Synthesis, Characterization, and Study the Biological Activity of New Di-azetidinone Derivatives

Main Article Content

Dhurgham Aziz
Mohauman Mohammed Majeed
Ahmed Thamer Salim

Keywords

β-lactam, Di-azetidinone, barbital, Schiff base, anticancer

Abstract

A series of new β-lactam derivatives were synthesized in two steps: The first step involves the synthesis of Schiff base derivatives from Veronal (Barbital) which is used as a sleeping aid (hypnotic) from 1903 until the mid-1950s, the compound (L3A) is synthesized by loading two molecules of formaldehyde on macrocycles compound as an initial step with absolute ethanol as solvent to form Hemiaminal compound, the reaction occurred on the two secondary amine molecules), after that treated the reaction product (L3A) with p-Toluenesulfonyl chloride in anhydrous pyridine to produce compound (L3B). While the preparation of the compound (L3C) involves removing the sulfonate groups of two sites in the compound (L3B) by gradually adding sodium amide with water. Imine derivatives (L3C1, L3C2, L3C3, and L3C4) were synthesized by reaction of Barbital derivatives free amino groups and corresponding substituted benzaldehyde in the presence of glacial acetic acid.
The second step is done through added chloroacetyl chloride to the Schiff base derivatives very slowly to prevent the compound from turning into something like bitumen, this is followed by adding the trimethylamine base to remove the proton and complete the closing process and form a β-lactam ring of derivatives (L3C5, L3C6, L3C7, and L3C8). Finally, in vitro anticancer activity of (L3C7, and L3C8) derivatives were investigated using SK-OV-3: Human Ovarian Cancer Cell Lines compared with 5-floro uracil (5-FU), the results showed the ability of these compounds to inhibit the infected cells in different proportions, depending on the concentrations used.

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