Unfavourable acceptor-acceptor
Conventional hydrogen bond
Halogen (Fluorine)
π-Alkyl
affinity score, synthesized compound 5d only was performed
to anticancer activity using various concentration (100, 50,
showed that 2-pyrazoline derivatives also exhibited good activity
against the studied four strains.
2
5, 12.5, 6.25 µg/mL). From this result, compound 5d exhibit
CONFLICT OF INTEREST
good activity at low concentration (6.25 µg/mL) compared
with other concentration. The LC50 value of this compound is
7
The authors declare that there is no conflict of interests
regarding the publication of this article.
4.27 µg/mL. The experiments were conducted in triplicate
and the mean value was calculated.
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against S. pyogenes and E. coli (Fig. 2). However, compound
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d exhibits good zone of inhibition against Pseudomonas sp.
3
4
.
.
Thus, most of the pyrazoline derivatives exhibited better activity
compared with standard drug.
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2
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5a
5b
5c
5d
5e
Compound
9
1
.
Fig. 2. Antibacterial activity with different strains for 2-pyrazoline
4
derivatives (5a-e)
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2-Pyrazoline derivatives were synthesized using biphenyl
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chalcone react with hydrazine hydrate and n-butyric acid by
Michael addition method. The docking study was carried out
for 2-pyrazoline derivatives using bacterial protein and breast
cancer protein. The results showed that the receptor and the
compound have greater potency of interactions in a binding
site. Especially, compound 5d exhibited good binding score
with the cancer protein. The LC50 value of compound 5d is
found to be 74.27 µg/mL. The antimicrobial activity results
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