Molecules 2020, 25, 3570
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3.3.3. 4-(2-(4-methoxyphenyl)-4-oxothiazolidin-3-yl)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (7c
)
Compound 7c was obtained from the cyclocondensation reaction between
4, 5c, and 6 for 12 h.
White solid; m.p.: 242–234 ◦C; Yield: 84%; 1H NMR (400 MHz, DMSO-d6,
δ
ppm): 9.42 (s, 1H, NH),
8.02–8.01 (m, 2H, Ar-H), 7.25–7.24 (m, 2H, Ar-H), 7.21–7.20 (m, 2H, Ar-H), 6.85–6.84 (m, 2H, Ar-H),
6.56 (s, 1H, S-CH-N), 5.80 (s, 1H, -C=CH), 3.79 (s, 1H, -OCH3), 3.72 (d, 1H, CH2, J = 12 Hz), 3.69 (d, 1H,
CH2, J = 12 Hz) and 2.35 (s, 3H, -CH3); 13C NMR (100 MHz, DMSO-d6,
δ ppm): 178.60, 168.20, 157.10,
143.22, 139.70, 132.71, 130.85, 129.58, 129.37, 127.39, 125.19, 102.19, 66.07, 52.53, 32.06 and 13.08; HRMS
(ESI-qTOF): Calcd. for C20H20N3O5S2 [M + H]+, 446.0521: found: 446.0546.
3.3.4. 4-(2-(4-fluorophenyl)-4-oxothiazolidin-3-yl)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (7d
Compound 7d was obtained from the cyclocondensation reaction between 5d, and for 12 h.
Yellow solid; m.p.: 216–218 ◦C; Yield: 80%; 1H NMR (400 MHz, DMSO-d6,
ppm): 9.54 (s, 1H, NH),
)
4,
6
δ
8.02–8.01 (m, 2H, Ar-H), 7.33–7.32 (m, 2H, Ar-H), 7.27–7.25 (m, 2H, Ar-H), 7.07–7.04 (m, 2H, Ar-H),
6.60 (s, 1H, S-CH-N), 6.18 (s, 1H, -C=CH), 3.77 (d, 1H, CH2, J = 12 Hz), 3.73 (d, 1H, CH2, J = 12 Hz) and
2.39 (s, 3H, -CH3); 13C NMR (100 MHz, DMSO-d6,
δ ppm): 176.31, 168.22, 161.79, 160.24, 154.29, 143.81,
143.36, 129.57, 129.52, 129.36, 127.42, 125.69, 115.63, 105.09, 68.12, 33.58 and 12.70; HRMS (ESI-qTOF):
Calcd. for C19H17FN3O4S2 [M + H]+, 434.0858: found: 434.0893.
3.3.5. 4-(2-(2-chlorophenyl)-4-oxothiazolidin-3-yl)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (7e
Compound 7e was obtained from the cyclocondensation reaction between 5e, and for 12 h.
White solid; m.p.: 240–242 ◦C; Yield: 84%; 1H NMR (400 MHz, DMSO-d6,
ppm): 9.62 (s, 1H, NH),
)
4
,
6
δ
8.27–8.26 (m, 2H, Ar-H), 7.48–7.46 (m, 3H, Ar-H), 7.37–7.31 (m, 3H, Ar-H), 6.87 (s, 1H, S-CH-N),
6.35 (s, 1H, -C=CH), 3.92 (d, 1H, CH2, J = 12 Hz), 3.90 (d, 1H, CH2, J = 12 Hz) and 2.23 (s, 3H, -CH3);
13C NMR (100 MHz, DMSO-d6,
δ ppm): 171.64, 167.47, 156.19, 143.33, 141.16, 138.58, 135.94, 132.27,
130.80, 129.46, 127.47, 125.43, 122.06, 101.90, 65.58, 35.18 and 14.01; HRMS (ESI-qTOF): Calcd. for
C19H17ClN3O4S2 [M + H]+, 450.0786: found: 450.0796.
3.3.6. 4-(2-(3-chlorophenyl)-4-oxothiazolidin-3-yl)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (7f
Compound 7f was obtained from the cyclocondensation reaction between 5f, and for 12 h.
White solid; m.p.: 228–230 ◦C; Yield: 78%; 1H NMR (400 MHz, DMSO-d6,
ppm): 9.56 (s, 1H, NH),
)
4,
6
δ
8.04–8.02 (m, 2H, Ar-H), 7.35 (s, 1H, Ar-H), 7.27–7.25 (m, 4H, Ar-H), 7.14–7.11 (m, 1H, Ar-H), 6.65 (s, 1H,
S-CH-N), 6.46 (s, 1H, -C=CH), 3.78 (d, 1H, CH2, J = 12 Hz), 3.74 (d, 1H, CH2, J = 12 Hz) and 2.40 (s, 3H,
-CH3); 13C NMR (100 MHz, DMSO-d6,
δ ppm): 179.77, 167.82, 156.82, 143.99, 143.52, 133.04, 131.60,
129.69, 129.53, 127.56, 125.86, 124.57, 122.12, 103.76, 68.63, 34.98 and 13.79; HRMS (ESI-qTOF): Calcd.
for C19H17ClN3O4S2 [M + H]+, 450.1372: found: 450.1396.
3.3.7. 4-(2-(4-chlorophenyl)-4-oxothiazolidin-3-yl)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (7g
Compound 7g was obtained from the cyclocondensation reaction between 5g, and for 12 h.
White solid; m.p.: 245–247 ◦C; Yield: 80%; 1H NMR (400 MHz, DMSO-d6,
ppm): 9.76 (s, 1H, NH),
)
4
,
6
δ
8.02–8.01 (m, 2H, Ar-H), 7.33–7.32 (m, 2H, Ar-H), 7.24–7.23 (m, 2H, Ar-H), 7.19–7.17 (m, 2H, Ar-H),
6.60 (s, 1H, S-CH-N), 6.43 (s, 1H, -C=CH), 3.76 (d, 1H, CH2, J = 12 Hz), 3.73 (d, 1H, CH2, J = 12 Hz)
and 2.38 (s, 3H, -CH3); 13C NMR (100 MHz, DMSO-d6,
δ ppm): 182.76, 165.85, 157.74, 141.75, 139.99,
128.90, 128.41, 127.88, 124.50, 124.32, 124.19, 99.96, 66.56, 31.80 and 14.15; HRMS (ESI-qTOF): Calcd. for
C19H17ClN3O4S2 [M + H]+, 450.0042: found: 450.0025.
3.3.8. 4-(2-(4-bromophenyl)-4-oxothiazolidin-3-yl)-N-(5-methylisoxazol-3-yl)benzenesulfonamide (7h
)
Compound 7h was obtained from the cyclocondensation reaction between
4
,
5h, and
6 for 12 h.
1
Red solid; m.p.: 234–236 ◦C; Yield: 80%; H NMR (400 MHz, DMSO-d6,
δ ppm): 9.64 (s, 1H, NH),
8.10–8.09 (m, 2H, Ar-H), 7.48–7.46 (m, 3H, Ar-H), 7.24–7.22 (m, 2H, Ar-H), 7.17–7.15 (m, 2H, Ar-H),