M. Shaldam, W.M. Eldehna, A. Nocentini et al.
European Journal of Medicinal Chemistry 216 (2021) 113283
AreH, J ¼ 8 Hz), 7.74 (d, 2H, AreH, J ¼ 8 Hz), 8.88 (s, 1H, NH, D
2
O
1H, AreH, J ¼ 7.6 Hz), 7.56 (t, 2H, AreH, J ¼ 7.6, 8.4 Hz), 7.69 (s, 2H,
exchangeable), 9.35 (s, 1H, NH, D
2
O exchangeable), 12.6 (s, 1H, NH,
NH
2
, D
2
O exchangeable of eSO
2
NH
2
), 7.84 (d, 1H, AreH, J ¼ 8 Hz),
D
2
O exchangeable of eSO
2
NH); Anal. Calcd. for C19
H
16
N
4
O
4
S
2
: C,
8.16 (d, 1H, AreH, J ¼ 8.4 Hz), 8.86 (s, 1H, NH, D
2
O exchangeable),
O exchangeable); C NMR (DMSO‑d ppm:
.07, 105.86, 111.04, 119.58, 122.73, 122.92, 122.95, 124.28, 128.05,
130.14, 131.69, 133.14, 136.45, 144.34, 151.25, 152.71. Anal. Calcd. for
12BrN S: C, 43.92; H, 2.95; N, 10.24; found C, 44.17; H, 2.93;
N, 10.17.
13
5
3.26; H, 3.76; N, 13.08; found C, 53.11; H, 3.8; N, 12.99.
8.82 (s, 1H, NH, D
2
6
) d
8
4
.1.2.7. 1-(4-[(3,4-Dimethyl-1,2-oxazol-5-yl)sulfamoyl]phenyl)-3-(3-
methyl-1-benzofuran-2-yl)urea (13c). Compound 9a was obtained
following the general procedure mentioned-above using 4-amino-
N-(3,4-dimethylisoxazol-5-yl)benzenesulfonamide 12c (0.133 g,
C
15
H
3 4
O
ꢀ
ꢁ1
0
3
.50 mmol). 75% yield; m. p. 169e171 C; IR (KBr,
290 (NH, NH ), 1681 (C]O) and 1341, 1162 (SO
ppm: 1.05 (d, 3H, CH ), 1.66 (s, 3H, CH ), 2.11 (d, 3H,
), 7.27 (m, 2H, AreH), 7.47 (d, 1H, AreH, J ¼ 7.6 Hz), 7.55 (d, 1H,
n
cm ): 3342,
4.1.2.12. 3-(5-Bromo-1-benzofuran-2-yl)-1-(5-chloro-2,4-
disulfamoylphenyl)urea (27b). Compound 9a was obtained
following the general procedure mentioned-above using 4-amino-
6-chlorobenzene-1,3-disulfonamide 8b (0.14 g, 0.50 mmol). 75%
); 1H NMR
2
2
(
DMSO‑d
6
)
d
3
3
CH
3
ꢀ
ꢁ1
1
AreH, J ¼ 7.6 Hz), 7.69 (d, 4H, AreH, J ¼ 8 Hz), 8.59 (s, 1H, NH, D
exchangeable), 9.49 (s, 1H, NH, D O exchangeable), 10.9 (s, 1H, NH,
O exchangeable of eSO NH); Anal. Calcd. for C21 S: C,
7.26; H, 4.58; N, 12.72; found C, 57.53; H, 4.55; N, 12.78.
2
O
yield; m. p. 221e223 C; IR (KBr,
n
cm ): 3407, 3314, 3195 (NH,
2
NH ), 1702 (C]O) and 1327, 1136 (SO
2
2
); H NMR (DMSO‑d
6
)
d
ppm:
D
5
2
2
H
20
N
4
O
5
6.56 (s, 1H, AreH), 6.62 (s, 2H, AreH), 6.99 (s, 1H, AreH), 7.30 (d, H,
AreH, J ¼ 8.0 Hz), 7.36 (s, 2H, NH , D O exchangeable of eSO NH ),
.45 (d, 1H, AreH, J ¼ 8.0 Hz), 7.52 (s, 2H, NH , D O exchangeable of
eSO NH ), 7.72 (s, 1H, NH, D O exchangeable), 8.17 (s, 1H, NH, D
exchangeable); Anal. Calcd. for C15 12BrClN : C, 34.4; H, 2.31;
N, 10.7; found C, 34.51; H, 2.33; N, 10.64.
2
2
2
2
7
2
2
4.1.2.8. 4-Sulfamoylphenyl
N-(3-methyl-1-benzofuran-2-yl)carba-
2
2
2
2
O
mate (15). Compound 9a was obtained following the general pro-
cedure mentioned-above using 4-hydroxybenzenesulfonamide 14
H
4 6 2
O S
ꢀ
ꢁ1
(
3
(
(
0.086 g, 0.50 mmol). 60% yield; m. p. 259e260 C; IR (KBr, n cm ):
1
250, 3167 (NH, NH
DMSO‑d ppm: 2.13 (s, 3H, CH
s, 2H, NH , D O exchangeable of eSO
2
), 1668 (C]O) and 1346, 1188 (SO
), 6.90 (d, 2H, AreH, J ¼ 8 Hz), 7.12
NH ), 7.21e7.34 (m, 2H,
2
); H NMR
4.1.2.13. 3-(5-Bromo-1-benzofuran-2-yl)-1-(3-sulfamoylphenyl)urea
(28a). Compound 9a was obtained following the general procedure
mentioned-above using 3-aminobenzenesulfonamide 10a (0.086 g,
6
)
d
3
2
2
2
2
ꢀ
ꢁ1
AreH), 7.47 (d, 1H, AreH, J ¼ 8 Hz), 7.54 (d, 1H, AreH, J ¼ 7.2 Hz),
.67 (d, 2H, AreH, J ¼ 8 Hz), 9.23 (s (b), 1H, NH, D O exchangeable);
ppm: 8.08, 106.62, 111.05, 115.33, 115.65,
19.61, 122.82, 124.32, 128.30, 128.58, 128.68, 130.12, 135.00, 144.56,
51.29, 153.68, 160.79; Anal. Calcd. for C16 S: C, 55.48; H,
0.50 mmol). 69% yield; m. p. 181e183 C; IR (KBr,
3271 (NH, NH ), 1704 (C]O) and 1339, 1157 (SO
(DMSO‑d
ppm: 6.52 (s, 1H, AreH), 7.28 (d, 1H, AreH, J ¼ 8 Hz),
7.36e7.46 (m, 4H, AreH, NH , D O exchangeable of eSO NH ), 7.51
(d, 1H, AreH, J ¼ 6 Hz), 7.62 (d, 1H, AreH, J ¼ 6 Hz), 7.69 (s, 1H,
AreH), 8.13 (d, 1H, AreH, J ¼ 8 Hz), 9.22 (s, 1H, NH, D
n
cm ): 3358,
7
2
2
2
); 1H NMR
1
3
C NMR (DMSO‑d
6
)
d
6
) d
1
2
2
2
2
1
14 2 5
H N O
4
.07; N, 8.09; found C, 55.63; H, 4.05; N, 8.02.
2
O
13
exchangeable), 10.02 (s, 1H, NH, D
(DMSO‑d ppm: 87.04, 112.42, 115.77, 115.97, 120.10, 122.02,
122.33, 124.78, 130.03, 132.49,139.82,145.18,148.48, 150.84, 151.63;
Anal. Calcd. for C15 12BrN S: C, 43.92; H, 2.95; N, 10.24; found C,
44.21; H, 2.96; N, 10.31.
2
O exchangeable); C NMR
4
.1.2.9. 3-(3-Methyl-1-benzofuran-2-yl)-1-[2-(4-sulfamoylphenyl)
6
) d
ethyl]urea (17). Compound 9a was obtained following the general
procedure mentioned-above using 4-(2-aminoethyl)benzene-
H
3 4
O
ꢀ
sulfonamide 16 (0.1 g, 0.50 mmol). 68% yield; m. p. 238e239 C; IR
ꢁ
1
(
1
KBr,
153 (SO
n
cm ): 3421, 3356, 3280 (NH, NH
2
), 1691 (C]O) and 1334,
ppm: 2.05 (s, 3H, CH ), 2.85 (t, 2H,
-, J ¼ 8 Hz), 3.35 (t, 2H, eCH CH -, J ¼ 8 Hz), 6.48 (t, 1H,
, D O exchangeable
), 7.43 (d, 3H, AreH, J ¼ 8 Hz, NH, D O exchangeable),
.50 (d, 1H, AreH, J ¼ 6.8 Hz), 7.78 (d, 2H, AreH, J ¼ 8 Hz), 8.55 (s,
1
2
); H NMR (DMSO‑d
6
)
d
3
4.1.2.14. 3-(5-Bromo-1-benzofuran-2-yl)-1-(4-methyl-3-
sulfamoylphenyl)urea (28b). Compound 9a was obtained following
the general procedure mentioned-above using 5-amino-2-
methylbenzenesulfonamide 10b (0.093 g, 0.50 mmol). 71% yield;
eCH
2
CH
2
2
2
AreH, J ¼ 5.4 Hz) 7.19e7.29 (m, 4H, AreH, NH
2
2
of eSO NH
2
2
2
ꢀ
ꢁ1
7
m. p.196e198 C; IR (KBr,
(C]O) and 1331, 1142 (SO
CH
O exchangeable of eSO
(d, 1H, AreH, J ¼ 8.4 Hz), 7.68 (s, 1H, AreH), 8.08 (s, 1H, AreH), 9.12
(s, 1H, NH, D O exchangeable), 9.93 (s, 1H, NH, D O exchangeable);
C NMR (DMSO‑d ppm: 19.60, 86.86, 112.38, 115.95, 117.90,
122.04, 122.26, 124.70, 128.67, 129.97, 133.12, 137.30, 142.80, 148.44,
150.83, 151.74; Anal. Calcd. for C16 14BrN S: C, 45.3; H, 3.33; N,
9.9; found C, 45.18; H, 3.32; N, 9.85.
n
cm ): 3415, 3274, 3210 (NH, NH
2
),1695
1
1
H, NH, D
2
O exchangeable); Anal. Calcd. for C18
19
H N
3
O
4
S: C, 57.9; H,
2
); H NMR (DMSO‑d
), 6.50 (s, 1H, AreH), 7.21e7.34 (m, 2H, AreH), 7.40 (s, 2H, NH
6
)
d
ppm: 2.54 (s, 3H,
5
.13; N, 11.25; found C, 58.09; H, 5.07; N, 11.28.
3
2
,
D
2
2
NH
2
), 7.42 (d, 1H, AreH, J ¼ 8.4 Hz), 7.58
4
.1.2.10. N-([(3-methyl-1-benzofuran-2-yl)carbamoyl]amino)-4-
sulfamoylbenzamide (19). Compound 9a was obtained following
the general procedure mentioned-above using 4-(hydrazine-
carbonyl)benzenesulfonamide 18 (0.11 g, 0.50 mmol). 76% yield; m.
2
2
13
6
) d
ꢀ
ꢁ1
1
p. 252e253 C; IR (KBr,
(
n
cm ): 3420, 3352, 3254 (NH, NH
2
), 1692
H
3 4
O
C]O) and 1327, 1151 (SO
2
); H NMR (DMSO‑d
6
)
d
ppm: 2.11 (d, 3H,
CH
3
, J ¼ 14 Hz), 7.19e7.33 (m, 3H, AreH), 7.46 (t, 1H, AreH,
, D O exchangeable of eSO NH ), 7.55
d, 1H, AreH, J ¼ 8.4 Hz), 7.94 (d, 2H, AreH, J ¼ 8 Hz), 8.09 (d, 1H,
AreH, J ¼ 8.4 Hz), 8.67 (s, 1H, NH, D O exchangeable), 9.09 (d, 1H,
NH, D
O exchangeable, J ¼ 14 Hz), 10.56 (s, 1H, NH, D
exchangeable); . Anal. Calcd. for C17 S: C, 52.57; H, 4.15; N,
J ¼ 8.4 Hz), 7.53 (s, 2H, NH
2
2
2
2
4.1.2.15. 3-(5-Bromo-1-benzofuran-2-yl)-1-(4-sulfamoylphenyl)urea
(29a). Compound 9a was obtained following the general procedure
mentioned-above using 4-aminobenzenesulfonamide 12a (0.086 g,
(
2
ꢀ
2
2
O
0.50 mmol). 74% yield; m. p. 230e231 C; IR (KBr,
n
cm-1): 3327,
1
H
16
N
4
O
5
3238 (NH, NH
(DMSO‑d , 400 MHz)
exchangeable of eSO
AreH, J ¼ 8 Hz), 7.67 (t, 3H, AreH, J ¼ 8 Hz), 7.78 (d, 2H, AreH,
J ¼ 8 Hz), 9.25 (s, 1H, NH, D O exchangeable), 10.02 (s, 1H, NH,
O exchangeable); C NMR (DMSO‑d ppm: 87.16, 112.43,
115.98, 118.45, 118.45, 122.37, 124.85, 127.34, 127.34, 132.44, 138.09,
142.44, 148.48, 150.70, 151.47; Anal. Calcd. for C15 12BrN S: C,
43.92; H, 2.95; N, 10.24; found C, 44.09; H, 2.93; N, 10.29.
2
), 1696 (C]O) and 1330, 1150 (SO
ppm: 6.53 (s, 1H, AreH) 7.27 (s, 2H, NH
NH
) 7.28 (d, 1H, AreH, J ¼ 8 Hz), 7.43 (d, 1H,
2
); H NMR
14.43; found C, 52.69; H, 4.19; N, 14.35.
6
d
2 2
, D O
2
2
4
.1.2.11. 3-(5-Bromo-1-benzofuran-2-yl)-1-(2-sulfamoylphenyl)urea
(
27a). Compound 9a was obtained following the general procedure
2
13
mentioned-above using 2-aminobenzenesulfonamide 8a (0.086 g,
D
2
6
) d
ꢀ
ꢁ1
0
3
.5 mmol). 77% yield; m. p. 189e191 C; IR (KBr,
259, 3180 (NH, NH
ppm: 2.15 (s, 3H, CH
n
cm ): 3467,
1
2
), 1691 (C]O) and 1333, 1156 (SO
2
); H NMR
H
3 4
O
(
DMSO‑d
6
)
d
3
), 7.18e7.31 (m, 3H, AreH), 7.47 (d,
10