10.1002/cmdc.201800749
ChemMedChem
FULL PAPER
d6, 25 °C, TMS): δ = 6.49 (d, J = 7.9 Hz, 2H), 6.74–6.79 (m, 4H), 6.99 (t,
J = 7.3 Hz, 1H), 7.60 (d, J = 8.6 Hz, 2H), 7.77–7.88 (m, 3H), 8.00 (t, J =
5.8 Hz, 4H), 8.08 (d, J = 8.7 Hz, 3H), 8.26 (d, J = 8.1 Hz, 1H), 8.30 (s,
1H), 9.66 (s, 1H), 10.87 (s, 1H) ppm. 13C NMR (100 MHz, DMSO-d6): δ =
115.9, 120.4, 121.5, 124.4 (d, J = 3.65 Hz), 125.9, 126.0, 126.2, 126.3,
127.1, 128.0, 128.1, 128.3, 128.5 (q, J = 30.0 Hz), 129.4, 129.7, 130.8,
131.3, 132.0, 132.5, 133.4, 134.2, 134.5, 135.1, 136.5, 141.1, 141.6,
143.2, 164.6, 179.9, 180.9 ppm. 19F NMR (600 MHz, DMSO-d6): δ = –
60.9 ppm. Anal. calcd for C36H23F3N2O5S2 (684): C, 63.15; H, 3.39; N,
4.09; S, 9.36. Found: C, 63.29; H, 3.39; N, 4.06; S, 9.72.
125.9, 126.0, 126.2, 126.3, 127.1, 127.9, 128.1, 128.2, 129.4, 129.8,
130.8, 131.4, 132.5, 133.4, 134.4, 135.7, 141.0, 141.6, 143.8, 162.2,
165.3, 179.9, 180.9 ppm. Anal. calcd for C36H26N2O6S2 (646): C, 66.86; H,
4.05; N, 4.33; S, 9.91. Found: C, 66.50; H, 4.05; N, 4.70; S, 10.23.
N-(4-((4-((1,4-dioxo-3-(phenylthio)-1,4-dihydronaphthalen-2-
yl)amino)phenyl)sulfonyl)phenyl)-4-methylbenzamide (5i)
Blue violet solid (98%); mp >300 ºC; IR (KBr) ṽ [cm-1] = 724, 835, 1105,
1244, 1402, 1502, 1591, 1610, 1631, 3260. 1H NMR (400 MHz, DMSO-
d6, 25 °C, TMS): δ = 2.37 (s, 3H), 6.49 (d, J = 7.6 Hz, 2H), 6.74–6.78 (m,
4H), 6.99 (t, J = 7.1 Hz, 1H), 7.34 (d, J = 7.8 Hz, 2H), 7.59 (d, J = 8.8 Hz,
2H), 7.80–7.89 (m, 4H), 7.95 (d, J = 8.7 Hz, 2H), 8.01 (d, J = 7.4 Hz, 1H),
8.08 (d, J = 8.7 Hz, 3H), 9.65 (s, 1H), 10.58 (s, 1H) ppm. 13C NMR (100
MHz, DMSO-d6): δ = 21.0, 115.8, 120.1, 121.5, 125.9, 126.0, 126.2,
126.4, 127.9, 128.0, 128.1, 128.2, 128.9, 130.8, 131.3, 131.4, 132.5,
133.4, 134.4, 134.5, 135.9, 141.1, 141.6, 142.1, 143.7, 165.8, 180.0,
180.9 ppm. Anal. calcd for C36H26N2O5S2 (630): C, 68.55; H, 4.16; N,
4.44; S, 10.17. Found: C, 68.28; H, 4.03; N, 4.51; S, 9.82.
3,5-dichloro-N-(4-((4-((1,4-dioxo-3-(phenylthio)-1,4-dihydronaphthalen-2-
yl)amino)phenyl)sulfonyl)phenyl)benzamide (5e)
Light maroon solid (93%); mp >300 ºC; IR (KBr) ṽ [cm-1] = 663, 750, 1016,
1255, 1397, 1407, 1518, 1643, 1684, 3070, 3314, 3388. 1H NMR (400
MHz, DMSO-d6, 25 °C, TMS): δ = 6.48 (d, J = 7.6 Hz, 2H), 6.73–6.78 (m,
4H), 6.98 (t, J = 7.4 Hz, 1H), 7.59 (d, J = 8.6 Hz, 2H), 7.81–7.87 (m, 3H),
7.97–8.01 (m, 5H), 8.03 (s, 1H), 8.06 (d, J = 5.8 Hz, 2H), 9.65 (s, 1H),
10.80 (s, 1H) ppm. 13C NMR (100 MHz, DMSO-d6): δ = 115.9, 120.4,
121.5, 125.9, 126.0, 126.2, 126.3, 126.6, 127.1, 128.0, 128.1, 128.2,
129.4, 130.8, 131.2, 131.3, 132.4, 133.4, 134.2, 134.3, 134.4, 136.6,
137.4, 141.1, 141.5, 143.0, 163.2, 179.9, 180.9 ppm. Anal. calcd for
C35H22Cl2N2O5S2 (684): C, 61.32; H, 3.23; N, 4.09; S, 9.35. Found: C,
4-(tert-butyl)-N-(4-((4-((1,4-dioxo-3-(phenylthio)-1,4-dihydronaphthalen-2-
yl)amino)phenyl)sulfonyl)phenyl)benzamide (5j)
Blue violet solid (75%); mp >300 ºC; IR (KBr) ṽ [cm-1] = 718, 849, 1106,
1148, 1243, 1296, 1402, 1502, 1536, 1586, 1664, 1682, 2956, 3264,
3397. 1H NMR (400 MHz, DMSO-d6, 25 °C, TMS): δ = 1.30 (s, 9H), 6.49
(d, J = 7.4 Hz, 2H), 6.74–6.78 (m, 4H), 6.99 (t, J = 7.4 Hz, 1H), 7.55 (d, J
= 7.5 Hz, 2H), 7.59 (d, J = 8.6 Hz, 2H), 7.83 (qd, J = 7.7 Hz & J = 1.5 Hz,
2H), 7.89 (d, J = 8.4 Hz, 2H), 7.95 (d, J = 8.8 Hz, 2H), 8.01 (dd, J = 7.4
Hz & J = 1.5 Hz, 1H), 8.07 (d, J = 8.7 Hz, 3H), 9.65 (s, 1H), 10.60 (s, 1H)
ppm. 13C NMR (100 MHz, DMSO-d6): δ = 30.8, 34.6, 115.8, 120.0, 121.5,
125.1, 125.9, 126.0, 126.2, 126.3, 127.6, 127.9, 128.1, 128.2, 130.8,
131.4, 131.5, 132.4, 133.3, 134.4, 134.4, 135.9, 141.1, 141.7, 143.6,
154.9, 165.9, 179.9, 180.8 ppm. Anal. calcd for C39H32N2O5S2 (672): C,
69.62; H, 4.79; N, 4.16; S, 9.53. Found: C, 69.23; H, 4.69; N, 4.20; S,
9.48.
61.56; H, 3.27; N, 4.35; S, 9.72; Beilstein test: Cl positive [23]
.
N-(4-((4-((1,4-dioxo-3-(phenylthio)-1,4-dihydronaphthalen-2-
yl)amino)phenyl)sulfonyl)phenyl)-3,5-dinitrobenzamide (5f)
Violet solid (92%); mp >300 ºC; IR (KBr) ṽ [cm-1] = 717, 915, 1107, 1286,
1480, 1537, 1698, 3094, 3269, 3410. 1H NMR (400 MHz, DMSO-d6,
25 °C, TMS): δ = 6.48 (d, J = 7.4 Hz, 2H), 6.73–6.78 (m, 4H), 6.99 (t, J =
7.3 Hz, 1H), 7.60 (d, J = 8.7 Hz, 2H), 7.82 (dt, J = 6.4 Hz & J = 1.4 Hz,
1H), 7.86 (dt, J = 6.5 Hz & J = 1.4 Hz, 1H), 7.99–8.10 (m, 6H), 9.00 (t, J =
2.1 Hz, 1H), 9.16 (d, J = 2.1 Hz, 2H), 9.66 (s, 1H), 11.21 (s, 1H) ppm. 13
C
NMR (100 MHz, DMSO-d6): δ = 115.9, 120.7, 121.4, 125.9, 126.0, 126.3,
126.3, 127.1, 127.5, 128.0, 128.1, 128.2, 128.3, 129.4, 130.8, 131.2,
132.4, 133.4, 134.1, 134.5, 136.8, 137.0, 141.1, 141.4, 142.6, 148.0,
161.9, 179.9, 181.0 ppm. Anal. calcd for C35H22N4O9S2 (706): C, 59.49; H,
3.14; N, 7.93; S, 9.07. Found: C, 59.55; H, 3.11; N, 7.71; S, 9.45.
N-(4-((4-((1,4-dioxo-3-(phenylthio)-1,4-dihydronaphthalen-2-
yl)amino)phenyl)sulfonyl)phenyl)-4-fluorobenzamide (5k)
Blue violet solid (95%); mp >300 ºC; IR (KBr) ṽ [cm-1] = 725, 1105, 1296,
1402, 1502, 1537, 1665, 1687, 3258. 1H NMR (400 MHz, DMSO-d6,
25 °C, TMS): δ = 6.49 (d, J = 7.8 Hz, 2H), 6.74–6.79 (m, 4H), 6.99 (t, J =
7.4 Hz, 1H), 7.37 (t, J = 8.8 Hz, 2H), 7.59 (d, J = 8.6 Hz, 2H), 7.82 (t, J =
7.3 Hz, 1H), 7.85 (dt, J = 6.8 Hz & J = 1.2 Hz, 1H), 7.96 (d, J = 8.8 Hz,
2H), 8.00–8.07 (m, 6H), 9.64 (s, 1H), 10.67 (s, 1H) ppm. 13C NMR (100
MHz, DMSO-d6): δ = 115.3, 115.5, 115.8, 120.2, 121.5, 125.9, 126.0,
126.2, 126.4, 128.0, 128.1, 128.2, 129.4, 130.6, 130.7, 131.4, 132.5,
133.4, 134.3, 136.1, 141.1, 141.6, 143.5, 164.2, (d, J = 249.0 Hz), 164.9,
180.0, 180.9 ppm. 19F NMR (600 MHz, DMSO-d6): δ = –107.8 ppm. Anal.
calcd for C35H23FN2O5S2 (634): C, 66.23; H, 3.65; N, 4.41; S, 10.10.
Found: C, 65.87; H, 3.71; N, 4.54; S, 10.13.
N-(4-((4-((1,4-dioxo-3-(phenylthio)-1,4-dihydronaphthalen-2-
yl)amino)phenyl)sulfonyl)phenyl)-3-nitrobenzamide (5g)
Blue violet solid (96%); mp >300 ºC; IR (KBr) ṽ [cm-1] = 607, 717, 844,
1107, 1150, 1403, 1537, 1590, 1663, 3096, 3268. 1H NMR (400 MHz,
DMSO-d6, 25 °C, TMS): δ = 6.48 (d, J = 7.7 Hz, 2H), 6.73–6.78 (m, 4H),
6.99 (t, J = 7.2 Hz, 1H), 7.60 (d, J = 8.6 Hz, 2H), 7.81 (t, J = 7.2 Hz, 1H),
7.85 (t, J = 7.2 Hz, 1H), 7.99–8.10 (m, 7H), 9.00 (s, 1H), 9.16 (d, J = 1.6
Hz, 2H), 9.66 (s, 1H), 11.21 (s, 1H) ppm. 13C NMR (100 MHz, DMSO-
d6): δ = 115.9, 120.7, 121.4, 125.9, 126.0, 126.3, 126.3, 127.1, 127.5,
128.0, 128.1, 128.2, 128.3, 129.4, 130.8, 131.2, 132.4, 133.4, 134.1,
134.5, 136.8, 137.0, 141.1, 141.4, 142.6, 148.0, 161.8, 179.9, 180.9 ppm.
Anal. calcd for C35H23N3O7S2 (661): C, 63.53; H, 3.50; N, 6.35; S, 9.69.
Found: C, 63.15; H, 3.15; N, 6.73; S, 9.66.
4-chloro-N-(4-((4-((1,4-dioxo-3-(phenylthio)-1,4-dihydronaphthalen-2-
yl)amino)phenyl)sulfonyl)phenyl)benzamide (5l)
Blue violet solid (97%); mp >300 ºC; IR (KBr) ṽ [cm-1] = 1 565, 740, 845,
1106, 1148, 1402, 1501, 1631, 1686, 3254. 1H NMR (400 MHz, DMSO-
d6, 25 °C, TMS): δ = 6.49 (d, J = 8.1 Hz, 2H), 6.74–6.79 (m, 4H), 6.99 (t,
J = 6.6 Hz, 1H), 7.61 (dt, J = 8.6 Hz & J = 2.4 Hz, 4H), 7.82 (dt, J = 6.7
Hz & J = 1.4 Hz, 1H), 7.86 (dt, J = 7.1 Hz & J = 1.3 Hz, 1H), 7.93–7.96
(m, 2H), 7.98 (s, 2H), 8.00–8.02 (m, 2H), 8.06 (s, 1H), 8.08 (d, J = 1.3 Hz,
1H), 9.66 (s, 1H), 10.73 (s, 1H) ppm. 13C NMR (100 MHz, DMSO-d6): δ =
115.8, 120.2, 121.5, 125.9, 126.0, 126.2, 126.3, 127.1, 128.0, 128.1,
128.2, 128.5, 128.7, 129.4, 129.8, 131.1, 132.5, 132.9, 134.3, 136.2,
136.9, 141.1, 141.6, 143.4, 164.9, 180.0, 180.9 ppm. Anal. calcd for
N-(4-((4-((1,4-dioxo-3-(phenylthio)-1,4-dihydronaphthalen-2-
yl)amino)phenyl)sulfonyl)phenyl)-4-methoxybenzamide (5h)
Blue violet solid (88%); mp >300 ºC; IR (KBr) ṽ [cm-1] = 611, 724, 840,
1107, 1149, 1284, 1407, 1508, 1548, 1588, 1668, 3329, 3374. 1H NMR
(400 MHz, DMSO-d6, 25 °C, TMS): δ = 3.83 (s, 3H), 6.49 (d, J = 7.4 Hz,
2H), 6.73–6.78 (m, 4H), 6.99 (t, J = 7.3 Hz, 1H), 7.06 (d, J = 8.8 Hz, 2H),
7.59 (d, J = 8.7 Hz, 2H), 7.81 (dt, J = 6.7 Hz & J = 1.4 Hz, 1H), 7.85 (dt, J
= 7.8 Hz & J = 1.4 Hz, 1H), 7.96 (t, J = 9.0 Hz, 4H), 8.01 (dd, J = 7.9 Hz
& J = 1.4 Hz, 1H), 8.06–8.08 (m, 3H), 9.66 (s, 1H), 10.51 (s, 1H) ppm.
13C NMR (100 MHz, DMSO-d6): δ = 55.4, 113.6, 115.8, 120.0, 121.5,
7
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