Synthesis and spectral data
((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(p-tolyl)allylidene)hydrazinecarbothioamide(6a)
Yield: 55%; m.p.: 196–198 °C; IR (KBr cm−1): 3362 (NH2), 1593 (C=C), 1351 (C=S), 1170 (OCH3); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 2.62 (s, 3H, CH3), 7.05 (s, 1H, ArH), 7.37 (d, 2H, J = 8.4 Hz, ArH), 7.56 (m, 4H, ArH), 7.72–7.69 (m, 3H, ArH, -C=HC-), 7.83 (d, 1H, J = 15.6 Hz, -C=HC-), 7.85 (s, 1H, NH2), 7.88 (s, 1H, NH2), 7.91 (s, 1H, ArH), 8.18 (s, 1H, ArH), 8.42 (s, 1H, ArH), 8.55 (s, 1H, ArH), 9.95 (s, 1H, NH), 10.83 (s, 1H, =N-NH-C); LC-MS M/Z: 473 [M + H]+.
2-((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-methoxyphenyl)allylidene)hydrazinecarbothioamide(6b)
Yield: 53%; m.p.: 190–192 °C; IR (KBr cm−1): 3367 (NH2), 1593 (C=C), 1350 (C=S), 1172 (OCH3); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 3.82 (s, 3H, OCH3), 7.02 (s, 1H, ArH), 7.34 (d, 2H, J = 8.4 Hz, ArH), 7.53 (m, 4H, ArH), 7.70–7.63 (m, 3H, ArH, -C=HC-), 7.85 (d, 1H, J = 15.6 Hz, -C=HC-), 7.87 (s, 1H, NH2), 7.89 (s, 1H, NH2), 7.88 (s, 1H, ArH), 8.18 (s, 1H, ArH), 8.40 (s, 1H, ArH), 8.58 (s, 1H, ArH), 9.93 (s, 1H, NH), 10.81 (s, 1H, =N-NH-C); LC-MS M/Z: 489 [M + H]+.
2-((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(3,4-dimethoxyphenyl)allylidene)hydrazinecarbothioamide(6c)
Yield: 56%; m.p.: 148–150 °C; IR (KBr cm−1): 3367 (NH2), 1265 (OCH3), 1350 (C=S); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 3.81 (s, 3H, OCH3), 3.86 (s, 3H, −OCH3), 7.02 (s, 1H, ArH), 7.45 (s, 1H, ArH), 7.38 (s, 1H, ArH), 7.53 (m, 3H, ArH), 7.72–7.69 (m, 3H, ArH, -C=HC-), 7.85 (d, 1H, J = 15.6 Hz, -C=HC-), 7.91 (s, 1H, NH2), 7.96 (s, 1H, NH2), 7.98 (s, 1H, ArH), 8.23 (s, 1H, ArH), 8.47 (s, 1H, ArH), 8.61 (s,1H, ArH), 9.91 (s, 1H, NH), 10.82 (s, 1H, =N-NH-C); LC-MS M/Z: 519 [M + H]+.
2-((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(3,4,5-trimethoxyphenyl)allylidene)hydrazinecarbothioamide(6d)
Yield: 66%; m.p.: 138–140 °C; IR (KBr cm−1): 3343 (NH2), 1593 (C=C), 1352 (C=S), 1128 (OCH3), 1128 (OCH3); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 3.76 (s, 3H, OCH3), 3.86 (s, 6H, -OCH3), 6.42 (s, 1H, ArH), 7.27 (d, 2H, J = 8.4 Hz ArH), 7.42 (s, 1H, ArH), 7.52 (s, 1H, ArH), 7.71–7.64 (m, 3H, ArH, -C=HC-), 7.89 (d, 1H, J = 15.6 Hz, -C=HC-), 7.92 (s, 1H, NH2), 7.95 (s, 1H, NH2), 7.98(s, 1H, ArH), 8.23 (s, 1H, ArH), 8.40 (s, 1H, ArH), 8.59 (s, 1H, ArH), 9.68 (s, 1H, NH), 10.72 (s, 1H, =N-NH-C); LC-MS M/Z: 549 [M + H]+.
2-((E)-3-(4-chlorophenyl)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)allylidene)hydrazinecarbothioamide(6e)
Yield: 73%; m.p.: 142–144 °C; IR (KBr cm−1): 3365 (NH2), 1554 (C=C), 1350 (C=S); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 7.08 (s, 1H, ArH), 7.51–7.749 (m, 3H, ArH, -C=HC-), 7.62 (d, 2H, J = 8.8 Hz, ArH), 7.70 (d,1H, J = 15.6 Hz -C=HC-), 7.78 (s, 1H, ArH), 7.89 (s, 1H, NH2), 7.91 (s, 1H, NH2), 7.95 (s, 1H, ArH), 8.01 (d, 2H, J = 8.4 Hz, ArH), 8.20 (d, 2H, J = 8.8 Hz, ArH), 8.41 (s, 1H, ArH), 8.62 (s, 1H, ArH), 10.08 (s, 1H, NH), 11.06 (s, 1H, =N-NH-C); LC-MS M/Z: 494 [M + H]+.
2-((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-fluorophenyl)allylidene)hydrazinecarbothioamide(6f)
Yield: 58%; m.p.: 178–180 °C; IR (KBr cm−1): 3354 (NH2), 1575 (C=C), 1351 (C=S); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 7.01 (s, 1H, ArH), 7.32–7.24 (m, 3H, ArH, -C=HC-), 7.52 (d, 2H, J = 8.8 Hz, ArH), 7.64 (d,1H, J = 15.6 Hz -C=HC-), 7.66 (s, 1H, NH2), 7.75 (s, 1H, NH2), 7.98 (s, 1H, ArH), 7.98–7.95 (m, 3H, ArH), 8.23–8.20 (m, 2H, ArH), 8.46 (s, 1H, ArH), 8.60 (s, 1H, ArH), 10.02 (s, 1H, NH), 11.03 (s, 1H, =N-NH-C); LC-MS M/Z: 477 [M + H]+.
2-((E)-3-(4-bromophenyl)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)allylidene)hydrazinecarbothioamide(6 g)
Yield: 66%; m.p.: 186–188 °C; IR (KBr cm−1): 3375 (NH2), 1580 (C=C), 1352 (C=S); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 6.53 (s, 1H, ArH), 6.86 (d, 1H, J = 15.6 Hz, -C=HC-), 6.99 (d, 1H, J = 12.6 Hz, -C=HC-), 7.07 (s, 1H, ArH), 7.30 (s, 1H, ArH), 7.47 (s, 1H, ArH), 7.62 (s, 1H, NH2), 7.77–7.70 (m, 4H, ArH,), 7.81 (s, 1H, NH2) 7.85 (d, 2H, J = 8.4 Hz, ArH), 8.20 (s, 1H, ArH), 8.30 (s, 1H, ArH), 8.51 (s, 1H, ArH), 10.10 (s, 1H, NH), 11.07 (s, 1H, =N-NH-C); LC-MS M/Z: 538 [M + H]+.
2-((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-nitrophenyl)allylidene)hydrazinecarbothioamide(6 h)
Yield: 47%; m.p.: 216–218 °C; IR (KBr cm−1): 3361 (NH2), 1540 (C=C), 1350 (C=S); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 7.20 (d, 1H, J = 5.6 Hz, ArH), 7.23–7.10 (m, 4H, ArH, NH2), 7.47 (d, 2H, J = 8.8 Hz, ArH), 7.71–7.60 (m, 3H, ArH, -C=HC-), 7.96 (s, 1H, NH2), 8.13 (s, 1H, ArH), 8.26 (s, 1H, ArH), 8.44–8.38 (m, 4H, ArH), 9.87 (s, 1H, NH), 11.69 (s, 1H, =N-NH-C); LC-MS M/Z: 504 [M + H]+.
2-((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-hydroxyphenyl)allylidene)hydrazinecarbothioamide(6i)
Yield: 50%; m.p.: 230–232 °C; IR (KBr cm−1): 3365 (NH2), 1567 (C=C), 1353 (C=S); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 7.20 (s, 1H, ArH), 7.27 (d, 2H, J = 8.8 Hz, ArH), 7.45–7.40 (m, 3H, ArH, CH=C), 7.73–7.61 (m, 3H, ArH, -C=HC-), 7.93 (s, 1H, NH2), 7.96 (s, 1H, NH2), 8.13 (s, 1H, ArH), 8.25 (d, 1H, ArH), 8.44–8.38 (m, 4H, ArH), 9.86 (s, 1H, NH), 9.88 (s, 1H, OH), 11.55 (s, 1H, =N-NH-C); LC-MS M/Z: 475 [M + H]+.
2-((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(p-tolyl)allylidene)hydrazinecarboxamide(7a)
Yield: 72%; m.p.: 148–150 °C; IR (KBr cm−1): 3425 (NH2), 1693 (C=O); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) 2.88 (s, 3H, CH3), 6.51 (s, 2H, NH2), 6.83–6.81 (d, 2H, J = 8.8 Hz, ArH), 6.86 (s, 1H, ArH), 6.90 (s, 1H, ArH), 7.60 (d, 2H, J = 8.8, ArH), 7.73 (d, 1H,, J = 15.6 Hz, -C=HC-), 7.83 (d, 1H, J = 15.6 Hz, -C=HC-), 7.85 (s, 1H, ArH), 7.93 (d, 2H, J = 8.4 Hz, ArH), 8.06 (d, 2H, J = 8.4 Hz, ArH), 8.57 (s, 1H, ArH), 8.69 (s, 1H, ArH), 9.41 (s, 1H, NH), 10.91(s, 1H, =N-NH-C); LC-MS M/Z: 457 [M + H]+.
2-((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-methoxyphenyl)allylidene)hydrazinecarboxamide(7b)
Yield: 65%; m.p.: 238–240 °C; FTIR (KBr) cm−1: 3450 (NH2), 1685 (C=O), 1251 (OCH3); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 3.72 (s, 3H, OCH3), 6.48 (s, 2H, NH2), 6.88 (d, 2H, J = 8.8 Hz, ArH), 6.96 (s, 1H, ArH), 7.13 (d, 2H, J = 8.8, ArH), 7.51 (d, 2H, J = 8.4 Hz, ArH), 7.75 (d, 1H, J = 15.6 Hz, -C=HC-), 7.78 (d, 1H, J = 15.6 Hz, -C=HC-), 7.85 (s, 1H, ArH), 7.93 (d, 2H, J = 8.8 Hz, ArH), 8.0 (s, 1H, ArH), 8.54 (s, 1H, ArH), 8.72 (s, 1H, ArH), 9.38 (s, 1H, NH), 10.76 (s, 1H, =N-NH-C); LC-MS M/Z: 473 [M + H]+.
2-((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(3,4-dimethoxyphenyl)allylidene)hydrazinecarboxamide(7c)
Yield: 56%; m.p.: 214–216 °C; IR (KBr cm−1): 3442 (NH2), 1681 (C=O), 1255 (OCH3); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 3.72 (s, 3H, OCH3), 3.81 (s, 3H, -OCH3), 6.50 (s, 2H, NH2), 6.81 (s, 1H, ArH), 7.20–6.96 (m, 3H, J = 8.4, ArH), 7.53 (d, 2H, J = 8.8 Hz, ArH), 7.79 (d, 1H, J = 15.6 Hz, -C=HC-), 7.81 (d, 1H, J = 15.6 Hz, -C=HC-), 7.85 (s, 1H, ArH), 7.95 (d, 2H, J = 8.4 Hz, ArH), 8.07 (s, 1H, ArH), 8.56 (s, 1H, ArH), 8.72 (s, 1H, ArH), 10.20 (s, 1H, NH), 10.81 (s, 1H, =N-NH-C); LC-MS M/Z: 503 [M + H]+.
2-((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(3,4,5-trimethoxyphenyl)allylidene)hydrazinecarboxamide(7d)
Yield: 52%; m.p.: 238–240 °C; IR (KBr cm−1): 3442 (NH2), 1671 (C=O), 1251 (OCH3); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 3.82 (s, 6H, OCH3), 3.87 (s, 3H, OCH3), 6.49 (s, 2H, NH2), 6.76 (s, 1H, ArH), 6.88 (s, 1H, ArH), 7.54 (d, 2H, J = 8.8 Hz, ArH), 7.71 (s, 1H, ArH), 7.81 (d, 1H, J = 15.6 Hz, -C=HC-), 7.83 (d, 1H, J = 15.6 Hz, -C=HC-), 7.93 (d, 2H, J = 8.8, ArH), 8.02 (s, 2H, ArH), 8.54 (s, 1H, ArH), 8.76 (s, 1H, ArH), 10.09 (s, 1H, NH), 11.02 (s, 1H, =N-NH-C); LC-MS M/Z: 533 [M + H]+.
2-((E)-3-(4-chlorophenyl)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)allylidene)hydrazinecarboxamide(7e)
Yield: 45%; m.p.: 174–176 °C; IR (KBr cm−1): 3335 (NH2,), 1680 (C=O), 1226 (C-N); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 6.48 (s, 2H, NH2), 7.22 (s, 1H, Ar-H), 7.54 (d, 2H, J = 8.4, Ar-H), 7.62 (d, 2H, J = 8.4 Hz, Ar-H), 7.76 (s, 1H, Ar-H), 7.87 (d, 1H, J = 15.6 Hz, −CH=C), 7.89 (d, 1H, J = 15.6 Hz, −CH=C), 7.95 (d, 2H, J = 8.8, Ar-H), 7.99 (s, 1H, Ar-H), 8.05 (s, 1H, Ar-H), 8.29 (d, 2H, J = 8.8 Hz, Ar-H), 8.62 (s, 1H, Ar-H), 10.17 (s, 1H, NH), 10.76 (s, 1H, =N-NH-C); LC-MS M/Z: 477 [M + H]+.
2-((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-fluorophenyl)allylidene)hydrazinecarboxamide(7f)
Yield: 70%; m.p.: 230–232 °C; IR (KBr cm−1): 3433 (NH2), 1686 (C=O), 1370 (C-N); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 6.54 (s, 2H, NH2), 7.22 (s, 1H, ArH), 7.44 (d, 2H, J = 8.4, ArH), 7.52 (d, 2H, J = 8.8 Hz, ArH), 7.73 (d, 1H, J = 15.6 Hz, -C=HC-), 7.76 (s, 1H, A-H), 7.83 (d, 1H, J = 15.6 Hz, -C=HC-), 7.91 (d, 2H, J = 8.8, ArH), 7.7 (s, 1H, ArH), 7.80–7.85 (m, 3H, ArH), 8.01 (s, 1H, ArH), 10.11 (s, 1H, −NH), 10.41 (s, 1H, =N-NH-C); LC-MS M/Z: 461 [M + H]+.
2-((E)-3-(4-bromophenyl)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)allylidene)hydrazinecarboxamide(7 g)
Yield: 51%; m.p.: 244–246 °C; IR (KBr cm−1): 3452 (NH2,), 1680 (C=O), 1251 (C-N); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 6.52 (s, 2H, NH2), 7.16 (s, 1H, ArH), 7.61(d, 2H, J = 8.4, ArH), 7.68 (d, 2H, J = 8.4 Hz, ArH), 7.74 (d, 1H, J = 15.6 Hz, -C=HC-), 7.78 (s, 1H, ArH), 7.81 (d, 1H, J = 15.6 Hz, -C=HC-), 7.90 (d, 2H, J = 8.0, ArH), 8.00 (s, 1H, ArH), 8.06 (s, 1H, ArH), 8.27 (d, 2H, J = 8.8 Hz, ArH), 8.62 (s, 1H, ArH), 10.18 (s, 1H, NH), 10.83 (s, 1H, =N-NH-C); LC-MS M/Z: 522 [M + H]+.
2-((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-nitrophenyl)allylidene)hydrazinecarboxamide(7 h)
Yield: 70%; m.p.: 196–198 °C; IR (KBr cm−1): 3398 (NH2), 1675 (C=O), 1585 (NO2), 1371 (C- N); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 6.50 (s, 2H, NH2), 7.20 (s, 1H, ArH), 7.42 (d, 2H, J = 8.8 Hz, ArH), 7.62 (d, 2H, J = 8.8 Hz, ArH), 7.80 (d, 1H, J = 15.6 Hz, -C=HC-), 7.83 (d, 1H, J = 15.6 Hz, -C=HC-), 7.9 (s, 1H, ArH), 8.02 (d, 2H, J = 8.4, ArH), 8.16 (s, 1H, ArH), 8.29 (d, 2H, J = 8.4 Hz, ArH), 8.53 (s, 1H, ArH), 8.62 (s, 1H, ArH), 10.30 (s, 1H, NH), 10.76 (s, 1H, =N-NH-C); LC-MS M/Z: 488 [M + H]+.
2-((E)-1-(4-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-hydroxyphenyl)allylidene)hydrazinecarboxamide(7i)
Yield: 45%; m.p.: 240–242 °C; IR (KBr cm−1): 3360 (NH2), 1680 (C=O), 1251 (C-N); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 6.53 (s, 2H, NH2), 7.23 (s, 1H, ArH), 7.56 (d, 2H, J = 8.8 Hz, ArH), 7.68 (d, 2H, J = 8.8 Hz, ArH), 7.78 (d, 1H, J = 15.6 Hz, -C=HC-), 7.81 (d, 1H, J = 15.6 Hz, -C=HC-), 7.7 (s, 1H, ArH), 8.0 (d, 2H, J = 8.2, ArH), 8.16 (s, 1H, ArH), 8.26 (d, 2H, J = 8.4 Hz, ArH), 8.51 (s, 1H, ArH), 8.60 (s, 1H, ArH), 9.89 (s, 1H, OH), 10.32 (s, 1H, NH), 10.71 (s, 1H, =N-NH-C); LC-MS M/Z: 459 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(p-tolyl)allylidene)hydrazinecarbothioamide(8a)
Yield: 50%; m.p.: 238–240 °C; IR (KBr cm−1): 3350 (NH2), 1575 (C=C), 1352 (C=S), 1261 (C-N); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 2.62 (s, 3H, CH3), 6.99 (s, 1H, ArH), 7.20–7.15 (m, 4H, ArH), 7.25 (d, 1H, J = 15.6 Hz, -C=HC-), 7.37 (d, 2H, J = 8.4 Hz, ArH), 7.50 (d, 1H, J = 15.6 Hz, -C=HC-), 7.59 (d, 2H, J = 8.4 Hz, ArH), 7.76 (s, 1H, ArH), 7.85 (s, 1H, NH2), 7.88 (s, 1H, NH2), 7.92 (s, 1H, ArH), 8.26 (s, 1H, ArH), 8.46 (s, 1H, ArH), 9.25 (s, 1H, NH), 11.25 (s, 1H, =N-NH-C); LC-MS M/Z: 473 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-Methoxyphenyl)allylidene)hydrazinecarbothioamide(8b)
Yield: 43%; m.p.: 210–212 °C; IR (KBr cm−1): 3365 (NH2), 1568 (C=C), 1350 (C=S), 1255 (OCH3); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 3.81 (s, 3H, OCH3), 7.42–7.35 (m, 4H, ArH), 7.67–7.58 (m, 3H, ArH, −NH2), 7.71 (s, 1H, NH2), 7.72 (s, 1H, ArH), 7.73 (d, 1H, J = 15.6 Hz, -C=HC-), 7.76 (d, 1H, J = 15.6 Hz, -C=HC-), 7.84 (d, 2H, J = 8.8 Hz, ArH), 7.93 (s, 1H, ArH), 8.04 (s, 1H, ArH), 8.43 (s, 1H, ArH), 8.50 (s, 1H, ArH), 9.26 (s, 1H, NH), 11.75 (s, 1H, =N-NH-C); LC-MS M/Z: 489 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(3,4-dimethoxyphenyl)allylidene)hydrazinecarbothioamide(8c)
Yield: 41%; m.p.: 120–122 °C; IR (KBr cm−1): 3655 (NH2), 1516 (C=C), 1313 (C=S), 1267 (C-N), 1560 (C=C), 1183 (OCH3); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 3.81 (s, 3H, OCH3), 3.84 (s, 3H, −OCH3), 7.39 (s, 1H, ArH), 7.41 (s, 1H, ArH), 7.65 (s, 1H, −NH2), 7.70–7.66 (m, 3H, ArH), 7.73 (d, 1H, J = 15.6 Hz, -C=HC-), 7.80 (d, 1H, J = 15.6 Hz, -C=HC-), 7.92–7.85 (m, 3H, ArH), 7.94 (s, 1H, ArH), 8.01 (s, 1H, ArH), 8.1 (s, 1H, −NH2), 8.14 (s, 1H, ArH), 8.49 (s, 1H, ArH), 9.71 (s, 1H, NH), 11.95 (s, 1H, =N-NH-C); LC-MS M/Z: 519 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(3,4,5-trimethoxyphenyl)allylidene)hydrazinecarbothioamide(8d)
Yield: 60%; m.p.: 240–242 °C; IR (KBr cm−1): 3352 (NH2), 1560 (C=C), 1352 (C=S), 1246 (C-N), 1182 (OCH3); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 3.70 (s, 3H, OCH3), 3.84 (s, 6H, OCH3), 7.22 (s, 1H, ArH), 7.64–7.58 (m, 4H, ArH), 7.67 (s, 1H, ArH), 7.71(d, 1H, J = 15.6, -C=HC-), 7.84 (s, 1H, NH2), 7.85 (d, 1H, J = 15.6, -C=HC-), 7.91 (s, 1H, NH2), 7.97 (s 2H, ArH), 8.02 (s, 1H, ArH), 8.43 (s, 1H, ArH), 8.51 (s, 1H, ArH), 9.28 (s, 1H, NH), 10.96 (s, 1H, =N-NH-C); LC-MS M/Z: 549 [M + H]+.
2-((E)-3-(4-chlorophenyl)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)allylidene)hydrazinecarbothioamide(8e)
Yield: 66%; m.p.: 212–214 °C; IR (KBr cm−1): 3338 (NH2), 1597 (C=C), 1350 (C=S), 1261 (C-N); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 7.21 (s, 1H, ArH), 7.46 (d, 1H, J = 15.6 Hz, -C=HC-), 7.52 (d, 2H, J = 8.4 Hz, ArH), 7.59 (d,1H, J = 15.6 Hz, -C=HC-), 7.61 (d, 2H, J = 8.4 Hz, ArH), 7.79–7.63 (m, 4H, ArH), 7.81 (s, 1H, NH2), 7.85 (s, 1H, ArH), 7.93 (s, 1H, NH2), 8.20 (s, 1H, ArH), 8.24 (s, 1H, ArH), 8.47(s, 1H, ArH), 9.29 (s, 1H, NH), 11.12 (s, 1H, =N-NH-C); LC-MS M/Z: 494 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-fluorophenyl)allylidene)hydrazinecarbothioamide(8f)
Yield: 60%; m.p.: 234–236 °C; IR (KBr cm−1): 3358 (NH2), 1591 (C=C), 1350 (C=S); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 7.21 (s, 1H, ArH), 7.41–7.34 (m, 4H, ArH), 7.48 (d,1H, J = 15.6 Hz, -C=HC-), 7.57 (d, 2H, J = 8.4 Hz, ArH), 7.63 (d, 2H, J = 8.4 Hz, ArH), 7.76 (d, 1H, J = 15.6 Hz, -C=HC-), 7.88 (s, 1H, NH2), 7.83 (s, 1H, ArH), 7.95 (s, 1H, NH2), 8.22 (s, 1H, ArH), 8.31 (s, 1H, ArH), 8.45 (s, 1H, ArH), 9.25 (s, 1H, NH), 11.22 (s, 1H, =N-NH-C); LC-MS M/Z: 477 [M + H]+.
2-((E)-3-(4-bromophenyl)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)allylidene)hydrazinecarbothioamide(8 g)
Yield: 55%; m.p.: 238–240 °C; IR (KBr cm−1): 3364 (NH2), 1575 (C=C), 1355 (C=S); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 7.21 (s, 1H, ArH), 7.45–7.37 (m, 4H, ArH), 7.48 (d, 1H, J = 15.6 Hz, -C=HC-), 7.53 (d, 2H, J = 8.4 Hz, ArH), 7.68 (d, 2H, J = 8.4 Hz, ArH), 7.75 (d, 1H, J = 15.6 Hz, -C=HC-), 7.83 (s, 1H, NH2), 7.91 (s, 1H, ArH), 7.96 (s, 1H, NH2), 8.14 (s, 1H, ArH), 8.23 (s, 1H, ArH), 8.46 (s, 1H, ArH), 9.23 (s, 1H, NH), 11.21 (s, 1H, =N-NH-C); LC-MS M/Z: 538 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-nitrophenyl)allylidene)hydrazinecarbothioamide(8 h)
Yield: 47%; m.p.: 218–220 °C; IR (KBr cm−1): 3356 (NH2), 1593 (NO2), 1550 (C=C), 1350 (C=S); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 7.20 (s, 1H, ArH), 7.52–7.43 (m, 4H, ArH), 7.56 (d, 2H, J = 8.4 Hz, ArH), 7.61 (d, 1H, J = 15.6 Hz, -C=HC-), 7.64 (d, 2H, J = 7.6 Hz, ArH), 7.69 (d, 1H, J = 15.6 Hz, -C=HC-), 7.72 (s, 1H, NH2), 7.96 (s, 1H, NH2), 8.16 (s, 1H, ArH), 8.31 (s, 1H, ArH), 8.36 (s, 1H, ArH), 8.48 (s, 1H, ArH), 9.68 (s, 1H, NH), 11.23 (s, 1H, =N-NH-C); LC-MS M/Z: 504 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-hydroxyphenyl)allylidene)hydrazinecarbothioamide(8i)
Yield: 57%; m.p.: 250–242 °C; IR (KBr cm−1): 3478 (OH), 3360 (NH2), 1590 (C=C), 1361 (C=S), 1265 (C-N); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 7.2 (s, 1H, ArH), 7.20–7.15 (m, 4H, ArH), 7.25 (d, 1H, J = 15.6 Hz, -C=HC-), 7.38 (d, 2H, J = 8.4 Hz, ArH), 7.50 (d, 1H, J = 15.6 Hz, -C=HC-), 7.61 (d, 2H, J = 8.4 Hz, ArH), 7.76 (s, 1H, ArH), 7.87 (s, 1H, NH2), 7.93 (s, 1H, NH2), 7.97 (s, 1H, ArH), 8.31 (s, 1H, ArH), 8.43 (s, 1H, ArH), 9.35 (s, 1H, NH), 9.98 (s, 1H, OH), 11.22 (s, 1H, =N-NH-C); LC-MS M/Z: 475 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(p-tolyl)allylidene)hydrazinecarboxamide(9a)
Yield: 55%; m.p.: 192–194 °C; IR (KBr cm−1): 3365 (NH2), 1690 (C=O), 1575 (C=C), 1261(C-N); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 2.61 (s, 3H, CH3), 6.73 (s, 2H, NH2), 7.16 (s, 1H, ArH), 7.33–7.21 (m, 4H, ArH), 7.36 (d, 1H, J = 15.6 Hz, -C=HC-), 7.41 (d, 2H, J = 8.4 Hz, ArH), 7.53 (d, 1H, J = 15.6 Hz, -C=HC-), 7.61 (d, 2H, J = 8.4 Hz, ArH), 7.82 (s, 1H, ArH), 7.91 (s, 1H, ArH), 8.32 (s, 1H, ArH), 8.41 (s, 1H, ArH), 9.33 (s, 1H, NH), 10.93 (s, 1H, =N-NH-C); LC-MS M/Z: 457 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-methoxyphenyl) allylidene)hydrazinecarboxamide(9b)
Yield: 40%; m.p.: 188–190 °C; IR (KBr cm−1): 3365 (NH2), 1685 (C=O), 1590 (C=C), 1235 (OCH3); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 3.83 (s, 3H, OCH3), 6.69 (s, 2H, NH2), 7.52–7.43 (m, 4H, ArH), 7.65 (d, 2H, ArH), 7.68 (s, 1H, ArH), 7.71 (d, 1H, J = 15.6 Hz, -C=HC-), 7.75 (d, 1H, J = 15.6 Hz, -C=HC-), 7.81 (d, 2H, J = 8.8 Hz, ArH), 7.93 (s, 1H, ArH), 8.01 (s, 1H, ArH), 8.42 (s, 1H, ArH), 8.47 (s, 1H, ArH), 9.34 (s, 1H, NH), 11.10 (s, 1H, =N-NH-C); LC-MS M/Z: 473 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(3,4-dimethoxyphenyl)allylidene)hydrazinecarboxamide(9c)
Yield: 51%; m.p.: 254–256 °C; IR (KBr cm−1): 3648 (NH2), 1680 (C=O), 1580 (C=C), 1215 (OCH3); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 3.86 (s, 3H, OCH3), 3.89 (s, 3H, −OCH3), 6.69 (s, 2H, −NH2), 7.53 (s, 1H, ArH), 7.68–7.59 (m, 3H, ArH), 7.71 (d, 1H, J = 15.6 Hz, -C=HC-), 7.79 (d, 1H, J = 15.6 Hz, -C=HC-), 7.91–7.83 (m, 3H, ArH), 7.94 (s, 1H, ArH), 8.10 (s, 1H, ArH), 8.23 (s, 1H, ArH), 8.49 (s, 1H, ArH), 8.51(s, H, ArH), 9.36 (s, 1H, NH), 11.13 (s, 1H, =N-NH-C); LC-MS M/Z: 503 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(3,4,5-trimethoxyphenyl) allylidene)hydrazinecarboxamide(9d)
Yield: 60%; m.p.: 258–260 °C; IR (KBr cm−1): 3363 (NH2), 1690 (C=O), 1565 (C=C), 1248 (C-N), 1189 (OCH3); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 3.76 (s, 3H, OCH3), 3.85 (s, 6H, -OCH3), 6.79 (s, 2H, NH2), 7.41 (s, 1H, ArH), 7.81–7.7 (m, 4H, ArH), 7.92 (s, 1H, ArH), 7.83 (d, 1H, J = 15.6, -C=HC-), 7.87 (d, 1H, J = 15.6, -C=HC-), 7.96 (s 2H, ArH), 8.13 (s, 1H, ArH), 8.41 (s, 1H, ArH), 8.48 (s, 1H, ArH), 9.33 (s, 1H, NH), 10.83 (s, 1H, =N-NH-C); LC-MS M/Z: 533 [M + H]+.
2-((E)-3-(4-chlorophenyl)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)allylidene)hydrazinecarboxamide(9e)
Yield: 50%; m.p.: 226–228 °C; IR (KBr cm−1): 3354 (NH2), 1686 (C=O), 1583 (C=C), 1270 (C-N); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 6.73 (s, 2H, NH2), 7.13 (s, 1H, ArH), 7.48 (d, 1H, J = 15.6 Hz, -C=HC-), 7.53 (d, 2H, J = 8.4 Hz, ArH), 7.58 (d,1H, J = 15.6 Hz, -C=HC-), 7.65 (d, 2H, J = 8.4 Hz, ArH), 7.81–7.75 (m, 4H, ArH), 7.83 (s, 1H, ArH), 8.22 (s, 1H, ArH), 8.35 (s, 1H, ArH), 8.43 (s, 1H, ArH), 9.31 (s, 1H, NH), 10.86 (s, 1H, =N-NH-C); LC-MS M/Z: 477 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-fluorophenyl)allylidene)hydrazinecarboxamide(9f)
Yield: 55%; m.p.: 198–200 °C; IR (KBr cm−1): 3360 (NH2), 1685 (C=O), 1595 (C=C); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 6.73 (s, 2H, NH2), 7.28 (s, 1H, ArH), 7.45–7.36 (m, 4H, ArH), 7.49 (d,1H, J = 15.6 Hz, -C=HC-), 7.53 (d, 2H, J = 8.4 Hz, ArH), 7.59 (d, 2H, J = 8.4 Hz, ArH), 7.75 (d, 1H, J = 15.6 Hz, -C=HC-), 7.95 (s, 1H, ArH), 8.26 (s, 1H, ArH), 8.35 (s, 1H, ArH), 8.46 (s, 1H, ArH), 9.29 (s, 1H, NH), 10.98 (s, 1H, =N-NH-C); LC-MS M/Z: 461 [M + H]+.
2-((E)-3-(4-bromophenyl)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)allylidene)hydrazinecarboxamide(9 g)
Yield: 60%; m.p.: 306–308 °C; IR (KBr cm−1): 3360 (NH2), 1686 (C=O), 1570 (C=C); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 6.75 (s, 2H, NH2), 7.14 (s, 1H, ArH), 7.49–7.38 (m, 4H, ArH), 7.52 (d, 1H, J = 15.6 Hz, -C=HC-), 7.63 (d, 2H, J = 8.4 Hz, ArH), 7.71 (d, 2H, J = 8.4 Hz, ArH), 7.79 (d, 1H, J = 15.6 Hz, -C=HC-), 7.93 (s, 1H, ArH), 8.22 (s, 1H, ArH), 8.29 (s, 1H, ArH), 8.45 (s, 1H, ArH), 9.27 (s, 1H, NH), 10.96 (s, 1H, =N-NH-C); LC-MS M/Z: 522 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-nitrophenyl)allylidene)hydrazinecarboxamide(9 h)
Yield: 43%; m.p.: 246–248 °C; IR (KBr cm−1): 3360 (NH2), 1690 (C=O), 1595 (NO2), 1565 (C=C); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 6.72 (s, 2H, NH2), 7.20 (s, 1H, ArH), 7.53–7.48 (m, 4H, ArH), 7.56 (d 2H, J = 8.4 Hz, ArH), 7.65 (d, 2H, J = 7.6 Hz, ArH), 7.73 (d, 1H, J = 15.6 Hz, -C=HC-), 7.96 (d, 1H, J = 15.6 Hz, -C=HC-), 8.13 (s, 1H, ArH), 8.26 (s, 1H, ArH), 8.33 (s, 1H, ArH), 8.47 (s, 1H, ArH), 9.36 (s, 1H, NH), 10.87 (s, 1H, =N-NH-C); LC-MS M/Z: 488 [M + H]+.
2-((E)-1-(3-((7-chloroquinolin-4-yl)amino)phenyl)-3-(4-hydroxyphenyl)allylidene)hydrazinecarboxamide(9i)
Yield: 43%; m.p.: 234–236 °C; IR (KBr cm−1): 3362 (NH2), 1685 (C=O), 1593 (C=C), 1265(C-N); 1H-NMR (400 MHz, DMSO-d6) δ (ppm) = 6.67 (s, 2H, NH2), 7.10 (s, 1H, ArH), 7.23–7.14 (m, 4H, ArH), 7.27 (d, 1H, J = 15.6 Hz, -C=HC-), 7.49 (d, 2H, J = 8.4 Hz, ArH), 7.62 (d, 1H, J = 15.6 Hz, -C=HC-), 7.73 (d, 2H, J = 8.4 Hz, ArH), 7.98 (s, 1H, ArH), 8.15 (s, 1H, ArH), 8.36 (s, 1H, ArH), 8.46 (s, 1H, ArH), 9.29 (s, 1H, NH), 9.85 (s, 1H, OH), 10.93 (s, 1H, =N-NH-C); LC-MS M/Z: 459 [M + H]+.