N. Bouider et al. / Bioorg. Med. Chem. 23 (2015) 1735–1746
1743
5.1.5.6.
(15f). White powder (80%); mp 73–74 °C; IR(KBr)
(N–H), 2919 (C–H aliphatic), 1707, 1667 (C@O) cmꢁ1
N-Cyclohexyl-N0-(2-propyloxybenzenecarbonyl)urea
: 3355, 3280
1H NMR
7.34–7.51 (m, 5H, CH2C6H5) 7.55 (t, 1H, 4-H), 7.71 (dd, 1H, 6-H),
8.46 (d, 1H, NHC6H11), 10.08 (s, 1H, CONHCO). Anal. (C17H24N2O3)
theoretical: 71.57 C, 6.86 H, 7.95 N. Found: 71.60 C, 7.05 H, 7.74 N.
m
;
(DMSO-d6, 500 MHz) d: 1.03 (t, 3H, CH3CH2CH2), 1.20–1.90
(m, 10H, C6H10), 1.80 (m, 2H, CH3CH2CH2), 3.61 (b, 1H, CHNH),
4.12 (t, 3H, CH3CH2CH2), 7.07 (t, 1H, 5-H), 7.19 (d, 1H, 3-H), 7.55
(t, 1H, 4-H), 7.70 (dd, 1H, 6-H), 8.49 (d, 1H, NHC6H11), 10.08
(s, 1H, CONHCO). Anal. (C17H24N2O3) theoretical: 67.08 C, 7.95 H,
9.20 N. Found: 66.91 C, 8.20 H, 9.07 N.
5.1.5.13.
(15m). White powder (40%); mp 100–101 °C; IR (KBr)
3284 (N–H), 3031 (C–H aromatic), 1692, 1660 (C@O) cmꢁ1
NMR (DMSO-d6, 500 MHz) d: 4.41(s, 2H, NHCH2) 5.27 (s, 2H,
OCH2), 7.09 (t, 1H, 5-H), 7.19 (d, 1H, 3-H), 7.27–7.45(m, 10-H,
CH2C6H5), 7.55 (t, 1H, 4-H), 7.72 (dd, 1H, 6-H), 8.93 (t, 1H,
NHCH2), 10.30 (s, 1H, CONHCO). Anal. (C22H20N2O3) theoretical:
73.32 C, 5.59 H, 7.77 N. Found: 73.72 C, 5.40 H, 7.58 N.
N-Benzyl-N0-(2-benzyloxybenzenecarbonyl)urea
: 3324,
1H
m
;
5.1.5.7.
(15g).
N-Phenyl-N0-(2-propyloxybenzenecarbonyl)urea
White powder (64%); mp 72 °C; IR (KBr) : 3330 (N–H),
1H NMR (DMSO-d6, 500 MHz) d: 1.03 (t,
m
1715, 1664 (C@O) cmꢁ1
;
3H, CH3CH2CH2), 1.84 (m, 2H, CH3CH2CH2), 4.12 (t, 3H,
CH3CH2CH2), 7.13 (t, 2H, 5, 40-H), 7.23 (d, 1H, 3-H), 7.36 (t, 2H, 30,
50-H), 7.59 (t, 3H, 4, 20, 60-H), 7.84 (dd, 1H, 6-H), 10.45 (s, 1H,
NHC6H5), 10.70 (s, 1H, CONHCO). Anal. (C17H18N2O3) theoretical:
68.44 C, 6.08 H, 9.39 N. Found: 68.04 C, 6.50 H, 9.34 N.
5.1.5.14.
(15n). White powder (62%); mp 79.5 °C; IR(KBr)
N-Ethyl-N0-(2-methoxybenzenecarbonyl)thiourea
: 3316 (N–H),
m
2924 (C–H aliphatic), 1661 (C@O) cmꢁ1; 1H NMR (DMSO-d6,
500 MHz) d: 1.15 (t, 3H, CH3CH2), 3.61 (q, 2H, CH3CH2), 3.91 (s,
3H, OCH3), 7.11 (t, 1H, 5-H), 7.24 (d, 1H, 3-H), 7.60 (t, 1H, 4-H),
7.86 (dd, 1H, 6-H), 10.67 (t, 1H, NHCH2CH3), 10.93 (s, 1H,
CONHCS). Anal. (C11H14N2O2S) theoretical: 55.44 C, 5.92 H, 11.76
N, 13.45 S. Found: 55.70 C, 6.12 H, 11.56 N, 13.47 S.
5.1.5.8.
(15h).
N-Ethyl-N0-(2-benzyloxybenzenecarbonyl)urea
White powder (40%); mp 74–75 °C; IR (KBr) : 3335
m
(N–H), 2925 (C–H aliphatic), 1698, 1660 (C@O) cmꢁ1; 1H NMR
(DMSO-d6, 500 MHz) d: 1.09 (t, 3H, CH3CH2), 3.22 (q, 2H,
CH3CH2), 5.27 (s, 2H, CH2), 7.19 (t, 1H, 5-H), 7.28 (d, 1H, 3-H),
7.34–7.54 (m, 5H, CH2C6H5), 7.55 (t, 1H, 4-H), 7.71 (dd, 1H, 6-H),
8.47 (t, 1H, NHCH2CH3), 10.14(s, 1H, CONHCO). Anal.
(C11H14N2O3) theoretical: 68.44 C, 6.08 H, 9.39 N. Found: 68.44 C,
6.28 H, 9.10 N.
5.1.5.15. N-Isopropyl-N0-(2-methoxybenzenecarbonyl)thiourea
(15o).
White powder (60%); mp 109.5–110 °C; IR (KBr)
m:
3317 (N–H), 2929 (C–H aliphatic), 1655 (C@O) cmꢁ1
;
1H NMR
(DMSO-d6, 500 MHz) d: 1.26 (d, 6H, (CH3)2CH), 3.61 (q, 2H,
CH3CH2), 3.98 (s, 3H, OCH3), 4.37 (m, 1H, (CH3)2CH), 7.11 (t, 1H,
5-H), 7.24 (d, 1H, 3-H), 7.60 (t, 1H, 4-H), 7.86 (dd, 1H, 6-H), 10.67
(t, 1H, NHCH2CH3), 10.93 (s, 1H, CONHCS). Anal. (C12H16N2O2S)
theoretical: 57.12 C, 6.39 H, 11.10 N, 12.70 S. Found: 57.51 C,
6.50 H, 11.23 N, 12.78 S.
5.1.5.9. N-Isopropyl-N0-(2-benzyloxybenzenecarbonyl)urea
(15i).
White powder (87%); mp 84–85 °C; IR (KBr) m: 3341,
3286 (N–H), 2925 (C–H aliphatic), 1690, 1664 (C@O) cmꢁ1, 1H
NMR (DMSO-d6, 500 MHz) d: 1.15 (d, 6H, (CH3)2CH), 3.87 (m, 1H,
(CH3)2CH), 5.27 (s, 2H, CH2), 7.09 (t, 1H, 5-H), 7.28 (d, 1H, 3-H),
7.34–7.54 (m, 5H, CH2C6H5), 7.55 (t, 1H, 4-H), 7.71 (dd, 1H, 6-H),
8.36 (d, 1H, NHCH(CH3)2), 10.17 (s, 1H, CONHCO). Anal.
(C18H20N2O3) theoretical: 69.21 C, 6.48 H, 8.97 N. Found: 68.98 C,
6.96 H, 8.59 N.
5.1.5.16. N-Sec-butyl-N0-(2-methoxybenzenecarbonyl)thiourea
(15p). White powder (42%); mp 79 °C; IR (KBr)
m: 3308 (N–H),
2926 (C–H aliphatic), 1656 (C@O) cmꢁ1 1H NMR (DMSO-d6,
;
500 MHz) d: 0.91 (t, 3H, (CH3CH2)CH3CH), 1.22 (d, 3H,
(CH3CH2)CH3CH), 1.63 (m, 2H, (CH3CH2)CH3CH), 3,91 (s, 3H,
OCH3), 4.27 (m, 1H, (CH3CH2)CH3CH), 7.12 (t, 1H, 5-H), 7.25 (d,
1H, 3-H), 7.61 (t, 1H, 4-H), 7.88 (dd, 1H, 6-H), 10.66 (d, 1H,
NHCHCH3(CH2CH3)), 10.94 (s, 1H, CONHCS). Anal. (C13H18N2O2S)
theoretical: 58.62 C, 6.81 H, 10.52 N, 12.04 S. Found: 58.80 C,
6.88 H, 10.66 N, 11.88 S.
5.1.5.10.
(15j).
N-Pentyl-N0-(2-benzyloxybenzenecarbonyl)urea
White powder (45%); mp 74 °C; IR (KBr) : 3350, 3300
1H NMR
m
(N–H), 2900 (C–H aliphatic), 1695, 1652 (C@O) cmꢁ1
,
(DMSO-d6, 500 MHz) d: 0,96 (t, 3H, CH3(CH2)4), 1.29 (m, 2H,
CH3CH2CH2(CH2)2), 1.33 (m, 2H,CH3CH2(CH2)3), 1.50 (m, 2H,
CH3(CH2)2CH2CH2), 3.16 (q, 2H, CH3(CH2)3CH2), 5.27 (s, 2H, CH2),
7.09 (t, 1H, 5-H), 7.28 (d, 1H, 3-H), 7.34–7.51 (m, 5H, CH2C6H5),
7.55 (t, 1H, 4-H), 7.71 (dd, 1H, 6-H), 8.37 (d, 1H, NHCH), 10.15 (s,
1H, CONHCO). Anal. (C20H24N2O3) theoretical: 70.56 C, 7.11 H,
8.23 N. Found: 70.36 C, 6.98 H, 8.34 N.
5.1.5.17.
(15q). White powder (55%); mp 154 °C; IR (KBr)
1655 (C@O) cmꢁ1 1H NMR (DMSO-d6, 500 MHz) d: 3.90 (s, 3H,
N-Phenyl-N0-(2-methoxybenzenecarbonyl)thiourea
: 3325 (N–H),
m
;
OCH3), 6.98–7.50 (m, 9H, H arom), 8.65 (s, 1H, NHC6H5), 9.79 (s,
1H, CONHCS). Anal. (C15H14N2O2S) theoretical: 62.92 C, 4.93 H,
9.78 N, 11.20 S. Found: 62.90 C, 4.91 H, 9.80 N, 11.18 S.
5.1.5.11.
(15k). White powder (65%); mp 62–63 °C; IR (KBr)
N-Sec-butyl-N0-(2-benzyloxybenzenecarbonyl)urea
: 3334, 3270
m
5.1.5.18.
(15r). White powder (62%); mp 93–93.5 °C; IR (KBr)
N-Benzyl-N0-(2-methoxybenzenecarbonyl)thiourea
: 3333
(N–H), 2962 (C–H aliphatic), 1687, 1661 (C@O) cmꢁ1; 1H NMR
(DMSO-d6, 500 MHz) d: 0.87 (t, 3H, (CH3CH2)CH3CH), 1.12 (d,
1H, (CH3CH2)CH3CH), 1.49 (m, 2H, (CH3CH2)CH3CH), 3.71 (m, 1H,
(CH3CH2)CH3CH), 5.27 (s, 2H, CH2), 7.09 (t, 1H, 5-H), 7.28 (d,
1H, 3-H), 7.34–7.51 (m, 5H, CH2C6H5), 7.55 (t, 1H, 4-H), 7.71 (dd,
1H, 6-H), 8.35 (d, 1H, NHCH), 10.18 (s, 1H, CONHCO). Anal.
(C19H22N2O3) theoretical: 69.92 C, 6.79 H, 8.58 N. Found: 70.30 C,
7.13 H, 8.28 N.
m
(N–H), 1657 (C@O) cmꢁ1; 1H NMR (DMSO-d6, 500 MHz) d: 3.99
(s, 3H, OCH3), 4.87 (d, 2H, CH2), 7.14 (t, 1H, 5-H), 7.26 (d, 1H, 3-
H), 7.29–7.42 (m, 5H, CH2C6H5), 7.64 (t, 1H, 4-H), 7.87 (dd, 1H, 6-
H), 7.87 (d, 1H, NHCH2), 11.06 (s, 1H, CONHCS). Anal.
(C16H16N2O2S) theoretical: 63.98 C, 5.37 H, 9.33 N, 10.67 S.
Found: 63.80 C, 5.35 H, 9.61 N, 10.50 S.
N-Cyclohexyl-N0-(2-benzyloxybenzenecarbonyl)urea
White powder (82%); mp 91–92 °C; IR (KBr) : 3273 (N–
1H NMR
5.1.5.19.
(15s). White powder (67%); mp 86–87 °C; IR (KBr)
3238 (N–H), 2966 (C–H aliphatic), 1661 (C@O) cmꢁ1
N-Benzyl-N0-(2-propyloxybenzenecarbonyl)thiourea
: 3320,
1H NMR
5.1.5.12.
(15l).
m
m
;
H), 2929 (C–H aliphatic), 1689, 1666 (C@O) cmꢁ1
;
(DMSO-d6, 500 MHz) d: 1.08 (t, 3H, CH3CH2CH2), 1.92 (m, 2H,
CH3CH2CH2), 4.20 (t, 2H, CH3CH2CH2), 4.88 (d, 2H, NHCH2), 7.15
(DMSO-d6, 500 MHz) d: 1.20–1.90 (m, 10H, C6H10), 3.59 (b, 1H,
CHNH), 5.27 (s, 2H, CH2), 7.09 (t, 1H, 5-H), 7.28 (d, 1H, 3-H),