Bio-potent sulfonamides

Article abstract of DOI:10.4067/s0717-97072019000104386

Some 4-(substituted phenylsulfonamido)benzoic acids have been synthesized by fly-ash:H₃PO₃ nano catalyst catalyzed condensation of substituted benzenesulfonyl chlorides and 4-aminobenzoic acid in ultrasound irradiation conditions. The yields of the sulfonamides are more than 90%. The synthesized 4-(substituted phenylsulfonamido) benzoic acid derivatives were characterized by their physical constants, analytical and spectroscopic data. Antimicrobial activities of all sulfonamides were measured by Bauer-Kirby disc diffusion method.

Full text of DOI:10.4067/s0717-97072019000104386

J. Chil. Chem. Soc., 64, Nº 1 (2019)
BIO-POTENT SULFONAMIDES
SELVAKUMAR DINESHKUMAR AND GANESAMOORTHY THIRUNARAYANAN*
Department of Chemistry, Annamalai University, Annamalainagar-608 002, India
ABSTRACT
Some 4-(substituted phenylsulfonamido)benzoic acids have been synthesized by fly-ash:H3PO nano catalyst catalyzed condensation of substituted
benzenesulfonyl chlorides and 4-aminobenzoic acid in ultrasound irradiation conditions. The yields of3the sulfonamides are more than 90%. The synthesized
4-(substituted phenylsulfonamido) benzoic acid derivatives were characterized by their physical constants, analytical and spectroscopic data. Antimicrobial
activities of all sulfonamides were measured by Bauer-Kirby disc diffusion method.
Key words: 4-(substitutedphenylsulfonamido)benzoic acids; Ultrasonication; Antimicrobial activities.
ultrasonication under solvent-free conditions and its biological activities.
Therefore herein the authors interestingly investigated the ultrasound assisted
synthesis of some sulphonamides and evaluation of antimicrobial activities
using the standard Bauer-Kirby39 Disc diffusion method.
INTRODUCTION
Sulfonamides or sulphonamide are effective compounds combining
(–S(=O)2–NH–) group and they are generally formed by the condensation of
corresponding amine and sulfonyl chlorides. The most common method for
synthesizing sulfonamides is the condensation of aromatic sulfonyl chloride
with aliphatic or aromatic primary/secondary amines in the presence of base
catalysts. Usually sulfonamides are derived from amines with sulfonic acids
or sulfonyl halides by eradicating of halide group or hydroxyl group and
form important class of sulfur holding sulfonamides. Researchers have been
investigated various compounds containing sulfonamide moieties. They are
tryptamine1, chalcones2, adamantine3, azetidinone4, carbazole5, catenane6,
cinnamic acyl7, coumarin8, cyanopyridines, isoxazoles, pyrazoles, pyrimidines9,
epipodophyllotoxin10, furan containing vinyl sulfonamides11, isoquinoline
sulfonamide12, oxazolidinones13, quinolone14, thiadiazole15, thiazole,pyridone,
chromene, hydrazine16, thiouracil17 and triazole18. Due to its greater effectiveness
and less toxicity it establishes a main class of drugs with numerous types of
pharmacological potentials such as antibacterial19, antitumor20, anti-carbonic
anhydrase21-23, antiretro-viral24, anti-malarial25, anti-HIV[26]. Many catalysts
are used for the synthesis of sulfonamides such as, β-Cyclodextrin27, water28,
29, pyridine30, PPh331, DMAP32, CsF-Celite33, ZnO-nanoparticles34, MgO35.
Lakroutet al.,36 have prepared somesulfonamide derivatives by sulfonylation
of primary, secondary sulfonyl chlorides, amino acid esters and phenols
under solvent-free microwave irradiation techniques. Pan et al.,28 synthesized
EXPERIMENTAL
General
Sigma-Aldrich, Alfa Aesar and E-Merck chemical company chemicals
used in this investigation. Mettler FP51 melting point apparatus was used for
the determination melting points of all sulfonamides. The OMNIC Fourier-
transform spectrophotometer was employed for recording Infrared spectra.
The proton and carbon-13 spectra of all sulfonamides were recorded in
Bruker AV400 & 500 NMR spectrometer in DMSO solvent using TMS as
internal standard. Mass spectra were recorded on a SIMADZU GC-MS2010
spectrometer. The Thermo Finnigan CHN analyzer was used for elemental
analysis.
Typical procedure for the preparation of 4-(substituted
phenylsulfonamido) benzoic acids
An equimolar concentration of benzenesulfonyl chloride (1 mmol),
4-aminobenzoic acid (1 mmol), fly-ash:H3PO (0.02 mg) catalyst38 and 10
mL of ethanol were taken in 50 mL conical4 flask and mixed thoroughly.
This mixture was subjected to ultrasound irradiation for 20-25 minutes in a
ultrasonicator (Scheme 1) in room temperature. During the reaction 0.1 mg of
potassium carbonate was added to neutralize the formation of hydrochloride.
The completion of the reaction was monitored by Thin layer chromatography.
The resulting product was washed with n-hexane and separated the catalyst by
filtration and dried to obtain the solids. Further the crude was purified by column
chromatogram using dichloromethane and ethylacetate (3:1) as eluants.
a
fewsulfonamides via I2-mediated reaction of sodium sulfinates with
amines in an aqueous medium at room temperature. Recently Dineshkumar
and Thirunarayanan prepared more than 80% yields of mesalazines type
sulphonamides37. In the literature surey, there is no report available for the
ultrasonic assisted fly-ash:H3PO nano catalyst38 catalyzed condensation
of substituted benzenesulfonyl 3chlorides and 4-aminobenzoic acid in
Scheme-1 . Synthesis of 4-(substitutedphenylsulfonamido)benzoic acids
e-mail: drgtnarayanan@gmail.com
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J. Chil. Chem. Soc., 64, Nº 1 (2019)
Measurement of antimicrobial activities
Measurement of antibacterial activities
C). Anal. Calcd.forC13H10BrNO4S (%):C (50.09), H (3.23), N (4.49); Found
(%):C (50.12), H (3.20), N (4.47); MW: 311; Mass (m/z): 311 [M+], 313 [M2+].
4-((2-fluorophenyl)sulfonamido)benzoic acid(4): White powder, m.p.
267-268°C. IR(4000-400, ν, cm-1): 3258(NH), 1700(CO), 1336(SOsym),
Antibacterial activities of all synthesized sulphonamides were evaluated by
using standard wellknown Bauer-Kirby disc diffusion method37. In this study
the authors chosen the Gram-positive bacterial strains such as Micrococcus
luteus B. subtilis and Staphylococcus aureus the Gram-negative bacterial
strains such as E. coli, P.aeruginosa. Ampicillin as standard and the solvent is
dimethylsulfoxide.
1
1150(SOasym). H NMR ( ppm): 10.364(s, 1H, NH), 12.004(s, 1H, COOH),
7.301-7.749(m, 8H, Ar-H). 13C NMR ( ppm):167.50(CO), 118.365-143.78(Ar-
C). Anal. Calcd.forC13H10FNO4S (%):C (52.88), H (3.41), N (4.74); Found
(%):C (52.92), H (3.38), N (4.71); MW: 295; Mass (m/z): 295 [M+], 297 [M2+].
4-((4-fluorophenyl)sulfonamido)benzoic acid(5): White solid, m.p.
270-272°C. IR(4000-400, ν, cm-1): 3247(NH), 1693(CO), 1334(SOsym),
1159(SOasym). 1H NMR ( ppm): 10.083(s, 1H, NH), 11.043(s, 1H, COOH),
7.435-7.782(m, 8H, Ar-H).13C NMR ( ppm): 167.21(CO), 118.093-142.87(Ar-
C). Anal. Calcd.forC13H10FNO4S (%):C (52.88), H (3.41), N (4.74); Found
(%):C (52.96), H (3.36), N (4.72); MW: 295; Mass (m/z): 295 [M+], 297 [M2+].
4-((4-methoxyphenyl)sulfonamido)benzoic acid(6): White solid,
m.p.278-281°C. IR(4000-400, ν, cm-1): 3264(NH), 1700(CO), 1332(SOsym),
Measurement of antifungal activities
Antifungal activities of all synthesized mesalazine sulfonamides were
determined by using standard wellknown Bauer-Kirby disc diffusion method37.
ThetestorganismsweresubcultureusingPDAmedium. Inthisstudy, theauthors
had chosen two fungal stains such as Aspergillus niger and Trichoderma viride.
Micanazole was used as a standard drug and dimethylsulfoxide as a solvent.
RESULTS AND DISCUSSION
1
1150(SOasym). H NMR ( ppm): 10.700(s, 1H, NH), 10.002(s, 1H, COOH),
In our research laboratory, we attempt to synthesis some sulphonamides
using fly-ash:H3PO4 catalyst assisted ultrasonication method. An appropriate
molar quantities of electron donating and electron-withdrawing substituted
benzenesulfonyl chloride (1 mmol), 4-aminobenzoic acid (1 mmol), fly-
ash:H3PO4 (0.02 mg) catalyst and 10 mL of ethanol were taken in 50 mL
conical flask and mixed thoroughly. This mixture was subjected to ultrasound
irradiation for 20-25 minutes in a ultrasonicator in room temperature. During
the reaction 0.1 mg of potassium carbonate was added to neutralize the
formation of hydrochloride. The completion of the reaction was monitored by
Thin Layer Chromatography. The resulting product was washed with n-hexane
and separated the catalyst by filtration and dried to obtained 90-96% yields of
sulphonamide derivatives. The electron donating substituted benzene sulfonyl
chlorides gave higher percent yields than the compound containing electron-
withdrawing substituents. The complete characterization data of synthesized
sulphonamide derivatives (entries 1-9) are summarized below
4-(Phenylsulfonamido)benzoic acid (1): White solid, m.p. 276°C.
IR(4000-400, ν, cm-1): 3272(NH), 1677(CO), 1332(SOsym), 1163(SO asym).
1H NMR ( ppm): 10.824(s, 1H, NH), 12.750(s, 1H, COOH), 7.200-7.843(m,
9H, Ar-H); 13C NMR ( ppm): 167.19(CO), 118.63-142.40(Ar-C). Anal. Calcd.
forC13H11NO4S (%):C (56.31), H (4.00), N (5.05); Found (%):C (56.38), H
(4.05), N (4.98); MW: 277; Mass (m/z): 277 [M+].
4-((4-Bromophenyl)sulfonamido)benzoic acid(2): White solid, m.p.
292-293°C. IR(4000-400, ν, cm-1): 3263(NH), 1680(CO), 1337(SOsymm),
1161(SOasym). 1H NMR ( ppm): 10.913(s, 1H, NH), 11.326(s, 1H, COOH),
7.234-7.7364(m, 8H, Ar-H). 13C NMR ( ppm): 167.19(CO), 119.23-144.23(Ar-
C). Anal. Calcd.forC13H10BrNO4S (%):C (43.84), H (2.83), N (3.93); Found
(%):C (43.86), H (2.87), N (3.89); MW: 356; Mass (m/z): 356 [M+], 358 [M2+].
4-((4-chlorophenyl)sulfonamido)benzoic acid(3): White solid, m.p.
285-287°C. IR(4000-400, ν, cm-1): 3258(NH), 1678(CO), 1336(SO sym),
1161(SOasym).1H NMR ( ppm): 10.624(s, 1H, NH), 11.901(s, 1H, COOH),
7.134-7.726(m, 8H, Ar-H). 13C NMR ( ppm): 167.16(CO), 118.502-144.93(Ar-
2.504(s, 3H, CH3), 7.216-7.693(m, 8H, Ar-H). 13C NMR ( ppm): 167.26(CO),
63.87(OCH3), 118.02-144.06(Ar-C). Anal. Calcd.forC14H13NO5S (%):C
(54.72), H (3.41), N (4.74); Found (%):C (54.76), H (4.22), N (4.54); MW:
307; Mass (m/z): 307 [M+].
4-((4-methylphenyl)sulfonamido)benzoic acid(7): White powder, m.p.
265-267°C. IR(4000-400, ν, cm-1):3215(NH), 1704(CO), 1336(SOsym),
1154(SOasym). 1H NMR ( ppm): 11.116(s, 1H, NH), 12.348(s,1H, COOH),
2.083(s,3H, CH3),7.381-7.762(m, 8H, Ar-H). 13C NMR ( ppm): 167.17(CO),
22.46(CH3), 118.12-143-36(Ar-C). Anal. Calcd.forC14H13NO4S (%):C (57.72),
H (4.50), N (4.81); Found (%):C (57.79), H (4.48), N (4.78); MW: 291; Mass
(m/z): 291 [M+].
4-((2-nitrophenyl)sulfonamido)benzoic acid(8): White solid, m.p.280-
282°C. IR(4000-400, ν, cm-1): 3213(NH), 1697(CO), 1336(SOsym),
1
1162(SOasym). H NMR ( ppm): 11.234(s, 1H, NH), 11.471(s, 1H, COOH),
7.435-7.892(m, 8H, Ar-H). 13C NMR ( ppm): 167.14(CO), 118.56-144.25(Ar-
C). Anal. Calcd.forC13H10N2O6S (%):C (48.45), H (3.13), N (8.69); Found
(%):C (48.49), H (3.09), N (8.62); MW: 322; Mass (m/z): 322 [M+].
4-((4-nitrophenyl)sulfonamido)benzoic acid(9): White solid, m.p.275-
276°C. IR(4000-400, ν, cm-1):3257(NH), 1677(CO), 1338(SOsym),
1162(SOasym). 1H NMR ( ppm): 11.128(s, 1H, NH), 11.5.308(s, 1H, COOH),
7.465-7.832(m, 8H, Ar-H). 13C NMR ( ppm): 167.13(CO), 119.09-144.83(Ar-
C). Anal. Calcd.forC13H10N2O6S (%):C (48.45), H (3.13), N (8.69); Found
(%):C (48.46), H (3.10), N (8.64); MW: 322; Mass (m/z): 322 [M+].
Authors have studied this experiment with methods of conventional
heating for 6h and microwave irradiation for 3-5 minutes for the condensation
of benzene sulfonyl chlorides and 4-aminobenzoic acid(entries 1-9). In these
methods the obtained yields are less than 80%. The obtained yields (entries 1-9)
in conventional heating, microwave irradiation and ultrasonication methods are
presented in Table 1. Among the three methods, the ultrasonication synthesis
gave high yields than other two methods.
Table-1. The obtained yields of sulphonamides in the various method of synthesis.
Conventional heating
Time(h) Yield (%)
68
Microwave irradiation
Ultrasound irradiation
Time(m) Yield (%)
20 94
Entry
X
Time(m)
Yield (%)
1
2
3
4
5
6
7
8
9
H
4-Br
6
3
4
75
70
71
73
74
78
76
68
71
6
6
6
6
6
6
6
6
65
66
63
67
72
70
61
61
25
25
23
21
25
25
24
22
92
91
90
90
96
94
90
91
4-Cl
4
2-F
5
4-F
3.5
3
4-OCH3
4-CH3
2-NO2
4-NO2
3
5
5
Also the authors studied the effects of solvent on these synthesis of
sulphonamides in the above three methods within the same conditions such as
quantity of catalyst and reaction time. The solvents such as methanol, ethanol,
dichloromethane, tetrahydrofuron and dioxane were used for the evaluation of
effects of solvent on synthesis of sulphonamides. Here the electron donating
substituted sulfonylchlorides gave more percentage yield than electron with-
drawing substituted sulfonylchlorides. In overall, among the three methods the
ultrasonication synthetic method gave more yields than conventional heating
method. The obtained yields of the sulphonamuides with various solvents in the
conventional heating, and ultrasonic sound irradiation methods are presented in
Table 2.
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J. Chil. Chem. Soc., 64, Nº 1 (2019)
Table-2. The effects of solvents on the obtained yields of sulphonamides in conventional and ultrasound irradiation method of synthesis.
Yields (%) in Conventional heating with solvents
Yields (%) in Ultrasound irradiation with solvents
Entry
X
MeOH
67
EtOH
68
DCM
66
THF
68
64
66
62
64
70
69
63
65
DX
69
62
65
61
63
72
68
62
65
ACN
69
MeOH
90
EtOH
94
DCM
91
THF
90
95
94
93
92
96
93
92
93
DX
91
93
93
91
92
95
94
91
94
ACN
90
1
2
3
4
5
6
7
8
9
H
4-Br
66
65
65
65
92
92
93
91
4-Cl
63
66
64
70
95
91
94
95
2-F
62
63
63
71
91
90
91
92
4-F
63
67
65
68
93
90
93
92
4-OCH3
4-CH3
2-NO2
4-NO2
70
72
68
74
96
96
95
96
66
70
67
69
93
94
94
93
63
61
62
66
91
90
90
90
62
61
63
65
91
91
92
92
MeOH: Methanol; EtOH: Ethanol; DCM: Dichloromethane; THF: Tetrahydrofuron; DX: Dioxane; ACN: Acetonitrile
Antibacterial activity
The measured antibacterial activities by means of the measurement of mm
of zone of inhibitions39-41 of the synthesized sulfonmamides are presented in
Table 3. The mm of zone of inhibition in the petri-plates (plates 1-8) are shown
in Fig. 2. The comparative statistical diagram of mm of zone of inhibition was
illustrated in Fig. 3.
Table-3.Antibacterial activities of 4-(substituted phenylsulfonamido)
benzoic acids.
Zone of inhibition (mm)
Gram-positive
Gram-negative
Entry
X
P.
M. luteus S. aureus
E. coli aeruginosa
1
2
3
4
5
6
7
8
9
H
4-Br
-
6
7
6
6
9
7
7
8
17
-
6
6
6
7
-
-
4-Cl
7
8
6
2-F
7
9
8
4-F
-
7
-
4-OCH3
4-CH3
2-NO2
4-NO2
7
7
11
7
7
8
7
12
9
8
10
24
-
16
19
-
Standard Ampicillin
Control DMSO
20
-
The synthesized 4-(substituted phenylsulfonamido)benzoic acid
compounds with 4-OCH3 substituent shows satisfactory antibacterial activity,
the substituents 4-Br, 4-Cl, 2-F, 4-F, 4-CH3,2-NO2 and 4-NO2 have shown least
activity and the other substituted compounds have no antibacterial activity
against Micrococcus luteus.
Fig
2.
Antibacterial
activities
(petri-dishes)
of
4-(substitutedphenylsulfonamido)benzoic acid compounds.
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J. Chil. Chem. Soc., 64, Nº 1 (2019)
The 4-(substituted phenylsulfonamido)benzoic acid compounds (with parent, 4-Br, 4-Cl, 2-F, 4-F, 4-OCH3,4-CH3,2-NO2 and 4-NO2 have shown least
antibacterial activity against Streptococcus aureus.
Fig. 3. Antibacterial activities (clustered column chart) of 4-(substituted phenylsulfonamido)benzoic acid compounds .
Antifungal activity
The antifungal activity of 4-(substituted phenylsulfonamido)benzoic acid
compounds were shown(plates 9-12) in Fig 4. and the zone of inhibition39-41
values are given in 4. The corresponding clustered column chart is shown
in Fig.5. The 4-(substituted phenylsulfonamido)benzoic acid compounds
with 4-Br and 4-CH substituents have shown good antifungal activity and
the compounds with 3parent, 2-F and 4-F substituent have shown satisfactory
antifungal activity and the other substituted compounds no antifungal activity
against Aspergillus niger.
Table-4. Antifungal activities of 4–(substituted phenylsulfonamido)
benzoic acid compounds
Zone of inhibition (mm)
Entry
X
Aspergillus
niger
Trichodermaviride
1
H
4-Br
6
8
-
9
13
10
14
9
2
3
4-Cl
4
2-F
6
7
-
5
4-F
6
4-OCH3
4-CH3
2-NO2
4-NO2
Miconazole
DMSO
8
Fig 4. Antifungal activities of 4-(substituted phenylsulfonamido)benzoic
acid compounds
7
8
-
13
12
8
8
9
-
Standard
Control
12
-
20
-
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J. Chil. Chem. Soc., 64, Nº 1 (2019)
Fig.5. Antifungal activities (clustered column chart) of 4-(substituted phenylsulfonamido)benzoic acid compounds.
The 4-(substituted phenylsulfonamido)benzoic acid compounds with 4-Br,
2-F, 4-CH3 and 2-NO2 substituents have shown good antifungal activity and the
compounds with 4-Cl substituent have shown satisfactory antifungal activity
and the other substituted compounds have shown least antifungal activity
against Trichoderma viride.
ACKNOWLEDGEMENT
Authors thank DST-NMR Facility, Department of Chemistry, Annamalai
University,Annamalainagar-608002 for recording NMR spectra of compounds.
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The authors have demonstrated the ultrasonicated synthesis of some
4-(substituted phenylsulfonamido)benzoic acids by fly-ash:H3PO nano
catalyst catalyzed condensation of substituted benzenesulfonyl chlorid3es and
4-aminobenzoic acid. The yields of the sulfonamides are more than 90%. The
synthesized 4-(substituted phenylsulfonamido) benzoic acid derivatives were
characterized by their physical constants, analytical and spectroscopic data.
Antimicrobial activities of all sulfonamides were measured by Bauer-Kirby
disc diffusion method. compounds with 4-OCH3 substituent shows satisfactory
antibacterial activity, the substituents 4-Br, 4-Cl, 2-F, 4-F, 4-CH3,2-NO and
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phenylsulfonamido)benzoic acids with parent, 4-Br, 4-Cl, 2-F, 4-F, 4-OCH3,
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Streptococcus aureus. Compounds with 4-Br and 4-CH3 substituents have
shown good antifungal activity and the compounds with parent, 2-F and
4-F substituent have shown satisfactory antifungal activity and the other
substituted compounds no antifungal activity against Aspergillus niger. The
4-(substituted phenylsulfonamido)benzoic acids with 4-Br, 2-F, 4-CH3 and
2-NO2 substituents have shown good antifungal activity and the compounds
with 4-Cl substituent have shown satisfactory antifungal activity. The other
sulphonamides have shown least antifungal activity against Trichoderma
viride.
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J. Chil. Chem. Soc., 64, Nº 1 (2019)
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