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3.1.16. 4-Oxo-N-(4-sulfamoylbenzyl)-4H-chromene-2-carboxamide (6a)
◦
96% yield. MP = 284–286 C. 1H NMR (400 MHz, CF3COOD)
δ
: 8.31 (d, J = 6.7 Hz, 1H,
Ar), 8.08–7.95 (m, 3H, Ar), 7.77 (m, 4H, Ar), 7.56 (s, 1H, Ar), 4.88 (s, 2H, CH2). 13C NMR
(126 MHz, DMSO-d6) δ: 177.74, 159.47, 156.02, 155.51, 143.71, 142.64, 135.46, 129.60, 126.47,
126.23, 125.39, 124.07, 119.19, 110.89, 40.90, 34.86. MS (ESI): m/z (%) = 359.1 (20.3) [M + H]+.
Anal. Calcd. for C17H14N2O5S (%): C, 56.98; H, 3.94; N, 7.82; S, 8.95. Found (%): C, 57.02;
H, 3.87; N, 7.79; S, 8.94.
3.1.17. 6-Methyl-4-oxo-N-(4-sulfamoylbenzyl)-4H-chromene-2-carboxamide (6b)
91% yield. MP = 293–295 ◦C. 1H NMR (400 MHz, DMSO-d6)
δ: 9.75 (t, J = 6.0 Hz, 1H,
NH), 7.84 (d, J = 2.1 Hz, 1H, Ar), 7.83–7.78 (m, 2H, Ar), 7.70 (dd, J = 8.6, 2.3 Hz, 1H, Ar),
7.61 (d, J = 8.6 Hz, 1H, Ar), 7.57–7.50 (m, 2H, Ar), 7.34 (s, 2H, SO2NH2), 6.84 (d, J = 1.5 Hz,
1H, Ar), 4.58 (d, J = 6.0 Hz, 2H, CH2), 2.43 (s, 3H, CH3). 13C NMR (151 MHz, DMSO-d6)
δ:
177.67, 159.81, 155.75, 153.81, 143.34, 142.97, 136.50, 136.15, 128.22, 126.23, 124.63, 123.83,
118.99, 110.97, 42.83, 40.51, 20.91. MS (ESI): m/z (%) = 373.1 (21.5) [M + H]+. Anal. Calcd.
for C18H16N2O5S (%): C, 58.05; H, 4.33; N, 7.52; S, 8.61. Found (%): C, 58.10; H, 4.29; N,
7.50; S, 8.71.
3.1.18. 6-Chloro-4-oxo-N-(4-sulfamoylbenzyl)-4H-chromene-2-carboxamide (6c)
◦
1
84% yield. MP = 299–301 C. H NMR (400 MHz, DMSO-d6) δ: 9.74 (s, 1H, NH),
8.01–7.89 (m, 2H, Ar), 7.78 (ddd, J = 18.4, 8.6, 1.8 Hz, 3H, Ar), 7.53 (d, J = 7.9 Hz, 2H, Ar),
7.29 (s, 2H, SO2NH2), 6.89 (d, J = 1.7 Hz, 1H, Ar), 4.59 (d, J = 6.0 Hz, 2H, CH2). 13C NMR
(126 MHz, DMSO-d6) δ: 176.72, 159.49, 156.09, 154.12, 143.36, 142.87, 135.38, 130.91, 128.23,
126.23, 125.23, 124.39, 121.69, 111.05, 42.83. MS (ESI): m/z (%) = 394.0 (39.5) [M + H]+. Anal.
Calcd. for C17H13ClN2O5S (%): C, 51.98; H, 3.34; Cl, 9.03; N, 7.13; S, 8.16. Found (%): C,
52.04; H, 3.28; Cl, 9.09; N, 7.16; S, 8.22.
3.1.19. 4-Oxo-N-(4-sulfamoylphenethyl)-4H-chromene-2-carboxamide (6d)
◦
95% yield. MP = 248–250 C. 1H NMR (400 MHz, DMSO-d6)
δ: 9.24–9.17 (m, 1H, NH),
8.05 (dd, J = 8.0, 1.5 Hz, 1H, Ar), 7.89 (ddd, J = 8.5, 7.1, 1.7 Hz, 1H, Ar), 7.77 (d, J = 7.9 Hz,
2H, Ar), 7.71 (d, J = 8.5 Hz, 1H, Ar), 7.53 (t, J = 7.6 Hz, 1H, Ar), 7.46 (d, J = 8.0 Hz, 2H), 7.27
(s, 2H, SO2NH2), 6.82 (s, 1H, Ar), 3.58 (q, J = 6.9 Hz, 2H, NCH2), 2.98 (t, J = 7.4 Hz, 2H,
CH2Ar). MS (ESI): m/z (%) = 373.1 (21.5) [M + H]+. Anal. Calcd. for C18H16N2O5S (%): C,
58.05; H, 4.33; N, 7.52; S, 8.61. Found (%): C, 58.10; H, 4.29; N, 7.50; S, 8.71.
3.1.20. 6-Methyl-4-oxo-N-(4-sulfamoylphenethyl)-4H-chromene-2-carboxamide (6e)
◦
84% yield. MP = 257–259 C. 1H NMR (400 MHz, DMSO-d6)
δ: 9.18–9.14 (m, 1H, NH),
7.82 (s, 1H, Ar), 7.89 (d, J = 8.5 Hz, 2H, Ar), 7.77–7.61 (m, 2H, Ar), 7.42 (d, J = 8.5 Hz, 2H,
Ar), 7.19 (s, 2H, SO2NH2), 6.77 (s, 1H, Ar), 3.54 (q, J = 6.9 Hz, 2H, NCH2), 2.96 (t, J = 7.4 Hz,
2H, CH2Ar), 2.46 (s, 3H, CH3). MS (ESI): m/z (%) = 387.1 (22.5) [M + H]+. Anal. Calcd. for
C19H18N2O5S (%): C, 59.06; H, 4.70; N, 7.25; S, 8.30. Found (%): C, 59.10; H, 4.79; N, 7.23;
S, 8.33.
3.1.21. 7-Methyl-4-oxo-N-(4-sulfamoylphenethyl)-4H-chromene-2-carboxamide (6f)
◦
87% yield. MP = 253–255 C. 1H NMR (400 MHz, DMSO-d6)
δ: 9.23 (t, J = 6.9 Hz,
1H, NH), 7.92 (d, J = 8.4 Hz, 1H, Ar), 7.75 (d, J = 8.0 Hz, 2H, Ar), 7.50 (s, 1H, Ar), 7.44 (d,
J = 8.0 Hz, 2H, Ar), 7.35 (d, J = 8.4 Hz, 2H, Ar), 7.30 (s, 2H, SO2NH2), 6.76 (s, 1H, Ar), 3.55
(q, J = 6.9 Hz, 2H, NCH2), 2.96 (t, J = 7.4 Hz, 2H, CH2Ar), 2.47 (s, 3H, CH3). MS (ESI): m/z
(%) = 387.1 (22.5) [M + H]+. Anal. Calcd. for C19H18N2O5S (%): C, 59.06; H, 4.70; N, 7.25; S,
8.30. Found (%): C, 59.12; H, 4.73; N, 7.24; S, 8.35.
3.1.22. 6-Ethyl-4-oxo-N-(4-sulfamoylphenethyl)-4H-chromene-2-carboxamide (6g)
◦
1
90% yield. MP = 257–259 C. H NMR (400 MHz, DMSO-d6)
δ: 9.21 (s, 1H, NH),
7.85 (d, J = 2.2 Hz, 1H, Ar), 7.80–7.71 (m, 3H, Ar), 7.63 (d, J = 8.6 Hz, 1H, Ar), 7.46 (d,