Synthesis, characterization, and antimicrobial studies of bissydnones based on 4,4'-diaminodiphenyl methane

Article abstract of DOI:10.1080/00397910903162809

The aim of this investigation is to present the synthesis and characterization of some 3,3'-(methylenedi-1,4-phenylene)bis(4-substituted aminosulfonyl)sydnone (7a-j) and to evaluate their antimicrobial activity. All newly synthesized compounds were characterized by spectral data as well as by elemental analysis. Some compounds showed excellent activity against Gram-positive and Gram-negative bacteria. Copyright

Full text of DOI:10.1080/00397910903162809

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Synthesis, Characterization, and
Antimicrobial Studies of Bissydnones
Based on 4,4′-Diaminodiphenyl Methane
Shahrukh T. Asundaria a & Keshav C. Patel a
a Department of Chemistry , Veer Narmad South Gujarat University ,
Surat, India
Published online: 08 Jun 2010.
To cite this article: Shahrukh T. Asundaria & Keshav C. Patel (2010) Synthesis, Characterization,
and Antimicrobial Studies of Bissydnones Based on 4,4′-Diaminodiphenyl Methane, Synthetic
Communications: An International Journal for Rapid Communication of Synthetic Organic Chemistry,
40:13, 1899-1906, DOI: 10.1080/00397910903162809
To link to this article: http://dx.doi.org/10.1080/00397910903162809
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Synthetic Communications1, 40: 1899–1906, 2010
Copyright # Taylor & Francis Group, LLC
ISSN: 0039-7911 print=1532-2432 online
DOI: 10.1080/00397910903162809
SYNTHESIS, CHARACTERIZATION, AND
ANTIMICROBIAL STUDIES OF BISSYDNONES BASED
ON 4,40-DIAMINODIPHENYL METHANE
Shahrukh T. Asundaria and Keshav C. Patel
Department of Chemistry, Veer Narmad South Gujarat University,
Surat, India
The aim of this investigation is to present the synthesis and characterization of some
3,30-(methylenedi-1,4-phenylene)bis(4-substituted aminosulfonyl)sydnone (7a–j) and to
evaluate their antimicrobial activity. All newly synthesized compounds were characterized
by spectral data as well as by elemental analysis. Some compounds showed excellent
activity against Gram-positive and Gram-negative bacteria.
Keywords: Bissydnone; cyclization; 4,40-diaminodiphenyl methane; mesoionic; microbial
INTRODUCTION
Mesoionic compounds have attracted widespread interest for a long time
because of their unusual structure,[1] chemical properties,[2] and synthetic utility.[3]
Sydnones are typical mesoionic compounds.[4] Several synthetic methodologies for
sydnones have been developed in the past years. A hydrogen atom at the fourth
position of the sydnone ring allows substitution with a wide variety of electrophiles,
with retention of the ring, typical of aromatic substrates.[5] Since their discovery,
sydnones have shown a variety of biological activities[6] carried out from a variety
of standpoints.
Sydnones have played a crucial role in the development of theory in hetero-
cyclic chemistry and occupy a unique place in organic chemistry. These observations
encouraged us to continue our current work to synthesize new heterocyclic-
containing bissydnone sulfonamides based on 4,40-diamino diphenyl methane.
RESULTS AND DISCUSSION
Herein we describe the synthesis, characterization, and biological evaluation of
novel 3,30-(methylenedi-1,4-phenylene)bis(4-substituted amino sulfonyl)sydnone (7a–
j). The synthesis of 3,30-(4,40-diphenyl)-bissydnonyl methane (5) was accomplished
by a four-step procedure. Compound 5 was reacted with chlorosulfonic acid and then
Received March 28, 2009.
Address correspondence to Keshav C. Patel, Department of Chemistry, Veer Narmad South
Gujarat University, Udhna-Magdalla Road, Surat 395007, India. E-mail: shahrukh_sun@rediff.com
1899

1900
S. T. ASUNDARIA AND K. C. PATEL
condensed with different amines to give 3,30-(methylenedi-1,4-phenylene) bis(4-substi-
tuted aminosulfonyl) sydnone (7a–j), which is a well-established strategy for the
synthesis of sulfonamides. Compounds 7a–j were synthesized as shown in Scheme 1.
The structures of the synthesized compounds were established on the basis of analyti-
cal and spectral data. The infrared (IR) spectrum of compound 5 showed absorption
1
bands at 1745 cmꢀ1, characteristic of the C O group. The H NMR spectra of
=
compound 5 showed a singlet at d 7.76 ppm, characteristic of the proton at C4 of
the sydnone.
The IR spectrum of the compounds displayed absorption bands between 1719
and 1756 cmꢀ1, which is characteristic of the carbonyl group of sydnone, and also
showed 1362–1367, 1157–1165, and 2923–2939 cmꢀ1, characteristic of SO2asy
,
1
SO2sym, and CH2 groups. Furthermore, the H NMR spectra of compounds 7a–j
showed signals in the range of d 8.86–8.96 ppm and 4.61–5.25 ppm for the SO2NH
group and d 6.80–8.90 ppm for aromatic protons. Further, the 13C NMR spectra
exhibited confirmatory signals for the carbonyl carbon around d 167.00 ppm and
the methylene carbon around d 39.00 ppm. The test compounds 7a–j were evaluated
for their antibacterial activity on four important bacterial stains (Gram-possitive
bacteria Streptococcus pneumoniae and Staphylococcus aureus and Gram-negative
bacteria Escherichia coli and Psudomanas aeruginosa). From the results obtained,
most of the compounds possess antibacterial activity. Compound 7h was most active
against Gram-positive bacterial stains and P. aeruginosa whereas compound 7e was
Scheme 1. R ¼7a, 4-ClC6H4; 7b, CH3; 7c, C6H5; 7d, 3-ClC6H4; 7e, 2-FC6H4; 7f, CH2(CH2)2CH3; 7g,
3-CH3C6H4; 7h, CH2-C6H5; 7i, 2-CH3C6H4; and 7j, 4-NO2C6H4.

BISSYDNONES BASED ON 4,40-DIAMINODIPHENYL METHANE
1901
Table 1. Antimicrobial activity of 3,30-(methylenedi-1,4-phenylene)bis(4-substituted aminosulfonyl) syd-
none (7a–j)
Gram-positive organism
S. pneumoniae S. aureus
IZ MIC MIC
Gram-negative organism
E. coli P. aeruginosa
MIC
Compound
IZ
IZ
IZ
MIC
7a
7b
14
15
15
10
17
17
15
18
14
14
40
35
64
64
16
14
17
18
17
15
17
19
14
14
40
45
32
64
15
10
13
10
16
14
14
10
13
10
28
30
64
—
64
—
32
64
64
—
64
—
1.0
0.5
13
13
15
12
10
16
14
22
12
10
34
38
64
64
7c
7d
32
—
32
32
32
64
7e
16
16
32
64
—
32
7f
7g
32
16
32
16
64
16
7 h
7i
64
64
64
64
128
—
7j
Streptomycin
Penicillin-G
0.25
0.25
0.125
0.125
0.5
0.25
Notes. IZ, inhibition of zone; MIC, minimum inhibitory concentration. Zone diameter of growth
inhibition (mm) after 24 h.
most active against E. coli. However, compound 7d was inactive against S. pneumo-
niae, compounds 7b, 7h, and 7j were inactive against E. coli, and compound 7e and 7j
were inactive against P. aeruginosa. The rest of the compounds were moderate to less
active against these species.
Biological Activity
One of the purposes of the present work was to synthesize new heterocyclic
compounds that might be of biological interest. The synthesized compounds were
tested for their antibacterial activity against Gram-positive and Gram-negative
bacteria. Preliminary antimicrobial testing was carried out using the Kirby–Bauer
technique.[8] The reference drugs used were streptomycin and penicillin-G, respect-
ively. The activity of the samples and the reference drugs was assayed under identical
conditions at 200 mg=mL concentration in N,N-dimethylformamide (DMF), and the
zone of inhibition was measured in millimeters. The investigation results are listed
in Table 1. In general, all the synthesized 3,30-(methylenedi-1,4-phenylene)bis(4-
substituted aminosulfonyl)sydnones (7a–j) exerted a wide range of modest antibac-
terial activity in vitro activity against the tested organisms.
EXPERIMENTAL
General Procedures
Melting points were determined by the open capillary method and are uncor-
rected. All compounds were analyzed satisfactorily for C, H, O, N, and S. IR spectra
(KBr) were recorded on a Shimadzu (Japan) Fourier transform (FT)–IR spectro-
1
photometer. H NMR spectra were recorded on a Bruker Advance II 400-MHz

1902
S. T. ASUNDARIA AND K. C. PATEL
NMR spectrometer, and 13C NMR spectra were recorded on Bruker Advance II
400-MHz NMR spectrometer using dimethylsulfoxide (DMSO-d6) as a solvent
and tetramethylsilane (TMS) as an internal standard. Elemental analysis was carried
out on a Vairo-EL (Elementa) model. Purity of the compounds was checked by
thin-layer chromatography (TLC) on silica-gel plates.
Synthesis of 3,30-(Methylenedi-1,4-phenylene)bis(4-substituted
amino sulfonyl) Sydnone Based on 4,40-Diaminodiphenyl Methane
2,20-[Methylenebis(1,4-phenyleneimino)]diethyl
Acetate
(2). 4,40-
Diaminodiphenyl methane (1.98 g, 0.01 mol), ethylchloroacetate (2.13 mL,
0.02 mol) in dry ethanol (10 mL), and anhydrous sodium acetate (3.28 g, 0.04 mol)
were refluxed for 5 h. The mixture was diluted with water (10 mL). After standing
overnight in the refrigerator, crystalline ester was obtained. The crude solid was pur-
ified by recrystallization from ethanol. Yield: 3.01 g, 80%, Mp 110–112 ꢁC. IR (KBr):
1
2959, 2928, 2875, 2854, 1756, 1521, 1307 cmꢀ1. H NMR (400 MHz, DMSO-d6): d
1.34 (t, 6H, CH3), 3.95 (s, 2H, NH), 4.05 (s, 6H, CH2), 4.35 (q, 4H, OCH2),
6.50–7.00 (m, 8H, Ar-H). 13C NMR (40 MHz, DMSO-d6): d 14.64, 40.50, 44.26,
61.24, 112.65, 128.95, 129.01, 145.87, 170.97. Anal. calcd. (%) for C21H26N2O4: C,
68.09; H, 7.07; O, 17.28; N, 7.56. Found: C, 68.13; H, 7.11; O, 17.25; N, 7.58.
2,20-[Methylenebis(1,4-phenyleneimino)]diacetic Acid (3). Compound 2
(3.70 g, 0.01 mol) and sodium hydroxide (1.2 g, 0.03 mol) were dissolved in a solution
of distilled water and ethanol (36 mL=4 mL). The mixture was stirred at reflux tem-
perature for 30 min. The resultant mixture was cooled and acidified with hydrochloric
acid. White crystalline product was obtained and recrystallized from ethanol. Yield:
2.23 g, 70%, Mp 130–135 ꢁC. IR (KBr): 2925, 2856, 2570–3209, 1719, 1518,
1297 cmꢀ1. 1H NMR (400 MHz, DMSO-d6): d 4.05 (s, 2H, CH2), 4.10 (s, 4H, CH2),
6.35 (s, 2H, NH), 6.40 (s, 2H, OH), 6.50–7.10 (m, 8H, Ar-H). 13C NMR (40 MHz,
DMSO-d6): d 40.82, 44.75, 112.28, 129.22, 129.47, 145.63, 171.54. Anal. calcd. (%)
for C17H18N2O4: C, 64.96; H, 5.77; O, 20.36; N, 8.91. Found: C, 64.94; H, 5.79; O,
20.32; N, 8.96.
2,20-{Methylenebis[4,1-phenylene (nitrosoimino)]}diacetic Acid
(4)[7]. A freshly prepared sodium nitrate solution (3.32g, 0.049 mol) was added drop-
wise to an ice-cold and well-stirred solution of compound 3 (5.02g, 0.016mol) in water
(40 mL) over a period of 40min. Concentrated hydrochloric acid was added until
complete precipitation occured and was stirred in cold solution for several minutes.
The solid nitroso compound was filtered off, washed with cold water, and dried. Yieꢀld1:
3.80 g, 64%. Mp 130–135 ꢁC. IR (KBr): 2925, 2853, 2570–3200, 1719, 1554, 1325 cm
.
1H NMR (400 MHz, DMSO-d6): d 4.12 (s, 2H, CH2), 4.84 (s, 2H, N-CH2), 7.25–7.54
(m, 8H, Ar-H), 11.36 (s, 2H, COOH). 13C NMR (40 MHz, DMSO-d6): d 40.61, 48.94,
122.88, 129.54, 137.20, 138.63, 167.61. Anal. calcd. (%) for C17H16N4O6: C, 54.84; H,
4.33; O, 25.78; N, 15.05. Found: C, 54.81; H, 4.37; O, 25.81; N, 14.98.
3,30-(4,40-Diphenyl)bissydnonyl Methane (5). The dried compound 4
(4.00 g, 0.0107 mol) was stirred for 12 h in 40 mL acetic anhydride. The solution
was poured slowly into cold water, which was very well stirred. The pH of the

BISSYDNONES BASED ON 4,40-DIAMINODIPHENYL METHANE
1903
content was adjusted to 7.0 with 10% sodium bicarbonate solution. The solid crude
product was washed well with water and dried. The crude sydnone was recrystallized
from benzene–petroleum ether. The product obtained was an orange solid. Yield:
.
2.52 g, 70%. Mp 120–123 ꢁC. IR (KBr): 3157, 2925, 2853 1745 cmꢀ1 1H NMR
(400 MHz, DMSO-d6): d 4.26 (s, 2H, CH2), 7.76 (s, 2H, sydnone), 7.14–8.13 (m,
8H, Ar-H). 13C NMR (40 MHz, DMSO-d6): d 39.43, 121.89, 128.26, 129.20,
139.36, 141.15, 168.20. Anal. calcd. (%) for C17H12N4O4: C, 60.71; H, 3.60; O,
19.03; N, 16.66. Found: C, 60.68; H, 3.65; O, 19.98; N, 16.63.
3,30-(Methylenedi-1,4-phenylene)bis(4-chlorosulfonyl) Sydnone
(6). Chlorosulfonic acid (2.32 mL, 0.02 mol) was added dropwise into the mixture of
compound 5 (3.36 g, 0.01 mol) and a catalytic amount of P O over 30 min with con-
2
5
stant stirring at 0–5 ꢁC. The temperature of the well-stirred mixture did not rise above
5 ꢁC. When all the chlorosulphonic acid was added, the mixture was refluxed at about
60 ꢁC for about 1 h. The solution was then poured into a mixture of crushed ice and
water with vigorous stirring. Precipitation was collected by filtration, washed three
times with water, and dried. Yield: 3.94 g, 74%. Mp 239–241 ꢁC. IR (KBr): 2928,
1745, 1395, 1180 cmꢀ1 1H NMR (400 MHz, DMSO-d6): d 4.25 (s, 2H, CH2),
.
7.29–8.12 (m, 8H, Ar-H). 13C NMR (40 MHz, DMSO-d6): d 39.65, 121.76, 122.97,
128.58, 138.86, 140.85, 169.64. Anal. calcd. (%) for C17H12Cl2N4O8S2: C, 38.14; H,
2.26; O, 23.91; N, 10.47; S, 11.98. Found: C, 38.12; H, 2.31; O, 23.95; N, 10.43; S, 12.03.
General Procedure for the Synthesis of 3,30-(Methylenedi-1,4-
phenylene)bis(4-primary substituted amino sulfonyl) Sydnone (7a–j)
3,30-(Methylenedi-1,4-phenylene)bis(4-chlorosulfonyl)sydnone 6 (5.88 g, 0.011
mol) was dissolved in acetone at room temperature. A solution of appropriate primary
amine (0.022 mol) in acetone was added dropwise into compound 6 solution over a
period of 5 h with constant stirring; 1.0 mL of pyridine was added to the well-stirred
solution after 1 and 2 h during the reaction. The solution was poured onto ice with
stirring. The precipitate was collected by filtration, washed with water, and dried.
Recrystallization of the crude product was performed from benzene.
3,30-(Methylenedi-1,4-phenylene)bis(4-{[(4-chlorophenyl)amino]sulfo-
nyl} Sydnone (7a). Yield: 4.33 g, 55%. Mp 130–132 ꢁC; IR (KBr): 2927, 1739, 1365,
1159, 1076 cmꢀ1. 1H NMR (400 MHz, DMSO-d6): d 4.28 (s, 2H, CH2), 7.20–8.30 (m,
16H, Ar-H), 8.86 (s, 2H, SO2NH); 13C NMR (40 MHz, DMSO-d6): d 39.86, 121.03,
122.60, 129.52, 129.56, 130.92, 131.15, 135.50, 137.30, 141.12, 167.30. Anal. calcd.
(%) for C29H20Cl2N6O8S2: C, 48.68; H, 2.82; O, 17.89; N, 11.74; S, 8.96. Found:
C, 48.65; H, 2.76; O, 17.93; N, 11.78; S, 8.99.
3,30-(Methylenedi-1,4-phenylene)bis{4-[(methylamino)sulfonyl] Sydnone
(7b). Yield: 3.05 g, 53%. Mp 145–148 ꢁC; IR (KBr): 2965, 2923, 2868, 1736, 1367,
1157 cmꢀ1 1H NMR (400 MHz, DMSO-d6): d 3.10 (s, 6H, CH3), 4.29 (s, 2H,
.
CH2), 4.61 (s, 2H, SO2NH), 7.3–8.4 (m, 8H, Ar-H); 13C NMR (40 MHz, DMSO-d6):
d 31.50, 39.89, 122.12, 129.45, 129.90, 137.56, 141.62, 169.30. Anal. calcd. (%) for
C19H18N6O8S2: C, 43.67; H, 3.47; O, 24.50; N, 16.08; S, 12.27. Found: C, 43.63;
H, 3.43; O, 24.43; N, 15.98; S, 12.33.

1904
S. T. ASUNDARIA AND K. C. PATEL
3,30-(Methylenedi-1,4-phenylene)bis[4-(anilinosulfonyl)] Sydnoꢀn1e
(7c). Yield 4.84 g, 65%. Mp 154–156 ꢁC; IR (KBr): 2927, 1743, 1362, 1164 cm
.
1H NMR (400 MHz, DMSO-d6): d 4.25 (s, 2H, CH2), 6.94–8.33 (m, 18H, Ar-H),
8.94 (s, 2H, SO2NH); 13C NMR (40 MHz, DMSO-d6): d 39.46, 121.50, 122.8,
125.20, 129.15, 129.54, 130.6, 136.45, 137.28, 140.56, 168.57. Anal. calcd. (%) for
C29H22N6O8S2: C, 53.86; H, 3.43; O, 19.79; N, 13.00; S, 9.92. Found: C, 53.83; H,
3.50; O, 19.76; N, 13.04; S, 9.85.
3,30-(Methylenedi-1,4-phenylene)bis(4-{[(3-chlorophenyl)amino]sulfo-
nyl} Sydnone (7d). Yield 4.57 g, 58%. Mp 129–131 ꢁC; IR (KBr): 2932, 1735, 1365,
1157, 1096 cmꢀ1. 1H NMR (400 MHz, DMSO-d6): d 4.24 (s, 2H, CH2), 7.15–8.42 (m,
16H, Ar-H), 8.88 (s, 2H, SO2NH); 13C NMR (40 MHz, DMSO-d6): d 39.24, 119.10,
121.08, 121.89, 125.05, 129.34, 130.01, 131.13, 135.75, 138.32, 139.15, 141.6, 168.33.
Anal. calcd. (%) for C29H20Cl2N6O8S2: C, 48.68; H, 2.82; O, 17.89; N, 11.74; S, 8.96.
Found: C, 48.65; H, 2.85; O, 17.93; N, 11.78; S, 8.94.
3,30-(Methylenedi-1,4-phenylene)bis(4-{[(2-fluorophenyl)amino]sulfonyl}
Sydnone (7e). Yield: 4.21 g, 56%. Mp 134–136 ꢁC; IR (KBr): 2933, 1737, 1366,
1
1233, 1159 cmꢀ1. H NMR (400 MHz, DMSO-d6): d 4.29 (s, 2H, CH2), 6.80–8.90
(m, 16H, Ar-H), 8.90 (s, 2H, SO2NH); 13C NMR (40 MHz, DMSO-d6): d 39.18,
116.19, 120.89, 122.93, 124.65, 126.65, 127.08, 129.21, 129.84, 139.15, 141.75,
159.76, 168.33. Anal. calcd. (%) for C29H20F2N6O8S2: C, 51.02; H, 2.95; O, 18.75;
N, 12.31; S, 9.39. Found: C, 51.08; H, 2.93; O, 18.74; N, 12.36; S, 9.42.
3,30-(Methylenedi-1,4-phenylene)bis{4-[(butylamino)sulfonyl] Sydnone
(7f). Yield: 4.21 g, 63%. Mp 137–139 ꢁC; IR (KBr): 2967, 2929, 2869, 2855, 1734,
1
1363, 1161 cmꢀ1. H NMR (400 MHz, DMSO-d6): d 0.92 (t, 6H, CH3), 1.72 (m,
4H, CH2), 2.90 (t, 4H, NHCH2), 4.24 (s, 2H, CH2), 4.75 (s, 2H, SO2NH),
7.23–8.30 (m, 8H, Ar-H); 13C NMR (40 MHz, DMSO-d6): d 13.42, 21.05, 29.50,
39.31, 42.41, 121.82, 129.11, 129.54, 139.21, 141.12, 168.64. Anal. calcd. (%) for
C25H30N6O8S2: C, 49.49; H, 4.98; O, 21.10; N, 13.85; S, 10.57. Found: C, 49.53;
H, 4.94; O, 21.16; N, 13.83; S, 10.51.
3,30-(Methylenedi-1,4-phenylene)bis(4-{[(3-methylphenyl)amino]sulfonyl}
Sydnone (7g). Yield: 4.53 g, 61%. Mp 149–151 ꢁC; IR (KBr): 2950, 2939, 2879,
1
1739, 1366, 1165 cmꢀ1. H NMR (400 MHz, DMSO-d6): d 2.25 (s, 6H, CH3), 4.27
(s, 2H, CH2), 6.9–8.31 (m, 16H, Ar-H), 8.96 (s, 2H, SO2NH); 13C NMR (40 MHz,
DMSO-d6): d 21.75, 39.32, 118.32, 121.45, 121.97, 126.28, 128.76, 129.74, 129.76,
136.59, 139.78, 140.27, 141.54, 168.83. Anal. calcd. (%) for C31H26O8N6S2: C,
55.18; H, 3.88; O, 18.97; N, 12.46; S, 9.50. Found: C, 55.15; H, 3.93; O, 18.93; N,
12.53; S, 9.55.
3,30-(Methylenedi-1,4-phenylene)bis{4-[(benzylamino)sulfonyl]} Sydnone
(7h). Yield: 4.38 g, 59%. Mp 180–182 ꢁC; IR (KBr): 2939, 1742, 1365, 1162 cmꢀ1. 1H
NMR (400 MHz, DMSO-d6): d 4.26 (s, 2H, CH2), 4.37 (s, 4H, CH2), 5.25 (s, 2H,
SO2NH), 7.27–8.25 (m, 18H, Ar-H); 13C NMR (40 MHz, DMSO-d6): d 39.74,
45.25, 121.50, 127.53, 128.96, 129.35, 129.50, 129.91, 138.74, 141.63, 142.23,
168.95. Anal. calcd. (%) for C31H26N6O8S2: C, 55.18; H, 3.88; O, 18.97; N,12.46;
S, 9.50. Found: C, 55.09; H, 3.84; O, 18.92; N, 12.55; S, 9.56.

BISSYDNONES BASED ON 4,40-DIAMINODIPHENYL METHANE
1905
3,30-(Methylenedi-1,4-phenylene)bis(4-{[(2-methylphenyl)amino]sulfo-
nyl} Sydnone (7i). Yield: 4.01 g, 54%. Mp 169–171 ꢁC. IR (KBr): 2950, 2935, 2883,
1739, 1366, 1165 cmꢀ1. 1H NMR (400 MHz, DMSO-d6): d 2.26 (s, 6H, CH3), 4.30 (s,
2H, CH2), 7.26–8.33 (m, 16H, Ar-H), 8.86 (s, 2H, SO2NH); 13C NMR (40 MHz,
DMSO-d6): d 18.09, 39.43, 121.74, 123.96, 125.87, 127.81, 129.42, 129.45, 131.20,
132.04, 134.97, 138.26, 141.88, 168.84. Anal. calcd. (%) for C31H26O8N6S2: C,
55.18; H, 3.88; O, 18.97; N, 12.46; S, 9.50. Found: C, 55.15; H, 3.83; O, 18.91; N,
12.52; S, 9.42.
3,30-(Methylenedi-1,4-phenylene)bis(4-{[(4-nitrophenyl)amino]sulfonyl}
Sydnone (7j). Yield 4.38 g, 54%. Mp 174–177 ꢁC; IR (KBr): 2936, 1527, 1734, 1367,
1351, 1162 cmꢀ1. 1H NMR (400 MHz, DMSO-d6): d 4.23 (s, 2H, CH2), 7.33–8.36 (m,
16H, Ar-H), 8.96 (s, 2H, SO2NH); 13C NMR (40 MHz, DMSO-d6): d 39.38, 119.24,
122.13, 126.85, 129.24, 129.95, 138.54, 141.68, 143.03, 145.21, 168.53. Anal. calcd.
(%) for C29H20N8O12S2: C, 47.28; H, 2.74; O, 26.06; N, 15.21; S, 8.71. Found: C,
47.23; H, 2.78; O, 26.11; N, 15.24; S, 8.78.
CONCLUSION
The new sulfonamide derivatives of sydnone were synthesized and evaluated
for their antibacterial activity. The activity varies with the different substituents
on sulfonamide linkage. The potential of the compounds increases and minimum
inhibitory concentration decreases.
ACKNOWLEDGMENT
The authors are thankful to Atul Limited, Valsad, for providing some useful
chemicals.
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