P. Vicini et al. / European Journal of Medicinal Chemistry 44 (2009) 1801e1807
1805
C, 58.73; H, 3.52; N, 9.78; S, 11.20. Found: C, 58.47; H, 3.81;
N, 9.38; S, 10.81.
(EtOH). TLC: eluent ¼ CH2Cl2/EtOH 98/2. IR(KBr) n: 3068
(aromatic CeH), 2980e2845 (aliphatic CeH), 1691 (C]O),
1
1601 (N]C) cmꢂ1. H NMR (300 MHz, DMSO-d6, d ppm):
5.1.1.3. 2-(Dodecylideneamino)-benzo[d]isothiazol-3(2H )-one
(1v). Yield: 72%; mp 38e40 ꢀC (Ligroin). TLC:
eluent ¼ Petroleum ether/AcOEt 1/1. IR(KBr) n: 3062 (aro-
matic CeH) 2930, 2858 (aliphatic CeH), 1675 (C]O),
8.29 (s, 1H, CH); 7.91 (d, 1H, J ¼ 8.1 Hz, H-7); 7.81 (s, 1H,
H-4); 7.71 (d, 1H, J ¼ 7.5 Hz, H-60); 7.66e7.51 (m, 3H, H-
20, H-40, H-6); 7.33 (t, 1H, J ¼ 8.4 Hz, H-50); 2.43 (s, 3H,
CH3). Anal. Calcd. for C15H11FN2OS (286.33): C, 62.92; H,
3.87; N, 9.78; S, 11.20. Found: C, 63.00; H, 4.15; N, 9.48;
S, 11.42.
1
1605 (N]C) cmꢂ1. H NMR (300 MHz, DMSO-d6, d ppm):
7.97 (d, 1H, J ¼ 8.2 Hz, H-4); 7.92 (d, 1H, J ¼ 7.8 Hz, H-7);
7.74 (t, 1H, J ¼ 7.4 Hz, H-5); 7.58 (t, 1H, J ¼ 5.0 Hz, CH);
7.46 (t, 1H, J ¼ 7.4 Hz, H-6); 2.43e2.36 (m, 2H, CH2);
1.55e1.22 (m, 18H, 9 CH2); 0.82 (t, 3H, CH3). Anal. Calcd.
for C19H28N2OS (332.50): C, 68.63; H, 8.49; N, 8.42; S,
9.64. Found: C, 69.04; H, 8.86; N, 8.10; S, 9.98.
5.1.1.8. 2-(4-Fluorobenzylideneamino)-5-methylbenzo[d]iso-
thiazol-3(2H )-one (4d). Yield: 63%; mp 193e194 ꢀC
(EtOH). TLC: eluent ¼ CH2Cl2/EtOH 95/5. IR(KBr) n:
3070e3052 (aromatic CeH), 2973, 2918, 2860 (aliphatic
CeH), 1666 (C]O), 1603 (N]C) cmꢂ1
.
1H NMR
5.1.1.4. N0-Dodecylidenebenzo[d]isothiazole-3-carboxydrazide
(2u). Yield: 55%; mp 65e67 ꢀC (Ligroin). TLC:
eluent ¼ Petroleum ether/AcOEt 1/1. IR(KBr) n: 3190 (Ne
H), 3055 (aromatic CeH) 2918, 2850 (aliphatic CeH), 1662
(300 MHz, DMSO-d6, d ppm): 8.30 (s, 1H, CH); 7.95e7.90
(m, 3H, H-20, H-60, H-7); 7.80 (s, 1H, H-4); 7.62 (d, 1H,
H-6); 7.37e7.31 (m, 2H, H-30, H-50); 2.43 (s, 3H, CH3).
Anal. Calcd. for C15H11FN2OS (286.33): C, 62.92; H, 3.87;
N, 9.78; S, 11.20. Found: C, 63.02; H, 4.08; N, 9.46; S,
11.38.
1
(C]O), 1623 (N]C) cmꢂ1. H NMR (300 MHz, DMSO-
d6, d ppm): 11.90 (s, 1H, NH); 8.71 (d, 1H, J ¼ 8.1 Hz, H-
4); 8.29 (d, 1H, J ¼ 8.1 Hz, H-7); 7.88 (t, 1H, J ¼ 5.5 Hz,
CH); 7.68e7.56 (m, 2H, H-5, H-6); 2.24 (td, 2H,
J ¼ 7.5 Hz, J ¼ 5.5 Hz CH2); 1.44 (quint, 2H, J ¼ 6.9 Hz
CH2); 1.24e1.19 (m, 16H, 8 CH2); 0.80 (t, 3H, J ¼ 6.6 Hz
CH3). Anal. Calcd. for C20H29N3OS (359.53): C, 66.81; H,
8.13; N, 11.69; S, 8.92. Found: C, 67.16; H, 8.42; N, 11.46,
S, 9.24.
5.1.1.9. 2-(3-Hydroxybenzylideneamino)-5-methylbenzo[d]iso-
thiazol-3(2H )-one (4m). Yield: 65%; mp 228e230 ꢀC (Diox-
ane). TLC: eluent ¼ CH2Cl2/MeOH 95/5. IR(KBr) n: 3182
(OeH), 2918, 2843 (aliphatic CeH), 1664 (C]O), 1610
1
(N]C) cmꢂ1. H NMR (300 MHz, DMSO-d6, d ppm): 9.68
(s, 1H, OH); 8.18 (s, 1H, CH); 7.89 (d, 1H, J ¼ 8.1 Hz, H-
7); 7.80 (s, 1H, H-4); 7.62 (d, 1H, J ¼ 8.1 Hz, H-6); 7.32e
7.26 (m, 3H, H-6’, H-20, H-50); 6.90e6.87 (m, 1H, H-40);
2.43 (s, 3H, CH3). Anal. Calcd. for C15H12N2O2S (284.33):
C, 63.36; H, 4.25; N, 9.85; S, 11.28. Found: C, 63.17; H,
4.32; N, 9.55; S, 11.19.
5.1.1.5. 2-(Benzo[d]isothiazol-3-yl)-N0-dodecylideneacetohy-
drazide (3o). Yield: 83%; mp 119e120 ꢀC (Ligroin-EtOH).
TLC: eluent ¼ Petroleum ether/AcOEt 1/1. IR(KBr) n: 3218
(NeH), 3080 (aromatic CeH) 2923, 2862 (aliphatic CeH),
1663 (C]O), 1575 (N]C) cmꢂ1 1H NMR (300 MHz,
.
DMSO-d6, d ppm): 11.39 and 11.13 (2 s, 1H, NH); 8.19e
8.14 (m, 1H, H-4); 8.07 (d, 1H, J ¼ 8.1 Hz, H-7); 7.61e7.53
(m, 1H, H-5); 7.53e7.45 (m, 2H, H-6, CH); 7.33 (t, 1H,
J ¼ 5.2 Hz, CH); 4.35 and 4.04 (2 s, 2H, CH2); 2.20e2.09
(m, 2H, CH2); 1.43e1.36 (m, 2H, CH2); 1.22e1.20 (m,
16H, 8 CH2); 0.84e0.80 (m, 3H, CH3). Anal. Calcd. for
C21H31N3OS (373.56): C, 67.52; H, 8.36; N, 11.25; S, 8.58.
Found: C, 67.16; H, 8.62; N, 11.48; S, 8.92.
5.1.1.10. 2-(4-Hydroxybenzylideneamino)-5-methylbenzo[d]i-
sothiazol-3(2H )-one (4n). Yield: 70%; mp 242e243 ꢀC (Diox-
ane). TLC: eluent ¼ CH2Cl2/EtOH 95/5. IR(KBr) n: 3181
(OeH), 3015 (aromatic CeH), 2963, 2888, 2850 (aliphatic
CeH), 1658 (C]O), 1596 (N]C) cmꢂ1
.
1H NMR
(300 MHz, DMSO-d6, d ppm): 10.05 (s, 1H, OH); 8.19 (s,
1H, CH); 7.87 (d, 1H, J ¼ 8.1 Hz, H-7); 7.78 (s, 1H, H-4);
7.69 (d, 2H, J ¼ 8.4 Hz, H-20, H-60); 7.49 (d, 1H, J ¼ 8.1 Hz,
H-6); 6.86 (d, 2H, J ¼ 8.7 Hz, H-30, H-50); 2.43 (s, 3H, CH3).
Anal. Calcd. for C15H12N2O2S (284.33): C, 63.36; H, 4.25; N,
9.85; S, 11.28. Found: C, 63.06; H, 4.25; N, 9.82; S, 11.18.
5.1.1.6. 2-(2-Fluorobenzylideneamino)-5-methylbenzo[d]iso-
thiazol-3(2H )-one (4b). Yield: 68%; mp 172e174 ꢀC
(EtOH). TLC: eluent ¼ CH2Cl2/EtOH 95/5. IR(KBr) n:
3065e3015 (aromatic CeH) 2960, 2920, 2845 (aliphatic
5.1.1.11. 2-(3,4-Dihydroxybenzylideneamino)-5-methylbenzo[-
d]isothiazol-3(2H )-one (4o). Yield: 62%; mp 240e243 ꢀC
(Dioxane). TLC: eluent ¼ CH2Cl2/EtOH 9/1. IR(KBr) n:
3459 (OH) 3350e3002 (bonded OeH), 2955, 2920, 2843 (al-
CeH), 1675 (C]O), 1601 (N]C) cmꢂ1
.
1H NMR
(300 MHz, DMSO-d6, d ppm): 8.28 (s, 1H, CH); 7.99e7.89
(m, 2H, H-60, H-7); 7.80 (s, 1H, 4); 7.63e7.52 (m, 2H, H-
30, H-50); 7.39e7.32 (m, 2H, H-40, H-6); 2.43 (s, 3H, CH3).
Anal. Calcd. for C15H11FN2OS (286.33): C, 62.92; H, 3.87;
N, 9.78; S, 11.20. Found: C, 62.58; H, 4.11; N, 9.38; S,
11.60.
1
iphatic CeH), 1664 (C]O), 1586 (N]C) cmꢂ1. H NMR
(300 MHz, DMSO-d6, d ppm): 9.51 (s, 1H, OH); 9.35 (s,
1H, OH); 8.09 (s, 1H, CH); 7.86 (d, 1H, J ¼ 8.1 Hz, H-7);
7.78 (d, 1H, J ¼ 1.2 Hz, H-4); 7.49 (dd, 1H, J ¼ 1.2 Hz,
J ¼ 8.1 Hz, H-6); 7.34 (d, 1H, J ¼ 2.1 Hz, H-20); 7.17 (dd,
1H, J ¼ 1.8 Hz, J ¼ 8.1 Hz, H-60); 6.81 (d, 1H, J ¼ 8.1 Hz,
H-50); 2.43 (s, 3H, CH3). Anal. Calcd. for C15H12N2O3S
5.1.1.7. 2-(3-Fluorobenzylideneamino)-5-methylbenzo[d]iso-
thiazol-3(2H )-one (4c). Yield: 56%; mp 190e191 ꢀC