Medicinal Chemistry Research
1721m, 1645m, 1586s, 1553m, 1528m, 1489m, 1467s,
1433m, 1412s, 1396m, 1381m, 1333s, 1272s, 1249s,
1198m, 1179s, 1160m, 1132s, 1075s, 1040m, 1011m,
3,6-Bis(diethylamino)-9[2-(1-thiomorpholinyl)carbonyl]-
xanthylium chloride (5)
1
974m, 923m, 824m, 708m, 682s, 668 m cm−1; H NMR
Yield: 471 mg (83%); m.p. 233 °C; RF = 0.35 (SiO2, CHCl3/
MeOH, 9:1); IR (ATR): ν = 3311w, 3060w, 2972w, 2906w,
1628m, 1585s, 1527m, 1508m, 1481m, 1467s, 1411s,
1394m, 1335s, 1305m, 1273s, 1245s, 1178s, 1131s, 1093m,
1072s, 1049m, 1036m, 1008m, 951m, 920m, 742m, 682s,
(500 MHz, CDCl3): δ = 8.29–8.25 (m, 1H, 23H), 7.79 (dt,
J = 7.6, 1.4 Hz, 1H, 25H), 7.72 (dt, J = 7.7, 1.3 Hz, 1H,
24H4), 7.30 (dd, J = 7.6, 1.3 Hz, 1H, 26H), 7.06 (d,
J = 9.3 Hz, 2H, 30H + 30′H), 6.86 (d, J = 2.5 Hz, 2H,
21H + 21′H), 6.85–6.83 (m, 2H, 33H + 33′H), 3.98 (t,
J = 6.7 Hz, 2H, 20H), 3.62 (q, J = 7.4 Hz, 8H, 35H + 35′
H + 35′′H + 35′′′H), 1.42–1.37 (m, 2H, 18Ha + 18Hb),
1.31 (t, J = 7.1 Hz, 12H, 36H + 36′H + 36′′H + 36′′′H),
1.29–1.26 (m, 2H, 2Ha + 2Hb), 1.24–1.14 (m, 28H, 3Ha +
3Hb + 4H–17H), 1.13–1.07 (m, 2H, 19Ha + 19Hb), 0.86 (t,
J = 6.9 Hz, 3H, 1H) ppm; 13C NMR (126 MHz, CDCl3): δ
= 165.2 (C-21), 158.9 (C-22), 157.8 (C-34 + C-34′),
155.6 (C-32 + C-32′), 133.4 (C-27), 133.0 (C-25), 131.3
(C-30 + C-30′), 131.2 (C-23), 130.3 (C-24), 130.3 (C-26),
130.2 (C-28), 114.1 (C-21 + C-21′), 113.6 (C-29 + C-29′),
96.5 (C-33 + C-33′), 65.8 (C-20), 46.1 (C-35 + C-35′ +
C-35′′ + C-35′′′), 31.9 (C-3), 29.7–29.2 (C-4–C-17), 28.3
(C-18), 25.8 (C-19), 22.7 (C-2), 14.1 (C-1), 12.6 (C-36
+C-36′ + C-36′′ + C-36′′′) ppm; MS (ESI, MeOH): m/z =
723.7 (100%, [M]+); analysis calcd for C48H71ClN2O3
(759.56): C 75.90, H 9.42, N 3.69; found: C 75.75, H 9.61,
N 3.55.
1
665 m cm−1; H NMR (500 MHz, CDCl3): δ = 7.64–7.60
(m, 2H, 7H7 + 8H), 7.48–7.45 (m, 1H, 5H), 7.29–7.27 (m,
1H, 6H), 7.17 (d, J = 9.5 Hz, 2H, 12H + 12′H), 6.93 (dd,
J = 9.5, 2.4 Hz, 2H, 13H + 13′H), 6.72 (d, J = 2.5 Hz, 2H,
15H + 15′H), 3.59 (qd, J = 7.3, 2.1 Hz, 8H, 17H + 17′H +
17′′H + 17′′′H), 3.58–3.46 (m, 4H, 2H + 2′H), 2.47–2.37
(m, 4H, 1H + 1′H), 1.27 (t, J = 7.1 Hz, 12H, 18H + 18′H +
18′′H + 18′′′H) ppm; 13C NMR (126 MHz, CDCl3): δ =
167.7 (C-3), 157.7 (C-14), 155.6 (C-16 + C-16′), 155.6 (C-
4), 135.3 (C-9), 132.1 (C-12 + C-12′), 130.5 (C-10), 130.3
(C-7), 130.2 (C-6), 130.0 (C-8), 127.3 (C-5), 114.2 (C-13 +
C-13′), 113.7 (C-11 + C-11′), 96.3 (C-15 + C-15′), 50.0 (C-
2a), 46.2 (C-17 + C-17′ + C-17′′ + C-17′′′), 44.1 (C-2b),
27.6 (C-1), 12.6 (C-18 + C-18′ + C-18′′ + C-18′′′) ppm; MS
(ESI, MeOH): m/z = 528.4 (100%, [M]+); analysis calcd for
C32H38ClN3O2S (564.19): C 68.13, H 6.79, N 7.45, S 5.68;
found: C 67.90, H 6.82, N 7.29, S 5.56.
3,6-Bis(diethylamino)-9[2-(1-(2,6-dimethylmorpholinyl)
carbonyl)]-xanthylium chloride (6)
3,6-Bis(diethylamino)-9[2-(1-morpholinyl)carbonyl]-
xanthylium chloride (4)
Yield: 483 mg (84%); m.p. 179–181 °C; RF = 0.38 (SiO2,
CHCl3/MeOH, 9:1); IR (ATR): ν = 2974w, 2933w, 2871w,
1644m, 1629m, 1585s, 1528m, 1507m, 1481m, 1467m,
1455m, 1431m, 1411s, 1394m, 1331s, 1272s, 1245s,
1196m, 1178s, 1159s, 1131s, 1094m, 1071s, 1039m,
Yield: 503 mg (92%); m.p. >250 °C; RF = 0.34 (SiO2,
CHCl3/MeOH, 9:1); IR (ATR): ν = 3356w, 3060w, 2976w,
2933w, 2871w, 2795w, 2605w, 2498w, 1644m, 1624m,
1584s, 1528m, 1508m, 1481s, 1465s, 1446s, 1431s, 1411s,
1394s, 1334s, 1271s, 1245s, 1196m, 1178s, 1161s, 1132s,
1094m, 1071s, 1008m, 976m, 921m, 822m, 740s, 682s,
1
1009m, 975m, 920m, 823m, 682s, 666 m cm−1; H NMR
(500 MHz, CDCl3): δ = 7.69–7.65 (m, 2H, 7H + 8H),
7.51–7.48 (m, 1H, 5H), 7.36–7.33 (m, 1H, 6H), 7.26–7.19
(m, 2H, 12H + 12′H), 6.96–6.87 (m, 2H, 13H + 13′H),
6.83–6.79 (m, 2H, 15H + 15′H), 4.12 (d, J = 13.2 Hz, 1H,
2Ha), 3.66–3.57 (m, 8H, 17H + 17′H + 17′′H + 17′′′H),
3.42 (d, J = 12.7 Hz, 1H, 2′Ha), 3.22–3.12 (m, 2H, 1H),
3.09–3.00 (m, 2H, 1′H), 2.58 (t, J = 11.9 Hz, 1H, 2H′b),
2.21 (t, J = 11.6 Hz, 1H, 2Hb), 1.30 (t, J = 7.1 Hz, 12H,
18H + 18′H+18′′H + 18′′′H), 1.08–0.98 (m, 6H, 19H +
19′H) ppm; 13C NMR (126 MHz, CDCl3): δ = 167.3 (C-3),
157.7 (C-14), 155.8 (C-16), 155.6 (C-16′), 155.5 (C-4),
135.2 (C-9), 132.4 (C-12), 131.9 (C-12′), 130.3 (C-10),
130.3 (C-7), 130.3 (C-6), 130.0 (C-8), 127.6 (C-5), 114.1
(C-13), 113.9 (C-13′), 113.7 (C-11), 113.6 (C-11′), 96.5 (C-
15 + C-15′), 71.9 (C-1), 71.7 (C-1′), 52.9 (C-2), 47.1 (C-2′),
46.1 (C-17 + C-17′ + C-17′′ + C-17′′′), 18.6 (C-19), 18.4
(C-19′), 12.60 (C-18 + C-18′ + C-18′′ + C-18′′′) ppm; MS
(ESI, MeOH): m/z = 540.4 (100%, [M]+); analysis calcd for
655m, 657 m cm−1 1H NMR (500 MHz, CDCl3): δ =
;
7.65–7.62 (m, 2H, 7H + 8H), 7.50–7.47 (m, 1H, 5H),
7.32–7.29 (m, 1H, 6H), 7.19 (d, J = 9.5 Hz, 2H, 12H + 12′
H), 6.95 (dd, J = 9.6, 2.4 Hz, 2H, 13H + 13′H), 6.73 (d, J
= 2.5 Hz, 2H, 15H + 15′H), 3.60 (q, J = 7.2 Hz, 8H, 17H
+ 17′H + 17′′H + 17′′′H), 3.45–3.40 (m, 4H, 1H + 1′H),
3.39–3.29 (m, 4H, 2H + 2′H), 1.28 (t, J = 7.1 Hz, 12H,
18H + 18′H + 18′′H + 18′′′H) ppm; 13C NMR (126 MHz,
CDCl3): δ = 167.4 (C-3), 157.7 (C-14), 155.7 (C-4), 155.6
(C-16 + C-16′), 135.0 (C-9), 132.0 (C-12 + C-12′), 130.7
(C-10), 130.3 (C-7), 130.2 (C-6), 130.1 (C-8), 127.6 (C-5),
114.2 (C-13 + C-13′), 113.7 (C-11 + C-11′), 96.3 (C-15 +
C-15′), 66.6 (C-1), 48.0 (C-2a), 46.2 (C-17 + C-17′ + C-17′
′ + C-17′′′), 42.2 (C-2b), 12.6 (C-18 + C-18′ + C-18′′ + C-
18′′′) ppm; MS (ESI, MeOH): m/z = 512.3 (100%, [M]+);
analysis calcd for C32H38ClN3O3 (548.12): C 70.12, H 6.99,
N 7.67; found: C 69.84, H 7.17, N 7.49.