Synthesis, antitumor evaluation, and molecular docking studies of indole–indazolyl…
887,793 cm-1
;
1H NMR (DMSO-d6, 500 MHz):
5-Nitro-N0-[(E)-(5-nitro-1H-indol-3-yl)methylidene]-1H-
indazole-3-carbohydrazide (10e, C17H11N7O5)
d = 11.75 (bs, 1H, NH), 11.57 (bs, 1H, NH), 10.92 (bs,
1H, NH), 8.95 (s, 1H), 8.38–8.32 (m, 1H), 8.22–8.13 (m,
1H), 7.91 (s, 1H), 7.78–7.76 (m, 1H), 7.51–7.41 (m, 1H),
7.24-7.08 (m, 3H) ppm; 13C NMR (solid state, 125 MHz):
d = 177, 160, 143, 138, 137, 134, 130, 126, 125, 124, 122,
113, 112 ppm; MS (ESI): m/z = 349 ([M?H]?).
This compound 10e was prepared following the method
described for the preparation of the compound 10a,
employing 500 mg 8 (1.0 eq.) with 2.26 mmol 5-nitroin-
dole-3-aldehyde (1.0 eq.) to afford 10e. Yellow color solid;
yield 92 %; m.p.: 300–302 °C; IR (neat): mꢀ = 3367, 3306,
1
3108, 3027, 1648, 1575, 1524, 1431, 827, 733 cm-1; H
N0-[(E)-(1-Methyl-1H-indol-3-yl)methylidene]-5-nitro-1H-
indazole-3-carbohydrazide (10b, C18H14N6O3)
NMR (DMSO-d6, 500 MHz): d = 11.33 (bs, 1H, NH),
11.13 (bs, 1H, NH), 9.06 (s, 2H), 8.20 (s, 1H), 8.06–7.97
(m, 3H), 7.63 (d, 2H, J = 8.85 Hz) ppm; 13C NMR (solid
state, 125 MHz): d = 177, 144, 142, 139, 137, 132, 126,
124, 121, 120, 119, 118, 116, 115, 114, 112 ppm; MS
(ESI): m/z = 394 ([M?H]?).
This compound 10b was prepared following the method
described for the preparation of the compound 10a,
employing 500 mg 8 (1.0 eq.) with 2.26 mmol 1-methylin-
dole-3-aldehyde (1.0 eq.) to afford 10b. Yellow color
ꢀ
solid; yield 90 %; m.p.: 153–155 °C; IR (neat): m = 3524,
3204, 3061, 1652, 1617, 1541, 1463, 915, 803, 730 cm-1
;
N0-[(E)-(5-Methoxy-1H-indol-3-yl)methylidene]-5-nitro-
1H-indazole-3-carbohydrazide (10f, C18H14N6O4)
1H NMR (DMSO-d6, 500 MHz): d = 11.81 (bs, 1H, NH),
11.23 (bs, 1H, NH), 8.37–8.11 (m, 2H), 7.88 (s, 1H),
7.73–7.71 (m, 1H), 7.53-7.46 (m, 2H), 7.31–7.13 (m, 3H),
3.84 (s, 3H) ppm; 13C NMR (solid state, 125 MHz):
d = 174, 158, 142, 139, 138, 127, 123, 112, 35 ppm; MS
(ESI): m/z = 363 ([M?H]?).
This compound 10f was prepared following the method
described for the preparation of the compound 10a,
employing 500 mg 8 (1.0 eq.) with 2.26 mmol 5-
methoxyindole-3-aldehyde (1.0 eq.) to afford 10e. Yellow
color solid; yield 84 %; m.p.: 210–212 °C; IR (neat):
ꢀ
m = 3458, 3363, 3199, 2989, 1637, 1574, 1534, 1486, 803,
N0-[(E)-(5-Bromo-1H-indol-3-yl)methylidene]-5-nitro-1H-
indazole-3-carbohydrazide (10c, C17H11BrN6O3)
712 cm-1 1H NMR (DMSO-d6, 500 MHz): d = 11.54
;
(bs, 1H, NH), 11.11 (bs, 1H, NH), 10.92 (bs, 1H, NH), 8.14
(s, 1H), 7.69–7.65 (m, 3H), 7.33 (d, 2H, J = 8.5 Hz),
6.83–6.81 (m, 2H), 3.76 (s, 3H) ppm; 13C NMR (solid
state, 125 MHz): d = 176, 157, 141, 133, 131, 127, 117,
114, 113, 103, 55 ppm; MS (ESI): m/z = 379 ([M?H]?).
This compound 10c was prepared following the method
described for the preparation of the compound 10a,
employing 500 mg 8 (1.0 eq.) with 2.26 mmol 5-bromoin-
dole-3-aldehyde (1.0 eq.) to afford 10c. Yellow color solid;
ꢀ
yield 89 %; m.p.: 235–237 °C; IR (neat): m = 3438, 3382,
3152, 3080, 1741,1650, 1541, 1341, 892,757 cm-1 1H
;
N0-[(E)-(5-Methoxy-1-methyl-1H-indol-3-yl)methylidene]-
5-nitro-1H-indazole-3-carbohydrazide
NMR (DMSO-d6, 500 MHz): d = 11.96, 11.17 (bs, 1H,
NH), 11.02 (bs, 1H, NH), 8.36–8.15 (m, 3H), 7.82 (s, 2H),
7.45-7.29 (m, 3H) ppm; 13C NMR (solid state, 125 MHz):
d = 177, 142, 136, 130, 127, 112 ppm; MS (ESI): m/
z = 428 ([M?H]?).
(10g, C19H16N6O4)
This compound 10g was prepared following the method
described for the preparation of the compound 10a,
employing 500 mg 8 (1.0 eq.) with 2.26 mmol 5-meth-
oxy-1-methylindole-3-aldehyde (1.0 eq.) to afford 10g.
Yellow color solid; yield 86 %; m.p.: 178–180 °C; IR
N0-[(E)-(5-Bromo-1-methyl-1H-indol-3-yl)methylidene]-5-
nitro-1H-indazole-3-carbohydrazide
ꢀ
(neat): m = 3497, 3184, 3026, 1665, 1610, 1532, 1486,
(10d, C18H13BrN6O3)
851, 795 cm-1 1H NMR (DMSO-d6, 500 MHz):
;
This compound 10d was prepared following the method
described for the preparation of the compound 10a,
employing 500 mg 8 (1.0 eq.) with 2.26 mmol 1-methyl-
5-bromoindole-3-aldehyde (1.0 eq.) to afford 10d. Yellow
color solid; yield 91 %; m.p.: 206–208 °C; IR (neat):
d = 11.14 (bs, 1H, NH), 10.96 (bs, 1H, NH), 8.11 (s,
1H), 7.68–7.62 (m, 3H), 7.39–7.34 (m, 2H), 6.91–6.87 (m,
2H), 3.77 (s, 6H) ppm; 13C NMR (solid state, 125 MHz):
d = 174, 169, 157, 144, 142, 136, 134, 133, 126, 124, 121,
118, 115, 114, 111, 102, 57, 33 ppm; MS (ESI): m/z = 393
([M?H]?).
ꢀ
m = 3441, 3186, 3085, 1660, 1541, 1400, 1368, 885,
785 cm-1 1H NMR (DMSO-d6, 500 MHz): d = 11.68
;
(bs, 1H, NH), 11.21 (bs, 1H, NH), 8.84 (s, 1H), 7.94–7.80
(m, 3H), 7.44 (s, 1H), 7.34–7.20 (m, 3H), 3.64 (s, 3H) ppm;
13C NMR (solid state, 125 MHz): d = 174, 158, 157, 139,
138, 136, 134, 128, 113, 34 ppm; MS (ESI): m/z = 442
(M?H)?.
5-Nitro-N0-[(E)-(5-nitro-1H-indazol-3-yl)methylidene]-1H-
indazole-3-carbohydrazide (10h, C16H10N8O5)
The compound 10h was prepared following the method
described for the preparation of the compound 10a,
employing 500 mg compound 8 (1.0 eq.) with 2.26 mmol
123