Article
Journal of Medicinal Chemistry, 2010, Vol. 53, No. 8 3061
N-(4-Cyanophenyl)hydrazinecarbothioamide (B19). Yield: 91%.
7.20-7.18 (d, J = 3.0 Hz, 1H), 2.31 (s, 3H). MS (EI, m/z): 320
[M]þ. HRMS (EI): calcd for C18H16N4S [M]þ, 320.1096; found
320.1104.
1H NMR (300 MHz, DMSO-d6): δ 9.24 (s, 1H), 7.86-7.79 (m,
2H), 7.43-7.39 (m, 2H).
N-(2,6-Diisopropylphenyl)hydrazinecarbothioamide (B20). Yield:
72%. 1H NMR (300 MHz, DMSO-d6): δ 7.25-7.10 (m, 3H), 4.75
(br, 2H), 3.08-2.98 (m, 2H), 1.07 (dd, J = 11.4 Hz, 6.9 Hz, 12H).
N-(2-Methoxy-5-methylphenyl)hydrazinecarbothioamide (B21).
Yield: 95%. 1H NMR (300 MHz, DMSO-d6): δ 9.92 (br, 1H),
9.18 (s, 1H), 8.62 (br, 1H), 6.93-6.82 (m, 2H), 4.84 (br, 1H), 3.80
(s, 3H), 2.22 (s, 3H).
N-(4-Methylphenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
boamide (TSC8). TSC8 was prepared from B8 according to
general procedure (method A). Yield: 55%. 1H NMR (300
MHz, DMSO-d6): δ 11.14 (s, 1H), 9.05 (s, 1H), 8.55 (d, J =
6.0 Hz, 1H), 8.41 (d, J = 4.5 Hz, 1H), 8.14 (s, 1H), 8.03-7.99 (m,
1H), 7.79-7.77 (m, 1H), 7.66-7.56 (m, 3H), 7.14 (d, J = 4.5 Hz,
1H). MS (EI, m/z): 304 [M]þ. HRMS (EI): calcd for C18H16N4O
[M]þ, 304.1324; found 304.1332.
N-(2-Fluorophenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC9). TSC9 was prepared from B9 according to
general procedure (method A). Yield: 47%. 1H NMR (300
MHz, DMSO-d6): δ 12.34 (s, 1H), 10.26 (s, 1H), 8.57 (d, J =
4.5 Hz, 1H), 8.38 (d, J = 4.5 Hz, 1H), 8.31 (s, 1H), 8.03-7.97 (m,
2H), 7.77-7.75 (m, 1H), 7.64-7.62 (m, 1H), 7.47-7.46 (m, 1H),
7.35-7.23 (m, 2H). MS (EI, m/z): 324 [M]þ. HRMS (EI): calcd
for C17H13FN4S [M]þ, 324.0845; found 324.0844.
N-Benzylhydrazinecarbothioamide (B22). Yield: 93%. 1H
NMR (DMSO-d6): δ 8.76 (s, 1H), 8.30 (br, 1H), 7.31-7.20
(m, 5H), 4.71 (d, J = 6.0 Hz, 2H).
N-Phenyl-2-(quinolin-2-ylmethylene)hydrazinecarbothioamide
(TSC1). TSC1 was prepared from B1 according to general
procedure (method A). Yield: 70%. 1H NMR (300 MHz,
DMSO-d6): δ 12.21 (s, 1H), 10.41 (s, 1H), 8.64 (d, J = 8.4 Hz,
1H), 8.41 (d, J = 9.0 Hz, 1H), 8.35 (s, 1H), 8.03 (t, J = 8.7 Hz,
2H), 7.83-7.77 (m, 1H), 7.67-7.56 (m, 3H), 7.42 (t, J = 7.5 Hz,
2H), 7.26 (t, J = 7.5 Hz, 1H). MS (EI, m/z): 306 [M]þ. HRMS
(EI): calcd for C17H14N4S [M]þ, 306.0939; found 306.0932.
N-(2-Methoxyphenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC2). TSC2 was prepared from B2 according to
general procedure (method A). Yield: 61%. 1H NMR (300
MHz, DMSO-d6): δ 12.24 (s, 1H), 10.13 (s, 1H), 8.60 (d, J =
8.1 Hz, 1H), 8.40 (d, J = 8.4 Hz, 1H), 8.30 (s, 1H), 8.03 (t, J =
9.0 Hz, 2H), 7.88-7.76 (m, 2H), 7.64-7.60 (m, 2H), 7.12-7.10
(m, 1H), 6.99-6.95 (m. 1H), 3.88 (s, 3H). MS (EI, m/z): 336
[M]þ. HRMS (EI): calcd for C18H16N4OS [M]þ, 336.1045;
found 336.1044.
N-(3-Fluorophenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC10). TSC10 was prepared from B10 according
to general procedure (method A). Yield: 41%. H NMR (300
1
MHz, DMSO-d6): δ 12.33 (s, 1H), 10.45 (s, 1H), 8.65 (d, J = 4.5
Hz, 1H), 8.43 (d, J = 9.0 Hz, 1H), 8.36 (s, 1H), 8.03 (t, J = 9.0
Hz, 2H), 7.79 (t, J = 6.0 Hz, 1H), 7.67-7.57 (m, 2H), 7.47-7.44
(m, 2H), 7.10-7.09 (m, 1H). MS (EI, m/z): 324 [M]þ. HRMS
(EI): calcd for C17H13FN4S [M]þ, 324.0845; found 324.0848.
N-(4-Fluorophenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC11). TSC11 was prepared from B11 according
1
to general procedure (method A). Yield: 40%. H NMR (300
N-(3-Methoxyphenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC3). TSC3 was prepared from B3 according to
general procedure (method A). Yield: 44%. 1H NMR (300
MHz, DMSO-d6): δ 12.22 (s, 1H), 10.35 (s, 1H), 8.63 (d, J =
8.4 Hz, 1H), 8.41 (d, J = 8.7 Hz, 1H), 8.40 (s, 1H), 8.03 (t, J =
9.0 Hz, 2H), 7.83-7.77 (m, 1H), 7.67-7.62 (m, 1H), 7.34-7.18
(m, 3H), 6.86-6.82 (m, 1H), 3.78 (s, 3H). MS (EI, m/z): 336
[M]þ. HRMS (EI): calcd for C18H16N4OS [M]þ, 336.1045;
found 336.1036.
N-(4-Methoxyphenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC4). TSC4 was prepared from B4 according to
general procedure (method A). Yield: 59%. 1H NMR (300
MHz, DMSO-d6): δ 12.14 (s, 1H), 10.31 (s, 1H), 8.64 (d, J =
8.7 Hz, 1H), 8.40 (d, J = 8.4 Hz, 1H), 8.33 (s, 1H), 8.02 (t, J =
8.4 Hz, 2H), 7.82-7.77 (m, 1H), 7.66-7.61 (m, 1H), 7.41 (t, J =
6.9 Hz, 2H), 6.97 (t, J = 6.9 Hz, 2H), 3.78 (s, 3H). MS (EI, m/z):
336 [M]þ. HRMS (EI): calcd for C18H16N4OS [M]þ, 336.1045;
found 336.1045.
N-(2-Methylphenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC5). TSC5 was prepared from B5 according to
general procedure (method A). Yield: 47%. 1H NMR (300
MHz, DMSO-d6): δ 12.18 (s, 1H), 10.28 (s, 1H), 8.63 (d, J =
6.0 Hz, 1H), 8.38 (d, J = 4.5 Hz, 1H), 8.33 (s, 1H), 7.78 (m, 1H),
7.65 (m, 1H), 7.32-7.24 (m, 4H), 2.27 (s, 1H). MS (EI, m/z): 320
[M]þ. HRMS (EI): calcd for C18H16N4S [M]þ, 320.1096; found
320.1101.
N-(3-Methylphenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC6). TSC6 was prepared from B6 according to
general procedure (method A). Yield: 53%. 1H NMR (300
MHz, DMSO-d6): δ 11.14 (s, 1H), 9.06 (s, 1H), 8.55 (d, J =
6.0 Hz, 1H), 8.41 (d, J = 4.5 Hz, 1H), 8.14 (s, 1H), 8.03-8.00 (m,
1H), 7.79-7.78 (m, 1H), 7.66-7.56 (m, 3H), 7.14 (d, J = 4.5 Hz,
1H). MS (EI, m/z): 320 [M]þ. HRMS (EI): calcd for C18H16N4S
[M]þ, 320.1096; found 320.1092.
MHz, DMSO-d6): δ 12.24 (s, 1H), 10.40 (s, 1H), 8.63 (d, J = 4.5
Hz, 1H), 8.42 (d, J = 6.0 Hz, 1H), 8.35 (s, 1H), 8.03 (t, J = 9.0
Hz, 2H), 7.83-7.78 (m, 1H), 7.67-7.54 (m, 3H), 7.25 (t, J = 9.0
Hz, 2H). MS (EI, m/z): 324 [M]þ. HRMS (EI): calcd for
C17H13FN4S [M]þ, 324.0845; found 324.0840.
N-(3-Chlorophenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC12). TSC12 was prepared from B12 according
to general procedure (method A). Yield: 46%. H NMR (300
1
MHz, DMSO-d6): δ 12.34 (s, 1H), 10.45 (s, 1H), 8.62 (d, J = 8.7
Hz, 1H), 8.43 (d, J = 9.0 Hz, 1H), 8.36 (s, 1H), 8.06-8.00 (m,
2H), 7.83-7.74 (m, 2H), 7.67-7.60 (m, 2H), 7.47-7.42 (m, 1H),
7.34-7.30 (m, 1H), MS (EI, m/z): 340 [M]þ. HRMS (EI): calcd
for C17H13ClN4S [M]þ, 340.0549; found 340.0558.
N-(4-Chlorophenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC13). TSC13 was prepared from B13 according
to general procedure (method A). Yield: 49%. H NMR (300
1
MHz, DMSO-d6): δ 12.28 (s, 1H), 10.41 (s, 1H), 8.59 (d, J = 6.0
Hz, 1H), 8.39 (d, J = 6.0 Hz, 1H), 8.32 (s, 1H), 8.03-7.97 (m,
2H), 7.79-7.75 (m, 1H), 7.64-7.58 (m, 3H), 7.47-7.44 (m, 2H).
MS (EI, m/z): 340 [M]þ. HRMS (EI): calcd for C17H13ClN4S
[M]þ, 340.0549; found 340.0548.
N-(2-Bromophenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC14). TSC14 was prepared from B14 according
to general procedure (method A). Yield: 44%. H NMR (300
1
MHz, DMSO-d6): δ 12.37 (s, 1H), 10.31 (s, 1H), 8.50 (d, J = 6.3
Hz, 1H), 8.38 (d, J = 6.6 Hz, 1H), 8.32 (s, 1H), 8.03-7.96 (m,
2H), 7.80-7.72 (m, 3H), 7.64-7.55 (m, 3H). MS (EI, m/z): 324
[M]þ. HRMS (EI): calcd for C17H13BrN4S [M]þ, 384.0044;
found 383.9959.
N-(3-Bromophenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC15). TSC15 was prepared from B15 according
to general procedure (method A). Yield: 56%. H NMR (300
1
MHz, DMSO-d6): δ 12.32 (s, 1H), 10.43 (s, 1H), 8.61 (d, J = 8.7
Hz, 1H), 8.41 (d, J = 8.7 Hz, 1H), 8.35 (s, 1H), 8.02 (t, J = 9.0
Hz, 2H), 7.86-7.74 (m, 1H), 7.66-7.61 (m, 2H), 7.46-7.34 (m,
2H). MS (EI, m/z): 384 [M]þ. HRMS (EI): calcd for C17H13-
BrN4S [M]þ, 384.0044; found 384.0029.
N-(4-Methylphenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC7). TSC7 was prepared from B7 according to
general procedure (method A). Yield: 44%. 1H NMR (300
MHz, DMSO-d6): δ 12.16 (s, 1H), 10.33 (s, 1H), 8.61 (d, J =
6.0 Hz, 1H), 8.37 (d, J = 6.0 Hz, 1H), 8.31 (s, 1H), 8.02-7.97 (m,
2H), 7.78-7.74 (m, 1H), 7.63-7.59 (m, 1H), 7.40-7.38 (m, 2H),
N-(4-Bromophenyl)-2-(quinolin-2-ylmethylene)hydrazinecar-
bothioamide (TSC16). TSC16 was prepared from B16 accord-
ing to general procedure (method A). Yield: 52%. H NMR
1