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26.3, “one signal is hidden”, 25.9, 25.4, 24.9, 14.7. ESI-MS: found
[M þ Na]þ 485.66; C29H54O2N2 [M þ Na]þ requires 485.68.
6.2.8. 1-[(Z)-Octadec-9-enoyl]-1,3-dicyclohexylurea (4d)
Yellow oily liquid, Yield ¼ 40%, IR (KBr, cmꢃ1): 3318 (NeH
stretch), 2923 (CeH asym), 2859 (CeH sym), 1649, 1597 (C]O),
1457 (NeH bend), 1226 (CeN). 1H NMR (CDCl3, dH) 7.19 (s, 1H, NH),
5.28 (m, 2H, eCH]CHe), 3.81e3.76 (m, 1H, CH of C6H11), 3.62e3.60
(m, 1H, CH of C6H11), 2.54 (t, 2H, J ¼ 7.4 Hz, CH2eCO), 1.96 (m, 4H,
eCH2eCH]CHeCH2), 1.69 (m, 14H, 7CH2), 1.65 (m, 2H,
CH2eCH2eCO), 1.35 (m, 26H, 13CH2), 0.81 (dist.t, 3H, terminal
eCH3). 13C NMR (CDCl3, dC) 154.7, 135.5, 129.7, 49.9, 48.7, 35.9, 35.4,
34.9, 34.3, 33.9, 33.7, 32.6, 31.5, 30.3, 29.5, 29.4, 27.9, 27.7, 26.7, 26.5,
“one signal hidden”, 26.2, 26.0, 25.8, 25.5, 25.4, 24.9, “two signal
hidden”, 24.3, 23.7, 14.3. ESI-MS: found [M þ Na]þ 511.70;
C31H56O2N2 [M þ Na]þ requires 511.72.
6.2.3. o-Hydroxy-octadecanilide (3b)
Yellow oily liquid, Yield ¼ 48%, IR (KBr, cmꢃ1): 3428 (OeH), 3308
(NeH stretch), 2927 (CeH asym), 2845 (CeH sym), 1715, 1658
(anilide). 1H NMR (CDCl3, dH) 9.25 (s, 1H, OH) 8.18 (s, 1H, NH),
7.07e7.03 (m, 4H, Ph), 2.27 (t, 2H, J ¼ 7.4 Hz, CH2eCO), 1.62 (m, 2H,
CH2eCH2eCO), 1.27 (br.s, 24H, chain CH2), 0.88 (dist.t, 3H, terminal
eCH3). 13C NMR (CDCl3, dC) 170.3, 131.4, 127.5, 126.7, 125.6, 122.7,
120.6, 33.6, 33.5, 30.3, 29.5, 29.3, 29.2, 28.7, 28.2, 27.5, 27.3, 26.6,
26.3, 25.1, 24.8, 24.3, 25.0, 14.0. ESI-MS: found [M þ Na]þ 398.51;
C24H41O2N [M þ Na]þ requires 398.53.
6.2.4. 1-(Octadecanoyl)-1,3-dicyclohexylurea (4b)
6.2.9. o-Hydroxy-(9Z,12R)-12-hydroxyoctadec-9-anilide (3e)
Yellow oily liquid, Yield ¼ 44%, IR (KBr, cmꢃ1): 3446 (OeH), 3302
(NeH stretch), 2928 (CeH asym), 2860 (CeH sym), 1715, 1654
(anilide). 1H NMR (CDCl3, dH) 9.11 (s, 1H, OH), 8.46 (s, 1H, NH),
7.06e7.04 (m, 4H, Ph), 5.38 (m, 2H, eCH]CHe), 3.55 (m, 1H,
eCHeOH), 2.29 (t, 2H, J ¼ 7.4 Hz, CH2eCO), 2.27 (s, 1H, CHeOH),
1.94 (m, 4H, eCH2eCH]CHeCH2), 1.65 (m, 2H, CH2eCH2eCO), 1.20
(br.s, 18H, chain CH2), 0.81 (dist.t, 3H, terminal eCH3). 13C NMR
(CDCl3, dC) 170.7, 131.7, 127.6, 126.5, 125.3, 122.3, 120.1, 119.3, 76.4,
42.7, 36.6, “two signals hidden”, 32.8, 31.5, 31.4, 30.8, “one signal
hidden”, 29.5, 29.3, 29.1, 27.3, 26.6, 14.0. ESI-MS: found [M þ Na]þ
412.51; C24H39O3N [M þ Na]þ requires 412.52.
Yellow oily liquid, Yield ¼ 39%, IR (KBr, cmꢃ1): 3325 (NeH
stretch), 2923(CeH asym), 2857 (CeHsym),1635(C]O),1525 (NeH
bend), 1228 (CeN). 1H NMR (CDCl3, dH) 7.20 (s, 1H, NH), 3.88e0.86
(m, 1H, CH of C6H11), 3.68e3.65 (m, 1H, CH of C6H11), 2.33 (t, 2H,
J ¼ 7.4 Hz, CH2eCO), 1.67 (m, 8H, 4CH2), 1.55 (m, 2H, CH2eCH2eCO),
1.37 (m, 40H, chain 20CH2), 0.86 (dist.t, 3H, terminal eCH3).13C NMR
(CDCl3, dC)154.4,135.2, 49.2,48.1, 33.9, 33.5, 32.9, 32.7, 32.1, 31.9, 31.5,
30.6, 30.5, 29.9, 29.7, 29.3, 29.5, 29.1, 28.9, 28.5, 28.2, 27.9, 27.3, 26.3,
26.1, “one signal hidden”, 25.7, 25.2, 25.7, 24.2, 14.6. ESI-MS: found
[M þ Na]þ 513.70; C31H58O2N2 [M þ Na]þ requires 513.73.
6.2.5. o-Hydroxy-undec-10-anilide (3c)
Yellow oily liquid, Yield ¼ 47%, IR (KBr, cmꢃ1): 3424 (OeH), 3305
(NeH stretch), 2926 (CeH asym), 2855 (CeH sym), 1705, 1669
(anilide). 1H NMR (CDCl3, dH) 9.19 (s, 1H, OH), 8.10 (s, 1H, NH),
6.2.10. 1-[(9Z,12R)-12-Hydroxyoctadec-9-enoyl]-1,3-
dicyclohexylurea (4e)
Yellow oily liquid, Yield ¼ 41%, IR (KBr, cmꢃ1): 3316 (NeH
stretch), 2927 (CeH asym), 2857 (CeH sym), 1639 (C]O), 1530
(NeH bend), 1231 (CeN). 1H NMR (CDCl3, dH) 7.25 (s, 1H, NH), 5.42
(m, 2H, eCH]CHe), 3.87e3.84 (m, 1H, CH of C6H11), 3.69e3.65 (m,
1H, CH of C6H11), 3.55 (m, 1H, eCHeOH), 2.38 (t, 2H, J ¼ 7.4 Hz,
CH2eCO), 2.28 (s, 1H, CHeOH), 1.95 (m, 4H, eCH2eCH]CHeCH2),
1.66 (m, 10H, 5CH2), 1.64(m, 2H, CH2eCH2eCO), 1.38 (m, 28H,
14CH2), 0.81 (dist.t, 3H, terminal eCH3). 13C NMR (CDCl3, dC) 154.9,
135.6, 129.3, 71.7, 49.6, 48.1, 37.5, 36.9, 36.1, 35.2, 34.7, 34.5, 33.9,
33.3, 31.4, 31.2, 30.7, 30.3, 29.6, 29.4, 29.1, 28.9, 28.8, “two signals
hidden”, 28.5, 27.2, 26.1, “one signal hidden”, 25.2, 24.7,14.4. ESI-MS:
found [M þ Na]þ 527.70; C31H56O3N2 [M þ Na]þ requires 527.72.
7.08e7.05 (m, 4H, Ph), 5.74 (tdd,1H, JHꢃ CH ¼ 6.6 Hz, JHꢃH ¼10.1 Hz,
8
Z
2
JHꢃH ¼ 17.0 Hz, CH2]CHe), 4.93 (dd, 1H, J
¼ 10.1 Hz,
HZꢃH
HEꢃH
E
JH ꢃH ¼ 2.6 Hz, HZC ¼ CH), 4.91 (dd, 1H, J
¼ 17.1 Hz,
Z
E
JH ꢃH ¼ 2.8 Hz, HEC]CHe), 2.28 (t, 2H, J ¼ 7.4 Hz, CH2eCO), 2.10 (m,
E
Z
2H, eCH2eCH]CH2), 1.65 (m, 2H, CH2eCH2eCO), 1.27 (br.s, 10H,
chain CH2). 13C NMR (CDCl3, dC) 170.2,131.4, 127.5, 126.6, 125.8, 122.9,
120.7, 129.3, 33.9, 33.5, 29.8, 28.3, 27.5, 24.7, 23.5, 22.9, 14.0. ESI-MS:
found [M þ Na]þ 298.32; C17H25O2N [M þ Na]þ requires 298.34.
6.2.6. 1-(Undec-10-enoyl)-1,3-dicyclohexylurea (4c)
Yellow oily liquid, Yield ¼ 41%, IR (KBr, cmꢃ1): 3315 (NeH stretch),
2925 (CeH asym), 2852 (CeH sym), 1639 (C]O), 1520 (NeH bend),
1225 (CeN). 1H NMR (CDCl3, dH) 7.26 (s, 1H, NH), 5.80 (tdd, 1H,
6.2.11. o-Hydroxy-(9R,12Z)-9-hydroxyoctadec-12-anilide (3f)
Yellow oily liquid, Yield ¼ 46%, IR (KBr, cmꢃ1): 3440 (OeH), 3309
(NeH stretch), 2926 (CeH asym), 2855 (CeH sym), 1705, 1655 (ani-
lide). 1H NMR (CDCl3, dH) 9.28 (s, 1H, OH), 8.50 (s, 1H, NH), 7.04e7.02
(m, 4H, Ph), 5.28 (m, 2H, eCH]CHe), 3.54 (m, 1H, eCHeOH), 2.25
(t, 2H, J ¼ 7.1 Hz, CH2eCO), 2.21 (s, 1H, OH), 1.94 (m, 4H, eCH2eCH]
CHeCH2),1.64 (m, 2H, CH2eCH2eCO),1.22 (br.s,18H, chain CH2), 0.81
(dist.t, 3H, terminal eCH3). 13C NMR (CDCl3, dC) 170.5, 131.3, 127.6,
126.8, 125.8, 122.0, 120.3, 119.5, 76.7, 42.7, 36.9, 35.8, 34.7, 32.7, 31.9,
31.5, 30.9, 29.7, 29.3, 29.1, 28.6, 27.1, 26.3, 14.5. ESI-MS: found
[M þ Na]þ 412.49; C24H39O3N [M þ Na]þ requires 412.52.
JHꢃ CH ¼ 6.7 Hz, JHꢃH ¼ 10.8 Hz, JHꢃH ¼ 16.9 Hz, CH2]CHe), 4.97
8
Z
E
2
(dd, 1H, JH ꢃH ¼ 10.0 Hz, JH ꢃH ¼ 2.3 Hz, HZC]CH), 4.94 (dd, 1H,
Z
Z
E
JH ꢃH ¼ 17.4 Hz, JH ꢃH ¼ 2.0 Hz, HEC]CHe), 3.88e3.84 (m,1H, CH of
E
E
Z
C6H11), 3.70e3.66(m,1H, CHofC6H11),2.40(t, 2H, J¼ 7.4 Hz, CH2eCO),
2.12 (m, 2H, eCH2eCH]CH2), 1.70 (m, 10H, 5CH2), 1.65 (m, 2H,
CH2eCH2eCO),1.36 (m, 20H,10CH2).13C NMR (CDCl3, dC) 154.6,135.9,
129.7, 115.3, 49.3, 48.3, 33.9, 33.7, 33.4, 32.9, 32.3, 32.0, 31.5, 31.1,
30.8, 30.2, 29.3, “one signal hidden”, 28.2, 26.3, 26.4, 25.0, 25.3,
25.0. ESI-MS: found [M þ Na]þ 413.51; C24H42O2N2 [M þ Na]þ
requires 413.54.
6.2.7. o-Hydroxy-(Z)-octadec-9-anilide (3d)
6.2.12. 1-[(9R,12Z)-9-Hydroxyoctadec-12-enoyl]-1,3-
Yellow oily liquid, Yield ¼ 45%, IR (KBr, cmꢃ1): 3412 (OeH), 3306
(NeH stretch), 2925 (CeH asym), 2852 (CeH sym), 1706, 1643
(anilide). 1H NMR (CDCl3, dH) 9.22 (s, 1H, OH), 8.80 (s, 1H, NH),
7.07e7.05 (m, 4H, Ph), 5.28 (m, 2H, eCH]CHe), 2.26 (t, 2H, J ¼ 7.4 Hz,
CH2eCO), 1.94 (m, 4H, eCH2eCH]CHeCH2), 1.67 (m, 2H,
CH2eCH2eCO), 1.27 (br.s, 20H, chain CH2), 0.80 (dist.t, 3H, terminal
eCH3). 13C NMR (CDCl3, dC) 170.6, 131.5, 127.2, 126.2, 125.5, 122.9,
120.6, 129.7, 35.9, 29.7, “two signal hidden”, 29.4, 28.7, 27.1, 27.0, 26.8,
26.7, 25.3, 24.8, 23.4, 23.2, 22.9, 22.8, 14.1. ESI-MS: found [M þ Na]þ
396.50; C24H39O2N [M þ Na]þ requires 396.52.
dicyclohexylurea (4f)
Yellow oily liquid, Yield ¼ 40%, IR (KBr, cmꢃ1): 3321 (NeH
stretch), 2926 (CeH asym), 2855 (CeH sym), 1629 (C]O), 1574
(NeH bend), 1227 (CeN). 1H NMR (CDCl3, dH) 7.21 (s, 1H, NH), 5.30
(m, 2H, eCH]CHe), 3.86e3.78 (m, 1H, CH of C6H11), 3.65e3.61 (m,
1H, CH of C6H11), 3.56 (m, 1H, eCHeOH), 2.32 (t, 2H, J ¼ 7.4 Hz,
CH2eCO), 2.25 (s, 1H, CHeOH), 1.97 (m, 4H, eCH2eCH]CHeCH2),
1.71 (m, 12H, 6CH2), 1.64 (m, 2H, CH2eCH2eCO), 1.34 (m, 26H,
13CH2), 0.81 (dist.t, 3H, terminal eCH3). 13C NMR (CDCl3, dC) 154.1,
135.8, 129.1, 71.6, 49.0, 48.3, 37.3, 36.5, 36.0, 35.7, 34.5, 34.3, 33.8,