DOI: 10.21276/sajp

Pages: 300-303

While designing some anti-convulsant hybrid molecules from a natural product, novel hydantoin (5) / thiohydantoin (8) based analogs were synthesized rationally from cuminaldehyde (1), the principal product of Cuminum cyminum (cumin) and also secondary components present in eucalyptus, cassia, and myrrh. The research was planned as literature reports potent anti-seizure activity of cumin oil, probably due to the presence of cuminaldehyde. The starting material, cuminaldehyde (1), the safe natural product was converted into intermediate Schiff’s base analogs (3) and (7) employing semicarbazide (2) / thiosemicarbazide (6). The molecule (8) demonstrated the most potent anti-MES activity at 30 mg/kg (0.5 hr) and 100 mg/kg (4 hr), respectively. Successively, the analog was cyclized by ethyl chloroacetate (4) in thr presence of fused alcoholic sodium acetate to form the compound of interest. The sophisticated analytical tools (FT-IR, 1H-NMR, and Mass) and elemental analyses provided all essential characteristics and evidence of the fabricated analogs. The hydantoin hybrids were screened for their anticonvulsant activity employing the Maximal Electroshock Seizure (MES) Test. The derivative (5) exhibited lower anti-MES activity as compared to the derivative (8) and standard drug, phenytoin. The compound presented anti-MES activity at 100 mg/kg (0.5 hr) and 300 mg/kg (4 hr), respectively. The lipophilicity accounts to be the decisive factor in the expression of anti-convulsant activity. The study demonstrated new possibilities in designing pharmacologically active analogs from a natural product in the near future.