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.
Highlights
Schiff bases are important intermediates for the synthesis of some bioactive compounds such as βlactams, and they form a significant class of compounds in medicinal and pharmaceutical chemistry with a variety of interesting biological actions including antibacterial, antifungal, antimouse hepatitis virus (MHV), and adenovirus type 5 (Ad 5), anticancer and herbicidal activities[1,2,3,4,5]
Phthalimides which are bicyclic non-aromatic nitrogen heterocycles are important compounds with a variety of applications and a wide range of properties [6,7,8]. They are used as starting materials and intermediates for the synthesis of many types of alkaloids and pharmacophores, synthesis of pesticides and lately are being under intense biomedical research due to their important biological effects [912]
Vol.11(2)2014 newly synthesized compounds containing both phthalimide and Schiff base moieties linked together through phenyl sulfonate component. Performing this target was made via multistep synthesis which described in Scheme (1)
Summary
Schiff bases are important intermediates for the synthesis of some bioactive compounds such as βlactams, and they form a significant class of compounds in medicinal and pharmaceutical chemistry with a variety of interesting biological actions including antibacterial, antifungal, antimouse hepatitis virus (MHV), and adenovirus type 5 (Ad 5), anticancer and herbicidal activities[1,2,3,4,5]. phthalimides which are bicyclic non-aromatic nitrogen heterocycles are important compounds with a variety of applications and a wide range of properties [6,7,8]. In light of the interesting variety of biological activities seen in compounds containing phthalimidies and azomethine linkages it was thought of interest to examine the effect of having these two functionalities present simultaneously in one structure. Based on this notion we decide to synthesize several new Schiff bases linked to phthalimidyl sulfonate moiety and to test them against types of bacteria and fungi
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