A.M. El-Naggar et al.
Bioorganic Chemistry 108 (2021) 104615
Fig. 17. 2D interaction of compound 27c with the active site of CDK2.
NMR (DMSO‑d6) δ ppm: 2.22 (s, 3H, CH3), 2.29 (s, 3H, CH3), 6.55 (s, 1H,
Ar-H of thiazol ring), 6.62–6.63 (dd, 1H, Ar-H thiophene ring, J = 1.76, 3.52
Hz,), 7.00 (br. s, 1H), 7.82 (d, 1H, Ar-H thiophene ring, J = 1.32 Hz); Anal.
Calcd. for C10H11N3OS (221.3): C, 54.28; H, 5.01; N, 18.99; Found: C,
54.18; H, 4.90; N, 18.87.
(M+.-1, 1.9), 178 (28.6), 79.0 (100); Anal. Calcd. for C14H17N3O2S
(291.4): C, 57.71; H, 5.88; N, 14.42; Found: C, 57.58; H, 5.80; N, 14.52.
5.1.2.10. (E)-2-(2-(1-(4-chlorophenyl)ethylidene)hydrazinyl)-4-phenyl-
thiazole (27j). Off white crystals; m.p. 265–267 ◦C; IR (KBr, cmꢀ 1):
1
–
3210 (NH), 3033 (CH-aromatic), 2943 (CH aliphatic), 1618 (C N); H
–
5.1.2.7. (E)-1-(2-(2-(1-(furan-2-yl)ethylidene)hydrazinyl)-4-methyl-
NMR (DMSO‑d6) δ ppm: 2.32 (s, 3H, CH3), 7.30 (s, 1H, NH), 7.33 (s, 1H,
Ar-H thiazole ring), 7.39–7.41 (m, 3H, Ar-H phenyl), 7.47–7.49 (d, 2H, phenyl
J = 8 Hz), 7.79–7.81 (d, 2H, Ar-Hchlorophenyl , J = 8.31 Hz), 7.86–7.88 (d,
2H, Ar-Hchlorophenyl ,J = 8 Hz,); Anal. Calcd. for C17H14ClN3S (327.8): C,
62.28; H, 4.30; N, 12.82; Found: C, 62.06; H, 4.21; N, 12.70.
thiazol-5-yl)ethan-1-one (27g). Pale yellow crystals; m.p. 215–217 ◦C; IR
(KBr, cmꢀ 1): 3416 (NH), 3091 (CH-aromatic), 1684 (C O), 1612
–
–
1
–
–
(C N); H NMR (DMSO‑d ) δ ppm: 2.24 (s, 3H, CH ), 2.39 (s, 3H, CH ),
2.49 (s, 3H, CH3), 6.59 (d6d, 1H, Ar-H thiophene ring, J = 1.76, 3.52 Hz,),
6.90–6.91 (dd, 1H, Ar-H thiophene ring, J = 0.88, 3.52 Hz), 7.79 (d, 1H, Ar-
H thiophene ring, J = 1.32 Hz); 13C NMR (100 MHz, DMSO‑d6) δ ppm: 13.9,
20.3, 29.4, 110.9, 111.9, 112.0, 143.5, 144.4, 144.5, 151.6, 159.8,
188.7; Anal. Calcd. for C12H13N3O2S (263.3): C, 54.74; H, 4.98; N,
15.96; Found: C, 54.65; H, 4.83; N, 15.84.
3
3
5.1.2.11. (E)-2-(2-(1-(4-chlorophenyl)ethylidene)hydrazinyl)-4-methyl-
thiazole (27k). Off white crystals; m.p. Sublimation at 131–133 ◦C; IR
(KBr, cmꢀ 1): 3364, 3125 (NH), 3042 (CH-aromatic), 2933 (CH
1
–
aliphatic), 1612 (C N); H NMR (DMSO‑d ) δ ppm: 2.26 (s, 3H, CH ),
–
6
2.41 (s, 3H, CH3), 6.66 (s, 1H, Ar-H of thiazol ring), 7.50–7.52 (dd, 2H, Ar3-H
5.1.2.8. (E)-2-(2-(1-(3,4-dimethoxyphenyl)ethylidene)hydrazinyl)-4-phe-
Chlorophenyl, J = 8.4 Hz,), 7.94 (d, 2H, Ar-H Chlorophenyl, J = 8.35 Hz); 13
C
nylthiazole (27h). Yellow crystals; m.p. 235–237 ◦C; IR (KBr, cmꢀ 1):
NMR (100 MHz, DMSO‑d6) δ 135.8, 134.4, 130.1, 128.7 (2), 128.4 (2),
128.3, 127.6, 104.0, 15.0, 14.6; Anal. Calcd. for C12H12ClN3S (265.8): C,
54.23; H, 4.55;N, 15.81; Found: C, 54.05; H, 4.42; N, 15.70.
1
–
3218 (NH), 3054 (CH-aromatic), 2937 (CH aliphatic), 1628 (C N); H
–
NMR (DMSO‑d6) δ ppm: 2.31 (s, 3H, CH3). 3.79 (s, 3H, OCH3), 3.82 (s,
3H, OCH3), 6.98 (d, 1H, Ar-H, J = 8.35 Hz), 7.31–7.39 (m, 3H, Ar-H),
7.41–7.45 (m, 3H, Ar-H), 7.86–7.87 (dd, 2H, Ar-H); Anal. Calcd. for
C19H19N3O2S (353.4): C, 64.57; H, 5.42; N, 11.89; Found: C, 64.43; H,
5.33; N, 11.77.
5.1.2.12. (E)-1-(2-(2-(1-(4-chlorophenyl)ethylidene)hydrazinyl)-4-meth-
ylthiazol-5-yl)ethan-1-one (27l). Yellow crystals; m.p. Sublimation
114–116 ◦C; IR (KBr, cmꢀ 1): 3426 (NH), 2923 (CH aromatic), 2854 (CH
1
–
–
–
aliphatic), 1650 (C O), 1606 (C N); H NMR (DMSO‑d ) δ ppm: 2.32
–
6
5.1.2.9. (E)-2-(2-(1-(3,4-dimethoxyphenyl)ethylidene)hydrazinyl)-4-
(s, 3H, CH3), 2.40 (s, 3H, CH3), 2.49 (s, 3H, CH3), 7.48 (d, 2H, Ar-H
chloropheny J = 8.79 Hz), 7.82 (d, 2H, Ar-H chloropheny J = 8.79 Hz); MS
(m/z, %): 309 (M+ + 2, 75.7), 307 (M+, 100), 306 (14.6); Anal. Calcd.
for C14H14ClN3OS (307.8): C, 54.63; H, 4.58; N, 13.65; Found: C, 54.45;
H, 4.51; N, 13.53.
methylthiazole (27i). Yellow crystals (yield 82%); m.p. 190–192 ◦C; IR
(KBr, cmꢀ 1): 3201, 3119 (NH), 3010 (CH-aromatic), 2942 (CH
1
–
aliphatic), 1613 (C N); H NMR (DMSO‑d ) δ ppm: 2.26 (s, 3H, CH ),
–
6
3.40 (s, 3H, CH3), 3.80 (s, 3H, OCH3), 3.82 (s, 3H, OCH3), 6.66 (s, 13H,
Ar-Hthiazole ring), 7.01 (d, 1H, Ar-H, J = 8.79 Hz), 7.42 (d, 1H, Ar-H, J =
8.35 Hz), 7.52 (s, 1H, Ar-H); 13C NMR (100 MHz, DMSO‑d6) δ 150.6,
148.5, 129.9, 129.4, 123.1, 120.2, 111.2, 110.8, 110.2, 103.8, 55.7,
55.6, 26.4, 15.1; MS (m/z, %): 292 (M+ + 1, 2.1), 291 (M+, 10.6), 291
5.1.2.13. (E)-4-phenyl-2-(2-(1-(p-tolyl)ethylidene)hydrazinyl)thiazole
(27m). Yellow crystals; m.p. 223–225 ◦C; IR (KBr, cmꢀ 1): 3221 (NH),
3028 (CH-aromatic), 2921 (CH aliphatic), 1619 (C N); 1H NMR
–
–
12