Molecules 2013, 18
2874
1H-NMR (300 MHz, DMSO-d6) δ 8.39 (s, 1H), 7.71 (d, J = 8.1 Hz, 2H), 7.61 (m, 4H), 7.34 (m, 4H),
7.15 (d, J = 8.2 Hz, 2H), 6.83 (d, J = 8.2 Hz, 2H), 5.29 (s, 1H), 4.87 (m, 1H), 4.69 (m, 2H), 3.83 (m,
2H), 3.47 (m, 2H), 2.40 (m, 2H), 2.31 (s, 1H), 2.15 (m, 1H), 2.07 (s, 3H), 1.95 (m, 2H), 1.70 (m, 2H),
1.51 (m, 1H), 1.27 (m, 4H), 1.04 (m, 2H), 0.80 (d, J = 7.3 Hz, 3H), 0.72 (d, J = 4.7 Hz, 3H). Anal.
Calcd. for C40H48N2O9S: C 65.55, H 6.60, N 3.82. Found: C 65.48, H 6.57, N 3.85.
(E)-N-(2-(10β-Dihydroartemisinoxy)ethyl)-4((4-(2-(N-(4-chlorophenyl)sulfamoyl)vinyl)phenoxy)methyl)
benzamide (6f). Yellow solid (39% yield); m.p.: 138–141 °C; MS (ESI) m/z: 751.1 (M-H)–; IR (KBr)
1
cm−1: 3397.1, 2923.1, 1603.4, 1509.9, 1345.8, 1146.5, 1026.2, 982.5, 871.4, 800.5, 594.3; H-NMR
(300 MHz, DMSO-d6) δ 8.39 (br, 1H), 7.72 (d, J = 8.2 Hz, 2H), 7.59 (d, J = 8.5 Hz, 2H), 7.48 (d,
J = 13.1 Hz, 2H), 7.32 (d, J = 8.2 Hz, 2H), 7.28 (d, J = 4.6 Hz, 2H), 7.17 (d, J = 8.1 Hz, 2H), 6.80 (d,
J = 8.2 Hz, 2H), 5.24 (s, 1H), 4.83 (s, 2H), 4.62 (d, J = 3.2 Hz, 1H), 4.41 (m, 1H), 4.30 (m, 1H), 3.81
(s, 2H), 3.60 (m, 1H), 2.33 (m, 1H), 2.08 (m, 1H), 1.93 (m, 1H), 1.61 (m, 3H), 1.47 (m, 2H), 1.26 (m,
6H), 0.78 (d, J = 7.2 Hz, 3H), 0.64 (d, J = 5.8 Hz, 3H). Anal. Calcd. for C39H45ClN2O9S: C 62.18, H
6.02, N 3.72. Found: C 62.23, H 5.98, N 3.76.
(E)-N-(2-(10β-Dihydroartemisinoxy)ethyl)-4((4-(2-(N-(2-chlorophenyl)sulfamoyl)vinyl)phenoxy)methyl)
benzamide (6g). Light yellow solid (38% yield); m.p.: 147–150 °C; MS (ESI) m/z: 775.2 (M+Na)+; IR
(KBr) cm−1: 3394.1,2925.3, 1605.5, 1499.1, 1339.3, 1144.8, 1028.8, 979.5, 881.7, 806.7, 598.2;
1H-NMR (300 MHz, DMSO-d6) δ 7.59 (m, 2H), 7.40 (d, J = 8.6 Hz, 4H), 7.32 (m, 3H), 6.94 (s, 2H),
6.79 (m, 3H), 5.62 (s, 1H), 5.35 (d, J = 10.3 Hz, 1H), 4.80 (s, 2H), 4.68 (d, J = 3.1 Hz, 1H), 3.81 (m,
2H), 3.45 (m, 2H), 2.18 (m, 1H), 2.05 (m, 2H), 1.94 (m, 2H), 1.63 (m, 2H), 1.52 (m, 2H), 1.33 (s, 3H),
0.98 (m, 2H), 0.83 (d, J = 7.4 Hz, 3H), 0.71 (d, J = 5.7 Hz, 3H). Anal. Calcd. for C39H45ClN2O9S:
C 62.18, H 6.02, N 3.72. Found: C 62.12, H 5.97, N 3.79.
(E)-N-(2-(10β-Dihydroartemisinoxy)ethyl)-4((4-(2-(N-(2,6-dichlorophenyl)sulfamoyl)vinyl)phenoxy)m
ethyl)benzamide (6h). Light yellow solid (40% yield); m.p.: 151–153 °C; MS (ESI) m/z: 784.9 (M-H)–;
IR (KBr) cm−1: 3420.8, 2922.6, 1602.6, 1508.2, 1348.2, 1147.1, 1027.8, 984.7, 874.3, 541.5; 1H-NMR
(300 MHz, DMSO-d6) δ 8.40 (br, 1H), 7.75 (d, J = 8.1 Hz, 1H), 7.62 (d, J = 8.3 Hz, 2H), 7.59 (m, 4H),
7.28 (m, 4H), 6.84 (d, J = 7.5 Hz, 2H), 5.26 (s, 1H), 4.80 (s, 2H), 4.69 (d, J = 3.3 Hz, 1H), 3.85 (m,
2H), 3.59 (m, 2H), 2.35 (m, 1H), 2.13 (m, 1H), 1.97 (m, 2H), 1.67 (m, 3H), 1.52 (m, 2H), 1.27 (s, 3H),
1.24 (s, 2H), 1.04 (m, 1H), 0.81 (d, J = 7.4 Hz, 3H), 0.69 (d, J = 4.5 Hz, 3H). Anal. Calcd. for
C39H44Cl2N2O9S: C 59.46, H 5.63, N 3.56. Found: C 59.42, H 5.59, N 3.50.
(E)-N-(2-(10β-Dihydroartemisinoxy)ethyl)-4((4-(2-(N-(3-methoxyphenyl)sulfamoyl)vinyl)phenoxy)met
hyl)benzamide (6i). Light yellow solid (48% yield); m.p.: 144–145 °C; MS (ESI) m/z: 747.2 (M−H)–;
IR (KBr) cm−1: 3392.7, 2923.7, 1603.2, 1512.6, 1340.0, 1142.2, 1025.9, 982.8, 871.7, 840.7, 596.3;
1H-NMR (300 MHz, DMSO-d6) δ 8.40 (br, 1H), 7.74 (d, J = 8.2 Hz, 2H), 7.60 (d, J = 8.5 Hz, 2H),
7.50 (s, 1H), 7.43 (s, 1H), 7.37 (d, J = 8.2 Hz, 2H), 7.32 (d, J = 4.6 Hz, 2H), 7.26 (d, J = 8.1 Hz, 2H),
6.82 (d, J = 8.6 Hz, 2H), 5.25 (s, 1H), 4.92 (d, J = 5.4 Hz, 2H), 4.68 (m, 1H), 3.95(s, 3H), 3.82 (m,
2H), 3.51(m, 2H), 2.34 (m, 2H), 2.12 (m, 2H), 2.00 (m, 2H), 1.66 (m, 2H), 1.49 (m, 1H), 1.26 (s, 3H),
1.21 (m, 3H), 0.81 (d, J = 7.3 Hz, 3H), 0.69 (d, J = 5.2 Hz, 3H). Anal. Calcd. for C40H48N2O10S:
C 64.15, H 6.46, N 3.74. Found: C 64.09, H 6.41, N 3.67.