RCHH HARM
A P
Arch. Pharm. Chem. Life Sci. 2017, 350, e1700044
W. Li et al.
Archiv der Pharmazie
40,7-Dimethoxy-5-hydroxy-6-[(piperidin-1-yl)methyl]-
flavothione (5d)
CH2NCH2), 1.03 (t, J ¼ 7.1 Hz, 6H, 2CH3); 13C NMR (100 MHz,
CDCl3) d 196.05, 163.09, 159.64, 152.91, 152.56, 151.48, 148.43,
121.73, 119.49, 117.13, 112.66, 110.99, 110.26, 107.79,
Yellow solid, yield: 84%; m.p.: 180–181°C; 1H NMR (400 MHz,
CDCl3) d 7.76 (d, J ¼ 8.7 Hz, 2H, H-20 and 60), 7.23 (s, 1H, H-3),
6.91 (d, J ¼ 8.7 Hz, 2H, H-30 and 50), 6.41 (s, 1H, H-8), 3.85, 3.81
(s, 6H, 2OCH3), 3.57 (s, 2H, 6-CH2N), 2.42–2.46 (m, 4H,
CH2NCH2), 1.54–1.45 (m, 4H, 2CH2), 1.31 (d, J ¼ 4.7 Hz, 2H,
CH2); 13C NMR (100 MHz, CDCl3) d 197.07, 164.09, 162.77,
160.70, 154.02, 153.57, 128.26, 122.42, 117.80, 114.66, 113.54,
110.49, 89.81, 56.06, 55.58, 54.36, 49.82, 25.94, 24.25. IR (KBr)
v/cmꢂ1: 2929, 1597, 1506, 1263, 1180, 1026, 831, 578. ESI-MS
(m/z): 412 [MþH]þ.
88.89, 55.20, 55.11, 45.90, 42.89, 10.15. IR (KBr) v/cmꢂ1
:
2926, 1631, 1512, 1458, 1327, 1141, 1024, 806. ESI-MS (m/z):
430 [MþH]þ.
30,40,7-Trimethoxy-5-hydroxy-6-[(pyrrolidin-1-yl)methyl]-
flavothione (6c)
Yellow solid, yield: 84%; m.p.: 214–215°C; 1H NMR (400 MHz,
CDCl3) d 7.51 (d, J ¼ 8.5 Hz, 1H, H-60), 7.28 (s, 2H, H-3 and 20),
6.90 (d, J ¼ 8.5 Hz, 1H, H-50), 6.46 (s, 1H, H-8), 3.92, 3.90, 3.89 (s,
9H, 3OCH3), 3.73 (s, 2H, 6-CH2N), 2.58 (m, 4H, CH2NCH2), 1.69
(m, 4H, CH2CH2); 13C NMR (100 MHz, CDCl3) d 196.12, 162.89,
159.50, 153.06, 152.61, 151.53, 148.46, 121.73, 119.53, 117.12,
112.65, 110.29, 110.22, 107.82, 88.85, 55.21, 55.12, 53.01,
45.04, 22.46. IR (KBr) v/cmꢂ1: 2924, 1629, 1512, 1458, 1261,
1143, 1022, 804, 613. ESI-MS (m/z): 428 [MþH]þ.
40,7-Dimethoxy-5-hydroxy-6-[(morpholine-1-yl)methyl]-
flavothione (5e)
Yellow solid, yield: 88%; m.p.: 225–226°C; 1H NMR (400 MHz,
CDCl3) d 13.83 (s, 1H, OH-5), 7.76 (d, J ¼ 8.5 Hz, 2H, H-20 and 60),
7.23 (s, 1H, H-3), 6.91 (d, J ¼ 8.5 Hz, 2H, H-30 and 50), 6.42 (s, 1H,
H-8), 3.86, 3.81 (s, 6H, 2OCH3), 3.64–3.61 (m, 4H, CH2OCH2),
3.60 (s, 2H, 6-CH2N), 2.50 (s, 4H, CH2NCH2); 13C NMR (100 MHz,
CDCl3) d 196.01, 162.92, 161.81, 159.67, 153.13, 152.66, 127.26,
121.27, 116.73, 113.65, 112.41, 108.64, 88.87, 66.01, 55.06,
54.55, 52.44, 50.99, 48.42. IR (KBr) v/cmꢂ1: 2935, 1595, 1506,
1261, 1110, 823, 580. EIMS: m/z 413 [M]þ, HR-EIMS: m/z calcd.
for C22H23O5NS, 413.1291 [M]þ, found 413.1275.
30,40,7-Trimethoxy-5-hydroxy-6-[(piperidin-1-yl)methyl]-
flavothione (6d)
Yellow solid, yield: 84%; m.p.: 216–218°C; 1H NMR (400 MHz,
CDCl3) d 7.50 (d, J ¼ 8.5 Hz, 1H, H-60), 7.28 (s, 2H, H-3 and 20),
6.90 (d, J ¼ 8.5 Hz, 1H, H-50), 6.45 (s, 1H, H-8), 3.92, 3.90, 3.88 (s,
9H, 3OCH3), 3.61 (s, 2H, 6-CH2N), 2.48–2.44 (m, 4H, CH2NCH2),
1.5–1.45 (m, 4H, CH2CH2CH2), 1.33 (d, J ¼ 4.8 Hz, 2H, CH2);
13C NMR (100 MHz, CDCl3) d 196.11, 163.14, 159.77, 152.99,
152.63, 151.51, 148.45, 121.73, 119.51, 117.14, 112.64, 110.27,
107.80, 88.82, 55.21, 55.12, 55.09, 53.35, 48.82, 24.87, 23.20. IR
(KBr) v/cmꢂ1: 2916, 2312, 1629, 1508, 1446, 1266, 1097, 802.
EIMS: m/z 441 [M]þ, HR-EIMS: m/z calcd. for C24H27O5NS
441.1604 [M]þ, found 441.1600.
40,7-Dimethoxy-5-hydroxy-6-[(4-methylpiperazin-1-yl)-
methyl]-flavothione (5f)
Yellow solid, yield: 86%; m.p.: 208–210°C; 1H NMR (400 MHz,
CDCl3) d 7.78 (d, J ¼ 8.6 Hz, 2H, H-20 and 60), 7.25 (s, 1H, H-3),
6.92 (d, J ¼ 8.6 Hz, 2H, H-30 and 50), 6.42 (s, 1H, H-8), 3.85, 3.82
(s, 6H, 2OCH3), 3.64 (s, 2H, 6-CH2N), 2.69–2.28 (m, 8H,
2CH2NCH2), 2.18 (s, 3H, CH3); 13C NMR (100 MHz, CDCl3) d
197.11, 164.01, 162.81, 160.72, 154.12, 153.65, 128.31, 122.41,
117.81, 114.68, 113.51, 110.06, 89.82, 56.03, 55.58, 55.11,
52.86, 48.89, 46.03. IR (KBr) v/cmꢂ1: 2927, 1631, 1508, 1456,
1261, 1134, 1020, 823, 580. ESI-MS (m/z): 427 [MþH]þ.
30,40,7-Trimethoxy-5-hydroxy-6-[(morpholino-1-yl)
methyl]-flavothione (6e)
Yellow solid, yield: 88%; m.p.: 219–220°C; 1H NMR (400 MHz,
CDCl3) d 13.83 (s, 1H, OH-5), 7.49 (d, J ¼ 8.6 Hz, 1H, H-60), 7.27 (s,
2H, H-3 and 20), 6.90 (d, J ¼ 8.6 Hz, 1H, H-50), 6.45 (s, 1H, H-8),
3.92, 3.90, 3.89 (s, 9H, 3OCH3), 3.64 (s, 2H, 6-CH2N), 3.63 (m, 4H,
CH2OCH2), 2.55–2.46 (m, 4H, CH2NCH2); 13C NMR (100 MHz,
CDCl3) d 196.06, 163.01, 159.75, 153.14, 152.72, 151.59, 148.46,
121.60, 119.56, 117.08, 112.53, 110.28, 108.81, 107.79, 88.89,
66.04, 55.21, 55.13, 55.11, 52.48, 48.45. IR (KBr) v/cmꢂ1: 2918,
1631, 1512, 1286, 1105, 860, 804. EIMS: m/z 443 [M]þ, HR-
30,40,7-Trimethoxy-5-hydroxy-6-[(dimethylamino)methyl]-
flavothione (6a)
Yellow solid, yield: 80%; m.p.: 230–231°C; 1H NMR (400 MHz,
CDCl3) d 13.85 (s, 1H, OH-5), 7.56 (d, J ¼ 8.6 Hz, 1H, H-60), 7.38 (s,
1H, H-20), 7.29 (s, 1H, H-3), 6.93 (d, J ¼ 8.5 Hz, 1H, H-50), 6.45 (s,
1H, H-8), 3.93, 3.91, 3.88 (s, 9H, 3OCH3), 3.65 (s, 2H, 6-CH2N),
2.26 (s, 6H, 2NCH3); 13C NMR (100 MHz, CDCl3) d 196.43,
162.85, 161.56, 153.49, 151.58, 151.07, 148.48, 122.02, 119.73,
116.31, 112.07, 110.38, 107.97, 98.95, 95.78, 55.34, 55.21,
55.14, 49.61, 44.46. IR (KBr) v/cmꢂ1: 2926, 1633, 1589, 1514,
1458, 1375, 1263, 1139, 1022, 812. ESI-MS (m/z): 402 [MþH]þ.
EIMS: m/z calcd. for
C
23H25O6NS 443.1397[M]þ, found
443.1403.
30,40,7-Trimethoxy-5-hydroxy-6-[(4-methylpiperazin-1-yl)-
methyl]-flavothione (6f)
Yellow solid, yield: 86%; m.p.: 221–223°C; 1H NMR (400 MHz,
CDCl3) d 7.50 (d, J ¼ 8.4 Hz, 1H, H-60), 7.27 (s, 2H, H-3 and 20),
6.90 (d, J ¼ 8.5 Hz, 1H, H-50), 6.44 (s, 1H, H-8), 3.92, 3.90, 3.87 (s,
9H, 3OCH3), 3.66 (s, 2H, 6-CH2N), 2.48 (m, 8H, 2CH2NCH2), 2.20
(s, 3H, NCH3); 13C NMR (100 MHz, CDCl3) d 196.07, 163.05,
159.75, 153.08, 152.68, 151.55, 148.46, 121.66, 119.55, 117.09,
112.56, 110.28, 109.10, 107.81, 88.82, 55.21, 55.13, 55.05,
30,40,7-Trimethoxy-5-hydroxy-6-[(diethylamino)methyl]-
flavothione (6b)
Yellow solid, yield: 80%; m.p.: 119–120°C; 1H NMR (400 MHz,
CDCl3) d 7.48 (d, J ¼ 8.5 Hz, 1H, H-60), 7.26 (s, 2H, H-3 and 20),
6.89 (d, J ¼ 8.5 Hz, 1H, H-50), 6.44 (s, 1H, H-8), 3.92, 3.89, 3.88 (s,
9H, 3OCH3), 3.60 (s, 2H, 6-CH2N), 2.56 (q, J ¼ 7.1 Hz, 4H,
ß 2017 Deutsche Pharmazeutische Gesellschaft
(6 of 7) e1700044