Synthesis, antimicrobial and antioxidant activity of bis sulfonamide/carbamate derivatives of bis-(4-aminophenyl) methane

Article abstract of DOI:10.1002/jccs.201900434

A series of new bis sulfonamide/carbamate derivatives of bis-(4-aminophenyl)methane 3(a–d)/5(a–f) were synthesized from bis-(4-aminophenyl)methane (1) using various pharmacologically active sulfonyl chlorides 2(a–d) and carbonochloridates 4(a–f) in high yields. The structures of all the newly synthesized compounds were characterized by the Infrared spectroscopy, NMR (¹H and ¹³C), mass, and elemental analyses. Further, all the synthesized compounds were tested for the antioxidant activity by using 2, 2-diphenyl-1-picrylhydrazyl, NO, and H₂O₂ scavenging methods and antimicrobial activity. Most of the compounds exhibited good antioxidant and antimicrobial activities.

Full text of DOI:10.1002/jccs.201900434

Received: 16 October 2019
DOI: 10.1002/jccs.201900434
Revised: 8 January 2020
Accepted: 9 January 2020
A R T I C L E
Synthesis, antimicrobial and antioxidant activity
of bis sulfonamide/carbamate derivatives
of bis-(4-aminophenyl) methane
Vadabingi Nagalakshmamma1 | Mavallur Varalakshmi2 | Kollu Umapriya4
|
Mallepogu Venkataswamy3 | Chintha Venkataramaiah5 | Kedam Thyaga Raju3
Ponne Venkata Chalapathi1 | Chamarthi NagaRaju4
|
1Department of Chemistry, Sri
Abstract
Venkateswara Arts College (TTD's),
Tirupati, Andhra Pradesh, India
A series of new bis sulfonamide/carbamate derivatives of bis-(4-aminophenyl)
2Centre for Applied Sciences, Sree
Vidyanikethan Engineering College,
Tirupati, Andhra Pradesh, India
3Department of Biochemistry, Sri
Venkateswara University, Tirupati,
Andhra Pradesh, India
4Department of Chemistry, Sri
Venkateswara University, Tirupati,
Andhra Pradesh, India
5Department of Zoology, Sri
Venkateswara University, Tirupati,
Andhra Pradesh, India
methane 3(a–d)/5(a–f) were synthesized from bis-(4-aminophenyl)methane
(1) using various pharmacologically active sulfonyl chlorides 2(a–d) and
carbonochloridates 4(a–f) in high yields. The structures of all the newly syn-
thesized compounds were characterized by the Infrared spectroscopy, NMR
(1H and 13C), mass, and elemental analyses. Further, all the synthesized
compounds were tested for the antioxidant activity by using 2, 2-diphenyl-1-
picrylhydrazyl, NO, and H2O2 scavenging methods and antimicrobial activity.
Most of the compounds exhibited good antioxidant and antimicrobial
activities.
K E Y W O R D S
Correspondence
antimicrobial activity, antioxidant activity, bis-(4-aminophenyl) methane, carbonyl chloridates,
sulfonyl chlorides
Ponne Venkata Chalapathi, Department
of Chemistry, Sri Venkateswara Arts
College (TTD's), Tirupati, 517502, Andhra
Pradesh, India.
Email: pvchalapathisumathi@gmail.com
Funding information
UGC-RGNF, Grant/Award Number:
Letter Number: F1-17.1/2015-16/RGNF-
2015-17-SC-AND
1 | INTRODUCTION
represents one of the landmarks in modern medicine.[2]
Nowadays, investigations of new antimicrobial substances
Antibiotics have obtained great importance in preventing
and controlling of infectious diseases. The utility of antibi-
otics has increased worldwide because of its usage as a com-
mon medicine in treatment of various diseases such as
orthopedics, cancer, and transplantation.[1] The introduc-
tion of antimicrobial agents into general clinical application
have become essential because there are no medicine for
which bacteria will not become resistant.[3] Sulfonamides
were the first antimicrobial drugs which lead to the antibi-
otic revolution in medicine. For the medicinal chemist, the
–SO2NH2 moiety has become privileged building block,
found in many drug molecules.[4] Sulfonamides represent
© 2020 The Chemical Society Located in Taipei & Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
J Chin Chem Soc. 2020;1–7.
http://www.jccs.wiley-vch.de
1

2
NAGALAKSHMAMMA ET AL.
an important class of drugs which exhibit various biological
activities like antimicrobial,[5] antidiabetics,[6] anti-
inflammatory,[7] antihypertensive,[8,9] and antileish-
manial[10] activities. Further, these derivatives are used as
angiogenesis inhibitors for the treatment of cancer,[11] in
the treatment of Alzheimer's disease,[12] as antiviral-HIV
protease inhibitors (amprenavir), and anti-hepatitis C virus
(HCV) agents.[13]
Based on the above facts, herein we report the synthe-
sis of new bis sulfonamide/carbamate derivatives and
evaluated their antioxidant and antimicrobial potencies.
2 | RESULTS AND DISCUSSION
2.1 | Chemistry
Molecules possessing carbamate moiety occupy a sig-
nificant role in modern drug discovery and medicinal
chemistry. Carbamates are used as a peptide bond surro-
gate in medicinal chemistry because of its chemical sta-
bility and capability to permeate cell membrane.
Substitution of –O and –N termini of carbamates offer
many opportunities for the modulation of biological
properties and pharmacokinetic properties due to its par-
ticipation in hydrogen bonding through carboxyl group
and the back bone NH.[14] Carbamates and their deriva-
tives are widely used as agrochemicals,[12] prodrugs,[15,16]
as an intermediates in organic synthesis,[17–20] in peptide
syntheses.[21,22] Some of the examples of the sulfonamide
and carbamate drugs possessing various activities are
shown in Figure 1.
The newly synthesized bis sulfonamide/carbamate deriv-
atives of bis-(4-aminophenyl)methane 3(a–d)/5(a–f) are
shown in Scheme 1.
The structures of all the newly synthesized compounds
were characterized by infrared spectroscopy (IR), NMR
(1H, 13C), mass, and elemental analyses. The details are
provided in the experimental section and supporting infor-
mation. In the IR spectrum of compound 3a, the absorp-
tion band appeared in the region of 3740, 1,346 cm−1
corresponds to the functional groups of –NH stretching
and –SO2 stretching frequencies, respectively. In 1H NMR
spectra, the chemical shift in the region of δ 8.17 ppm
appeared as a singlet and assigned to the -NH proton. The
methylene protons resonated as a singlet at 3.78 ppm. The
chemical shifts at the region of 6.61–7.54 ppm appeared as
multiplets and correspond to the aromatic protons. Fur-
ther, the structure of compound 3a was confirmed by the
1H NMR, 13C NMR, mass, and elemental analysis.
2.2 | Bioactivity evaluation
2.2.1 | Antioxidant activity
All the newly synthesized title compounds 3(a–d)/5(a–f)
were tested for their antioxidant activity by using 2,
2-diphenyl-1-picrylhydrazyl (DPPH), H2O2, and NO scav-
enging activity. Ascorbic acid was used as a standard.
FIGURE 1 Some examples of sulfonamides and carbamate
drugs
SCHEME 1 Synthesis of new
bis sulfonamide/carbamate derivatives
3(a–d)/5(a–f)

NAGALAKSHMAMMA ET AL.
3
TABLE 1 The percentage of
inhibition and IC50 values of bis
sulfonamide/carbamate derivatives
3(a–d)/5(a–f) in DPPH method
% of inhibition
Compound
25 (μg/ml)
53.27 1.2
52.50 3.2
58.20 1.5
59.70 2.4
59.02 1.5
56.07 1.3
50.10 2.1
54.70 2.7
55.80 1.5
55.50 1.8
72.00 0.1
50 (μg/ml)
75 (μg/ml)
58.84 2.5
75.50 2.2
68.80 3.8
74.90 1.2
67.50 3.9
70.40 2.8
62.70 1.6
62.50 2.8
60.90 3.1
62.50 2.8
78.29 0.1
100 (μg/ml)
66.80 1.8
83.30 2.9
71.10 3.1
81.10 3.6
70.10 2.3
73.50 1.5
65.03 3.8
64.70 1.4
63.50 3.5
67.60 2.5
80.14 0.1
IC50 (μg/ml)
23.46
3a
55.45 3.6
60.80 1.5
65.17 2.6
68.50 3.2
64.90 2.6
62.80 3.4
58.40 1.2
58.80 3.1
58.10 2.6
59.40 3.1
76.18 0.1
3b
23.80
3c
21.47
3d
20.93
5a
21.17
5b
22.29
5c
24.95
5d
22.85
5e
22.40
5f
22.52
Ascorbic acid
17.36
Note: Data represents mean SD of triplicates.
scavenging activity with the IC50 values 21.49, 22.0, 20.77,
and, 19.49 when compared to the remaining compounds.
The percentage of inhibition and the IC50 values of the of
bis sulfonamide/carbamate derivatives 3(a–d)/5(a–f) are
presented in Table 2 and Figure 3.
In the NO scavenging method, compounds 5a, 5b
exhibited good activity when compared to the remaining
compounds. The percentage of inhibition and the IC50
values of the bis sulfonamide/carbamate derivatives 3
(a–d)/5(a–f) are presented in Table 3 and Figure 4. In
overall, the results regarding the biological aspects con-
cerning to the synthesized compounds revealed that the
title compounds would stand as the promising antioxi-
dant and antimicrobial drugs in future when compared
to the native sulfonamide/carbamate derivatives.[15,16]
FIGURE 2 IC50 values of bis sulfonamide/carbamate
derivatives 3(a–d)/5(a–f) in DPPH method
Compounds 3c, 3d, 5a, and 5b have exhibited good activity
with the IC50 values 21.47, 20.93, 21.17, and 22.29 because
of the presence of nitro and chloro substituents in the ring.
Based on the results, it is clear that all the newly synthe-
sized compounds have exhibited good activity at the lower
concentrations. The percentage of inhibition and the IC50
values of the newly synthesized compounds are presented
in Table 1 and Figure 2.
H2O2 is the most important because of its ability to
penetrate into biological membranes. H2O2 itself is not
very reactive, but it can sometimes be toxic to cell because
it may give rise to hydroxyl radicals in the cells.[23] Scav-
enging of H2O2 by compounds is attributed to their
hydroxyl radicals in its, structure which can donate elec-
trons to H2O2, thus neutralizing it to water.[24] The results
show that all the compounds have shown potent
H2O2scavenging activity. As the antioxidant components
present in its structure of compounds are good electron
donors, they may accelerate the conversion of H2O2 to
H2O. Compounds 3c, 3d, 5a, and 5b have exhibited good
2.2.2 | Antimicrobial activity
Antibacterial activity
All the newly synthesized title compounds were screened
for the antibacterial activity against four bacterial strains
such as Escherichia coli, Bacillus subtilis, Pseudomonas
aeruginosa, and Klebsiella pneumoniae by using the agar
well diffusion method. Gatifloxacin was used as a stan-
dard. The compounds 3c, 3d, 5a, 5b, and 5e showed
potent antibacterial activity against all the tested patho-
gens. The zones of inhibition of all the title compounds
were presented in Table 4.
2.2.3 | Antifungal activity
In vitro antifungal activity of all the newly synthesized
title compounds was tested against two fungal strains

4
NAGALAKSHMAMMA ET AL.
TABLE 2 Percentage of inhibition
and IC50 values of bis sulfonamide/
carbamate derivatives 3(a–d)/5(a–f) in
H2O2 method
% of inhibition
Compound
25 (μg/ml)
49.45 2.3
54.40 2.4
58.16 1.6
56.80 2.5
60.18 2.0
63.30 1.4
54.56 3.9
52.40 3.8
50.50 2.0
58.50 3.4
71.19 0.1
50 (μg/ml)
75 (μg/ml)
68.46 3.4
76.8 2.1
72.5 2.5
78.5 2.9
71.34 3.6
69.48 3.3
63.26 2.8
60.38 2.8
57.32 3.0
68.39 3.9
78.29 0.1
100 (μg/ml)
84.58 2.4
82.90 3.0
74.40 3.1
85.20 2.3
74.45 2.8
70.54 1.6
65.15 3.2
65.5 4.8
IC50 (μg/ml)
25.51
3a
58.53 2.8
59.50 2.8
65.61 2.0
62.70 3.6
63.45 2.4
65.58 2.4
58.8 2.4
3b
22.90
3c
21.49
3d
22.00
5a
20.77
5b
19.49
5c
22.91
5d
57.54 2.5
53.46 2.8
65.48 4.0
76.18 0.1
23.85
5e
62.42 1.5
73.85 1.8
80.14 0.1
24.75
5f
21.36
Ascorbic acid
17.60
Note: Data represents mean SD of triplicates.
orbital and remaining SP2 orbitals of carbon atoms. From
the results, it is clear that, the compounds which have
the nitro and chloro substituents on the phenyl ring have
shown significant antioxidant and antimicrobial activity.
3 | EXPERIMENTAL
3.1 | Chemistry
All the required chemicals were purchased from Sigma-
Aldrich and Merck and were used as such without
further purification. The completion and purity of the
reactions were monitored by thin layer chromatography,
performed on silica gel aluminium 60 F-254 thin-layer
plates procured from Merck, and visualization on TLC
was achieved by UV light and iodine indicator. The melt-
ing points of the compounds were determined on Guna
digital melting point apparatus using open capillary
method and are uncorrected. The Infrared spectra were
recorded on FT-IR Bruker Alpha interferometer and
wave numbers are given in cm−1.1H and 13C NMR spec-
tra were recorded on a Bruker FT-NMR 400 MHz in
CDCl3 solvent and the spectrometer operating at
400 MHz for 1H NMR and 100 MHz for 13C NMR in
DMSO-d6. Tetramethylsilane (TMS) was used as internal
FIGURE 3 IC50 values of bis sulfonamide/carbamate
derivatives 3(a–d)/5(a–f) in H2O2 method
such as Candida albicans and Saccharomyces cerevisiae
by using the poison plate method. Ketoconazole was used
as a standard. Compounds 5a, 5b, and 5e showed potent
antifungal activity against the tested pathogens. The zone
of inhibition of the title compounds are presented in
Table 5.
2.2.4 | Structure–activity relationship
studies
1
The detailed analysis of the structure of bis sulfonamide/
carbamate derivatives of bis-(4-aminophenyl) methane is
envisaging that the compounds exhibit dynamic intercon-
version from one form to another. Here, the nitrogen
atom is the adjunction point for the continuous conjuga-
tion in the phenyl substituted moiety system. In this way,
nitrogen is protecting the continuous conjugation of
π-electron density over entire molecule with its empty p
standards in the recording of H and 13C NMR spectra,
respectively. The chemical shift (δ) and coupling constant
(J) were expressed in ppm and Hertz, respectively. The
following abbreviations were used s, d, t, and m as sin-
glet, doublet, triplet, and multiplet. The mass spectra
were recorded on LCMS-2010A Shimadzu mass spec-
trometer in positive mode. The CHN analysis was carried
out on Flash EA 1112 instrument.

NAGALAKSHMAMMA ET AL.
5
TABLE 3 Percentage of inhibition
and IC50 values of bis sulfonamide/
carbamate derivatives 3(a-d)/5(a-f) in
NO method
% of inhibition (μg/ml)
Compound
25 (μg/ml)
32.60 1.5
28.24 1.6
42.15 2.6
40.70 3.2
58.50 2.6
55.10 1.2
43.70 1.9
50.70 2.0
54.90 1.2
52.05 3.4
75.00 01
50 (μg/ml)
36.28 2.0
39.26 2.2
50.43 1.9
48.50 2.8
62.40 2.2
58.20 2.8
50.80 2.4
54.80 3.5
59.20 2.4
60.60 3.2
80.18 0.1
75 (μg/ml)
45.14 1.8
53.15 1.5
58.38 2.1
60.20 3.0
65.50 3.2
65.60 3.5
56.40 1.6
60.80 2.4
62.50 1.6
66.80 2.2
83.29 0.1
100 (μg/ml)
51.52 2.4
61.92 1.0
65.46 2.0
66.4 1.5
IC50 (μg/ml)
97.04
3a
3b
70.55
3c
49.57
3d
51.54
5a
75.70 3.3
72.80 2.9
65.50 2.7
65.60 1.8
70.40 2.8
78.15 3.1
86.14 0.1
21.30
5b
22.68
5c
49.21
5d
45.62
5e
22.76
5f
23.80
Ascorbic acid
33.33
of the remaining target compounds 3(b–d)/5(a–f) using dif-
ferent substituted sulfonyl chlorides and chloroformates.
Spectral data
N,N0-(methylenebis[4,1-phenylene])bis(4-bromobenzene-
sulfonamide) (3a): Off-white solid, Yield: 89%,
m.p. 200-202ꢀC; IR (KBr, cm−1): 3,740 (N–H), 2,925(Ar-
CH), 1,507 (C=C), 1,346 (S=O), 1,273 (C–N), 938 (S–N),
1
746 (C–Br); H NMR (400 MHz, CDCl3): δ 8.16 (2H, s,
N–H), 7.48–7.60 (8H, m, Ar-H), 6.99 (4H, d, J = 7 Hz,
Ar-H), 6.94 (4H, d, J = 7 Hz, Ar-H), 3.79 (2H, s, CH2); 13
C
NMR (100 MHz, CDCl3): δ 46.1, 115.4, 121.1, 123.2, 125.0,
128.8, 131.4, 132.4, 138.3; LC–MS (m/z): 636 (M)+. Anal.
Calcd for C25H20 Br2N2O4 S2: C 47.19, H 3.17, N 4.40.
Found: C- 47.25, H- 3.19, N- 4.36.
FIGURE 4 IC50 values of bis sulfonamide/carbamate
derivatives 3(a–d)/5(a–f) in NO method
3.2 | Procedure for the synthesis of bis
sulfonamide/carbamate derivatives 3(a–d)/
5(a–e)
Dipentyl(methylene)bis(4,1-phenylene))dicarbamate (5f):
White solid, Yield: 88%; m.p. 212–214ꢀC. IR (KBr, cm−1):
3,321(N-H), 1,711 (C=O), 1,224 (C–O); 1H NMR (400 MHz,
CDCl3): δ 9.86 (2H, s, N–H), 7.26 (4H, t, J = 7.6 Hz, Ar–H),
7.08 (4H, d, J = 7.6 Hz, Ar–H), 4.12 (4H, t, J = 6.8 Hz, –
OCH2), 3.86 (2H, s, CH2), 1.612–1.682 (4H, m Ali-H),
1.29–1.62 (8H, m, Ali-H), 0.89 (6H, t, J = 6.8 Hz, –CH3);
13C NMR (100 MHz, CDCl3): δ 14.1, 24.3, 28.0, 28.6, 44.2,
63.5, 120.3, 126.0, 129.4, 134.4, 153.7. LC–MS (m/z):
427 (M + H)+. Anal. Calcd. for C25H34N2O4: C 70.40, H
8.03, N 6.57; Found: C 70.32, H 8.09, N 6.63.
3.2.1 | N,N0-(methylenebis
[4,1-phenylene])bis
(4-bromobenzenesulfonamide) (3a)
To a stirred solution of Bis-(4-aminophenyl)methane (1)
(0.001 mol, 0.198 g) dissolved in THF (10 ml), 4-Bromo
benzene sulfonyl chloride (2a) (0.002 mol, 0.225 g,
0.22 ml) was added dropwise at 0–10ꢀC with constant stir-
ring and reflux at 45–50ꢀC for 4 hr in the presence of
triethylamine. The progress of the reaction was monitored
by TLC. After the completion of reaction, the reaction
mixture was concentrated under rota evaporator. The
crude reaction mixture was purified by column chroma-
tography using ethyl acetate and hexane (2,1) as mobile
phase to obtain N,N0-(methylenebis[4,1-phenylene])bis
(4-bromobenzenesulfonamide) (3a) as a pure product. The
same experimental procedure was adopted for the synthesis
3.3 | Biological activity
3.3.1 | Antioxidant activity
The antioxidant activity of the all the newly synthesized
title compounds 3(a–d)/5(a–f) was carried out by using
[27]
DPPH,[24–26] H2O2, and
NO[28] scavenging activity
methods. Ascorbic acid was used as a standard. The

6
NAGALAKSHMAMMA ET AL.
TABLE 4 Zone of the inhibition of bis sulfonamide/carbamate derivatives 3(a–d)/5(a–f) against tested bacterial strains by agar well
diffusion method
Zone of inhibition (mm)
Compound
(100 μg/ml)
E. coli
B. subtilis
5.5 0.4
3.0 1.5
10.0 2.0
9.2 0.2
10.3 0.6
10.2 0.2
3.0 0.4
4.7 0.1
10.8 2.6
6.3 0.1
—
P. aeruginosa
2.7 0.3
6.1 0.1
11.2 0.2
11.3 0.1
12.6 0.4
12.9 0.5
6.7 0.3
4.2 0.3
12.0 0.4
7.3 0.2
—
K. pneumoniae
3.0 1.5
2.7 0.3
10.4 0.6
9.8 0.6
11.3 0.2
10.6 0.1
3.6 0.4
5.5 0.25
10.0 0.3
4.2 0.1
—
3a
3.2 0.2
4.5 0.4
9.2 0.2
9.1 0.4
10.2 0.3
12.6 0.2
5.0 0.5
8.6 0.4
15.5 0.1
6.1 0.3
—
3b
3c
3d
5a
5b
5c
5d
5e
5f
Control
Gatifloxacin
19.8 0.3
11.2 0.3
13 0.2
11.6 0.2
Note: Data represents mean SD of triplicates.
TABLE 5 Zone of the inhibition of the bis sulfonamide/
carbamate derivatives 3(a–d)/5(a–f) by using poison plate method
bacterial strains such as E. coli, B. subtilis, P. aeruginosa,
and K. pneumoniae by using the agar well diffusion
method.[29] Gatifloxacin was used as a standard. The zones
of inhibition are summarized in Table 4. The detailed pro-
cedure has been provided in the supporting information.
Zone of inhibition (mm)
Compound
(100 μg/ml)
Candida
albicans
Saccharomyces
cerevisiae
3a
ND
ND
3b
ND
3.5 1.5
7.2 0.4
8.6 0.5
12.2 0.3
11.1 0.1
4.2 0.4
8.4 0.2
12.5 0.2
7.8 0.6
—
3.3.3 | Antifungal activity
3c
4.8 0.2
5.0 0.4
9.2 0.5
9.7 0.5
3.2 0.2
6.8 0.4
8.4 0.2
5.4 0.3
—
3d
All the title compounds were screened for their in vitro
antifungal activity against the fungal strains Candida
albicans and Saccharomyces cerevisiae by using the poi-
son plate method.[30] Ketoconazole was used as a stan-
dard. The zone of inhibition is summarized in Table 5.
The detailed procedure has been provided in the
supporting information.
5a
5b
5c
5d
5e
5f
Control
Ketoconazole
3.3.4 | Statistical analysis
10.2 0.4
13.3 0.3
Note: Data represents mean SD of triplicates.
All the statistical analyses regarding the biological
aspects were carried out using the SPSS 20.0 package.
Abbreviations: ND, not determined.
results are presented in Table 1 and Figure 2, Table 2 and
Figure 3, and Table 3 and Figure 4. The detailed proce-
dure has been provided in the supporting information.
4 | CONCLUSIONS
Synthesis of a series new of bis sulfonamide/carbamate
derivatives 3(a–d)/5(a–f). All the newly synthesized com-
pounds were investigated for their antioxidant and antimi-
crobial activities to understand their biological potency.
The biological activity results showed that most of the
3.3.2 | Antibacterial activity
All the newly synthesized compounds were evaluated for
their in vitro antibacterial activity against the growth of four

NAGALAKSHMAMMA ET AL.
7
[14] K. Arun Ghosh, M. Brindisi, J. Med. Chem. 2015, 58, 2895.
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D. W. Boykin, Eur. J. Med. Chem. 2008, 43, 174. https://doi.
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[17] A. J. Wills, Y. K. Ghosh, S. J. Balasubramanian, J. Org. Chem.
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compounds exhibited good antibacterial activity than that
of the standard drug. In contrast to bacterial activity, the
compounds 3c, 3d, 5a, and 5b exhibited potent antioxidant
activity. Finally it is concluded that, on the basis of the bio-
logical results, further investigations in vivo to be carried
out for these compounds in order to produce the best anti-
oxidant agents in near future and they can be further
explored as a new class of drug candidates.
[19] A. B. Smith, B. S. Freez, M. J. LaMarche, T. Hirose, I. Brouard,
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ACKNOWLEDGMENTS
The authors are grateful to the UGC, for sanctioning
RGNF (SRF) and Department of Chemistry and Zoology,
Sri Venkateswara University, Tirupati for providing lab
facilities.
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How to cite this article: Nagalakshmamma V,
Varalakshmi M, Umapriya K, et al. Synthesis,
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