Synthesis, Characterization and Antimicrobial Screening of New Schiff Bases Linked to Phthalimidyl Phenyl Sulfonate Moiety

Abstract

A series of Schiff bases linked to phthalimidyl phenyl sulfonate moiety have been synthesized via multistep synthesis. The first step involved reaction of phthalic anhydride with aniline producing N-phenyl phthalamic acid which was subsequently dehydrated to the corresponding N-phenyl phthalimide via treatment with acetic anhydride and anhydrous sodium acetate. The synthesized imide was treated with chlorosulfonic acid in the third step producing 4-(N-phthalimidyl) phenyl sulfonyl chloride which was introduced in reaction with 4-hydroxy acetophenone in the fourth step producing 4-[4-(N-phthalimidyl) phenyl sulfonate] acetophenone and this in turn was introduced successfully in condensation reaction with various aromatic primary amines affording the desired new Schiff bases. The newly synthesized compounds were characterized through spectral data including FTIR, 1HNMR and 13CNMR. Antimicrobial activity of the prepared Schiff bases was evaluated against two types of bacteria and one type of fungi and the new Schiff bases were found to exhibit good antimicrobial activity against the tested organisms.

Phthalimide Derivative Shows Anti-angiogenic Activity in a 3D Microfluidic Model and No Teratogenicity in Zebrafish Embryos

“…Phthalimide, an imido derivative of phthalic acid, consists of two carbonyl groups bound to nitrogen. This compound is structurally related to acid anhydrides and its hydrophobicity and neutrality allow membrane-permeability in vivo (Al-Azzawi and Al-Razzak, 2014). Phthalimide, together with N-substituted phthalimides, represents an important class of compounds that possess important biological activities including anti-inflammatory (Machado et al, 2005), analgesic (Antunes et al, 1998) and hypolipidemic (Sena et al, 2003) functions.…”