4706
H.-J. Zhang et al. / European Journal of Medicinal Chemistry 46 (2011) 4702e4708
4.3.3. (Z)-2-((E)-3-(2-bromophenyl)-1-phenylallylidene)hydrazine
8.16 (d, J ¼ 8.6 Hz,1H). ESI-MS: 361.0 (C16H15BrN3S, [M þ H]þ). Anal.
Calcd for C16H14BrN3S: C, 53.34%; H, 3.92%; N, 11.66%. Found: C,
53.69%; H, 4.30%; N, 12.03%.
carbothioamide (4c)
1H NMR (300 MHz, DMSO-d6,
d ppm): 2.50 (s, 1H), 3.32 (s, 1H),
6.39 (d, J ¼ 16.5 Hz, 1H), 6.86 (d, J ¼ 16.3 Hz, 1H), 7.19 (d, J ¼ 16.4 Hz,
1H), 7.36 (d, J ¼ 7.5 Hz, 1H), 7.42e7.50 (m, 2H), 7.55e7.76 (m, 6H).
4.3.11. (Z)-2-((E)-1-phenyl-3-p-tolylallylidene)hydrazinecarbothio
ESI-MS: 361.0 (C16H15BrN3S, [M
C16H14BrN3S: C, 53.34%; H, 3.92%; N, 11.66%. Found: C, 53.68%; H,
4.30%; N, 11.99%.
þ
H]þ). Anal. Calcd for
amide (4k)
1H NMR (300 MHz, DMSO-d6,
d ppm): 2.33 (s, 3H, CH3),
3.83e3.93 (m,1H), 5.88 (dd, J1 ¼ 3.1 Hz, J2 ¼ 3.1 Hz,1H), 7.01 (d,
J ¼ 8.0 Hz, 2H), 7.11 (d, J ¼ 7.9 Hz, 2H), 7.21 (d, J ¼ 8.1 Hz, 1H),
7.44e7.46 (m, 3H), 7.86e7.88 (m, 3H), 7.80 (s, 1H, NH). ESI-MS:
296.1 (C17H18N3S, [M þ H]þ). Anal. Calcd for C17H17N3S: C, 69.12%;
H, 5.80%; N, 14.22%. Found: C, 69.48%; H, 6.15%; N, 14.58%.
4.3.4. (Z)-2-((E)-3-(2-methoxyphenyl)-1-phenylallylidene)hydrazin-
ecarbothioamide (4d)
1H NMR (300 MHz, DMSO-d6,
d ppm): 3.43 (s, 3H, OCH3), 3.83 (s,
2H), 6.06 (dd, J1 ¼3.1 Hz, J2 ¼ 3.3 Hz,1H), 6.80e6.88 (m, 2H), 7.03 (d,
J ¼ 8.0 Hz, 1H), 7.22 (t, J ¼ 8.6 Hz, 1H), 7.43 (d, J ¼ 6.3 Hz,3H), 7.86
(dd, J1 ¼ 2.5 Hz, J2 ¼ 1.6 Hz, 3H), 8.02 (s, 1H, NH). ESI-MS: 312.1
(C17H18N3OS, [M þ H]þ). Anal. Calcd for C17H17N3OS: C, 65.57%; H,
5.50%; N, 13.49%. Found: C, 65.92%; H, 5.83%; N, 13.85%.
4.3.12. (Z)-2-((E)-3-(4-methoxyphenyl)-1-phenylallylidene)hydraz
inecarbothioamide (4l)
1H NMR (300 MHz, DMSO-d6,
d ppm): 3.72 (s, 3H, OCH3),
3.83e3.92 (m,1H), 5.87 (dd, J1 ¼ 3.3 Hz, J2 ¼ 3.1 Hz, 1H), 6.87 (d,
J ¼ 8.6 Hz, 2H), 7.05 (d, J ¼ 8.6 Hz, 2H), 7.47 (t, J ¼ 3.5 Hz, 3H), 7.98 (s,
1H, NH), 7.87e7.90 (m, 3H). ESI-MS: 312.1 (C17H18N3OS, [M þ H]þ).
Anal. Calcd for C17H17N3OS: C, 65.57%; H, 5.50%; N,13.49%. Found: C,
65.95%; H, 5.86%; N, 13.83%.
4.3.5. (Z)-2-((E)-3-(3-fluorophenyl)-1-phenylallylidene)hydrazinec-
arbothioamide (4e)
1H NMR (300 MHz, DMSO-d6,
d ppm): 2.50 (s, 1H), 3.31 (s, 1H),
7.50e7.98 (m, 12H). ESI-MS: 300.1 (C16H15FN3S, [M þ H]þ). Anal.
Calcd for C16H14FN3S: C, 64.19%; H, 4.71%; N, 14.04%. Found: C,
64.56%; H, 5.09%; N, 14.39%.
4.3.13. (Z)-2-((E)-3-(4-nitrophenyl)-1-phenylallylidene)hydrazine
carbothioamide (4m)
1H NMR (300 MHz, DMSO-d6,
d
ppm): 6.90 (d, J ¼ 16.0 Hz, 1H),
4.3.6. (Z)-2-((E)-3-(3-methoxyphenyl)-1-phenylallylidene)
7.65 (d, J ¼ 7.0 Hz, 4H), 8.01 (d, J ¼ 6.9 Hz, 3H), 8.19e8.27 (m, 5H),
8.38 (s, 1H, NH). ESI-MS: 327.1 (C16H15N4O2S, [M þ H]þ). Anal. Calcd
for C16H14N4O2S: C, 58.88%; H, 4.32%; N, 17.17%. Found: C, 59.26%; H,
4.67%; N, 17.52%.
hydrazinecarbothioamide (4f)
1H NMR (300 MHz, DMSO-d6,
d ppm): 3.81 (s, 3H, OCH3), 3.72-
3.40 (m,1H), 6.75 (d, J ¼ 16.1 Hz, 1H), 6.95 (d, J ¼ 6.6 Hz, 1H), 7.05 (d,
J ¼ 7.9 Hz, 1H), 7.30 (s, 3H), 7.45 (s, 3H), 7.61e7.66 (m, 2H), 7.78 (d,
J ¼ 16.1 Hz, 1H), 8.30 (s, 1H, NH). ESI-MS: 312.1 (C17H18N3OS,
[M þ H]þ). Anal. Calcd for C17H17N3OS: C, 65.57%; H, 5.50%; N,
13.49%. Found: C, 65.95%; H, 5.86%; N, 13.83%.
4.3.14. (Z)-2-((E)-3-(biphenyl-4-yl)-1-phenylallylidene)
hydrazinecarbothioamide (4n)
1H NMR (300 MHz, DMSO-d6,
d
ppm): 3.20 (dd, J1 ¼ 3.1 Hz,
J2 ¼ 3.3 Hz, 1H), 3.89e4.04 (m, 1H), 5.75 (s, 1H), 5.98 (d,
J ¼ 11.3 Hz, 1H), 7.23 (d, J ¼ 8.0 Hz, 2H), 7.35 (d, J ¼ 7.0 Hz,
1H), 7.45 (t, J ¼ 7.3 Hz, 6H),7.73 (d, J ¼ 8.2 Hz, 1H), 7.83 (d,
J ¼ 7.7 Hz, 1H), 7.89 (t, J ¼ 3.8 Hz, 3H), 8.06 (s, 1H, NH). ESI-
MS: 358.1 (C22H20N3S, [M þ H]þ). Anal. Calcd for C22H19N3S:C,
73.92%; H, 5.36%; N, 11.75%. Found: C, 74.30%; H, 5.69%; N,
12.08%.
4.3.7. (Z)-2-((E)-3-(3-nitrophenyl)-1-phenylallylidene)hydrazi-
necarbothioamide (4g)
1H NMR (300 MHz, DMSO-d6,
d ppm): 2.52 (s, 1H), 3.31 (s, 1H),
6.60 (d, J ¼ 16.5 Hz, 1H), 6.90 (d, J ¼ 16.4 Hz, 1H), 7.37 (t, J ¼ 9.0 Hz,
2H), 7.45e7.47 (m, 4H), 8.19 (d, J ¼ 8.8 Hz, 1H), 8.25 (d, J ¼ 9.0 Hz,
2H), 8.37 (s, 1H, NH). ESI-MS: 327.1 (C16H15N4O2S, [M þ H]þ). Anal.
Calcd for C16H14N4O2S: C, 58.88%; H, 4.32%; N, 17.17%. Found: C,
59.26%; H, 4.68%; N, 17.52%.
4.3.15. (Z)-2-((E)-3-(4-(benzyloxy)phenyl)-1-phenylallylidene)
hydrazinecarbothioamide (4o)
4.3.8. (Z)-2-((E)-3-(4-fluorophenyl)-1-phenylallylidene)hydrazine
carbothioamide (4h)
1H NMR (300 MHz, DMSO-d6,
d
ppm): 3.13 (dd, J1 ¼ 3.1 Hz,
J2 ¼ 3.2 Hz, 1H), 3.82e3.92 (m, 1H), 5.06 (s, 2H), 5.84e5.89 (m, 1H),
6.95 (d, J ¼ 8.6 Hz, 2H), 7.06 (d, J ¼ 8.6 Hz, 2H), 7.29e7.47 (m, 8H),
7.87 (t, J ¼ 3.8 Hz, 3H), 7.99 (s, 1H, NH). ESI-MS: 388.1 (C23H22N3OS,
[M þ H]þ). Anal. Calcd for C23H21N3OS: C, 71.29%; H, 5.46%; N,
10.84%. Found: C, 71.65%; H, 5.80%; N, 11.19%.
1H NMR (300 MHz, DMSO-d6,
d ppm): 3.12e3.19 (m, 1H),
3.86e3.96 (m, 1H), 5.93 (dd, J1 ¼ 3.5 Hz, J2 ¼ 3.3 Hz, 1H), 7.10e7.20
(m, 4H), 7.46 (t, J ¼ 3.5 Hz, 3H), 7.87e7.90 (m, 3H), 8.05 (s, 1H, NH).
ESI-MS: 300.1 (C16H15FN3S, [M þ H]þ). Anal. Calcd for C16H14FN3S:
C, 64.19%; H, 4.71%; N,14.04%. Found: C, 64.44%; H, 5.05%; N,14.39%.
4.3.16. (Z)-2-((E)-1,3-diphenylallylidene)hydrazinecarbothioamide
4.3.9. (Z)-2-((E)-3-(4-chlorophenyl)-1-phenylallylidene)hydrazine
carbothioamide (4i)
(4p)
1H NMR (500 MHz, DMSO-d6,
d
ppm): 6.78 (d, J ¼ 16.0 Hz, 1H),
1H NMR (300 MHz, DMSO-d6,
d
ppm): 3.14 (dd, J1 ¼ 3.5 Hz,
7.35e7.43 (m, 3H), 7.45e7.48 (m, 3H), 7.63-7.66 (m, 2H), 7.74 (d,
J ¼ 7.0 Hz, 2H), 7.80 (s, 1H), 7.81 (d, J ¼ 16.0 Hz, 1H), 8.31 (s, 1H),
11.09 (s, 1H). ESI-MS: 282.1 (C16H16N3S, [M þ H]þ). Anal. Calcd for
C16H15N3S: C, 68.30%; H, 5.37%; N, 14.93%. Found: C, 68.64%; H,
5.73%; N, 15.31%.
J2 ¼ 3.5 Hz, 1H), 3.85e3.95 (m, 1H), 5.93 (dd, J1 ¼ 3.3 Hz, J2 ¼ 3.3 Hz,
1H), 7.12 (d, J ¼ 7.1 Hz, 2H), 7.20e7.34 (m, 3H), 7.52 (d, J ¼ 8.4 Hz,
2H),7.90 (d, J ¼ 8.4 Hz, 2H), 8.00 (d, J ¼ 26.7 Hz, 2H). ESI-MS: 317.1
(C16H15ClN3S, [M þ H]þ). Anal. Calcd for C16H14ClN3S: C, 60.85%; H,
4.47%; N, 13.31%. Found: C, 61.21%; H, 4.85%; N, 13.69%.
4.3.17. (Z)-2-((E)-1-(4-bromophenyl)-3-phenylallylidene)
4.3.10. (Z)-2-((E)-3-(4-bromophenyl)-1-phenylallylidene)hydraz
hydrazinecarbothioamide (4q)
inecarbothioamide (4j)
1H NMR (300 MHz, DMSO-d6,
d
ppm): 3.14 (d, J ¼ 18.7 Hz, 1H),
1H NMR (300 MHz, DMSO-d6,
d
ppm): 2.50 (s, 1H), 3.60 (s, 1H),
3.85e3.95 (m,1H), 5.93 (d, J ¼ 8.2 Hz,1H), 7.13 (d, J ¼ 7.3 Hz, 2H),
7.24 (d, J ¼ 7.9 Hz, 1H), 7.31 (t, J ¼ 7.6 Hz, 2H), 7.52 (d, J ¼ 8.4 Hz,
2H), 7.90 (d, J ¼ 8.4 Hz, 2H), 7.97 (s, 1H), 8.05(s, 1H, NH). ESI-MS:
7.37 (t, J ¼ 8.2 Hz, 1H), 7.47e7.52 (m, 1H), 7.58 (t, J ¼ 7.7 Hz, 2H),
7.66e7.75 (m, 4H), 7.87 (d, J ¼ 15.5 Hz, 2H), 7.97 (d, J ¼ 15.5 Hz, 1H),