X. Dou et al. / European Journal of Medicinal Chemistry 201 (2020) 112445
13
calcd for C16H12ClN2O2: 299.0587; found: 299.0597.
8.48 (s, 1H), 8.08 (d, J ¼ 8.0 Hz, 1H), 8.02 (d, J ¼ 7.3 Hz, 2H), 7.73 (d,
J ¼ 7.7 Hz, 1H), 7.62 (t, J ¼ 7.2 Hz, 1H), 7.54 (dt, J ¼ 15.6, 7.7 Hz, 4H),
4.1.17. (Z)-3-(2-(3-bromophenyl)-2-oxoethylidene)-3,4-
dihydroquinoxalin-2(1H)-one (J46e27)
7.16 (s, 3H), 6.86 (s, 1H). 13C NMR (101 MHz, DMSO‑d6)
d 188.64,
166.17, 156.21, 146.09, 140.09, 139.56, 135.23, 132.14, 129.53, 128.87,
128.16, 127.19, 124.60, 124.48, 124.14, 123.90, 122.60, 119.36, 117.06,
115.84, 89.62. HRMS (ESI) [MþH]þ calcd for C23H18N3O3: 384.1348;
found: 384.1353.
Compound J46e27 was prepared in a manner similar to that
described for J46 as a yellow solid. Yield: 55%. Mp 283e284 ꢁC. 1H
NMR (400 MHz, DMSO‑d6)
7.96 (d, J ¼ 7.8 Hz, 1H), 7.76 (d, J ¼ 7.9 Hz, 1H), 7.58e7.44 (m, 2H),
7.15 (s, 3H), 6.76 (s, 1H). 13C NMR (101 MHz, DMSO‑d6)
186.85,
d 13.63 (s, 1H), 12.10 (s, 1H), 8.05 (s, 1H),
d
4.1.23. Tert-butyl (Z)-(3-(2-(3-oxo-3,4-dihydroquinoxalin-2(1H)-
ylidene)acetyl)phenyl)carbamate (J46e34)
155.95, 146.51, 141.22, 134.87, 131.42, 129.93, 127.32, 126.47, 124.75,
124.34, 124.14, 122.65, 117.21, 115.85, 89.40. HRMS (ESI) [MþH]þ
calcd for C16H12BrN2O2: 343.0082; found: 343.0089.
Compound J46e34 was prepared in a manner similar to that
described for J46 as a yellow solid. Yield: 42%. Mp 231e232 ꢁC. 1H
NMR (400 MHz, DMSO‑d6) d 13.66 (s, 1H), 12.05 (s, 1H), 9.57 (s, 1H),
4.1.18. (Z)-3-(2-oxo-2-(m-tolyl)ethylidene)-3,4-dihydroquinoxalin-
2(1H)-one (J46e28)
8.19 (s, 1H), 7.64 (d, J ¼ 8.0 Hz, 1H), 7.58 (d, J ¼ 7.8 Hz, 1H), 7.52 (dd,
J ¼ 5.7, 3.7 Hz, 1H), 7.41 (t, J ¼ 7.9 Hz, 1H), 7.15 (s, 3H), 6.78 (s, 1H),
Compound J46e28 was prepared in a manner similar to that
1.50 (s, 9H). 13C NMR (101 MHz, DMSO‑d6)
d 188.80, 156.20, 153.27,
146.00, 140.47, 139.63, 129.52, 127.16, 124.60, 124.46, 124.15, 121.81,
121.12, 117.03, 115.83, 89.57, 79.75, 28.60. HRMS (ESI) [MþH]þ calcd
for C21H22N3O4: 380.1610; found: 380.1606.
described for J46 as a yellow solid. Yield: 64%. Mp 259e260 ꢁC. 1H
NMR (400 MHz, DMSO‑d6)
J ¼ 8.7 Hz, 2H), 7.48 (s, 1H), 7.39 (d, J ¼ 7.4 Hz, 2H), 7.13 (s, 3H), 6.80
(s, 1H), 2.39 (s, 3H). 13C NMR (101 MHz, DMSO‑d6)
189.00, 156.19,
d 13.65 (s, 1H), 12.04 (s, 1H), 7.76 (d,
d
145.92, 139.11, 138.44, 132.98, 129.06, 127.93, 127.12, 124.66, 124.57,
124.38, 124.10, 116.96, 115.80, 89.67, 21.46. HRMS (ESI) [MþH]þ
calcd for C17H15N2O2: 279.1134; found: 279.1135.
4.1.24. (Z)-3-(2-(2,3-dichlorophenyl)-2-oxoethylidene)-3,4-
dihydroquinoxalin-2(1H)-one (J46e35)
Compound J46e35 was prepared in a manner similar to that
described for J46 as a yellow solid. Yield: 74%. Mp 298e299 ꢁC. 1H
4.1.19. (Z)-3-(2-oxo-2-(3-(trifluoromethyl)phenyl)ethylidene)-3,4-
dihydroquinoxalin-2(1H)-one (J46e29)
NMR (400 MHz, DMSO‑d6) d 13.24 (s, 1H), 12.13 (s, 1H), 7.74 (d,
J ¼ 7.8 Hz, 1H), 7.61 (d, J ¼ 7.2 Hz, 1H), 7.54 (d, J ¼ 7.5 Hz, 1H), 7.47 (t,
Compound J46e29 was prepared in a manner similar to that
J ¼ 7.8 Hz, 1H), 7.16 (d, J ¼ 7.1 Hz, 3H), 6.31 (s, 1H). 13C NMR
described for J46 as a yellow solid. Yield: 38%. Mp 278e279 ꢁC. 1H
(101 MHz, DMSO‑d6)
d 189.59, 155.73, 145.89, 142.79, 133.03,
NMR (400 MHz, DMSO‑d6)
d
13.71 (s, 1H), 12.14 (s, 1H), 8.28 (d,
132.02, 129.10, 128.25, 128.03, 127.31, 124.93, 124.17, 117.34, 115.88,
93.40. HRMS (ESI) [MþH]þ calcd for C16H11Cl2N2O2: 333.0198;
found: 333.0202.
J ¼ 7.8 Hz, 1H), 8.20 (s, 1H), 7.94 (d, J ¼ 7.7 Hz, 1H), 7.77 (t, J ¼ 7.7 Hz,
1H), 7.55 (d, J ¼ 6.5 Hz, 1H), 7.16 (s, 3H), 6.83 (s, 1H). 13C NMR
(101 MHz, DMSO‑d6) d 186.71, 155.91, 146.79, 139.83, 131.39, 130.54,
130.03 (q, J ¼ 30.0 Hz, 1C), 128.61 (q, J ¼ 3.6 Hz, 1C), 127.39, 124.85,
4.1.25. (Z)-3-(2-(naphthalen-1-yl)-2-oxoethylidene)-6-nitro-3,4-
dihydroquinoxalin-2(1H)-one (J46e36)
124.44 (d, J ¼ 273.4 Hz, 1C), 124.30, 124.16, 123.62 (q, J ¼ 3.8 Hz, 1C),
117.27, 115.87, 89.31.19F NMR (376 MHz, DMSO‑d6)
d
ꢀ61.30. HRMS
Compound J46e36 was prepared in a manner similar to that
(ESI) [MþH]þ calcd for C17H12F3N2O2: 333.0851; found: 333.0860.
described for J46 as a yellow solid. Yield: 71%. Mp 312e313 ꢁC. 1H
NMR (400 MHz, DMSO‑d6)
(m, 2H), 8.16e7.76 (m, 4H), 7.57 (s, 3H), 7.18 (d, J ¼ 8.4 Hz, 1H), 6.62
(s, 1H). 13C NMR (101 MHz, DMSO‑d6)
193.63, 156.56, 144.02,
d 13.16 (s, 1H), 12.36 (s, 1H), 8.71e8.42
4.1.20. (Z)-3-(2-(3-methoxyphenyl)-2-oxoethylidene)-3,4-
dihydroquinoxalin-2(1H)-one (J46e30)
d
Compound J46e30 was prepared in a manner similar to that
143.11, 138.12, 133.91, 132.50, 131.72, 129.94, 128.91, 127.52, 127.09,
126.72, 125.83, 125.50, 125.03, 119.32, 115.95, 112.67, 95.64. HRMS
(ESI) [MþH]þ calcd for C20H14N3O4: 360.0984; found: 360.0989.
described for J46 as a yellow solid. Yield: 48%. Mp 233e234 ꢁC. 1H
NMR (400 MHz, DMSO‑d6)
J ¼ 7.6 Hz, 1H), 7.51 (d, J ¼ 4.7 Hz, 1H), 7.45 (d, J ¼ 7.6 Hz, 2H), 7.14 (s,
4H), 6.79 (s,1H), 3.83 (s, 3H). 13C NMR (101 MHz, DMSO‑d6)
188.51,
d 13.69 (s, 1H), 12.06 (s, 1H), 7.56 (d,
d
4.1.26. (Z)-3-(2-(naphthalen-1-yl)-2-oxoethylidene)-2-oxo-1,2,3,4-
tetrahydroquinoxaline-6-carbonitrile (J46e37)
159.96, 156.14, 146.08, 140.60, 130.34, 127.18, 124.52, 124.49, 124.14,
119.88, 118.28, 117.03, 115.82, 112.09, 89.65, 55.66. HRMS (ESI)
[MþH]þ calcd for C17H15N2O3: 295.1083; found: 295.1086.
Compound J46e37 was prepared in a manner similar to that
described for J46 as a yellow solid. Yield: 78%. Mp 327e328 ꢁC. 1H
NMR (400 MHz, DMSO‑d6)
d 13.23 (s, 1H), 12.28 (s, 1H), 8.63e8.43
4.1.21. (Z)-3-(2-(3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)
acetyl)benzonitrile (J46e31)
(m, 1H), 8.15 (d, J ¼ 1.5 Hz, 1H), 8.09 (d, J ¼ 8.2 Hz, 1H), 8.01 (dd,
J ¼ 6.5, 2.8 Hz, 1H), 7.86 (d, J ¼ 6.3 Hz, 1H), 7.59 (qd, J ¼ 7.3, 6.9,
2.8 Hz, 3H), 7.53 (dd, J ¼ 8.3, 1.7 Hz, 1H), 7.21 (d, J ¼ 8.3 Hz, 1H), 6.62
Compound J46e31 was prepared in a manner similar to that
described for J46 as a yellow solid. Yield: 44%. Mp 276e277 ꢁC. 1H
(s, 1H). 13C NMR (101 MHz, DMSO‑d6)
d 193.79, 156.42, 144.49,
NMR (400 MHz, DMSO‑d6)
d
13.69 (s, 1H), 12.11 (s, 1H), 8.33 (s, 1H),
138.23, 133.93, 131.71, 130.95, 129.94, 128.95, 127.81, 127.57, 127.08,
126.77, 125.83, 125.58, 125.30, 120.74, 119.21, 116.55, 105.74, 95.32.
HRMS (ESI) [MþH]þ calcd for C21H14N3O2: 340.1086; found:
340.1085.
8.26 (d, J ¼ 7.9 Hz, 1H), 8.01 (d, J ¼ 7.6 Hz, 1H), 7.72 (t, J ¼ 7.7 Hz, 1H),
7.53 (d, J ¼ 7.4 Hz, 1H), 7.15 (s, 3H), 6.82 (s, 1H). 13C NMR (101 MHz,
DMSO‑d6)
d 186.31, 155.87, 146.82, 139.85, 135.49, 131.93, 131.06,
130.52, 127.40, 124.90, 124.24, 124.15, 118.83, 117.32, 115.85, 112.43,
89.40. HRMS (ESI) [MþH]þ calcd for C17H12N3O2: 290.0930; found:
290.0937.
4.1.27. (Z)-8-methyl-3-(2-(naphthalen-1-yl)-2-oxoethylidene)-3,4-
dihydroquinoxalin-2(1H)-one (J46e38)
Compound J46e38 was prepared in a manner similar to that
4.1.22. (Z)-3-(2-(3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene)
acetyl)benzonitrile (J46e33)
described for J46 as a yellow solid. Yield: 66%. Mp 336e337 ꢁC. 1H
NMR (400 MHz, DMSO‑d6)
d 13.61 (s, 1H), 11.39 (s, 1H), 8.53 (d,
Compound J46e33 was prepared in a manner similar to that
J ¼ 7.8 Hz, 1H), 8.08 (d, J ¼ 8.2 Hz, 1H), 8.02 (d, J ¼ 7.8 Hz, 1H), 7.87
described for J46 as a yellow solid. Yield: 50%. Mp 332e333 ꢁC. 1H
(d, J ¼ 7.1 Hz, 1H), 7.61 (t, J ¼ 7.2 Hz, 3H), 7.43 (d, J ¼ 7.9 Hz, 1H), 7.08
NMR (400 MHz, DMSO‑d6)
d
13.68 (s,1H),12.06 (s,1H),10.46 (s,1H),
(t, J ¼ 7.7 Hz,1H), 7.02 (d, J ¼ 7.6 Hz,1H), 6.58 (s, 1H), 2.39 (s, 3H). 13
C