Molecules 2016, 21, 1488
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J = 43.5 Hz, 1H), 8.34 (d, J = 7.7 Hz, 1H), 7.73–7.42 (m, 3H), 7.17 (t, J = 7.5 Hz, 1H), 7.05 (d, J = 8.3 Hz,
1H), 6.40 (dd, J = 17.4 Hz, 11.0, 1H), 5.75 (d, J = 8.3 Hz, 1H), 5.18 (dd, J = 51.6 Hz, 14.2, 2H), 4.09
(d, J = 10.7 Hz, 3H), 3.94 (d, J = 4.8 Hz, 2H), 3.31 (s, 1H), 2.41–2.23 (m, 2H), 2.23–2.12 (m, 2H), 2.05
(s, 1H), 2.04 (s, 1H), 1.96 (dd, J = 15.8 Hz, 8.4, 1H), 1.73 (t, J = 13.6 Hz, 1H), 1.61 (d, J = 9.9 Hz, 2H),
1.55–1.20 (m, 9H), 1.06 (s, 4H), 0.86 (d, J = 6.9 Hz, 3H), 0.70 (d, J = 6.8 Hz, 3H); 13C-NMR (101 MHz,
CDCl3)
δ 215.94,167.41, 167.32, 162.45, 156.29, 147.67, 137.80, 132.32, 131.53, 120.79, 116.26, 110.62,
73.61, 69.51, 59.39, 57.11, 55.30, 44.43, 43.44, 42.97, 40.85, 35.73, 35.04, 34.17, 33.44, 29.41, 25.86, 25.43,
23.83, 20.02,18.17, 15.76, 13.79, 13.18, 10.46; HRMS (ES) calcd [M + H]+ for C37H45N3O5S 644.3162,
found 644.3183.
14-O-((2-Methoxybenzamide-5-aminobenzimidazole-2-yl) thioacetyl) mutilin (4g). Synthesized according to
the general procedure for 36 h. White solid; yield 68% (0.90 g). IR (KBr): 3357, 2934, 1729, 1653, 1600,
1
1551, 1457, 1406, 1292, 1237, 1162, 1117, 1019, 980, 938, 916, 756 cm−1; H-NMR (400 MHz, CDCl3)
δ
8.04 (s, 1H), 7.88 (d, J = 6.7 Hz, 2H), 7.57–7.20 (m, 4H), 6.11–5.98 (m, 1H), 5.53 (d, J = 7.1 Hz, 1H),
5.01 (dd, J = 74.0 Hz, 14.3, 2H), 4.47 (s, 1H), 4.09 (s, 2H), 3.38 (s, 1H), 2.39 (s, 3H), 2.36 (s, 1H), 2.16 (d,
J = 11.1 Hz, 1H), 2.11–1.87 (m, 4H), 1.62 (dd, J = 25.4 Hz, 12.7, 2H), 1.47 (s, 1H), 1.42–1.11 (m, 9H), 0.99
(d, J = 28.2 Hz, 4H), 0.80 (d, J = 5.3 Hz, 3H), 0.62 (d, J = 3.2 Hz, 3H); 13C-NMR (101 MHz, CDCl3)
δ
217.68, 167.48, 165.71, 149.15, 141.90, 141.22, 140.67, 136.04, 134.44, 132.93, 129.44, 128.21, 117.52, 115.93,
115.52, 102.88, 73.21, 70.74, 60.34, 57.84, 45.55, 44.75, 43.71, 42.14, 36.96, 34.59, 30.71, 29.28, 27.21, 25.06,
21.60, 16.68, 15.12, 14.69, 12.10; HRMS (ES) calcd [M + H]+ for C37H45N3O6S 660.3145, found 660.3149.
14-O-((3-Methoxybenzamide-5-aminobenzimidazole-2-yl) thioacetyl) mutilin (4h). Synthesized according to
the general procedure for 40 h. White solid; yield 57% (0.75 g). IR (KBr): 3385, 2936, 1727, 1654, 1598,
1541, 1447, 1349, 1287, 1154, 1117, 1039, 980, 937, 918, 804 cm−1; 1H-NMR (400 MHz, CDCl3) δ 8.30 (s,
1H), 8.10 (s, 1H), 7.38 (s, 2H), 7.36 (s, 1H), 7.27 (t, J = 7.8, 1H), 6.98 (d, J = 6.0, 1H), 6.32 (dd, J = 17.4 Hz,
11.1, 1H), 5.68 (d, J = 8.3 Hz, 1H), 5.10 (dd, J = 43.3 Hz, 14.2, 2H), 4.05 (dt, J = 7.1 Hz, 6.2, 1H), 3.84
(d, J = 15.7 Hz, 2H), 3.76 (s, 3H), 3.24 (s, 1H), 2.29–2.17 (m, 1H), 2.16–2.04 (m, 2H), 1.97 (d, J = 1.0 Hz,
1H), 1.94–1.85 (m, 1H), 1.66 (d, J = 14.4 Hz, 1H), 1.53 (d, J = 9.8 Hz, 1H), 1.44–1.17 (m, 8H), 1.00 (s, 4H),
0.79 (d, J = 6.7 Hz, 3H), 0.64 (d, J = 6.7 Hz, 4H); 13C-NMR (101 MHz, CDCl3)
δ 216.18, 170.22, 167.42,
165.11, 158.89, 147.98, 137.72, 135.42, 131.85, 128.78, 117.97, 116.89, 116.30, 111.55, 76.31,73.56, 69.58,
59.42, 57.08, 54.47, 44.41, 43.37, 42.94, 40.82, 35.69, 34.99, 34.07, 33.44, 29.36, 25.82, 25.42, 23.80, 20.06,
15.80, 13.80, 13.19, 10.51; HRMS (ES) calcd [M + H]+ for C37H45N3O6S 660.3145, found 660.3098.
14-O-((4-Methoxybenzamide-5-aminobenzimidazole-2-yl) thioacetyl) mutilin (4i). Synthesized according to
the general procedure for 36 h. White solid; yield 58% (0.76 g). IR (KBr): 3386, 2932, 1725, 1647, 1606,
1544, 1508, 1458, 1406, 1351, 1286, 1254, 1179, 1119, 1076, 980, 939, 917, 762 cm−1; 1H-NMR (400 MHz,
CDCl3) δ 8.21 (s, 1H), 8.06 (d, J = 24.1 Hz, 1H), 7.81 (d, J = 8.8 Hz, 2H), 7.24 (s, 1H), 6.86 (d, J = 8.7 Hz,
2H), 6.32 (dd, J = 17.4 Hz, 11.0, 1H), 5.67 (d, J = 8.4 Hz, 1H), 5.09 (dd, J = 43.1 Hz, 14.2, 2H), 3.87 (d,
J = 3.7 Hz, 2H), 3.78 (s, 3H), 3.25 (s, 1H), 2.20 (dd, J = 13.7 Hz, 7.1, 1H), 2.10 (dt, J = 17.5 Hz, 7.3, 2H),
1.97 (s, 1H), 1.97 (s, 1H), 1.90 (dd, J = 16.0 Hz, 8.5, 1H), 1.66 (d, J = 14.0 Hz, 1H), 1.54 (d, J = 7.1 Hz, 1H),
1.49–1.12 (m, 9H), 0.99 (s, 4H), 0.78 (d, J = 6.9 Hz, 3H), 0.64 (d, J = 6.9 Hz, 3H);13C-NMR (101 MHz,
CDCl3)
δ 216.05, 167.41, 164.80, 161.49, 147.85, 137.78, 132.08, 128.05, 126.11, 116.27, 112.99,76.23,
73.60, 69.61, 59.39, 57.11, 54.45, 44.43, 43.45, 42.98, 40.95,40.85, 35.72, 35.03, 34.15, 33.45, 29.39, 25.85,
25.45, 23.82, 20.02, 15.79, 13.80, 13.18, 10.47; HRMS (ES) calcd [M + H]+ for C37H45N3O6S 660.3145,
found 660.3143.
14-O-((Cyclohexanecarboxamide-5-aminobenzimidazole-2-yl) thioacetyl) mutilin (4j). Synthesized according
to the general procedure for 36 h. White solid; yield 81% (1.03 g). IR (KBr): 3365, 2931, 1728, 1664,
1601, 1541, 1448, 1407, 1345, 1277, 1208, 1152, 1117, 1018, 980, 938, 917, 807 cm−1; 1H-NMR (400 MHz,
CDCl3) δ 8.16 (s, 1H), 7.61 (s, 1H), 7.39 (d, J = 7.9 Hz, 1H), 6.93 (s, 1H), 6.39 (dd, J = 17.4 Hz, 11.0, 1H),
5.74 (d, J = 8.4 Hz, 1H), 5.33–5.00 (m, 3H), 3.96 (d, J = 6.1 Hz, 1H), 3.30 (d, J = 4.6 Hz, 1H), 2.39–2.10
(m, 4H), 2.08–1.95 (m, 4H), 1.69 (dd, J = 72.2 Hz, 26.0, 10H), 1.41–1.15 (m, 9H), 1.05 (s, 4H), 0.86 (d,