Med Chem Res (2011) 20:601–606
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N-(3-hydroxypropyl)palmitamide (1a)
N-(3-hydroxypropyl)cinnamamide (3a)
Yield = 82%, mp: 96–98°C. IR (KBr) cm-1: 1712 (C=O),
3090 (NH), 3320 (OH). H-NMR (CDCl3): 0.87 (t, 3H,
Yield = 57%, mp: 91–92°C. IR (KBr) cm-1: 1709 (C=O),
3127 (NH), 3315 (OH). H-NMR (CDCl3): 1.74 (m, 2H,
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J = 6.9 Hz, CH3), 1.26–1.69 (m, 26H, (CH2)13), 1.85 (m,
2H, CH2), 2.19 (t, 2H, J = 7.5 Hz, CH2CO), 3.40 (m, 2H,
CH2), 3.48 (s, 1H, OH), 3.63 (m, 2H, CH2), 5.95 (s, 1H,
NH). C19H39NO2. MS: m/z 314 (M ? 1).
CH2), 3,49 (s, 1H, OH), 3.58 (t, 2H, –CH2NHCO), 3.68 (t,
2H, –CH2OH), 6.40 (d, 1H, J = 15.6 Hz, =CHCO), 7.65
(d, 1H, J = 15.6 Hz, CH=C), 7.36–7.51 (m, 5H, –C6H5).
C12H15NO2. MS: m/z 206 (M ? 1).
N,N-dimethylcinnamamide (3b)
N,N-bis(2-hydroxyethyl)palmitamide (1b)
Yield = 52%, mp: 101–103°C. IR (KBr) cm-1: 1705
(C=O), 1172 (C–N). 1H-NMR (CDCl3): 3.08 (s, 3H, CH3),
3.18 (s, 3H, CH3), 6.90 (d, 1H, J = 15.5 Hz, =CHCO),
7.68 (d, 1H, J = 15.5 Hz, CH=C), 7.36–7.55 (m, 5H,
–C6H5). C11H13NO. MS : m/z 176 (M ? 1).
Yield = 67%, mp: 89–91°C. IR (KBr) cm-1: 1705
(C = O), 1123 (C–N), 3317 (OH). 1H-NMR (CDCl3): 0.88
(t, 3H, J = 6.4 Hz, CH3), 1.25-1.63 (m, 26H, (CH2)13),
2.39 (t, 2H, J = 7.6 Hz, CH2CO), 3.50 (t, 2H, J = 6.0 Hz,
CH2), 3.56 (t, 2H, J = 6.0 Hz, CH2), 3.61 (s, H, OH), 3.65
(s, H, OH), 3.79 (t, 2H, J = 6.0 Hz, CH2), 3.85 (t, 2H,
J = 6.0 Hz, CH2). C20H41NO3. MS: m/z 344 (M ? 1).
N-(2-hydroxyethyl)-N-methylcinnamamide (3c)
Yield = 56%, mp: 96–97°C. IR (KBr) cm-1: 1698 (C=O),
1120 (C–N), 3309 (OH). H-NMR (CDCl3): 3.25 (s, 3H,
N,N-diethylpalmitamide (1c)
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Yield = 75%, oil. 1H-NMR (CDCl3): 0.87 (t, 3H,
J = 6.5 Hz, CH3), 1.08–1.19 (m, 6H, (CH3)2), 1.25–1.65
(m, 26H, (CH2)14), 2.28 (t, 2H, J = 7.7 Hz, CH2CO),
3.26–3.40 (m, 4H, (CH2)2). C20H41NO. MS: m/z 312
(M ? 1).
CH3), 3.41 (s, 1H, OH), 3.68 (m, 2H, –CH2NCO), 3.85 (m,
2H, –CH2OH), 6.88 (d, 1H, J = 15.4 Hz, =CHCO), 7.71
(d, 1H, J = 15.4 Hz, CH=C), 7.38–7.52 (m, 5H, –C6H5).
C12H15NO2. MS: m/z 206 (M ? 1).
N,N-diethylcinnamamide (3d)
N-(3-hydroxypropyl)stearamide (2a)
Yield = 47%, mp: 86–87°C. IR (KBr) cm-1: 1706 (C=O),
1124 (C–N); 1H-NMR (CDCl3): 1.23 (m, 6H, (CH3)2), 3.49
(m, 4H, (CH2)2), 6.82 (d, 1H, J = 15.4 Hz, =CHCO), 7.72
(d, 1H, J = 15.4 Hz, CH=C), 7.36–7.54 (m, 5H, –C6H5).
C13H17NO. MS: m/z 204 (M ? 1).
Yield = 79%, mp: 90–92°C. IR (KBr) cm-1: 1709 (C=O),
3209 (NH), 3324 (OH). H-NMR (CDCl3): 0.87 (t, 3H,
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J = 6.9 Hz, CH3), 1.64 (m, 2H, CH2), 1.24–1.68 (m, 30H,
(CH2)15), 2.18 (t, 2H, J = 7.5 Hz, CH2CO), 3.37 (m, 2H,
CH2), 3.41 (s, 1H, OH), 3.63 (m, 2H, CH2), 5.99 (s, 1H,
NH). C21H43NO2. MS: m/z 342 (M ? 1).
Anticonvulsant activity
The MES test and the rotarod test were carried out
according to the standard protocols described in the ADD
Program of the National Institute of Neurological and
N-(2-hydroxyethyl)-N-methylstearamide (2b)
Yield = 63%, mp: 96–97°C. IR (KBr) cm-1: 1684 (C=O),
1176 (C–N), 3326 (OH). H-NMR (CDCl3): 0.87 (t, 3H,
¨
Communicative Disorders and Stroke (NINCDS) (Schafer,
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1985; Krall et al., 1978). All the compounds were tested for
anticonvulsant activities with Kunming mice in the 18–
25 g weight range purchased from the Laboratory of Ani-
mal Research, College of Pharmacy, Yanbian University.
Mice were housed collectively in groups of 10 in poly-
carbonate cages. They were maintained on a 12-h light/
dark cycle in a temperature-controlled (23 2°C) labora-
tory. Food and water were available ad libitum. The tested
compounds were prepared as a suspension in a 0.5%
aqueous solution of methylcellulose and injected i.p. in a
standard volume of 0.05 ml/20 g body weight.
J = 6.3 Hz, CH3), 1.25–1.63 (m, 30H, (CH2)15), 2.33 (t,
2H, J = 7.6 Hz, CH2CO), 3.06 (s, 1H, OH), 3.46 (m, 3H,
CH3), 3.55 (m, 2H, CH2), 3.77 (m, 2H, CH2). C21H43NO2.
MS: m/z 342 (M ? 1).
N,N-diethylstearamide (2c)
Yield = 71%, oil. 1H-NMR (CDCl3): 0.86 (t, 3H,
J = 6.7 Hz,CH3), 1.06–1.18 (m, 6H, (CH3)2), 1.24–1.64
(m, 30H, (CH2)15), 2.27 (t, 2H, J = 7.3 Hz, CH2CO),
3.25–3.39 (m, 4H, (CH2)2). C22H45NO. MS : m/z 340
(M ? 1).
In Phase-I screening (Table 1), each compound was
administered at the dose levels of 30, 100, and 300 mg/kg
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