Molecules 2019, 24, 1154
12 of 16
2.6 Hz, 1H), 6.60 (s, 1H), 6.40 (s, 1H), 6.35–6.31 (m, 2H), 5.90 (s, 1H), 3.83–3.78 (m, 4H), 3.65 (s, 3H),
3.61–3.56 (m, 1H), 3.51–3.47 (m, 1H), 3.47–3.39 (m, 1H), 3.34–3.30 (m, 1H), 3.29 (s, 3H), 3.22–3.17 (m,
1H), 3.16–3.07 (m, 2H), 3.03–2.96 (m, 1H), 2.87–2.60 (m, 7H), 2.38 (s, 3H), 2.36–2.28 (m, 2H), 2.17 (s,
3H), 1.32–1.22 (m, 2H); 13C-NMR (DMSO-d6)
δ 165.0, 152.9, 151.0, 149.0, 147.9, 147.8, 146.7, 143.2, 136.4,
135.9, 135.6, 134.2, 133.4, 132.6, 130.5, 129.0 (2), 128.4, 128.4 (2), 128.3, 127.8, 123.0, 122.3, 121.6, 121.4,
119.7, 115.3, 112.8, 111.9, 106.4, 70.2, 62.9, 61.1, 55.7, 55.7 (2), 44.9, 43.2, 42.1, 42.0, 41.5, 38.5, 36.5, 29.1,
24.5, 21.1; HRMS: calcd for C47H51ClN3O7 [M + H]+: 804.3410, found: 803.3411.
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7O-o-Picolinamidepropylfangchinoline (8g) 102 mg, 22% yield; light yellow solid; mp: 146–148 C.
1H-NMR (DMSO-d6)
δ 8.64 (d, J = 4.6 Hz, 1H), 8.58 (t, J = 6.0 Hz, 1H), 8.08–7.99 (m, 2H), 7.65–7.59 (m,
1H), 7.32 (dd, J = 8.2, 1.7 Hz, 1H), 7.06 (dd, J = 8.1, 2.4 Hz, 1H), 6.92 (d, J = 8.2 Hz, 1H), 6.77 (dd, J = 8.2,
1.2 Hz, 1H), 6.69 (dd, J = 8.2, 2.4 Hz, 1H), 6.60 (s, 1H), 6.40 (s, 1H), 6.35–6.30 (m, 2H), 5.90 (s, 1H), 3.81
(s, 3H), 3.79–3.73 (m, 1H), 3.67 (s, 3H), 3.63–3.56 (m, 1H), 3.53–3.39 (m, 2H), 3.33–3.25 (m, 4H), 3.19–3.01
(m, 4H), 2.88–2.60 (m, 7H), 2.42–2.27 (m, 5H), 2.16 (s, 3H), 1.27–1.20 (m, 2H); 13C-NMR (DMSO-d6)
δ
163.7, 153.1, 151.2, 150.2, 149.1, 148.6, 148.1, 148.0, 146.8, 143.3, 138.0, 136.4, 135.8, 134.4, 132.8, 130.7,
128.7, 128.5, 128.0, 126.7, 123.1, 122.4, 122.0, 121.8, 121.6, 119.9, 115.5, 112.9, 112.1, 106.4, 70.3, 63.1,
61.3, 55.8 (2), 55.2, 45.1, 43.4, 42.3, 42.2, 41.6, 38.5, 36.2, 29.3, 24.7, 21.3; HRMS: calcd for C46H51N4O7
[M + H]+: 771.3752, found: 771.3751. ]
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7O-o-Furamidepropylfangchinoline (8h) 100 mg, 22% yield; light yellow solid; mp: 142–144 C. 1H-NMR
(DMSO-d6) 8.11 (t, J = 5.8 Hz, 1H), 7.84 (dd, J = 1.7, 0.7 Hz, 1H), 7.40 (dd, J = 8.2, 2.1 Hz, 1H), 7.08–7.04
δ
(m, 2H), 6.92 (d, J = 8.3 Hz, 1H), 6.77 (dd, J = 8.2, 1.8 Hz, 1H), 6.69 (dd, J = 8.2, 2.6 Hz, 1H), 6.63 (dd,
J = 3.4, 1.8 Hz, 1H), 6.59 (s, 1H), 6.39 (s, 1H), 6.36–6.31 (m, 2H), 5.90 (s, 1H), 3.83–3.78 (m, 4H), 3.65
(s, 3H), 3.58–3.52 (m, 1H), 3.51–3.46 (m, 1H), 3.46–3.38 (m, 1H), 3.32–3.27 (m, 4H), 3.19–3.11 (m, 2H),
3.09–3.01 (m, 1H), 3.00–2.91 (m, 1H), 2.87–2.60 (m, 7H), 2.41 (s, 3H), 2.38–2.26 (m, 2H), 2.17 (s, 3H),
1.24–1.19 (m, 2H); 13C-NMR (DMSO-d6) δ 157.4, 152.8, 150.8, 148.8, 148.0, 147.7 (2), 146.5, 144.7, 143.0,
136.1, 135.5, 134.1, 132.5, 130.4, 128.3, 128.2, 127.7, 122.8, 122.1, 121.5, 121.2, 119.6, 115.1, 113.0, 112.6,
111.8, 111.7, 106.2, 70.1, 62.8, 61.0, 55.5 (3), 44.8, 43.1, 42.0, 41.8, 41.3, 38.1, 35.6, 29.1, 24.4, 21.0; HRMS:
calcd for C45H50N3O8 [M + H]+: 760.3592, found: 760.3591.
7O-Morp◦holine-4”-carboxamidepropylfangchinoline (8i) 211 mg, 45% yield; light yellow solid; mp:
1
152–154 C. H-NMR (DMSO-d6)
δ 7.46 (dd, J = 8.2, 2.1 Hz, 1H), 7.09 (dd, J = 8.2, 2.6 Hz, 1H),
6.91 (d, J = 8.3 Hz, 1H), 6.76 (dd, J = 8.2, 1.8 Hz, 1H), 6.69 (dd, J = 8.2, 2.6 Hz, 1H), 6.60 (s, 1H), 6.39
(s, 1H), 6.36–6.29 (m, 3H), 5.90 (s, 1H), 3.86–3.80 (m, 4H), 3.67 (s, 3H), 3.54–3.41 (m, 7H), 3.29 (s, 3H),
3.22–3.10 (m, 6H), 2.89–2.59 (m, 10H), 2.47 (s, 3H), 2.39–2.25 (m, 2H), 2.16 (s, 3H), 1.24–1.09 (m, 2H);
13C-NMR (DMSO-d6)
δ 157.4, 152.8, 150.9, 148.8, 147.7 (2), 146.5, 143.0, 136.2, 135.5, 134.0, 132.5, 130.4,
128.3, 128.1, 127.6, 122.8, 122.1, 121.5, 121.2, 119.6, 115.1, 112.7, 111.8, 106.2, 70.2, 65.8 (2), 62.9, 61.0, 55.6,
55.5 (2), 44.8, 43.7 (2), 43.1, 42.1, 41.8, 41.3, 38.6, 37.1, 29.6, 24.2, 21.0. HRMS: calcd for C45H55N4O8
[M + H]+: 779.4014, found: 771.4016.
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7O-3”,4”-Dichlorobenzamidepropylfangchinoline (8j) 318 mg, 63% yield; light yellow solid; mp: 145–147 C.
1H-NMR (DMSO-d6)
δ 8.48 (t, J = 5.6 Hz, 1H), 8.03 (d, J = 1.5 Hz, 1H), 7.8 –7.75 (m, 2H), 7.36 (dd, J = 8.2,
2.1 Hz, 1H), 7.05 (dd, J = 8.2, 2.6 Hz, 1H), 6.92 (d, J = 8.3 Hz, 1H), 6.77 (dd, J = 8.2, 1.8 Hz, 1H), 6.68 (dd,
J = 8.2, 2.6 Hz, 1H), 6.60 (s, 1H), 6.40 (s, 1H), 6.34–6.30 (m, 2H), 5.89 (s, 1H), 3.82–3.76 (m, 4H), 3.65 (s,
3H), 3.61–3.56 (m, 1H), 3.51–3.47 (m, 1H), 3.47–3.39 (m, 1H), 3.34–3.30 (m, 1H), 3.29 (s, 3H), 3.23–3.17
(m, 1H), 3.16–3.07 (m, 2H), 3.05–2.96 (m, 1H), 2.88–2.60 (m, 7H), 2.38 (s, 3H), 2.36–2.27 (m, 2H), 2.17 (s,
3H), 1.33–1.22 (m, 2H); 13C-NMR (DMSO-d6)
δ 163.7, 153.0, 151.0, 149.0, 147.9, 147.8, 146.7, 143.2, 136.4,
135.6, 135.0, 134.2, 133.9, 132.7, 131.3, 130.8, 130.5, 129.1, 128.5, 128.3, 127.9, 127.5, 123.0, 122.3, 121.6,
121.4, 119.7, 115.3, 112.8, 111.9, 106.4, 70.1, 62.9, 61.2, 55.7, 55.7 (2), 45.0, 43.2, 42.2, 42.0, 41.5, 38.4, 36.6,
29.0, 24.5, 21.1; HRMS: calcd for C47H51Cl2N3O7 [M + H]+: 839.3099, found: 839.3104.
7O-Benzenesulfonamidepropylfangchinoline (8k) 102 mg, 21% yield; light yellow solid; mp: 146–148 ◦C.
1H-NMR (DMSO-d6)
δ 7.79–7.73 (m, 2H), 7.67–7.57 (m, 4H), 7.46 (dd, J = 8.3, 2.1 Hz, 1H), 7.09 (dd,