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G. Nasr et al. / Bioorg. Med. Chem. 22 (2014) 2867–2874
using sodium sulfate. 1H NMR spectra were recorded on an ARX
300 MHz Bruker spectrometer in CDCl3 with the use of the residual
solvent CHCl3 peak as reference. Elemental analyses were per-
formed at Service d’Analyse de l’Université Montpellier II.
5.1.2.8. 4Bim: Methyl 4-(2-hydroxy-5-methoxybenzylideneimi-
no)benzoate.
1H NMR (300 MHz, 9:1 CDCl3:CD3OD) d: 3.725
(s, 3H, OCH3), 3.846 (s, 3H, COOCH3), 6.816–6.925 (m, 3H, Ar-H);
7.240–7.268, 7.984–8.012 (d, 2H, Ar-H from methyl benzoate),
8.953 (s, 1H, CH@N). Elem. anal calcd for C16H15NO4: C, 67.36; H,
5.30; N, 4.91; O, 22.43; found C, 67.12; H, 5.29; N, 4.7.
5.1.1. General synthesis of imine compounds
1 mmol of amine A–E and 1.1 mmol of aldehyde 1–4 were
introduced in 50 ml of CHCl3:MeOH (5:1, v/v). The solution was
stirred at reflux for 18 h. The solvent was then evaporated and
the pure imine compounds were obtained after precipitated by
ether.
5.1.2.9. 1Cim: 4-(Benzylidene-imino)-benzenesulfonamide. 1H
NMR (300 MHz, 9:1 CDCl3:CD3OD) d: 7.128–7.155 (d, 2H, Ar-H
from benzenesulfonamide) 7.38 (m, 3H, Ar-H), 7.79 (m, 4H, 2
Ar-H and 2 Ar-H from benzenesulfonamide), 8.319 (s, 1H, CH=N).
Elem. anal calcd for C13H12N2O2S: C, 59.98; H, 4.65; N, 10.76; O,
12.29; S, 12.32; found C, 59.95; H, 4.91; N, 10.38; S, 12.14.
5.1.2. Imines
5.1.2.1. 1Aim: 4-(Benzylideneimino) benzoic acid.
1H NMR
(300 MHz, CDCl3) d: 7.251–7.279 (d, 2H, Ar-H from benzoic acid
moiety), 7.491–7.585 (m, 3H, Ar-H), 7.92 (dd, 2H, Ar-H), 8.168–
8.191 (d, 2H, Ar-H from benzoic acid), 8.472 (s, 1H, CH@N). Elem.
anal. calcd for C14H11NO2: C, 74.65; H, 4.92; N, 6.22; O, 14.21;
found C, 74.36; H, 5.11; N, 6.09.
5.1.2.10. 2Cim
sulfonamide.
:
4-[(4-tert-Butyl-benzylidene)-imino]-benzene-
1H NMR (300 MHz, 9:1 CDCl3: CD3OD) d:
1.189 (s, 9H, tBu). 7.079–7.108 (d, 2H Ar-H from benzenesulfon-
amide), 7.346–7.374, 7.650–7.678 (d, 2H, Ar-H), 7.741–7.770 (d,
2H, Ar-H from benzenesulfonamide), 8.255 (s, 1H, CH@N). Elem.
anal. calcd for C17H20N2O2S: C, 64.53; H, 6.37; N, 8.85; O, 10.11;
S, 10.13; found C, 64.63; H, 6.47; N, 8.55; S, 9.70.
5.1.2.2.
acid.
2Aim
:
4-(4-tert-Butylbenzylideneimino)
benzoic
1H NMR (300 MHz, CDCl3) d: 1.191 (s, 9H, tBu), 7.042–
7.07 (d, 2H, Ar-H from benzoic acid), 7.349–7.377 (d, 2H, Ar-H),
7.656–7.684 (d, 2H, Ar-H), 7.894–7.922 (d, 2H, Ar-H from benzoic
acid), 8.282 (s, 1H, CH@N). Elem. anal. calcd for C18H19NO2: C,
76.84; H, 6.81; N, 4.98; O, 11.37; found C, 75.90; H, 6.60; N, 4.75.
5.1.2.11. 3Cim: 4-[(4-Hydroxy-benzylidene)-imino]-benzenesul-
fonamide.
6.567 (d, 2H, Ar-H), 6.895–6.924 (d, 2H, Ar-H from benzene sulfon-
amide), 7.402–7.431 (d, 2H, Ar-H), 7.543–7.571 (d, 2H, Ar-H from
benzene sulfonamide), 8.017 (s, 1H, CH@N). Elem. anal. calcd for
1H NMR (300 MHz, 9:1 CDCl3:CD3OD) d: 6.538–
5.1.2.3.
acid.
3Aim
:
4-(4-Hydroxybenzylideneimino)
benzoic
1H NMR (300 MHz, CDCl3) d: 6.880–6.852 (d, 2H, Ar-
C13H12N2O3S: C, 56.51; H, 4.38; N, 10.14; O, 17.37; S, 11.60; found
C, 56.31; H, 4.46; N, 10.05; S, 11.75.
H), 7.147–7.120 (d, 2H, Ar-H from benzoic acid), 7.727–7.700 (d,
2H, Ar-H), 7.981–7.953 (d, 2H, Ar-H from benzoic acid), 8.316 (s,
1H, CH@N). Elem. anal calcd for C14H11NO3: C, 69.70; H, 4.60; N,
5.81; O, 19.90; found C, 69.76; H, 4.96; N, 5.80.
5.1.2.12. 4Cim: 4-[(2-Hydroxy-5-methoxy-benzylidene)-imino]-
benzenesulfonamide.
1H NMR (300 MHz, 9:1 CDCl3:CD3OD)
d: 3.684 (s, 3H, OCH3), 6.918–7.049 (m, 3H, H-Ar), 7.352–7.381,
7.936–7.965 (d, 2H, Ar-H from benzenesulfonamide), 8.642 (s,
1H, CH@N). Elem. anal calcd for C14H14N2O4S: C, 54.89; H, 4.61;
N, 9.14; O, 20.89; S, 10.47; found C, 55.00; H, 4.87; N, 8.71; S, 10.22.
5.1.2.4. 4Aim: 4-(2-Hydroxy-5-methoxybenzylideneimino)ben-
zoic acid.
1H NMR (300 MHz, CDCl3) d: 3.772 (s, 3H, OCH3),
6.891–6.900 (d, 1H, Ar-H), 6.910–6.940 (d, 1H, Ar-H), 6.973–
6.982, 7.004–7.012 (dd, 1H, Ar-H), 7.252–7.279 (d, 2H, Ar-H from
benzoic acid), 8.055–8.082 (d, 2H, Ar-H from benzoic acid), 8.569
(s, 1H, CH@N). Elem. anal. calcd for C15H13NO4: C, 66.41; H, 4.83;
N, 5.16; O, 23.59; found C, 66.30; H 5.2; N 4.93.
5.1.2.13. 1Dim: 4-[(Benzylidene-imino)-methyl]-benzenesulfon-
amide.
1H NMR (300 MHz, 9 CDCl3:1 CD3OD) d: 5 (s, 2H, CH2),
7.066–7.095 (d, 2H, Ar-H from benzenesulfonamide), 7.275–7.375
(m, 3H, Ar-H), 7.692–7.760 (m, 4H, 2Ar-H from benzenesulfon-
amide and 2Ar-H), 8.25 (s, 1H, CH@N). Elem. anal calcd for C14H14-
N2O2S: C, 61.29; H, 5.14; N, 10.21; O, 11.66; S, 11.69; found C,
61.08; H, 5.17; N, 9.87; S, 11.38.
5.1.2.5. 1Bim
:
Methyl 4-(benzylideneimino)benzoate.
1H
NMR (300 MHz, 9:1 CDCl3:CD3OD) d: 3.930 (s, 3H, COOCH3),
7.198–7.227 (d, 2H, Ar-H from methyl benzoate), 7.5 (m, 3H, Ar-
H), 7.901–7.928 (d, 2H, Ar-H), 8.066–8.095 (d, 2H, Ar-H from
methyl benzoate), 8.441 (s, 1H, CH@N). Elem. Anal calcd for
5.1.2.14. 2Dim: 4-{[(4-tert-Butyl-benzylidene)-imino]-methyl}-
benzenesulfonamide.
1H NMR (300 MHz, 9 CDCl3:1 CH3OD)
C15H13NO2: C, 75.30; H, 5.48; N, 5.85; O, 13.37; found C, 75.25;
d: 1.177 (s, 9H, tBu), 3.162 (s, 2H, CH2), 7.073–7.102 (d, 2H, Ar-H
from benzenesulfonamide), 7.337–7.365, 7.639–7.667 (d, 2H, Ar-
H), 7.732–7.760 (d, 2H, Ar-H from benzenesulfonamide), 8.248 (s,
1H, CH@N). Elem. anal calcd for C18H22N2O2S: C, 66.26; H, 8.34;
N, 7.73; O, 8.83; S, 8.85; found C, 66.53; H, 8.84; N, 7.96.
H, 5.69; N, 5.61.
5.1.2.6. 2Bim: Methyl 4-(4-tert-butylbenzylideneimino)benzo-
ate.
1H NMR (300 MHz, 9:1 CDCl3/CD3OD) d: 1.363 (s, 9H,
tBu), 3.889 (s, 3H, COOCH3), 7.244–7.271 (d, 2H, Ar-H from methyl
benzoate), 7.564–7.592, 7.859–7.886 (d, 2H, Ar-H), 8.025–8.053 (d,
2H, Ar-H from methyl benzoate), 8.497 (s, 1H, CH@N). Elem. anal
calcd for C19H21NO2: C, 77.26; H, 7.17; N, 4.74; O, 10.83; found C,
77.07; H, 7.38; N, 4.43.
5.1.2.15. 3Dim
benzenesulfonamide.
:
4-{[(4-Hydroxy-benzylidene)-imino]-methyl}-
1H NMR (300 MHz, 9 CDCl3: 1 CD3OD)
d: 4.77 (s, 2H, CH2), 6.584–6.613 (d, 2H, Ar-H), 6.714–6.742 (d, 2H,
Ar-H from benzenesulfonamide), 7.157–7.185 (d, 2H, Ar-H), 7.524–
7.554 (d, 2H, Ar-H from benzenesulfonamide), 8.266 (s, 1H, CH@N).
Elem. anal calcd for C14H14N2O3S: C, 57.92; H, 4.86; N, 9.65; O,
16.53; S, 11.04; found C, 56.26; H, 4.98; N, 8.81; S, 11.40.
5.1.2.7. 3Bim
: Methyl 4-(4-hydroxybenzylideneimino)benzo-
ate.
1H NMR (300 MHz, 9:1 CDCl3:CD3OD) d: 3.946 (s, 3H,
COOCH3), 6.940–6.968 (d, 2H, Ar-H), 7.196–7.224 (d, 2H, Ar-H from
methyl benzoate), 7.828–7.857 (d, 2H, Ar-H), 8.070–8.098 (d, 2H,
Ar-H from methyl benzoate), 8.377 (s, 1H, CH@N). Elem. anal calcd
for C15H13NO3: C, 70.58; H, 5.13; N, 5.49; O, 18.80; found C, 69.81;
H, 5.01; N, 5.31.
5.1.2.16. 4Dim: 4-{[(2-Hydroxy-5-methoxy-benzylidene)-imino]-
methyl}-benzenesulfonamide.
1 CD3OD) d: 3.821 (s, 3H, OCH3), 6.914–6.923 (d, 1H, Ar-H),
6.977–7.007 (d, 1H, Ar-H), 7.043–7.053, 7.073–7.083 (dd, 1H,
1H NMR (300 MHz, 9 CDCl3: