Med Chem Res
N’-(4-methoxybenzylidene)-4-methylbenzenesulfonohydrazide
(3e) Red crystal; mp 105 °C; IR (KBr) tmax, cm-1: 3265
(NH), 3045 (Ar–H), 2868 (=CH), 1628 (C=N), 1370, 1160
(C, C-4), 125.8 (C, C-3, C-5), 129.6 (C, C-2, C-6), 135.5
(C, C-13), 137.3 (C, C-10), 141.4 (C, C-1), 148.8 (C, C-12,
C-14), 154.9 (HC=N, C-8); MS (70 eV, m/z): 365.51
(M ? 1). Anal. calcd for C17H20N2O5S: C, 56.03; H, 5.53;
N, 7.69. Found: C, 55.90; H, 5.60; N, 7.75.
1
(SO2); H NMR (300 MHz, CDCl3): d ppm 2.39 (s, 3H,
CH3), 3.81 (s, 3H, OCH3), 6.82–6.89 (m, 2H, Ar–H), 7.29
(d, 2H, Ar–H, J 8.1), 7.48–7.54 (m, 2H, Ar–H), 7.86 (d,
2H, Ar–H, J 8.1), 7.73 (s, 1H, –N=CH–Ar), 8.10 (s, 1H,
NH); 13C NMR (75 MHz, CDCl3): d ppm 21.5 (CH3, C-7),
55.3 (OCH3, C-18), 114.0 (C, C-12, C-14), 122.4 (C, C-4),
127.9 (C, C-3, C-5), 129.0 (C, C-11, C-15), 129.6 (C, C-2,
C-6), 135.2 (C, C-10), 144.1 (C, C-1), 148.5 (HC=N, C-8),
162.5 (C, C-13); MS (70 eV, m/z): 305.39 (M ? 1). Anal.
calcd for C15H16N2O3S: C, 59.19; H, 5.30; N, 9.20. Found:
C, 58.90; H, 5.21; N, 8.95.
N’-(2,4-dimethoxybenzylidene)-4-methylbenzenesulfonohy-
drazide (3i) Yellow powder; mp 125 °C; IR (KBr) tmax
,
cm-1: 3270 (NH), 3040 (Ar–H), 2970 (=CH), 1620 (C=N),
1
1340, 1125 (SO2); H NMR (300 MHz, CDCl3): d ppm
2.35 (s, 3H, CH3), 3.40 (s, 3H, OCH3), 3.78 (s, 3H, OCH3),
6.72–7.85 (m, 7H, Ar–H), 7.80 (s, 1H, =CH), 8.08 (s, 1H,
NH); 13C NMR (75 MHz, CDCl3): d ppm 20.1 (CH3, C-7),
58.3 (-OCH3, C-18), 64.5 (-OCH3, C-16), 99.9 (C, C-14),
106.1 (C, C-12), 110.5 (C, C-11), 122.3 (C, C-4), 126.4 (C,
C-3, C-5), 129.9 (C, C-2, C-6), 135.9 (C, C-10), 141.8 (C,
C-1), 154.9 (HC=N, C-8), 164.2 (C, C-13), 168.2 (C,
C-15); MS (70 eV, m/z): 335.42 (M ? 1). Anal. calcd for
C16H18N2O4S: C, 57.47; H, 5.43; N, 8.38. Found: C, 57.55;
H, 5.30; N, 8.47.
N’-(3-methoxybenzylidene)-4-methylbenzenesulfonohydrazide
(3f) Yellow powder; mp 130 °C; IR (KBr) tmax, cm-1
3265 (NH), 3060 (Ar–H), 2980 (=CH), 1620 (C=N), 1365,
:
1
1155 (SO2); H NMR (300 MHz, CDCl3): d ppm 2.33 (s,
3H, CH3), 3.74 (s, 3H, OCH3), 6.82–6.86 (m, 1H, Ar–H),
7.02–7.08 (m, 2H, Ar–H), 7.16 (s, 1H, Ar–H), 7.23 (d, 2H,
Ar–H, J 8.4), 7.65 (s, 1H, –N=CH–Ar), 7.80 (d, 2H, Ar–H,
J 8.4), 7.98 (s, 1H, NH); 13C NMR (75 MHz, CDCl3): d
ppm 21.1 (CH3, C-7), 56.3 (OCH3, C-17), 114.2 (C, C-13),
116.2 (C, C-15), 120.8 (C, C-11), 122.1 (C, C-4), 126.2 (C,
C-3, C-5), 128.3 (C, C-12), 129.7 (C, C-2, C-6), 136.4 (C,
C-10), 141.8 (C, C-1), 156.0 (HC=N,C-8), 162.1 (C, C-14);
MS (70 eV, m/z): 305.12 (M ? 1). Anal. calcd for C15-
H16N2O3S: C, 59.19; H, 5.30; N, 9.20. Found: C, 59.25; H,
5.15; N 9.32.
N’-(1-(4-aminophenyl)ethylidene)-4-methylbenzenesulfonohy-
drazide (3j) Yellow powder; mp 188 °C; IR (KBr) tmax
,
cm-1: 3260 (NH), 3010 (Ar–H), 3050, 3450 (NH2) 1615
1
(C=N), 1360, 1165 (SO2); H NMR (300 MHz, CDCl3): d
ppm 2.10 (s, 3H, CH3), 2.32 (s, 3H, CH3), 2.5 (s, 2H, NH2),
6.70–7.77 (m, 8H, Ar–H), 10.2 (s, 1H, NH); 13C NMR
(75 MHz, CDCl3): d ppm 17.7 (CH3, C-9), 21.1 (CH3,
C-7), 126.2 (C, C-3, C-5), 121.2 (C, C-4), 115.3 (C, C-11,
C-15), 130.7 (C-2, C-6), 129.9 (C, C-12, C-14), 136.5 (C,
C-10), 141.5 (C, C-1), 149.5 (C, C-13), 155.6 (H3C-C=N,
C-8); MS (70 eV, m/z): 334.41 (M ? 1). Anal. calcd for
C15H17N3O2S: C, 59.38; H, 5.65; N, 13.85. Found: C,
59.48; H, 5.58; N, 13.94.
N’-(3,4-dimethoxybenzylidene)-4-methylbenzenesulfonohy-
drazide (3g) Yellow solid; mp 129 °C; IR (KBr) tmax
,
cm-1: 3260 (NH), 3058 (Ar–H), 2945 (=CH), 1625 (C=N),
1
1375, 1173 (SO2); H NMR (300 MHz, CDCl3): d ppm
N’-(1-(4-nitrophenyl)ethylidene)-4-methylbenzenesulfonohy-
2.23 (s, 3H, CH3), 3.43 (s, 6H, OCH3), 6.75–7.87 (m, 7H,
Ar–H), 7.75 (s, 1H, –N=CH–Ar), 8.02 (s, 1H, NH); 13C
NMR (75 MHz, CDCl3): d ppm 20.0 (CH3, C-7), 56.4
(OCH3, C-17, C-18), 108.9 (C, C-12), 111.1 (C, C-15),
115.2 (C, C-11), 122.2 (C, C-4), 128.1 (C, C-3, C-5), 129.9
(C, C-2, C-6), 136.8 (C, C-10), 143.9 (C, C-1), 147.8 (C,
C-14), 149.6 (C, C-13), 151.3 (HC=N, C-8); MS (70 eV,
m/z): 335.41 (M ? 1). Anal. calcd for C16H18N2O4S: C,
57.47; H, 5.43; N, 8.38. Found: C, 58.23; H, 5.65; N, 8.45.
drazide (3k) Orange powder; mp 173 °C; IR (KBr) tmax
,
cm-1: 3282 (NH), 3120 (Ar–H), 1645 (C=N), 1350, 1145
(SO2), 1520, 1325 (NO2); 1H NMR (300 MHz, DMSO-d6):
d ppm 2.01 (s, 3H, CH3), 2.35 (s, 3H, CH3), 7.20–7.99 (m,
8H, Ar–H), 9.75 (s, 1H, NH); 13C NMR (75 MHz, DMSO-
d6): d ppm 17.8 (CH3, C-9), 21.2 (CH3, C-7), 121.5 (C,
C-4), 123.8 (C, C-3, C-5), 124.7 (C, C-11, C-15), 128.3 (C,
C-2, C-6), 129.9 (C, C-12, C-14), 137.5 (C, C-10), 142.0
(C, C-1), 150.8 (C, C-13), 157.1 (H3C-C=N, C-8); MS
(70 eV, m/z): 304.21 (M ? 1). Anal. calcd for C15H15N3-
O4S: C, 54.04; H, 4.54; N, 12.60. Found: C, 54.15; H, 4.85;
N, 12.32.
N’-(3,4,5-trimethoxybenzylidene)-4-methylbenzenesulfono-
hydrazide (3h) Red powder; mp 142 °C; IR (KBr) tmax
,
cm-1: 3268 (NH), 3085 (Ar–H), 2940 (=CH), 1630 (C=N),
1
1360, 1160 (SO2); H NMR (300 MHz, CDCl3): d ppm
2.25 (s, 3H, CH3), 3.74 (s, 9H, OCH3), 6.76–7.81 (m, 6H,
Ar–H), 7.76 (s, 1H, –N=CH–Ar), 8.05 (s, 1H, NH); 13C
NMR (75 MHz, CDCl3): d ppm 20.6 (CH3, C-7), 56.7
(OCH3, C-17, C-18, C-19), 107.9 (C, C-11, C-15), 125.5
Antibacterial activity
The antibacterial activities of the synthesized compounds
3a–k were determined by agar diffusion method as
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