8
I. Tomassoli et al. / European Journal of Medicinal Chemistry 46 (2011) 1e10
(KBr)
y
3205, 1658, 1558 cmꢁ1
;
1H NMR (DMSO-d6, 300 MHz)
Anal. Calcd. for C19H17N3O5: C, 62.12; H, 4.66; N, 11.44. Found: C,
d
13.19 (s, 1H), 12.01 (s, 1H), 11.08 (s, 1H), 10.10 (s, 1H), 8.51 (s, 1H),
62.19; H, 4.63; N, 11.41.
7.96 (d, J ¼ 7.9 Hz, 1H), 7.66 (t, J ¼ 7.7 Hz, 1H), 7.34 (t, J ¼ 7.3 Hz, 2H),
7.27 (t, J ¼ 7.7 Hz, 1H), 6.34 (d, J ¼ 8.4 Hz, 1H), 6.29 (s, 1H). Anal.
Calcd. for C17H13N3O5: C, 60.18; H, 3.86; N,12.38. Found: C, 60.24; H,
3.84; N, 12.31.
4.7.7. 4-Hydroxy-N’-[(1E)-(2-nitrophenyl)methylene]-2-oxo-1,2-
dihydroquinoline-3-carbohydrazide (6g)
Following the General procedure in section 5.6, the reaction of 2-
nitrobenzaldehyde (0.31 g, 2.05 mmol) with compound 5a (0.20 g,
4.7.2. 4-Hydroxy-N’-[(1E)-(2-hydroxy-5-methylphenyl)
0.91 mmol) gave product 6g (0.18 g, 56%): mp >260 ꢀC; IR (KBr)
y
methylene]-2-oxo-1,2-dihydroquinoline-3-carbohydrazide (6b)
Following the General procedure in section 5.6, the reaction of 2-
hydroxy-5-methyl-benzaldehyde (0.15 g,1.10 mmol) with compound
5a (0.25 g, 1.14 mmol) gave product 6b (0.31 g, 81%): mp >260 ꢀC, IR
;
3328, 3298, 3031, 1635, 1604, 1554 cmꢁ1 1H NMR (DMSO-d6,
300 MHz) 16.45 (s, 1H), 13.56 (s, 1H), 12.14 (s, 1H), 8.81 (s, 1H), 8.05
d
(m, 3H), 7.86 (m, 1H), 7.74 (m, 2H), 7.39 (m, 2H). Anal. Calcd. for
C17H12N4O5: C, 57.96; H, 3.43; N, 15.90. Found: C, 57.92; H, 3.45; N,
15.94.
(KBr)
300 MHz)
y ;
3001, 1651, 1612, 1581, 1546 cmꢁ1 1H NMR (DMSO-d6,
d
13.65 (s, 1H), 8.87 (s, 1H), 8.27 (d, J ¼ 7.9 Hz, 1H), 7.97
(t, J ¼ 7.5 Hz,1H) 7.67 (s,1H), 7.57 (t, J ¼ 7.5 Hz,1H), 7.39 (d, J ¼ 8.1 Hz,
1H), 7.11 (t, J ¼ 8.6 Hz,1H), 2.75 (s, 3H). Anal. Calcd. for C18H15N3O4: C,
64.09; H, 4.48; N, 12.46. Found: C, 64.12; H, 4.46; N, 12.38.
4.7.8. 4-Hydroxy-1-methyl-N’-[(1E)-(2-nitrophenyl)methylene]-2-
oxo-1,2-dihydroquinoline-3-carbohydrazide (6h)
Following the General procedure in section 5.6, the reaction of
2-nitrobenzaldehyde (0.78 g, 5.16 mmol) with compound 5b
(0.20 g, 0.86 mmol) gave product 6h (0.29 g, 92%): mp >260 ꢀC; IR
4.7.3. 4-Hydroxy-N’-[(1E)-(2-hydroxy-5-methoxyphenyl)
methylene]-2-oxo-1,2-dihydroquinoline-3-carbohydrazide (6c)
Following the General procedure in section 5.6, the reaction of
2-hydroxy-5-methoxy-benzaldehyde (0.28 g, 1.84 mmol) with
compound 5a (0.40 g, 1.83 mmol) gave product 6c (0.59 g, 92%): mp
(KBr) y d 8.67
1670, 1566, 1523 cmꢁ1; 1H NMR (DMSO-d6, 300 MHz)
(s, 1H), 8.15 (s, 1H), 8.11 (d, J ¼ 7.6 Hz, 1H), 8.07 (s, 1H), 7.83 (t,
J ¼ 6.9 Hz, 1H), 7.67 (m, 2H), 7.48 (s, 1H), 7.26 (s, 1H), 3.58 (s, 3H).
Anal. Calcd. for C18H14N4O5: C, 59.02; H, 3.85; N, 15.29. Found: C,
59.11; H, 3.82; N, 15.25.
>260 ꢀC; IR (KBr)
(DMSO-d6, 300 MHz)
y
3355, 1670, 1651, 1577, 1542 cmꢁ1
;
1H NMR
d
13.41 (s, 1H), 10.43 (s, 1H), 8.92 (s, 1H), 8.58
(s, 1H), 7.98 (d, J ¼ 7.9 Hz, 1H), 7.68 (t, J ¼ 7.9 Hz, 1H), 7.36 (d,
J ¼ 8.3 Hz, 1H), 7.23 (m, 1H), 7.12 (d, J ¼ 2.8 Hz, 1H), 6.90 (m, 3H),
3.69 (s, 3H). Anal. Calcd. for C18H15N3O5: C, 61.19; H, 4.28; N, 11.89.
Found: C, 61.26; H, 4.25; N, 11.82.
4.7.9. N’-[(1E)-(2,6-dichloro-3-nitrophenyl)methylene]-4-hydroxy-
2-oxo-1,2-dihydroquinoline-3-carbohydrazide (6i)
Followingthe Generalprocedure insection 5.6, the reactionof 2,6-
dichloro-3-nitro-benzaldehyde (1 g, 4.55 mmol) with compound 5a
(0.50 g, 2.30 mmol) gave product 6i (0.87 g, 92%): mp >260 ꢀC; IR
4.7.4. N’-[(E)-(2,4-dihydroxyphenyl)methylidene]-4-hydroxy-1-
methyl-2-oxo-1,2-dihydroquinoline-3-carbohydrazide (6d)
(KBr)
300 MHz)
y
3298, 3093, 1735, 1620, 1596, 1539 cmꢁ1; 1H NMR (DMSO-d6,
d
13.92 (s, 1H), 11.80 (s, 1H), 8.60 (s, 1H), 8.16 (d, J ¼ 8.5 Hz,
Following the General procedure in section 5.6, the reaction of
2,4-dihydroxybenzaldehyde (0.15 g, 1.1 mmol) with compound 5b
(0.25 g, 1.1 mmol) gave product 6d (0.30 g, 79%): mp >260 ꢀC; IR
1H), 8.01 (d, J ¼ 8.1 Hz,1H), 7.88 (d, J ¼ 8.7 Hz,1H), 7.66 (s,1H), 7.35 (s,
1H), 7.26 (s, 1H). Anal. Calcd. for C17H10Cl2N4O5: C, 48.48; H, 2.39; Cl,
16.83; N, 13.30. Found: C, 48.44; H, 2.37; Cl, 16.86; N, 13.25.
(KBr)
13.25 (s, 1H), 11.15 (s, 1H), 10.10 (s, 1H), 8.58 (s, 1H), 8.12
y ;
3460, 1624, 1581 cmꢁ1 1H NMR (DMSO-d6, 300 MHz)
d
4.7.10. N’-[(1E)-(2,6-dichloro-3-nitrophenyl)methylene]-4-
hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbohydrazide
(6j)
(d, J ¼ 7.7 Hz, 1H), 7.83 (t, J ¼ 7.7 Hz, 1H), 7.64 (d, J ¼ 8.6 Hz, 1H), 7.41
(d, J ¼ 7.5 Hz, 1H), 7.35 (d, J ¼ 8.6 Hz, 1H), 6.38 (d, J ¼ 8.4 Hz, 1H),
6.33 (s, 1H), 3.66 (s, 3H). Anal. Calcd. for C18H15N3O5: C, 61.19; H,
4.28; N, 11.89. Found: C, 61.25; H, 4.23; N, 11.84.
Following the General procedure in section 5.6, the reaction of
2,6-dichloro-3-nitro-benzaldehyde (0.78 g, 3.55 mmol) with
compound 5b (0.30 g, 1.28 mmol) gave product 6j (0.51 g, 91%): mp
4.7.5. 4-Hydroxy-N’-[(1E)-(2-hydroxy-5-methylphenyl)
methylene]-1-methyl-2-oxo-1,2-dihydroquinoline-3-
carbohydrazide (6e)
230 ꢀC; IR (KBr)
(DMSO-d6, 300 MHz)
J ¼ 8.7 Hz, 1H), 7.79 (s, 1H), 7.60 (s, 1H), 7.36 (s, 1H), 3.64 (s, 3H).
Anal. Calcd. for C18H12Cl2N4O5: C, 49.67; H, 2.78; Cl, 16.29; N, 12.87.
Found: C, 49.71; H, 2.76; Cl, 16.31; N, 12.82.
y ;
3058, 1635, 1577, 1558, 1519 cmꢁ1 1H NMR
d
8.66 (s, 1H), 8.15 (d, J ¼ 7.2 Hz, 2H), 7.87 (d,
Following the General procedure in section 5.6, the reaction of
2-hydroxy-5-methyl-benzaldehyde (0.15 g, 1.10 mmol) with
compound 5b (0.25 g, 1.07 mmol) gave product 6e (0.34 g, 93%): mp
>260 ꢀC; IR (KBr)
(DMSO-d6, 300 MHz)
y
2985, 1624, 1589, 1558, 1519 cmꢁ1
;
1H NMR
4.7.11. 5-Chloro-N’-[(E)-(2,4-dihydroxyphenyl)methylidene]-4-
hydroxy-2-oxo-1,2-dihydroquinoline-3-carbohydrazide (6k)
Following the General procedure section 5.6, the reaction of 2,4-
dihydroxybenzaldehyde (0.04 g, 0.20 mmol) with compound 5c
(0.05 g, 0.20 mmol) gave product 6k (0.04 g, 54%): mp >260 ꢀC; IR
d
12.55 (s,1H), 9.95 (s,1H), 7.81 (s,1H), 7.30 (d,
J ¼ 7.7 Hz, 1H), 7.00 (t, J ¼ 8.1 Hz, 1H), 6.82 (d, J ¼ 8.6 Hz, 1H), 6.58
(d, J ¼ 7.5 Hz, 1H), 6.53 (s, 1H), 6.30 (d, J ¼ 8.3 Hz, 1H), 6.01 (d,
J ¼ 8.3 Hz, 1H), 2.83 (s, 3H), 1.41 (s, 3H). Anal. Calcd. for C19H17N3O4:
C, 64.95; H, 4.88; N, 11.96. Found: C, 64.92; H, 4.86; N, 11.95.
(KBr)
y
3159, 2896, 1639, 1589, 1554 cmꢁ1
;
1H NMR (DMSO-d6,
300 MHz)
d
13.10 (s, 1H), 11.97 (s, 1H), 10.84 (s, 1H), 9.87 (s, 1H), 8.35
4.7.6. 4-Hydroxy-N’-[(1E)-(2-hydroxy-5-methoxyphenyl)
methylene]-1-methyl-2-oxo-1,2-dihydroquinoline-3-
carbohydrazide (6f)
(s, 1H), 7.39 (t, J ¼ 8.1 Hz, 1H), 7.17 (d, J ¼ 7.8 Hz, 2H), 7.11 (d,
J ¼ 8.8 Hz, 2H), 6.15 (d, J ¼ 8.4 Hz, 1H), 6.11 (s, 1H). Anal. Calcd. for
C17H12ClN3O5: C, 54.63; H, 3.24; Cl, 9.49; N, 11.24. Found: C, 54.58;
H, 3.21; Cl, 9.52; N, 11.27.
Following the General procedure in section 5.6, the reaction of
2-hydroxy-5-methoxy-benzaldehyde (0.16 g, 1.05 mmol) with
compound 5b (0.25 g, 1.07 mmol) gave product 6f (0.33 g, 84%): mp
4.7.12. 5-Chloro-N’-[(E)-(2,4-dihydroxyphenyl)methylidene]-4-
hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carbohydrazide
(6l)
>260 ꢀC; IR (KBr)
d6, 300 MHz)
y
2966, 1643, 1562, 1535 cmꢁ1: 1H NMR (DMSO-
13.49 (s, 1H), 10.51 (s, 1H), 8.65 (s, 1H), 8.15 (d,
d
J ¼ 7.5 Hz, 1H), 7.82 (d, J ¼ 7.0 Hz, 1H), 7.65 (d, J ¼ 8.1 Hz, 1H), 7.40 (t,
Following the procedure section 5.6, the reaction of 2,4-dihy-
droxybenzaldehyde (20 mg, 0.14 mmol) with compound 5d (40 mg,
J ¼ 7.2 Hz, 1H), 7.15 (s, 1H), 6.92 (m, 2H) 3.74 (s, 3H), 3.67 (s, 3H).