In Vitro Biological Evaluation of Some Synthesized Novel 5-Substituted-2-(substituted)hydazineyl-1,3-thiazolidin-4-ones.

The 2-[2-(1-(4-chlorophenyl)ethylidene]hydrazineyl-1,3-thiazolidin-4-one (V) compound was synthesized via the condensation of thiosemicarbazone derivatives (III) with chloroacetyl chloride which gave a 1,3-disubstituted thiourea derivative (IV) as an intermediate compound, this was followed by cyclization of (IV) in situ boiling ethanol solvent in the presence of anhydrous potassium carbonate. The treatment of thiazole derivative (V) with 4-hydroxybenzaldehyde yielded the corresponding 2,5-disubstituted-1,3-thiazolidin-4-one (VI). Compound (VI) was reacted with 4-chlorophenacyl bromide that afforded 5-(4-hydroxybenzylidene)-2-(1,2-disubstituted) hydrazineyl-1,3-thiazolid-in-4-one (VIII). Acetylation of compounds (VI) and (VIII) with acetic anhydride formed acetyl derivatives (VII) and (IX). The structures of synthesized compounds were characterized and confirmed based on spectroscopic methods and microanalytical method (elemental analysis). It was found that most of the 1,3-thiazole derivatives (V–IX) showed enzyme activity, while compound (VIII) exhibited an excellent activity with IC50 value (4.22 μM) for α-amylase. Also, compound (VIII) gave a good inhibitory activity against free radical scavenging (DPPH), DPP-4, and human breast cancer (MCF-7). Based on the achieved results, it was suggested that compound (VIII) acts as a vital structure for the development of the most potent α-amylase inhibitors. [ABSTRACT FROM AUTHOR]