S. Ke et al. / European Journal of Medicinal Chemistry 44 (2009) 2985–2993
2991
(N–H), 1703, 1617 (C]O) cmꢁ1
;
1H NMR (400 MHz, DMSO-d6):
4.3.10. N0-(4-Ethylbenzoyl)-2-methoxy-N-(nonan-5-yl)
benzohydrazide (6j)
This compound was obtained following the above method as
white solid, yield 75%, m.p. 83.5–84.9 ꢀC; IR (KBr):
¼ 3303 (N–H),
1684, 1632 (C]O) cmꢁ1; 1H NMR (400 MHz, DMSO-d6):
¼ 9.89 (s,
d
¼ 10.68 (s, 1H, N–H), 7.22–7.49 (m, 7H, Ar–H), 6.57 (d, J ¼ 7.2 Hz,
1H, Ar–H), 4.52 (br, 1H, CH), 1.27–1.61 (m, 12H, CH2), 0.87 (t,
J ¼ 7 Hz, 6H, CH3); 13C NMR (100 MHz, DMSO-d6):
d
¼ 170.76,
n
165.66, 165.56, 162.88, 160.46, 138.77, 138.70, 134.76, 134.70, 131.97,
131.34, 130.47, 130.39, 130.28, 130.18, 128.64, 127.52, 123.71, 117.03,
116.82, 114.42, 114.19, 56.33, 32.03, 31.51, 28.90, 28.63, 22.71, 22.40,
14.44,14.33; MS: m/z ¼ 418 (Mþ), 361, 292, 221,139, 123, 111, 95, 57;
EI-HRMS: calcd for C23H28ClFN2O2 (Mþ), 418.1823; found, 418.1823.
d
1H, N–H), 6.78–7.86 (m, 8H, Ar–H), 4.56 (br, 1H, CH), 3.79 (s, 3H,
OCH3), 2.56 (q, 2H, Ph–CH2),1.18–1.63(m,12H, CH2),1.11(t, J ¼ 7.6 Hz,
3H, Ph–CH2CH3), 0.88 (t, J ¼ 9.0 Hz, 6H, CH3); 13C NMR (100 MHz,
DMSO-d6):
d
¼ 170.57, 167.23, 155.55, 147.94, 131.09, 130.40, 128.44,
128.09, 127.86, 126.84, 126.03, 120.68, 120.03, 111.76, 60.98, 55.79,
32.26, 31.61, 29.04, 28.83, 28.45, 22.63, 22.25,15.80,14.63,14.43; MS:
m/z ¼ 424 (Mþ), 367, 298, 276, 233, 191, 135, 105, 92, 77; EI-HRMS:
calcd for C26H36N2O3 (Mþ), 424.2726; found, 424.2726.
4.3.6. N0-(4-Chlorobenzoyl)-3,5-dimethyl-N-(nonan-5-yl)
benzohydrazide (6f)
This compound was obtained following the above method as
white solid, yield 71%, m.p. 136.2–137.7 ꢀC; IR (KBr):
n
¼ 3259
1H NMR (400 MHz, DMSO-d6):
¼ 10.45 (s, 1H, N–H), 6.95–7.91 (m, 7H, Ar–H), 4.53 (br, 1H, CH),
2.20 (s, 6H, Ph–CH3), 1.28–1.62 (m, 12H, CH2), 0.84 (t, J ¼ 6.8 Hz, 6H,
CH3); 13C NMR (100 MHz, DMSO-d6):
(N–H), 1684, 1628 (C]O) cmꢁ1
;
4.3.11. N0-(4-Ethylbenzoyl)-N-(nonan-5-yl)benzo[d][1,3]dioxole-5-
carbohydrazide (6k)
d
This compound was obtained following the above method as
d
¼ 172.26, 165.82, 136.96,
white solid, yield 58%, m.p. 134.8–136.2 ꢀC; IR (KBr):
n
¼ 3192
136.85, 136.41, 132.03, 131.97, 131.24, 130.25, 129.58, 128.89, 125.04,
56.11, 31.90, 31.73, 28.97, 28.81, 22.71, 22.50, 21.16, 14.48, 14.33; MS:
m/z ¼ 428 (Mþ), 371, 280, 237, 195, 133, 105, 79, 55; EI-HRMS: calcd
for C25H33ClN2O2 (Mþ), 428.2231; found, 428.2231.
(N–H), 1691, 1669 (C]O) cmꢁ1 1H NMR (400 MHz, DMSO-d6):
;
d
¼ 10.34 (s, 1H, N–H), 6.83–7.50 (m, 7H, Ar–H), 5.98 (s, 2H, OCH2O),
4.49 (br, 1H, CH), 2.61 (q, 2H, Ph–CH2), 1.26–1.62 (m, 12H, CH2), 1.15
(t, J ¼ 7.6 Hz, 3H, Ph–CH2CH3), 0.85 (t, J ¼ 7.2 Hz, 6H, CH3); 13C NMR
(100 MHz, DMSO-d6):
d
¼ 171.33, 166.51, 148.56, 148.41, 146.67,
4.3.7. N0-(4-Chlorobenzoyl)-2-methoxy-N-(nonan-5-yl)
benzohydrazide (6g)
130.63, 130.25, 128.19, 127.91, 122.23, 108.19, 107.83, 101.70, 56.35,
31.79, 29.02, 28.83, 28.50, 22.72, 22.52, 15.78, 14.48, 14.34; MS:
m/z ¼ 438 (Mþ), 381, 355, 281, 231, 207,149,133,121,105; EI-HRMS:
calcd for C26H34N2O4 (Mþ), 438.2519; found, 438.2520.
This compound was obtained following the above method as
white solid, yield 73%, m.p. 132.2–134.4 ꢀC; IR (KBr):
n
¼ 3303
1H NMR (400 MHz, DMSO-d6):
¼ 10.06 (s, 1H, N–H), 6.79–7.94 (m, 8H, Ar–H), 4.55 (br, 1H, CH),
3.78 (s, 3H, OCH3), 1.14–1.61 (m, 12H, CH2), 0.85 (t, J ¼ 7.2 Hz, 6H,
CH3); 13C NMR (100 MHz, DMSO-d6):
(N–H), 1688, 1628 (C]O) cmꢁ1
;
d
4.3.12. N0-(2-chloroacetyl)-4-ethyl-N0-(nonan-5-yl)benzohydrazide
(6l)
d
¼ 170.48, 166.42, 137.09,
This compound was obtained following the above method as
136.65, 132.25, 132.19, 131.99, 131.09, 130.50, 130.24, 129.62, 128.90,
128.64, 128.06, 56.00, 55.78, 32.22, 31.60, 29.00, 28.46, 22.73, 22.48,
14.63, 14.38; MS: m/z ¼ 430 (Mþ), 373, 304, 276, 233, 191, 135, 111,
92, 77; EI-HRMS: calcd for C24H31ClN2O3 (Mþ), 430.2023; found,
430.2023.
white solid, yield 82%, m.p. 152.1–152.9 ꢀC; IR (KBr):
n
d
¼ 3244
(N–H), 1688, 1643 (C]O) cmꢁ1; 1H NMR (400 MHz, CDCl3):
¼ 7.75
(d, J ¼ 8 Hz, 2H, Ar–H), 7.69 (s, 1H, N–H), 7.35 (d, J ¼ 8 Hz, 2H, Ar–H),
4.63 (br, 1H, CH), 4.08 (q, 2H, COCH2), 2.75 (q, 2H, Ph–CH2),
1.33–1.60 (m, 12H, CH2), 1.28 (t, J ¼ 7.6 Hz, 3H, Ph–CH2CH3), 0.91 (t,
J ¼ 6.4 Hz, 6H, CH3); 13C NMR (100 MHz, CDCl3):
¼ 168.81, 166.52,
d
4.3.8. 2-Chloro-N0-(4-ethylbenzoyl)-N-(nonan-5-yl)
benzohydrazide (6h)
149.91, 129.01, 128.63, 127.34, 56.98, 41.98, 32.16, 31.41, 28.89,
28.64, 28.45, 22.63, 22.47, 15.23, 13.97; MS: m/z ¼ 330 ([M–Cl]þ),
273, 217, 204, 190, 159, 133, 105; ESI-HRMS: calcd for C20H31ClN2O2
([M þ H]þ), 367.2152; found, 367.2151.
This compound was obtained following the above method as
white solid, yield 68%, m.p. 92.3–93.7 ꢀC; IR (KBr):
n
¼ 3281 (N–H),
1691, 1632 (C]O) cmꢁ1; 1H NMR (400 MHz, CDCl3):
d
¼ 7.70 (s, 1H,
N–H), 7.53 (d, J ¼ 7.2 Hz, 1H, Ph–H), 7.16–7.31 (m, 7H, Ph–H),
4.72–4.77 (m, 1H, CH), 2.65 (q, 2H, Ph–CH2), 1.20–1.63 (m, 12H,
CH2), 1.21 (t, J ¼ 7.4 Hz, 3H, Ph–CH2CH3), 0.95 (t, J ¼ 7 Hz, 6H, CH3);
4.3.13. N0-(4-Ethylbenzoyl)-2,3,5-trifluoro-4-methoxy-N-(nonan-
5-yl)benzohydrazide (6m)
This compound was obtained following the above method as
13C NMR (100 MHz, CDCl3):
d
¼ 170.24, 166.27, 148.97, 136.12,
white solid, yield 67%, m.p. 117.0–118.4 ꢀC; IR (KBr):
n
¼ 3274 (N–H),
130.25, 129.63, 129.58, 128.37, 128.25, 127.07, 126.68, 56.94, 28.86,
28.75, 22.65, 15.14, 14.06; MS: m/z ¼ 428 (Mþ), 371, 280, 237, 133,
105, 90, 55; EI-HRMS: calcd for C25H33ClN2O2 (Mþ), 428.2231;
found, 428.2231.
1684, 1636 (C]O) cmꢁ1; 1H NMR (400 MHz, CDCl3):
d
¼ 7.67 (s, 1H,
N–H), 7.43 (d, J ¼ 8.4 Hz, 2H, Ph–H), 7.24 (d, J ¼ 8 Hz, 2H, Ph–H),
7.12–7.18 (m, 1H, Ph–H), 4.70–4.74 (m, 1H, CH), 3.91 (s, 3H, OCH3),
2.68 (q, 2H, Ph–CH2), 1.21–1.63 (m, 12H, CH2), 1.23 (t, J ¼ 7.6 Hz, 3H,
Ph–CH2CH3), 0.94 (t, J ¼ 7 Hz, 6H, CH3); 13C NMR (100 MHz, CDCl3):
4.3.9. N0-(4-Ethylbenzoyl)-3,5-dimethyl-N-(nonan-5-yl)
benzohydrazide (6i)
d
¼ 166.67, 165.89, 149.57, 129.03, 128.49, 126.78, 111.16, 110.91,
62.09, 57.35, 32.31, 31.90, 31.09, 28.81, 22.50, 15.20, 14.00; MS:
m/z ¼ 478 (Mþ), 421, 330, 287, 245, 214, 189, 133, 105, 79; EI-HRMS:
calcd for C26H33F3N2O3 (Mþ), 478.2443; found, 478.2443.
This compound was obtained following the above method as
white solid, yield 79%, m.p. 98.4–99.5 ꢀC; IR (KBr):
n
¼ 3288 (N–H),
1684, 1628 (C]O) cmꢁ1
;
1H NMR (400 MHz, DMSO-d6):
d
¼ 10.30
(s, 1H, N–H), 6.94–7.82 (m, 7H, Ar–H), 4.53 (br, 1H, CH), 2.59 (q, 2H,
Ph–CH2), 2.20 (s, 6H, Ph–CH3), 1.27–1.63 (m, 12H, CH2), 1.13 (t,
J ¼ 7.6 Hz, 3H, Ph–CH2CH3), 0.89 (t, J ¼ 6.8 Hz, 3H, CH3), 0.84 (t,
4.3.14. N0-Benzoyl-3-methoxy-N0-(nonan-5-yl)benzohydrazide
(6n)
This compound was obtained following the above method as
J ¼ 7.0 Hz, 3H, CH3); 13C NMR (100 MHz, DMSO-d6):
d
¼ 172.37,
white solid, yield 64%, m.p. 89.4–90.2 ꢀC; IR (KBr):
n
¼ 3281 (N–H),
166.79, 148.25, 136.74, 136.60, 131.15, 130.86, 128.44, 128.07, 127.80,
125.12, 56.11, 31.91, 31.74, 28.99, 28.81, 28.47, 22.74, 22.52, 21.17,
15.78,14.48,14.34; MS: m/z ¼ 422 (Mþ), 365, 296, 274, 231,189,133,
105, 79, 57; EI-HRMS: calcd for C27H38N2O2 (Mþ), 422.2933; found,
422.2933.
1684, 1613 (C]O) cmꢁ1
;
1H NMR (400 MHz, DMSO-d6):
d
¼ 10.39
(s, 1H, N–H), 6.88–7.95 (m, 9H, Ar–H), 4.53 (br, 1H, CH), 3.72 (s, 3H,
OCH3), 1.14–1.64 (m, 12H, CH2), 0.87 (t, J ¼ 9.6 Hz, 6H, CH3); 13C
NMR (100 MHz, DMSO-d6):
133.32, 131.13, 129.99, 129.69, 129.01, 127.88, 127.26, 119.82, 117.52,
d
¼ 167.66, 159.38, 136.79, 134.58,