A. Kamal et al. / Bioorg. Med. Chem. 15 (2007) 1004–1013
1011
was obtained from 2-(4-chloroanilino)-3-pyridinecarbo-
hydrazide (5a, 263 mg, 1 mmol) and 4-methyl
benzenesulfonyl chloride (6a, 228 mg, 1.2 mmol) as de-
scribed in Section 6.4.
Yield 75%; mp 237–239 ꢁC; 1H NMR (200 MHz,
CDCl3+DMSO-d6): d 10.96 (d, J = 5.00, 1H), 10.29 (br
s, 1H), 9.42 (d, J = 5.00, 1H), 8.52 (d, J = 9.29. 1H),
8.22 (dd, J = 5.00, 1.43, 1H), 8.08 (dd, J = 7.86,
1.43 Hz, 1H), 7.88 (dd, J = 8.58,5.00 Hz, 2H), 7.28 (d,
J = 2.14 Hz, 1H), 7.12 (d, J = 2.14 Hz, 1H), 7.04 (t,
J = 8.58 Hz, 1H), 6.74(dd, J = 7.86, 4.29 Hz, 1H); LC–
Yield 68%; mp 241–243 ꢁC; 1H NMR (200 MHz,
CDCl3+DMSO-d6): d 10.96 (1H, d, J = 4.46 Hz), 9.79
(br s, 1H), 9.36 (d, J = 4.46 Hz, 1H), 8.23 (dd,
J = 5.20, 1.48 Hz, 1H), 8.02 (dd, J = 7.43, 1.48 Hz,
1H), 7.75 (d, J = 8.17 Hz, 2H), 7.50 (d, J = 8.176 Hz,
2H), 7.20 (dd, J = 15.61, 8.92 Hz, 4H), 6.71 (dd,
J = 8.17, 5.20 Hz, 1H), 2.30 (s, 3H); FABMS m/z 417
(M+1)+; IR (KBr) (mmax/cmꢀ1): 1150, 1328 (SO2), 1248
(C–N), 1521, 1602, 1648 (C@O), 1721, 3036 (methyl),
3323 (NH). Anal. Calcd for C19H17ClN4O3S: C, 54.74;
H, 4.11; N, 13.44. Found: C, 54.79; H, 4.21; N, 13.35.
MS m/z 454.9 (M+), 476.9 (M++Na); IR (KBr) (mmax
/
cmꢀ1): 1164, 1326 (SO2), 1247 (C–N), 1500, 1604, 1660
(C@O), 3103 (Ar–H), 3268, 3355 (NH). Anal. Calcd
for C18H13Cl2FN4O3S: C, 47.49; H, 2.88; N, 12.31.
Found: C, 47.52; H, 2.86; N, 12.28.
6.4.5. N0-1-[2-(4-Fluoroanilino)-3-pyridyl]carbonyl-4-chlo-
ro-1-benzenesulfonohydrazide (7e). The title compound
was obtained from 2-(4-fluoroanilino)-3-pyridinecarbo-
hydrazide (5c, 246 mg, 1 mmol) and 4-chloro benzene-
sulfony lchloride (6c, 252 mg, 1.2 mmol) as described
in Section 6.4.
6.4.2.
N0-1-[2-(4-Methoxyanilino)-3-pyridyl]carbonyl-
4-methyl-1-benzenesulfonohydrazide (7b). The title
compound was obtained from 2-(4-methoxyanilino)-3-
pyridinecarbohydrazide (5b, 258 mg, 1 mmol) and 4-
methyl benzenesulfonyl chloride (6a, 228 mg, 1.2 mmol)
as described in Section 6.4.
Yield 70%; mp 232–235 ꢁC (charred); 1H NMR
(200 MHz, CDCl3+DMSO-d6): d (ppm): 10.85 (br s,
1H), 9.66 (br s, 2H), 8.14 (dd, J = 4.45, 1.48, 1H), 7.95
(dd, J = 8.17, 1.48, 1H), 7.80 (d, J = 8.17, 2H), 7.38
(m, 4H), 6.68 (t, J = 8.91, 2H), 6.60 (dd, J = 8.17, 4.45,
1H); MS m/z 420.9 (M+), 443 (M++Na); IR (KBr)
(mmax/cmꢀ1): 1157, 1337 (SO2), 1253 (C–N), 1506,
1588, 1613, 1735 (C@O), 3021 (Ar–H), 3330 (NH).
Anal. Calcd for C18H14ClFN4O3S: C, 51.37; H, 3.35;
N, 13.31. Found: C, 51.32; H, 3.37; N, 13.28.
Yield 75%; mp 159–161 ꢁC; 1H NMR (200 MHz,
CDCl3+DMSO-d6): d 10.80 (1H, d, J = 4.29 Hz), 9.49
(d, J = 4.29 Hz, 1H), 9.45 (br s, 1H), 8.11 (dd,
J = 3.57 Hz, 1.43, 1H), 7.92 (1H, dd, J = 7.15, 1.43, 1H),
7.70 (dd, J = 7.86, 0.71 Hz, 2H), 7.30 (d, J = 8.58 Hz,
2,), 7.18 (d, J = 7.86 Hz, 2H), 6.72 (d, J = 8.58 Hz, 2H),
6.58 (dd, J = 5.00, 7.86 Hz, 1H), 3.70 (s, 3H), 2.25 (s,
3H); FABMS m/z 413 (M+1)+; IR (KBr) (mmax/cmꢀ1):
1163, 1337 (SO2), 1245 (C–N), 1517, 1603, 1659 (C@O),
1740, 2854, 2924 (methyl), 3213, 3325 (NH). Anal. Calcd
for C20H20N4O4S: C, 58.24; H, 4.89; N, 13.58. Found: C,
58.31; H, 4.84; N, 13.62.
6.4.6. N0-1-[2-(4-Chloroanilino)-3-pyridyl]carbonyl-2,4-
dichloro-1-benzenesulfono-hydrazide (7f). The title
compound was obtained from 2-(4-chloroanilino)-3-
pyridinecarbohydrazide (5a, 263 mg, 1 mmol) and 2,4-
dichloro benzenesulfonyl chloride (6d, 293 mg,
1.2 mmol) as described in Section 6.4.
6.4.3. N0-1-[2-(4-Fluoroanilino)-3-pyridyl]carbonyl-4-fluo-
ro-1-benzenesulfonohydrazide (7c). The title compound
was obtained from 2-(4-fluoroanilino)-3-pyridinecarbo-
hydrazide (5c, 246 mg, 1 mmol) and 4-fluoro benze-
nesulfonyl chloride (6b, 232 mg, 1.2 mmol) as
described in Section 6.4.
Yield 70%; mp 215–216 ꢁC; 1H NMR (200 MHz,
CDCl3+DMSO-d6): d 10.85 (br s, 1H), 9.86 (br s, 1H),
9.62 (br s, 1H), 8.18 (dd, J = 4.21, 1.68 Hz, 1H), 7.95
(d, J = 1.68 Hz, 1H), 7.89 (d, J = 8.43 Hz, 1H), 7.51
(d, J = 1.68 Hz, 1H), 7.46 (d, J = 8.43 Hz, 2H), 7.25
(dd, J = 8.43, 1.68 Hz, 1H), 7.12 ( d, J = 8.43 Hz, 2H),
6.64 (dd, J = 7.59,4.21 Hz, 1H); FABMS m/z 473
(M+2)+; IR (KBr) (mmax/cmꢀ1): 1162, 1339 (SO2), 1251
(C–N), 1518, 1607, 1644 (C@O), 1738, 3020 (Ar–H),
3339 (NH). Anal. Calcd for C18H13Cl3N4O3S: C,
45.83; H, 2.78; N, 11.88. Found: C, 45.78; H, 2.76; N,
11.81.
Yield 70%; mp 225–227 ꢁC; 1H NMR (200 MHz,
CDCl3+DMSO-d6): d 10.92 (d, J = 3.18 Hz, 1H), 9.78
(br s, 1H), 9.73 (d, J = 3.18 Hz, 1H), 8.22 (dd,
J = 4.77, 1.59 Hz, 1H), 8.02 (dd, J = 7.95, 1.59 Hz,
1H), 7.94 (dd, J = 8.76, 4.77 Hz, 2H), 7.48 (dd,
J = 8.76, 4.77 Hz, 1H), 7.15 (t, J = 8.76 Hz, 2H), 6.94
(t, J = 8.76 Hz, 2H), 6.70 (dd, J = 7.96, 4.77 Hz, 1H);
FABMS m/z 405 (M+1)+; IR (KBr) (mmax/cmꢀ1): 1154,
1344 (SO2), 1256 (C–N), 1506, 1585, 1691 (C@O),
3030 (Ar–H), 3232, 3355 (NH). Anal. Calcd for
C18H14F2N4O3S: C, 53.46; H, 3.49; N, 13.85. Found:
C, 53.51; H, 3.46; N, 13.76.
6.4.7. N-1-4-[(2-[2-(4-Chloroanilino)-3-pyridyl]carbonylhyd-
razino)sulfonyl]phenyl-acetamide (7g). The title compound
was obtained from 2-(4-chloroanilino)-3-pyridinecarbo-
hydrazide (5a, 263 mg, 1 mmol) and 4-acetylamino
benzenesulfonyl chloride (6e, 280 mg, 1.2 mmol) as
described in Section 6.4.
6.4.4. N0-1-[2-(2,4-Dichloroanilino)-3-pyridyl]carbonyl-
4-fluoro-1-benzenesulfono-hydrazide (7d). The title
compound was obtained from 2-(2,4-dichloroanilino)-
3-pyridinecarbohydrazide (5d, 297 mg, 1 mmol) and 4-
fluoro benzenesulfonyl chloride (6b, 232 mg, 1.2 mmol)
as described in Section 6.4.
Yield 65%; mp 245–247 ꢁC (charred); 1H NMR
(200 MHz, CDCl3+DMSO-d6): d 11.02 (d, J = 3.37,
1H), 10.26 (br s, 1H), 10.04 (d, J = 3.37 Hz, 1H), 9.72
(br s, 1H), 8.32 (dd, J = 5.06 Hz, 1H), 8.03 (dd,
J = 7.59, 1.68 Hz, 1H), 7.74 (m, 4H), 7.54 (d,