1154
Vol. 50, No. 9
Table 2. Physical and Analytical Data of Compounds 1—7
Pharmacology
Male Swiss mice weighing 20 to 25 g, supplied by Charles
River (Italy), were housed in colony cages (10 mice each)
under standard light (light on from 7.00 a.m. to 7.00 p.m.),
temperature (22Ϯ1 °C) and room humidity (60Ϯ10%) condi-
tions for at least 1 h before experimentation. Food and water
were available ad libitum.
On the testing day the compounds (1—7) used in the ex-
perimental sessions were dissolved in saline for administra-
tion. Drugs were injected in a volume of 10 ml/kg, i.p. Com-
pounds were administered at doses of 10—20—40 mg/kg/i.p.
1 h before the beginning of the tests.
Compound
mp (°C)
Yield (%)
Formula
1
2
3
4
5
6
7
146
93
48
73
85
45
80
62
74
C25H32N2O6
C20H31N3O2
C23H37ClN2O2
C23H33SClN2O2
C21H33ClN2O2
C24H30N2O6
138
210
120
142
170
C21H27ClN2O2
Table 3. IR Data of Compounds 1—7
Locomotor Activity, Motor Coordination, Pentobarbital
Sleeping time, Stereotyped Behavior, Catalepsy, Nociceptive
Assays were performed as previously reported.6—14)
All data (expressed as meanϮS.E.M.) were analysed by
the analysis of variance (ANOVA) and Dunnett’s procedure
for multiple comparisons with a single control group. When
the analysis was restricted to two means, Student’s t-test
(Two-tailed) was used. The Fisher exact test was used to
analyse the rotarod data. Significance was assumed at a 5%
level.
Compound
Ir (KBr) n cmϪ1
1
2
3282 (NH); 2330, 2450, 1730 (COOH)2; 1636 (CO);
1540, 1200, 1110, 709 lead band
3360, 3300 (NH); 1530 (CO); 1305, 1125, 924, 709
lead band
1634 (CO); 1457, 1269, 1132, 704, 708 lead band
3280 (NH); 1635 (CO), 1430, 1250, 710 lead band
3280 (NH); 1635 (CO), 1433, 1240, 709 lead band
3280 (NH); 2300, 2400, 1730 (COOH)2, 1640 (CO),
1540, 1400, 1200, 1100, 710 lead band
3
4
5
6
7
3240 (NH), 1635 (CO), 1530, 1115, 710, 700 lead band
References
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Table 4. 1H-NMR Data (d ppm) of Compounds 1—7 (DMSO-d6)
Compound
1
2
8.11 (1H, NH), 7.38—7.00 (m, 10H, HAr), 3.00 (1H,
CH), 2.98, 2.87, 2.71, 1.64, 1.42 (m, (CH2)5)
7.09—6.98 (m, 5H, HAr), 6.22, 6.21 (d, 1H, NH),
5.62—5.60 (t, 1H, NH), 4.28 (d, 1H, CH), 3.36 (m, 2H,
NH–CH2–), 3.34—2.79 (m, 2H, CH2–N), 2.76—2.08
(m, 2H, CH2–CH2–CH2), 2.00—1.23 (m, 8H, CH2),
1.13—1.11 (m, 5H, CH2 cyclopenthyl)
3
4
7.21—6.99 (m, 5H, HAr), 3.12 (1H, CH), 3.30, 3.16,
2.66, 2.10 (m, (CH2)3), 1.70 (q, 2H, CH2), 0.82 (t, 3H,
CH3, Jϭ7 Hz)
8.32 (1H, NH), 7.67, 7.65 (d, 2H, HAr), 7.66, 7.56 (d,
2H, HAr), 7.12, 7.06 (m, 2H, HAr), 7.03 (s, H,
thienyl), 3.40, 3.32, 2.78, 2.66, 2.10 (m, 18H (CH2))
8.23 (1H, NH), 7.24—7.16 (m, 5H, HAr), 4.12 (1H,
CH), 3.80., 3.70, 2.66, 1.06 (m, 18H(CH2)n)
5
6
8.12 (1H, NH), 7.40—7.02 (m, 10H, HAr), 4.47 (d, 2H,
CH), 2.98—2.50 (m, 6H, CH2), 2.71, 2.68, 1.64, 1.59
(m, 8H, (CH2)4)
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7
8.00 (1H, NH), 7.56, 7.50, 7.40, 7.38 (m, 10H, HAr),
4.00 (1H, CH), 3.12, 2.07 (m, (CH2)3), 3.13, 2.99 (m,
2H, morpholine), 1.55, 1.23 (m, 2H, morpholine)