Synthesis, Characterization, and Anti-Cancer Activity of Some New N'-(2-Oxoindolin-3-ylidene)-2-propylpentane hydrazide-hydrazones Derivatives

El-Faham, Ayman; Farooq, Muhammad; Khattab, Sherine N.; Abutaha, Nael; Wadaan, Mohammad A.; Ghabbour, Hazem A.; Fun, Hoong-Kun

Reaction of valporic acid hydrazide 2 with N-acetylisatin 3h proceeds in a different way, where the ring opening occurred to afford the product 4h. The IR and NMR data proved its structure in the open form, due to the attack of the hydrazide group on C2 instead of C3 [53] . The IR spectrum of 4h reveals absorption bands in the region 3310 and 3223 cm −1 corresponding to the NH, a band at 1720, 1709, 1688, and 1608 cm −1 corresponding to the C=O and C=N group, respectively. 1 H-NMR of 4h showed multiple peaks at δ 0.86-0.89, 1.27-1.29, 1.40-1.44, 1.56-1.60, and a broad singlet peak at δ 2.21 ppm corresponding to the valporic acid moiety (2 CH3, 2 CH2, and 2CH2, CH, respectively). The observed peak at δ 2.16 ppm is corresponding to the N-acetyl group. The observed peaks in the aromatic region at δ 7.28 (t, 1H), 7.68 (t, 1H), 7.99 (d, 1H), and 8.17(d, 1H) ppm, are related to the phenyl ring, while the two singlet peaks at δ 10.03 and 10.72 ppm corresponded to the two NH. The 13 C-NMR of 4h showed peaks at δ 14.6, 20.6, 29.9, 35.3, 43.8, and 46.5 ppm corresponding to the valporic acid moiety group, while the acetyl group was observed at δ 25.0 ppm, in addition to six peaks related to the aromatic carbons at δ 121.5, 121.8, 123.8, 133.6, 135.9, and 140.3 ppm. The three peaks observed at δ 164.1, 169.6, and 174.7 ppm related to the three CONH groups, while the peak observed at δ 193.0 ppm is related to the α-ketoamide group.