Synthesis and Preliminary Biological Activity Evaluation of New N- Substituted Phthalimide Derivatives

Abstract

<jats:p>A&#x0D; A new series of bases of Schiff (H2-H4) derived from phthalic anhydrideweresynthesized. These Schiff bases were prepared by the reaction of different amines (tyrosine methyl ester, phenylalanine methyl ester, and isoniazid) with the phthalimide derived aldehyde with the aid of glacial acetic acid or triethylamine ascatalysts. All the synthesized compounds were characterized by (FT-IR and 1HNMR) analyses and were in vitro evaluated for their antimicrobial activity against six various kinds of microorganisms. All the synthesized compounds had been screened for their antimicrobial activity against two Gram-positive bacteria “Staph. Aureus, and Bacillus subtilis”, two Gram-negative bacteria “Escherichia coli, and Klebsiella pneumoniae”, and two fungi species “Candida tropicalis and Candida albicans” using concentrations of 62.5, 125 and 250 µg\mLof derivative in dimethyl sulfoxide(DMSO). All the synthesized compounds showed no activity at all against Gram-positive bacteria, for Gram-negative bacteria and fungi they showed moderate or no activity except compound H1revealedhigh antifungal activityagainstCandida tropicalisat concentrations 125 and 250 µg\ mL.&#x0D; Keywords: Schiff base, phthalic anhydride, antimicrobial.&#x0D; </jats:p>

Synthesis, characterization and preliminary antimicrobial study of some new phthalimide phenyl hydrazide derivatives

“…4-(1,3-dioxoisoindolin-2-yl) benzoic acid 7 Phthalic anhydride and 4-aminobenzoic acid were reacted in an equimolar ratio of 1 mmoL each in 15 ml of glacial acetic acid.…”

“…6 Phthalimide derivatives are given a biological activity via the imide ring and structural core (-CO-N(R)-CO-). 7 Several pharmacophore subunits, including pyrazoles and diazoles, (oxo and thioxo) triazoles, benzo-(oxazoles, imidazoles, and thiazoles), and compounds containing the azomethine group (Schiff bases), were added using the molecular hybridization method to boost the biological action of phthalimide derivatives. 8 The most commonly used types of organic substances include Schiff bases -with the imine (-C=N-) - [14]; they are very helpful for creating several bioactive medicinal molecules from primary amine.…”

“…8 The most commonly used types of organic substances include Schiff bases -with the imine (-C=N-) - [14]; they are very helpful for creating several bioactive medicinal molecules from primary amine. 7 Schiff bases result from a certain series of conditions-driven chemical reactions between a primary amine and an aldehyde or ketone. Hugo Schiff described these molecules for the first time.…”

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“…Both phthalimide and Nsubstituted phthalimide possessed biological efficiency such as anti-inflammatory [1,2], analgesic, anti-depressant [3,4], antioxidant [5], antimicrobial agent [5][6][7], and other activates [8][9][10][11][12]. The important applications of phthalimide due to the structural properties that are possessed like a hydrophobic aryl ring, the group of electron-donor, and hydrophobic 5-membered ring help to improve the biological activity of Phthalimide [13]. The study [14] has shown that, the possibility of using phthalimide and its derivatives in the biological field and used as an anti-bacterial.…”

Sulfa drugs–based Norbornenyl imides and reductive Heck reactions: Synthesis and antimicrobial screening

“…[ 2,3 ] There has been an increasing interest in synthesizing new cyclic imide derivatives as prospective antimicrobial agents in recent years, as the structure is a promising scaffold. [ 2,4–6 ]…”