Medicinal Chemistry Research
537.0928 (M + Na); IR (νmax/cm−1): 2959, 2933, 2853,
1745, 1697, 1617, 1559, 1450, 1309, 1245, 1162; 1H NMR
(400 MHz, CDCl3) δ 8.53 (s, 1H, =CH), 8.06 (d, J = 3.7
Hz, 2H, Ph-H), 7.77 (s, 1H, Ph-H), 7.71–7.60 (m, 4H, Ph-
H), 7.36 (d, J = 5.7 Hz, 2H, Ph-H), 4.45 (s, 2H, O–CH2),
4.40 (s, 2H, O=CCH2), 1.93 (d, J = 1.3 Hz, 2H, CH2), 1.86
(d, J = 9.9 Hz 2H, CH2), 1.57 (s, 4H, CH2); 13C NMR (100
MHz, CDCl3) δ 163.25, 159.04, 156.63, 155.16, 148.61,
138.11, 135.62, 134.37, 129.65, 129.57 (2C), 128.47 (2C),
124.86, 118.34, 117.87, 116.74, 110.48, 71.42, 65.69,
28.44, 28.28, 25.43, 25.25.
O=CCH2, O–CH2), 2.10 (d, J = 4.7 Hz, 2H, O–CH2), 2.02
(d, J = 2.6 Hz, 2H, O–CH2); 13C NMR (100 MHz, DMSO-
d6) δ 163.01, 159.36, 156.36, 155.00, 149.29, 137.65,
136.52, 135.04, 130.71 (2C), 130.41, 128.71 (2C), 125.27,
118.16, 117.90, 116.61, 110.92, 71.33, 68.77, 68.29, 64.96.
4-(2-(2-oxo-2H-chromene-3-carboxamido)ethoxy)-3-
(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide (10i)
White solid, yield: 64.2%; m.p. 142.3–145.7℃; APCI-
HRMS (m/z): calcd for C20H15N3S (neutral M + H)
458.0580; found 458.0658; IR (νmax/cm−1): 3273, 3022,
2924, 1710, 1650, 1632, 1531, 1450, 1362, 1254, 1154 cm
−1; 1H NMR (400 MHz, CDCl3) δ 9.20 (s, 1H, =CH), 8.93
(s, 1H, O=C–NH), 8.14 (s, 2H, Ph-H), 7.76–7.70 (m, 3H,
Ph-H), 7.65 (d, J = 5.0 Hz, 2H, Ph-H), 7.43 (d, J = 8.7 Hz,
2H, Ph-H), 4.61 (s, 2H, O–CH2), 3.98 (d, J = 2.9 Hz, 2H,
O=C–NH–CH2); 13C NMR (100 MHz, DMSO-d6) δ
162.13, 160.78, 159.26, 154.43, 148.44, 134.76, 132.95,
130.82, 130.43, 129.37, 128.86, 126.95, 126.69, 125.31,
119.01, 118.89, 116.67, 111.08, 70.31, 38.28.
4-((4-((2-oxo-2H-chromene-3-carbonyl)oxy)but-2-yn-1-yl)
oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide (10f)
White solid; yield: 78.7%; m.p. 135.1–138.1 °C; APCI-
HRMS (m/z): calcd for C22H14N2O9S (neutral M + H)
483.0420; found 483.0532; IR (νmax/cm−1): 2914, 1762,
1
1609, 1556, 1490, 1372, 1208, 1168, 998 cm−1; H NMR
(400 MHz, CDCl3) δ 8.64 (s, 1H, =CH), 8.11 (d, J = 1.8
Hz, 2H, Ph-H), 7.79 (s, 1H, Ph-H), 7.68 (dd, J = 3.4, 0.8
Hz, 4H, Ph-H), 7.40 (d, J = 4.3 Hz, 2H, Ph-H), 5.16 (d, J =
1.0 Hz, 2H, O–CH2), 5.04 (d, J = 1.4 Hz, 2H, O=CCH2);
13C NMR (100 MHz, CDCl3) δ 149.85, 137.81, 137.79,
135.80, 135.76, 134.93, 129.83, 129.76, 129.73, 128.61
(2C), 125.08, 117.73, 116.85, 110.62, 88.28, 83.51, 58.90,
53.05, 50.90, 50.18, 29.68.
4-(3-(2-oxo-2H-chromene-3-carboxamido)propoxy)-3-
(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide (10j)
White solid, yield: 67.1%; m.p. 148.5–156.3 °C; APCI-
HRMS (m/z): calcd for C21H17N3O8S (neutral M + H)
472.0770; found 472.0805; IR (νmax/cm−1): 3355, 3045,
2913, 1699, 1648, 1533, 1449, 1369, 1248, 1161; 1H NMR
(400 MHz, DMSO-d6) δ 9.00 (s, 1H, =CH), 8.92 (s, 1H,
O=C–NH), 8.10 (d, J = 6.0 Hz, 2H, Ph-H), 7.74–7.63 (m,
5H, Ph-H), 7.42 (d, J = 7.0 Hz, 2H, Ph-H), 4.55 (s, 2H,
O–CH2), 3.70 (s, 2H, O=C–NH–CH2), 2.25 (s, 2H, CH2);
13C NMR (100 MHz, DMSO-d63) δ 161.94, 160.68, 159.38,
154.32, 147.75, 137.62, 136.61, 134.50, 130.69 (2C),
130.50, 128.90 (2C), 125.58, 119.69, 118.92, 116.59,
110.99, 69.89, 36.27, 28.67.
4-((1-((2-oxo-2H-chrom3ene-3-carbonyl)oxy)propan-2-yl)
oxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide (10g)
White solid, yield: 80.4%; m.p. 152.9–154.7 °C. ESI-MS
(m/z): calcd for C21H16N2O9S (neutral M + H) 473.0; IR
(νmax/cm−1): 2917, 2850, 1761, 1613, 1553, 1460, 1392,
1293, 1248, 1165, 1085, 1005; 1H NMR (400 MHz, CDCl3)
δ 8.57 (s, 1H, =CH), 8.06 (d, J = 2.0 Hz, 2H, Ph-H), 7.76
(s, 1H, Ph-H), 7.65 (dd, J = 2.8, 1.0 Hz, 4H, Ph-H), 7.36 (s,
J = 0.5 Hz, 2H, Ph-H), 4.61 (d, J = 32.7 Hz, 4H, O=CCH2,
O–CH), 2.38 (d, J = 5.2 Hz, 2H, CH3); 13C NMR (100
MHz, CDCl3) δ 163.14, 158.85, 156.51, 155.24, 149.05,
138.02, 135.66, 134.56, 129.72 (2C), 129.67, 128.50 (2C),
124.93, 117.93, 117.82, 116.78, 110.49, 68.11, 61.80,
27.91.
4-((1-(2-oxo-2H-chromene-3-carboxamido)propan-2-yl)oxy)-
3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide (10k)
White solid, yield: 65.2%; m.p. 152.9–154.7 °C; APCI-
HRMS (m/z): calcd for C21H17N3O8S (neutral M + H)
472.0770; found 472.0807; IR (νmax/cm−1) 3356, 2917,
2850, 1703, 1623, 1655, 1527, 1453, 1354, 1162; 1H NMR
(400 MHz, CDCl3) δ 8.98 (s, 1H, =CH), 8.90 (s, 1H,
O=C–NH), 8.10 (d, J = 4.8 Hz, 2H, Ph-H), 7.74–7.63 (m,
5H, Ph-H), 7.42 (d, J = 6.0 Hz, 2H, Ph-H), 4.50 (s, 1H,
O–CH), 3.52–3.37 (s, 2H, O=C–NH–CH2), 1.52 (s, 3H,
CH3); 13C NMR (100 MHz, DMSO-d6) δ 162.20, 160.81,
158.79, 154.39, 136.49, 134.73, 130.38 (3C), 128.93,
128.07, 125.95, 125.69, 125.55, 119.17, 118.88, 116.66,
111.10, 78.41, 43.17, 17.27.
4-(2-(2-((2-oxo-2H-chromene-3-carbonyl)oxy)ethoxy)
ethoxy)-3-(phenylsulfonyl)-1,2,5-oxadiazole-2-oxide (10h)
White solid, yield: 77.5%; m.p. 98.9–101.0℃; ESI-HRMS
(m/z): calcd for C22H18N2O10S (neutral M + H) 503.0682;
found 503.0797; IR (νmax/cm−1): 2834, 2895, 1723, 1564,
1
1449, 1345, 1169, 1020; H NMR (400 MHz, CDCl3) δ
8.58 (s, 1H, =CH), 8.08 (s, 2H, Ph-H), 7.77 (s, 1H, Ph-H),
7.66 (s, 4H, Ph-H), 7.38 (s, 2H, Ph-H), 4.54–4.43 (m, 4H,