10.1002/cbdv.201800470
Chemistry & Biodiversity
122.8 (C2), 125.2 (C4), 127.2 (C1’), 130.9 (C2’’, C6’’), 132.3 (C2’, C6’), 136.3 (C1’’), 142.3 (C9) , 143.6 (C=N), 156.9 (C4’’), 158.4 (C4’), 174.8 (C=S). Anal. Calcd. For C23H20N4O2S:
C, 66.33; H, 4.84; N, 13.45; Found: C, 66.41; H, 4.92; N, 13.51.
(E)‐4‐(4‐Methoxyphenyl)‐1‐((2‐(3,4,5‐trimethoxyphenyl)‐1H‐indol‐3‐yl)methylene) thiosemicarbazide (8j)
Pale yellow powder, Mp: 201‐203 C; Yield: 79%. IR (KBr, cm‐1): 3452, 3326 (N‐H stretching), 3136 (Aromatic C‐H stretching), 1606 (C=N), 1535 (C=C), 1261 (C‐N),
1196 (C=S), 1172 (C‐O). 1H NMR (500 MHz, DMSO‐d6) (, ppm): 3.81 (s, 3H, OCH3), 3.89 (s, 3H, OCH3), 3.95 (s, 3H, OCH3), 3.98 (s, 3H, OCH3), 6.78
(d, J = 8.4 Hz, 2H, H3'',5''), 6.90 (s, 1H, H2'), 7.17 (t, J = 8.9 Hz, 1H, H6), 7.27‐7.32 (m, 3H, H2'',6'',7), 7.39 (s,1H, H6'), 7.52 (d, J = 8.9 Hz , 1H, H8), 8.41(d, 1H, J = 8.9 Hz, H5),
8.97 (s, 1H, H‐C=N), 9.54 (s, 1H, NH‐Ph), 11.47 (s, 1H, NH‐C=S), 12.03 (s, 1H, NH‐indole). 13C NMR (125 MHz, DMSO‐d6) (, ppm): 54.2 (C4’’‐OCH3), 54.7
(C3’‐OCH3 , C5’‐OCH3), 55.5 (C4’‐OCH3), 105.0 (C3), 106.9 (C2’, C6’), 110.8 (C8), 120.2 (C3’’, C5’’), 121.9 (C5), 124.0 (C7), 124.9 (C6), 126.2 (C2), 126.9 (C4), 128.6 (C1’), 128.8
(C2’’, C6’’), 130.9 (C1’’), 131.5 (C9), 138.6 (C4’), 141.9 (C=N), 143.1 (C3’, C5’), 153.6 (C4’’), 174.2 (C=S). Anal. Calcd for C26H26N4O4S: C, 63.66; H, 5.34; N, 11.42; Found
C, 63.47; H, 5.22; N, 11.38.
(E)‐4‐(4‐Methoxyphenyl)‐1‐((2‐(4‐methoxyphenyl)‐1H‐indol‐3‐yl)methylene)thiosemicarbazide (8k)
Cream powder, Mp: 200‐202 C, Yield: 77%. IR (KBr, cm‐1): 3339 (N‐H stretching), 3130 (Aromatic C‐H stretching), 1601 (C=N), 1549 (C=C), 1275 (C‐N), 1237 (C=S),
1
1171 (C‐O). H NMR (500 MHz, DMSO‐d6) (, ppm): 3.77 (s, 3H, CH3), 4.03 (s, 3H, OCH3), 6.94 (d, J = 8.4 Hz, 2H, H3'',5''), 7.17 (t, J = 7.4, 1H, H6), 7.25
(t, J = 7.4 Hz, 1H, H7), 7.45‐7.47 (m, 3H, H3',5',8), 7.65‐7.69 (m, 4H, H2',6',2'',6''), 8.39 (d, J = 7.4 Hz, 1H, H5), 8.54 (s, 1H, H‐C=N), 9.44 (s, 1H, NH‐Ph), 11.46 (s, 1H, NH‐
C=S), 12.01 (s, 1H, NH‐indole). 13C NMR (DMSO‐d6) (, ppm): 55.2 (C4’‐OCH3), 55.4 (C4’’‐OCH3), 106.5 (C3), 111.3 (C8), 113.2 (C3’’, C5’’), 114.2 (C3’, C5’), 123.3 (C5), 124.9
(C7), 125.4 (C6), 126.4 (C2), 127.1 (C1’), 128.9 (C4), 130.7 (C2’’, C6’’), 136.3 (C2’, C6’), 137.0 (C1’’), 142.1 (C9), 142.9 (C=N), 158.7 (C4’’), 159.9 (C4’), 174.8 (C=S). Anal. Calcd.
For C24H22N4O2S: C, 66.96; H, 5.15; N, 13.01 Found: C, 67.10; H, 5.26; N, 12.90.
(E)‐1‐((2‐(4‐Chlorophenyl)‐1H‐indol‐3‐yl)methylene)‐4‐(4‐methoxyphenyl)thiosemicarbazide (8l)
Cream powder, MP 250 C, Yield: 81%. IR (KBr, cm‐1): 3339 (N‐H stretching), 3126 (Aromatic C‐H stretching), 1601 (C=N), 1542 (C=C), 1276 (C‐N), 1233 (C=S),
1175 (C‐O). 1H NMR (500 MHz, DMSO‐d6) (, ppm): 3.81 (s, 3H, OCH3), 6.98 (d, J = 7.9 Hz, 2H, H3'',5''), 7.21 (t, J = 7.0 Hz, 1H, H6), 7.29 (t, J = 7.0 Hz, 1H, H7), 7.48‐7.51
(m, 3H, H2'',6'',8), 7.68‐7.71 (m, 4H, H2',6',3',5'), 8.42 (d, J = 7.0 Hz, 1H, H5), 8.58 (s, 1H, H‐C=N), 9.46 (s, 1H, NH‐Ph), 11.48 (s, 1H, NH‐C=S), 12.03 (s, 1H, NH‐indole).
13C NMR (125 MHZ, DMSO‐d6) (, ppm): 54.9 (OCH3), 107.8 (C3), 111.2 (C8), 113.3 (C3’’, C5’’), 121.1 (C5), 122.8 (C7), 123.3 (C6), 125.2 (C2), 127.1 (C4), 128.9 (C2’’, C6’’),
129.8 (C2’, C6’), 131.0 (C3’, C5’), 132.2 (C1’’), 133.8 (C1’), 136.5 (C4’), 141.0 ( C9), 141.3 (C=N), 156.8 (C4’’), 174.9 (C=S). Anal. Calcd. for C23H19ClN4OS: C, 63.51; H, 4.40;
N, 12.88; Found: C, 63.45; H, 4.35; N, 12.75.
(E)‐1‐((2‐(4‐Bromophenyl)‐1H‐indol‐3‐yl)methylene)‐4‐(4‐methoxyphenyl)thiosemicarbazide (8m)
Pale yellow powder, Mp: 220‐222 C; Yield: 83%. IR (KBr, cm‐1): 3337 (N‐H stretching), 3128 (Aromatic C‐H stretching), 1600 (C=N), 1540 (C=C), 1272 (C‐N), 1234
(C=S), 1179 (C‐O). 1H NMR (500 MHz, DMSO‐d6) (, ppm): 3.77 (s, 3H, OCH3), 6.94 (d, J = 8.6 Hz, 2H, H3'',5''), 7.17 (t, J = 7.6 Hz, 1H, H6), 7.25 (t, J = 7.6 Hz, 1H, H7),
7.44‐7.47 (m, 3H, H2'',6'',8), 7.60 (d, J = 8.2 Hz, 2H, H3',5'), 7.79 (d, J = 8.2 Hz, 2H, H2',6'), 8.39 (d, J = 7.6 Hz, 1H, H5), 8.54 (s, 1H, H‐C=N), 9.44 (s, 1H, NH‐Ph), 11.46
(s, 1H, NH‐C=S), 12.02 (s, 1H, NH‐indole). 13C NMR (125 MHZ, DMSO‐d6) (, ppm): 55.2 (OCH3), 107.7 (C3), 111.6 (C8), 113.3 (C3’’, C5’’), 121.2 (C5), 122.4 (C7), 122.8
(C6), 123.4 (C2), 125.1 (C4), 127.2 (C2’’, C6’’), 130.1 (C2’, C6’), 131.3 (C3’, C5’), 131.9 (C1’’), 132.3 (C1’), 136.6 (C4’), 141.2 (C9), 141.4 (C=N), 156.8 (C4’’), 174.9 (C=S).
ESI‐MS (m/z): 480.08 ([M + H]+, C23H19BrN4OS; calc. 480.05). Anal. Calcd. for C23H19BrN4OS: C, 57.62; H, 3.99; N, 11.69 Found: C, 57.45; H, 4.20; N, 11.51.
(E)‐4‐(4‐Methoxyphenyl)‐1‐((2‐p‐tolyl‐1H‐indol‐3‐yl)methylene)thiosemicarbazide (8n)
Cream powder, Mp: 233‐234 C, Yield: 75%. IR (KBr, cm‐1): 3344 (N‐H stretching), 3130 (Aromatic C‐H stretching), 1602 (C=N), 1543 (C=C), 1276 (C‐N), 1233 (C=S),
1173 (C‐O). 1H NMR (500 MHz, DMSO‐d6): (, ppm) 2.41 (s, 3H, CH3), 3.77 (s, 3H, OCH3), 6.94 (d, J = 7.4 Hz, 2H, H3'',5''), 7.16 (t, J = 7.1 Hz, 1H, H6),
7.23 (t, J = 7.1 Hz, 1H, H7), 7.39‐7.44 (m, 3H, H3',5',8), 7.48 (d, J = 7.4 Hz, 2H, H2'',6''), 7.55 (d, J = 7.1 Hz, 2H, H2',6'), 8.35 (d, J = 7.1 Hz, 1H, H5), 8.57 (s, 1H, H‐C=N), 9.40
(s, 1H, NH‐Ph), 11.46 (s, 1H, NH‐C=S), 11.87 (s, 1H, NH‐indole). 13C NMR (125 MHZ, DMSO‐d6) (, ppm): 20.6 (CH3), 55.4 (OCH3), 107.1 (C3), 111.5 (C8), 113.3
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