Novel phthalimide derivatives with TNF-α and IL-1β expression inhibitory and apoptotic inducing properties

Coêlho, Lucas Cunha Duarte; Cardoso, Marcos Veríssimo de Oliveira; Moreira, Diogo Rodrigo Magalhães; Gomes, Paulo André Teixeira de Moraes; Cavalcanti, Suellen M. T.; Oliveira, Arsênio Rodrigues; Filho, Gevanio Bezerra de Oliveira; Siqueira, Lucianna Râbelo Pessôa de; Barbosa, Míria de Oliveira; Borba, Elizabeth Fernanda de Oliveira; Silva, Teresinha Gonçalves da; Kaskow, Belinda J.; Karimi, Mahdad; Abraham, Lawrence J.; Leite, Ana Cristina Lima

doi:10.1039/c4md00070f

Cited by 14 publications

(7 citation statements)

References 17 publications

(18 reference statements)

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“…Copyright@ G SilvaJunior Jose [11,29]. Another study using cyclic imides designed to have selective anti-inflammatory action against cyclooxygenase 2 [COX-2] was performed with 30 imidic compounds.…”

Section: Am J Biomed Sci and Resmentioning

confidence: 99%

Therapeutic Potential of Phthalimide Derivatives: A Review

Júnior

Holanda

RodriguesGambôa

et al. 2019

AJBSR

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Section: Am J Biomed Sci and Resmentioning

confidence: 99%

Therapeutic Potential of Phthalimide Derivatives: A Review

Júnior

Holanda

RodriguesGambôa

et al. 2019

AJBSR

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“…In 2012, Basaric et al found that phthalimides can produce tumor necrosis factor (TNFα) to suppress tumor cell proliferation [ 9 ]. Furthermore, phthalimide polymers are widely used in biomedical and biological fields with a variety of properties including antimalarial, anti-influenza, anticancer, anti-inflammatory, and antifungal activities, apoptotic-inducing properties, and in applications such as protein sensors, n-type organic semiconductors, and electroluminescence [ 10 , 11 , 12 , 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

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

Durairaju

Chinnasamy²,

Periyasami

et al. 2021

Polymers

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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.

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“…The phthalimide (Pht) scaffold has attracted great interest as the basis for the synthesis of various alkaloids and other biologically important pharmacophores [25][26][27][28][29]. Phts are lipophilic and neutral molecules that can easily cross biological membranes, and possess anti-microbial [30] and anti-inflammatory [31] activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Bioactivity of Phthalimide Analogs as Potential Drugs to Treat Schistosomiasis, a Neglected Disease of Poverty

et al. 2020

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The neglected tropical disease, schistosomiasis, is caused by trematode blood flukes of the Schistosoma genus and infects approximately 200 million people worldwide. With just one partially effective drug available for disease treatment, new drugs are urgently needed. Herein, a series of 47 phthalimide (Pht) analogues possessing high-value bioactive scaffolds (i.e., benzimidazole and 1,2,3,-triazoles) was synthesized by click-chemistry. Compounds were evaluated for anti-schistosomal activity in culture against somules (post-infective larvae) and adults of Schistosoma mansoni, their predicted ADME (absorption, distribution, metabolism, and excretion) properties, and toxicity vs. HepG2 cells. The majority showed favorable parameters for surface area, lipophilicity, bioavailability and Lipinski score. Thirteen compounds were active at 10 µM against both somules and adults (6d, 6f, 6i-6l, 6n-6p, 6s, 6r', 6t' and 6w). Against somules, the majority caused degeneracy and/or death after 72 h; whereas against adult parasites, five compounds (6l, 6d, 6f, 6r' and 6s) elicited degeneracy, tegumental (surface) damage and/or death. Strongest potency against both developmental stages was recorded for compounds possessing n-butyl or isobutyl as a linker, and a pentafluorophenyl group on triazole. Apart from five compounds for which anti-parasite activity tracked with toxicity to HepG2 cells, there was apparently no toxicity to HepG2 cells (EC 50 values ≥50 µM). The data overall suggest that phthaloyl-triazole compounds are favorable synthons for additional studies as anti-schistosomals.

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Novel phthalimide derivatives with TNF-α and IL-1β expression inhibitory and apoptotic inducing properties

Abstract: 24 compounds were synthesized and their immunomodulation of TNF-α and IL-1β was evaluated.

Cited by 14 publications

References 17 publications

Therapeutic Potential of Phthalimide Derivatives: A Review

Therapeutic Potential of Phthalimide Derivatives: A Review

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

Synthesis and Bioactivity of Phthalimide Analogs as Potential Drugs to Treat Schistosomiasis, a Neglected Disease of Poverty

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