Synthesis and In Vitro Antimicrobial Evaluation of Photoactive Multi—Block Chalcone Conjugate Phthalimide and 1,8-Naphthalimide Novolacs

Abstract

Herein we report new multiblock chalcone conjugate phthalimide and naphthalimide functionalized copolymers with a topologically novel architecture synthesis using nucleophilic substitution and polycondensation methodology. The structures of the synthesized novolacs were elucidated on the basis of their spectroscopic analysis including FTIR, 1H NMR, and 13C NMR spectroscopy. Further, the number-average and weight-average molecular weights of the novolac polymers were determined by gel permeation chromatography (GPC). We examined the solubility of the synthesized polymers in various organic solvents including CHCl3, CH3CN, THF, H2O, CH3OH, DMSO, and DMF and found they are insoluble in both methanol and water. The novolac polymers were evaluated for their photophysical properties and microbial activities. The investigation of the antimicrobial activities of these polymers reveals significant antimicrobial activity against the pathogens E. coli, S. aureus, C. albicans, and A. niger.

Antifungal, anti-biofilm, and anti-hyphal properties of N-substituted phthalimide derivatives against Candida species

“…Phthalimide is a versatile pharmacological scaffold with anticancer, anti-inflammatory, antiparasitic, and, importantly, antimicrobial activities ( Fernandes et al., 2023 ). Phthalimide and its derivatives also have various applications in the cosmetic and biomedicine industries ( Durairaju et al., 2021 ). N -substituted phthalimides have exhibited antifungal activity against Aspergillus niger and Aspergillus flavus ( Neelottama Kushwaha, 2016 ), and novel heterocycle-substituted phthalimides are potent against C. albicans ( Jelali et al., 2022 ).…”

Phthalimide as a versatile pharmacophore scaffold: Unlocking its diverse biological activities

“…N ‐substituted phthalimides have demonstrated strong antibacterial activity, with minimal inhibitory concentrations (MICs) comparable to clinically used antibiotics (Orzeszko et al, 2000a, 2000b). Recently, Durairaju et al (2021) developed new phthalimide–chalcone conjugates ( 252–254 ) (Figure 21) with antibacterial and antifungal effects against Escherichia coli , Staphylococcus aureus , Candida albicans , and Aspergillus niger . At 100 µg/mL, the compounds displayed significant zone of inhibition values: 10.0 ( 252 ), 16.0 ( 253 ), and 18.0 mm ( 254 ) against E. coli ; 10.0 ( 252 ), 18.0 ( 253 ), and 23.0 mm ( 254 ) against S. aureus ; 12.0 ( 252 ), 12.0 ( 253 ), and 22.0 mm ( 254 ) against C. albicans ; and 18.0 ( 252 ), 20.0 ( 253 ), and 24.0 mm ( 254 ) against A. niger (Durairaju et al, 2021).…”

Anticancer Activity of Chalcones and Its Derivatives: Review and In Silico Studies

“…Their privileged structure also opens up possibilities for substitutions in aromatic rings [ 2 ], directly impacting its biological activity and development of formulations capable of improving its pharmacokinetic characteristics [ 3 ]. Due to their high biological value, the literature also reports on the anti-inflammatory [ 4 ], antiviral [ 5 ], antimicrobial [ 6 ], anticancer [ 7 ], antioxidant [ 8 ], and antifungal [ 9 ] properties of these compounds.…”

“…Natural products such as chalcones of the type (1,3-diaryl-2-propen-1ones) have been the focus of research for the treatment of this disease, as they have a conjugated carbonyl system that acts by inhibiting the polymerization of tubulin in tumor Their privileged structure also opens up possibilities for substitutions in aromatic rings [2], directly impacting its biological activity and development of formulations capable of improving its pharmacokinetic characteristics [3]. Due to their high biological value, the literature also reports on the anti-inflammatory [4], antiviral [5], antimicrobial [6], anticancer [7], antioxidant [8], and antifungal [9] properties of these compounds.…”