M. Ansari, et al.
Bioorganic Chemistry 93 (2019) 103300
DMSO‑d
6
): δ 3.86 (s, 3H, OMe), 4.42 (s, 2H, CH
2
), 7.13 (d, 2H,
7.47 (s, 2H, H-2 and H-6), 7.55 (t, 2H, J = 8.8 Hz, H-3′ and H-5′), 8.22
+
J = 8.8 Hz, H-3′ and H-5′), 7.53–7.62 (m, 3H, H-3, H-4 and H-5), 7.99
(dd, 2H, J = 8.4 and 5.6 Hz, H-2′ and H-6′). MS (m/z, %) 400 (M
,
(
d, 2H, J = 8.8 Hz, H-2′ and H-6′), 8.02 (dd, 2H, J = 8.0 and 2.0 Hz, H-
100), 385 (30), 368 (27), 193 (54), 178 (33), 150 (12), 135 (25), 120
1
3
2
1
5
and H-6). C NMR (100 MHz, DMSO‑d
6
): δ 162.94, 156.78, 151.62,
(18), 95 (12), 75 (6). Anal. Calcd for C19
H
17FN
4
O
3
S: C, 56.99; H, 4.28;
43.71, 131.15, 130.09, 129.32, 128.60, 125.70, 125.65, 115.11,
N, 13.99. Found: C, 57.02; H, 4.13; N, 13.92.
+
1
6.09, 23.10. MS (m/z, %) 322 (M , 100), 307 (31), 147 (24), 133
Compound 10f: Yield: 65%; m.p: 215–217 °C; H NMR (400 MHz,
(
30), 118 (5), 103 (35), 77 (12), 58 (7). Anal. Calcd for C17
H
14
N
4
OS: C,
DMSO‑d
6
): δ 3.73 (s, 3H, OMe), 3.82 (s, 6H, OMe), 4.36 (s, 2H, CH ),
2
6
3.34; H, 4.38; N, 17.38. Found: C, 63.68; H, 4.29; N, 17.40.
7.30–7.35 (m, 1H, H-3′), 7.36 (s, 2H, H-2 and H-6), 7.52–7.59 (m, 1H,
1
+
Compound 9i: Yield: 66%; m.p: 264–266 °C; H NMR (400 MHz,
H-5′), 7.94–8.00 (m, 1H, H-6′). MS (m/z, %) 418 (M , 100), 403 (36),
DMSO‑d
6
): δ 2.40 (s, 3H, Me), 3.85 (s, 3H, OMe), 4.42 (s, 2H, CH
2
),
386 (26), 371 (9), 267 (9), 252 (5), 193 (55), 178 (35), 163 (5), 139
7
.13 (d, 2H, J = 8.8 Hz, H-3′ and H-5′), 7.39 (d, 2H, J = 8.0 Hz, H-3
(20), 120 (14), 64 (5). Anal. Calcd for C19
H
16
F
2
N
4
3
O S: C, 54.54; H,
and H-5), 7.90 (d, 2H, J = 8.4 Hz, H-2 and H-6), 7.99 (d, 2H,
3.85; N, 13.39. Found: C, 54.75; H, 3.86; N, 13.43.
+
1
J = 8.8 Hz, H-2′ and H-6′). MS (m/z, %) 336 (M , 40), 318 (100), 306
Compound 10g: Yield: 82%; m.p: 216–218 °C; H NMR (400 MHz,
DMSO‑d ): δ 3.86 (s, 3H, OMe), 3.94 (s, 6H, OMe), 4.55 (s, 2H, CH ),
7.47 (s, 2H, H-2 and H-6), 7.79 (d, 2H, J = 8.8 Hz, H-3′ and H-5′), 8.18
(
(
20), 265 (39), 237 (14), 205 (21), 161 (10), 150 (44), 133 (52), 117
50), 103 (14), 89 (31), 77 (25), 63 (20), 51 (12). Anal. Calcd for
6
2
1
3
C
18
6.58.
H
16
N
4
OS: C, 64.27; H, 4.79; N, 16.65. Found: C, 64.01; H, 4.81; N,
(d, 2H, J = 8.8 Hz, H-2′ and H-6′). C NMR (100 MHz, DMSO‑d ): δ
6
1
155.25, 153.40, 151.64, 142.73, 139.62, 137.33, 132.73, 129.73,
+
1
29.64, 121.61, 105.75, 60.63, 56.41, 22.92. MS (m/z, %) 416 (M
,
4
.1.4. General procedure for the preparation of compounds 10a-l
100), 401 (29), 281 (5), 264 (5), 193 (77), 178 (44), 150 (20), 135 (22),
A solution of compound 17 (282 mg, 1 mmol) and proper phenacyl
120 (20), 102 (13), 75 (12), 58 (5). Anal. Calcd for C19
H
17ClN
4
O S: C,
3
bromide 12a-l (1.2 mmol) in absolute ethanol (7 mL) was refluxed for
54.74; H, 4.11; N, 13.44. Found: C, 54.75; H, 3.96; N, 13.33.
1
1
–5 h. After cooling to room temperature, the reaction mixture was left
Compound 10h: Yield: 92%, m.p: 241–243 °C; H NMR (400 MHz,
in refrigerator overnight. The precipitated solid was separated and
washed with cool ethanol. The crude product was recrystallized from
ethanol to give corresponding pure compounds 10.
DMSO‑d
6
): δ 3.76 (s, 3H, OMe), 3.85 (s, 6H, OMe), 4.45 (s, 2H, CH
2
),
7.38 (s, 2H, H-2 and H-6), 7.83 (d, 2H, J = 8.8 Hz, H-3′ and H-5′), 8.00
1
3
(d, 2H, J = 8.8 Hz, H-2′ and H-6′). C NMR (100 MHz, DMSO‑d
6
): δ
1
Compound 10a: Yield: 87%; m.p: 198–200 °C; H NMR (250 MHz,
155.50, 153.40, 151.61, 142.84, 139.66, 133.06, 132.68, 129.81,
CDCl
3
): δ 3.92 (s, 6H, OMe), 3.94 (s, 3H, OMe), 4.14 (s, 2H, CH
2
), 7.53
126.34, 121.49, 105.79, 60.64, 56.44, 22.90. MS (m/z, %) 462 (M + 2,
+
(
s, 2H, H-2 and H-6), 7.54–7.75 (m, 3H, H-3′, H-4′ and H-5′), 7.96 (d,
69), 460 (M , 68), 447 (15), 416 (19), 401 (7), 281 (11), 264 (7), 208
1
3
2
1
1
1
7
H, J = 7.0 Hz, H-2′ and H-6′). C NMR (100 MHz, DMSO‑d
6
): δ
(14), 193 (93), 178 (53), 150 (26), 135 (28), 120 (26), 102 (30), 80
56.29, 153.40, 151.61, 142.85, 139.59, 133.89, 132.52, 129.64,
(100), 64 (12). Anal. Calcd for C19
H
17BrN
4
O
3
S: C, 49.47; H, 3.71; N,
+
27.88, 121.71, 105.74, 60.67, 56.41, 23.03. MS (m/z, %) 382 (M
,
12.14. Found: C, 49.45; H, 4.01; N, 12.37.
1
00), 364 (27), 264 (4), 193 (47), 178 (25), 163 (3), 135 (13), 103 (17),
Compound 10i: Yield: 72%; m.p: 263–265 °C; H NMR (400 MHz,
7 (17). Anal. Calcd for C19
H
18
N
4
O
3
S: C, 59.67; H, 4.74; N, 14.65.
DMSO‑d
6
): δ 3.85 (s, 3H, OMe), 3.96 (s, 6H, OMe), 4.48 (s, 2H, CH ),
2
Found: C, 59.50; H, 5.01; N, 14.65.
7.04 (d, 2H, J = 8.8 Hz, H-3′ and H-5′) 7.51 (s, 2H, H-2 and H-6), 8.04
1
13
Compound 10b: Yield: 76%; m.p: 230–232 °C; H NMR (400 MHz,
(d, 2H, J = 8.8 Hz, H-2′ and H-6′). C NMR (100 MHz, DMSO‑d
6
): δ
DMSO‑d
6
): δ 3.82 (s, 3H, OMe), 3.92 (s, 9H, OMe), 4.49 (s, 2H, CH
2
),
161.81, 156.47, 153.37, 151.07, 143.21, 139.73, 129.99, 124.07,
+
7
.22 (d, 2H, J = 8.8 Hz, H-3′ and H-5′), 7.48 (s, 2H, H-2 and H-6), 8.11
121.22, 116.46, 105.81, 60.66, 56.39, 22.75. MS (m/z, %) 398 (M
,
1
3
(
d, 2H, J = 8.8 Hz, H-2′ and H-6′). C NMR (100 MHz, DMSO‑d
6
): δ
15), 380 (14), 296 (13), 281 (100), 266 (47), 238 (16), 223 (14), 208
(16), 193 (54), 178 (38), 150 (23), 135 (38), 120 (58), 104 (9), 80 (18),
1
1
62.82, 155.83, 153.38, 151.40, 142.81, 139.53, 129.75, 125.90,
21.84, 115.07, 105.68, 60.64, 56.45, 56.03, 22.80. MS (m/z, %) 412
64 (20). Anal. Calcd for C19
H
18
N
4
O
4
S: C, 57.28; H, 4.55; N, 14.06.
+
(
M
, 100), 397 (21), 382 (29), 264 (8), 193 (57), 177 (30), 143 (14),
Found: C, 57.50; H, 4.56; N, 14.02.
1
1
33 (33), 103 (10), 77 (15), 51 (3). Anal. Calcd for C20
H
20
N
4
O
4
S: C,
Compound 10j: Yield: 77%; m.p: 255–257 °C; H NMR (400 MHz,
5
8.24; H, 4.89; N, 13.58. Found: C, 58.27; H, 5.00; N, 13.37.
DMSO‑d
6
): δ 3.85 (s, 3H, OMe), 3.95 (s, 6H, OMe), 4.44 (s, 2H, CH ),
2
1
Compound 10c: Yield: 84%; m.p: 238–240 °C; H NMR (400 MHz,
6.99 (d, 1H, J = 8.4 Hz, H-5′) 7.48 (s, 2H, H-2 and H-6), 7.49 (dd, 1H,
J = 8.4 and 2.4 Hz, H-6′), 7.65 (d, 1H, J = 2.4 Hz, H-2′). MS (m/z, %)
DMSO‑d
6
): δ 3.84 (s, 3H, OMe), 3.91 (s, 3H, OMe), 3.94 (s, 6H, OMe),
+
3
7
.95 (s, 3H, OMe), 4.53 (s, 2H, CH
2
), 7.26 (d, 1H, J = 8.4 Hz, H-5′),
414 (M , 19), 398 (19), 295 (15), 281 (100), 267 (46), 255 (45), 238
.49 (s, 2H, H-2 and H-6), 7.69 (d, 1H, J = 2.0 Hz, H-2′), 7.77 (dd, 1H,
(19), 223 (15), 207 (93), 196 (87), 178 (59), 150 (34), 135 (45), 120
+
J = 8.4 and 2.0 Hz, H-6′). MS (m/z, %) 442 (M , 26), 424 (100), 410
(40), 93 (21), 77 (22), 58 (47). Anal. Calcd for C19
H
18
N
4
O S: C, 55.06;
5
(
(
57), 281 (69), 267 (83), 252 (42), 224 (15), 209 (16), 193 (30), 178
26), 163 (26), 135 (14), 120 (16), 104 (7), 79 (9), 64 (16). Anal. Calcd
H, 4.38; N, 13.52. Found: C, 54.98; H, 4.39; N, 13.86.
1
Compound 10k: Yield: 78%; m.p: 230–232 °C; H NMR (400 MHz,
for C21
H
22
4
N O
5
S: C, 57.00; H, 5.01; N, 12.66. Found: C, 57.01; H, 4.89;
DMSO‑d
6
): δ 2.39 (s, 3H, Me), 3.76 (s, 3H, OMe), 4.36 (s, 6H, OMe),
N, 12.70.
4.44 (s, 2H, CH
2
), 7.40 (d, 4H, J = 8.0 Hz, H-3′ and H-5′), 7.41 (s, 2H,
1
13
Compound 10d: Yield: 72%; m.p: 210–212 °C; H NMR (400 MHz,
H-2 and H-6), 7.97 (d, 2H, J = 8.0 Hz, H-2′ and H-6′). C NMR
DMSO‑d
6
): δ 3.88 (s, 3H, OMe), 3.89 (s, 3H, OMe), 3.97 (s, 6H, OMe),
), 7.48 (s, 2H, H-2′ and H-6′), 7.52
): δ 156.43, 153.62,
(100 MHz, DMSO‑d ): δ 156.45, 153.38, 151.5, 142.95, 142.90, 139.70,
6
3
.98 (s, 6H, OMe), 4.59 (s, 2H, CH
2
130.93, 130.22, 127.88, 121.40, 105.80, 60.65, 56.45, 22.91, 21.53.
1
3
+
(
s, 2H, H-2 and H-6). C NMR (100 MHz, DMSO‑d
6
MS (m/z, %) 396 (M , 19), 381 (21), 281 (29), 266 (10), 207 (7), 193
1
1
53.42, 151.55, 143.22, 141.46, 139.87, 129.09, 121.62, 106.19,
(79), 178 (40), 150 (19), 135 (21), 117 (21), 91 (20), 64 (20). Anal.
+
05.88, 60.73, 56.64, 23.38. MS (m/z, %) 472 (M , 6), 454 (38), 439
Calcd for C20
H
20
N
4
O
3
S: C, 60.59; H, 5.08; N, 14.13. Found: C, 60.83; H,
(
(
(
15), 281 (100), 267 (82), 252 (44), 238 (20), 224 (20), 209 (15), 193
38), 178 (32), 164 (8), 150 (17), 135 (17), 120 (16), 93 (6), 79 (6), 64
5.36; N, 14.12.
1
Compound 10l: Yield: 83%; m.p: 248–250 °C; H NMR (400 MHz,
16). Anal. Calcd for C22
H
24
N
4
O
6
S: C, 55.92; H, 5.12; N, 11.86. Found:
DMSO‑d
6
): δ 3.78 (s, 3H, OMe), 3.89 (s, 6H, OMe), 4.52 (s, 2H, CH ),
2
C, 55.61; H, 5.06; N, 12.05.
7.44 (s, 2H, H-2 and H-6), 7.46 (t, 1H, J = 7.6 Hz, H-4″), 7.54 (t, 2H,
J = 7.2 Hz, H-3″ and H-5″), 7.80 (d, 2H, J = 7.2 Hz, H-2″ and H-6″),
7.94 (d, 2H, J = 8.8 Hz, H-3′ and H-5′), 8.18 (d, 2H, J = 8.4 Hz, H-2′
1
Compound 10e: Yield: 68%; m.p: 204–206 °C; H NMR (400 MHz,
DMSO‑d
6
): δ 3.84 (s, 3H, OMe), 3.93 (s, 6H, OMe), 4.54 (s, 2H, CH ),
2
10