Novel chalcone/aryl carboximidamide hybrids as potent anti-inflammatory via inhibition of prostaglandin E2 and inducible NO synthase activities: design, synthesis, molecular docking studies and ADMET prediction

Ibrahim, Tarek S.; Moustafa, Amr H.; Almalki, Ahmad J.; Allam, Rasha M.; Althagafi, Abdulhamid; Shadab,; Mohamed, Mamdouh F. A.

doi:10.1080/14756366.2021.1929201

Cited by 18 publications

(7 citation statements)

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“…Docking simulation study was carried out using Discovery Studio 2.5 software (Accelrys Inc., San Diego, CA, USA) [73]. For more details, see Supplementary Materials.…”

Section: In Silico Docking Studymentioning

confidence: 99%

Synthesis, Antimicrobial, Anti-Virulence and Anticancer Evaluation of New 5(4H)-Oxazolone-Based Sulfonamides

et al. 2022

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Since the synthesis of prontosil the first prodrug shares their chemical moiety, sulfonamides exhibit diverse modes of actions to serve as antimicrobials, diuretics, antidiabetics, and other clinical applications. This inspiring chemical nucleus has promoted several research groups to investigate the synthesis of new members exploring new clinical applications. In this study, a novel series of 5(4H)-oxazolone-based-sulfonamides (OBS) 9a-k were synthesized, and their antibacterial and antifungal activities were evaluated against a wide range of Gram-positive and -negative bacteria and fungi. Most of the tested compounds exhibited promising antibacterial activity against both Gram-positive and -negative bacteria particularly OBS 9b and 9f. Meanwhile, compound 9h showed the most potent antifungal activity. Moreover, the OBS 9a, 9b, and 9f that inhibited the bacterial growth at the lowest concentrations were subjected to further evaluation for their anti-virulence activities against Pseudomonas aeruginosa and Staphylococcus aureus. Interestingly, the three tested compounds reduced the biofilm formation and diminished the production of virulence factors in both P. aeruginosa and S. aureus. Bacteria use a signaling system, quorum sensing (QS), to regulate their virulence. In this context, in silico study has been conducted to assess the ability of OBS to compete with the QS receptors. The tested OBS showed marked ability to bind and hinder QS receptors, indicating that anti-virulence activities of OBS could be due to blocking QS, the system that controls the bacterial virulence. Furthermore, anticancer activity has been further performed for such derivatives. The OBS compounds showed variable anti-tumor activities, specifically 9a, 9b, 9f and 9k, against different cancer lines. Conclusively, the OBS compounds can serve as antimicrobials, anti-virulence and anti-tumor agents.

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“…Docking simulation study was carried out using Discovery Studio 2.5 software (Accelrys Inc., San Diego, CA, USA) [73]. For more details, see Supplementary Materials.…”

Section: In Silico Docking Studymentioning

confidence: 99%

Synthesis, Antimicrobial, Anti-Virulence and Anticancer Evaluation of New 5(4H)-Oxazolone-Based Sulfonamides

et al. 2022

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“…15 Recently, numerous studies have reported that both naturally occurring and synthetic chalcones and dihydrochalcones as anti-inflammatory agents are involved in the inhibition of cytokines and inflammatory mediator production in inflammatory disorders. 13,[16][17][18][19][20] However, limited studies are reported on evaluating the anti-inflammatory activity of chalcones and dihydrochalcones or their structure-activity relationships (SARs).…”

Section: Introductionmentioning

confidence: 99%

Identification of chalcone analogues as anti-inflammatory agents through the regulation of NF-κB and JNK activation

Zhang,

Wang,

et al. 2024

RSC Med. Chem.

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“…Chalcones are used in several biosynthetic pathways as initial intermediate structures in the production of flavonoids, isoflavonoids, and aurones . A significant part of medicinal chemistry research in the 21st century has been focused on both natural and synthetic chalcones because of their various pharmacological potential including activities and characteristics such as antibacterial, − anti-inflammatory, − analgesic, , anticholinergic, antiplatelet, antiulcer, antioxidant, , antimalarial, anticancer, , antiviral, − antileishmanial, antidiabetic, , immunomodulatory, , aldose reductase inhibition, estrogenic, acetylcholinesterase inhibition, and as non-purine xanthine oxidase inhibitors . Chalcones are highly attractive molecules because of their simple structure, ease of construction, and promising biological applications.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Chalcones Derivatives and Their Biological Activities: A Review

et al. 2022

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Chalcone derivatives are considered valuable species because they possess a ketoethylenic moiety, CO–CH=CH–. Due to the presence of a reactive α,β-unsaturated carbonyl group, chalcones and their derivatives possess a wide spectrum of antiproliferative, antifungal, antibacterial, antiviral, antileishmanial, and antimalarial pharmacological properties. Recent developments in heterocyclic chemistry have led to the synthesis of chalcone derivatives, which had been biologically investigated toward certain disease targets. The major aspect of this review is to present the most recent synthesis of chalcones bearing N, O, and/or S heterocycles, revealing their biological potential during the past decade (2010–2021). Based on a review of the literature, many chalcone–heterocycle hybrids appear to exhibit promise as future drug candidates owing to their similar or superior activities compared to those of the standards. Thus, this review may prove to be beneficial for the development and design of new potent therapeutic drugs based on previously developed strategies.

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Novel chalcone/aryl carboximidamide hybrids as potent anti-inflammatory via inhibition of prostaglandin E2 and inducible NO synthase activities: design, synthesis, molecular docking studies and ADMET prediction

Abstract: 2021) Novel chalcone/aryl carboximidamide hybrids as potent anti-inflammatory via inhibition of prostaglandin E2 and inducible NO synthase activities: design, synthesis, molecular docking studies and ADMET prediction,

Cited by 18 publications

References 69 publications

Synthesis, Antimicrobial, Anti-Virulence and Anticancer Evaluation of New 5(4H)-Oxazolone-Based Sulfonamides

Synthesis, Antimicrobial, Anti-Virulence and Anticancer Evaluation of New 5(4H)-Oxazolone-Based Sulfonamides

Identification of chalcone analogues as anti-inflammatory agents through the regulation of NF-κB and JNK activation

Synthesis of Chalcones Derivatives and Their Biological Activities: A Review

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