Month 2019
Synthesis, Antimicrobial and Antioxidant Activities of Some New Sulfonamide
Derivatives Containing Tetrazole and Oxadiazole Rings
NMR (75 MHz, CDCl ) 180.0, 170.1, 168.7, 137.2, 135.0,
2H, Ar–H, J = 8.2 Hz), 4.92 (s, 2H, CH ), 4.38 (s, 2H,
3
2
1
22.8, 111.4, 103.9, 53.9, 41.8, 39.6, 22.2; Anal. Calcd for
NH ), 3.91 (s, 1H, NH), 3.37 (s, 2H, CH ), 1.58 (s, 6H,
2
2
13
C H IN O S : C, 31.92; H, 3.04; N, 19.85. Found: C,
CH3); C-APT-NMR (75 MHz, CDCl ) 179.5, 170.0,
1
5
17
8
4
2
3
3
1.80; H, 3.00; N, 19.81%.
169.4, 144.8, 143.1, 136.8, 131.7, 129.8, 129.6, 128.4,
N-(1-((5-Mercapto-1,3,4-oxadiazol-2-yl)methyl)-1H-tetrazol-
1
27.2, 112.1, 47.2, 41.3, 40.0, 21.3; Anal. Calcd for
5
-yl)-2,2-dimethyl-3-((4-methylphenyl)sulfonamido)
C H N O S: C, 52.38; H, 4.81; N, 26.18. Found: C,
21 23 9 3
propanamide (7f). Yield 66%; mp: 155–156°C; IR (ATR,
νmax/cm ): 3350 (NH), 3040 (Ar. CH), 2980 (Al. CH),
2
5
2.32; H, 4.84; N, 26.12%.
ꢀ
1
1
3,3′-((Oxybis(4,1-phenylene))bis
(azanediyl)bis(N-(1-((5-
240 (SH), 1740 (C═O), 1390–1350 (S═O), H-NMR
mercapto-1,3,4-oxadiazol-2-yl)methyl)-1H-tetrazol-5-yl)-2,2-
(300 MHz, CDCl ) δ: 8.82 (br, 1H, SH), 8.35 (s, 1H,
3
dimethylpropanamide) (9b). Yield 72%; mp: 275–276°C;
NH), 8.02 (s, 1H, NH), 7.31 (dd, 2H, Ar–H, J = 8.8 Hz),
.90 (dd, 2H, Ar–H, J = 8.8 Hz), 5.18 (s, 2H, CH ), 3.47
ꢀ1
IR (ATR, νmax/cm ): 3450 (NH), 3350 (CONH ), 3040
2
6
2
(
1
Ar. CH), 2850 (Al. CH), 2240 (SH), 1750 (C═O),
13
(s, 2H, CH ), 2.56 (s, 3H, CH ), 1.78 (s, 6H, CH ); C-
1
2
3
3
275–1200 (C–O), H-NMR (300 MHz, CDCl ) δ: 8.81
3
APT-NMR (75 MHz, CDCl ) 180.1, 170.0, 169.2, 138.2,
3
(
br, 1H, SH), 8.60 (s, 1H, NH), 7.49 (dd, 2H, Ar–H, J =
.5 Hz), 7,31 (dd, 2H, Ar–H, J = 8,5 Hz), 5.40 (s, 1H,
NH), 4.98 (s, 2H, CH ), 3.37 (s, 2H, CH ), 1.75 (s, 6H,
132.5, 130.0, 128.1, 109.7, 55.5, 41.4, 39.2, 28.8, 21.5;
8
Anal. Calcd for C H N O S : C, 42.47; H, 4.45; N,
2
1
6 20 8 4 2
2
2
4.76. Found: C, 42.42; H, 4.39; N, 24.80%.
13
CH3); C-APT-NMR (75 MHz, CDCl ) 180.2, 170.1,
3
N-(1-((5-Mercapto-1,3,4-oxadiazol-2-yl)methyl)-1H-tetrazol-
1
3
4
69.3, 147.8, 136.2, 133.3, 130.0, 112.6, 51.2, 42.1,
5-yl)-3-((4-methoxyphenyl)sulfonamido)-2,2-
8.9, 22.4; Anal. Calcd for C H N O S : C, 47.24; H,
30 34 16 5 2
dimethylpropanamide (7g). Yield 54%; mp: 188–189°C;
.49; N, 29.38. Found: C, 47.14; H, 4.40; N, 29.30%.
ꢀ
1
IR (ATR, νmax/cm ): 3345 (NH), 3040 (Ar. CH), 2980
Al. CH), 2240 (SH), 1740 (C═O), 1390–1350 (S═O),
Antimicrobial activity. The antibacterial and antifungal
(
1
activities of the prepared compounds were targets against
both types of Gram-positive (B. subtilis, S. aureus) and
Gram-negative bacteria (E. coli and K. pneumoniae) and
fungal strains (S. cerevisiae and C. albicans).
Ciprofloxacin (50 μg; antibacterial) and ketoconazole (50
μg; antifungal) were used as the standard antibacterial
and antifungal agents for comparison. Antimicrobial tests
were performed by the agar well diffusion method [28].
1
8
7
250–1200 (C–O–C), H-NMR (300 MHz, CDCl ) δ:
3
.67 (br, 1H, SH), 8.21 (s, 1H, NH), 8.05 (s, 1H, NH),
.69 (dd, 2H, Ar–H, J = 8.3 Hz), 7,33 (dd, 2H, Ar–H, J
=
8.8 Hz), 5.17 (s, 2H, CH ), 3.62 (s, 3H, OCH ), 3.49
2 3
1
3
(s, 2H, CH ), 1.79 (s, 6H, CH ); C-APT-NMR (75
2 3
MHz, CDCl ) 179.8, 170.0, 168.3, 150.3, 132.8, 131.9,
1
C H N O S : C, 41.02; H, 4.30; N, 23.92. Found: C,
4
3
29.6, 112.1, 59.8, 54.7, 43.3, 39.8, 21.2; Anal. Calcd for
1
6 20 8 5 2
6
In this method, 100 μL of suspension containing 1 × 10
0.97; H, 4.25; N, 23.89%.
6
CFU/mL of pathological target bacteria, 1 × 10 /mL of
N-(1-((5-Mercapto-1,3,4-oxadiazol-2-yl)methyl)-1H-
yeast spread on nutrient agar, and Sabouraud dextrose
agar were used. After the media were cooled, the wells
(10 mm in diameter) were filled by the agar and then
loaded with 100 μL of the solution of test compound;
tetrazol-5-yl)-2,2-dimethyl-3-((4-sulfamoylphenyl)amino)
propanamide (8). Yield 64%; mp: 148–149°C; IR (ATR,
ꢀ
1
νmax/cm ): 3350 (NH), 3035 (Ar. CH), 2850 (Al. CH),
240 (SH), 1740 (C═O), 1370–1335 (S═O), 1250–1200
2
1
1
00 mg of each test compound was dissolved to 1 mL of
(C–O–C), H-NMR (300 MHz, CDCl ) δ: 8.80 (br, 1H,
3
SH), 8.32 (s, 1H, NH), 8.05 (s, 1H, NH), 7.13 (dd, 2H,
Ar–H, J = 8.1 Hz), 6.71 (dd, 2H, Ar–H, J = 8.1 Hz),
dimethyl sulfoxide (DMSO). The inoculated plates were
incubated for 24 h at 37°C for bacteria and 48 h at 28°C
for fungi. After incubation period, the plates were read to
obtain the zone diameters of target compounds,
ciprofloxacin and ketoconazole as standards. Negative
control was performed using DMSO to determine the
solvent effect. Finally, antimicrobial activities were
evaluated by measuring the zones (in mm) of inhibition
against the test organisms and compared with those of the
standard. The experiments were repeated three times, and
the average zone of inhibition was calculated.
5
.03 (s, 2H, CH ), 4.34 (birli, 1H, NH), 3.38 (s, 2H,
2
1
3
CH ), 2.33 (s, 2H, NH ), 1.71 (s, 6H, CH ); C-APT-
2
2
3
NMR (75 MHz, CDCl ) 178.9, 170.2, 169.1, 146.4,
3
132.3, 129.5, 120.2, 110.1, 59.6, 62.4, 39.6, 19.9; Anal.
Calcd for C H N O S : C, 39.73; H, 4.22; N, 27.80.
15 19 9 4 2
Found: C, 39.65; H, 4.20; N, 30.78%.
3
-((4-(4-Aminophenoxy)phenyl)amino)-N-(1-((5-mercapto-
,3,4-oxadiazol-2-yl)methyl)-1H-tetrazol-5-yl)-2,2-
dimethylpropanamide (9a). Yield 11%; mp: 230–232°C;
1
ꢀ
1
IR (ATR, νmax/cm ): 3350 (NH), 3300 (SO NH ), 3050
Minimum inhibitory concentration measurement.
The
2
2
(
1
Ar. CH), 2850 (Al. CH), 2240 (SH), 1740 (C═O),
390–1350 (S═O), 1275–1200 (C–O), H-NMR (300
microdilution susceptibility tests were performed by
Müeller-Hinton broth (Oxoid) for the antibacterial
activity and Sabouraud liquid medium (Oxoid) for
antifungal activity. Stock solutions of the target
1
MHz, CDCl ) δ: 8.49 (br, 1H, SH), 8.22 (s, 1H, NH),
7
3
.84 (dd, 2H, Ar–H, J = 8.4 Hz), 7.40 (dd, 2H, Ar–H, J
=
8.2 Hz), 7.33 (dd, 2H, Ar–H, J = 8.4 Hz), 7.21 (dd,
compounds, ciprofloxacin, and ketoconazole at
a
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet