Design and Synthesis of Novel 1,3,4-Oxadiazole and 1,2,4-Triazole Derivatives as Cyclooxygenase-2 Inhibitors with Anti-inflammatory and Antioxidant activity in LPS-stimulated RAW264.7 Macrophages

Hamoud, Mohamed M.S.; Osman, Nermine A.; Rezq, Samar; El-wahab, Hend A. A. Abd; Abdel-Fattah, Hanan A.; Romero, Damián G.; Ghanim, Amany M.

doi:10.1016/j.bioorg.2022.105808

Cited by 20 publications

(9 citation statements)

References 49 publications

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“…Zhang ( 120 ) synthesized a novel 5-aminothiazole ring-containing nuclear COX-2 inhibitor with higher anti-inflammatory effect than meloxicam. Hamoud MMS and other researchers ( 121 ) synthesized 1,3,4-oxadiazolyl derivatives (8a-g) and 1,2,4-triazolyl derivatives (10a,b and 11a-g), and through further experiments the newly designed compounds were found to have potent COX-2 inhibitory effects, possessing powerful with potent anti-inflammatory and antioxidant activities, capable of inhibiting TNF-α, NO and ROS production, and have the potential to be promising therapeutic agents for the treatment of inflammation-related psychiatric disorders. Novel chalcone compounds have excellent COX-2 inhibitory activity, can effectively suppress EGFR expression levels, and can overcome gastrointestinal side effects ( 122 , 123 ).…”

Section: Cyclo-oxygen-ase-2 Inhibitorsmentioning

confidence: 83%

Biology of cyclooxygenase-2: An application in depression therapeutics

Han

Liao

et al. 2022

Front. Psychiatry

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Depressive Disorder is a common mood disorder or affective disorder that is dominated by depressed mood. It is characterized by a high incidence and recurrence. The onset of depression is related to genetic, biological and psychosocial factors. However, the pathogenesis is still unclear. In recent years, there has been an increasing amount of research on the inflammatory hypothesis of depression, in which cyclo-oxygen-ase 2 (COX-2), a pro-inflammatory cytokine, is closely associated with depression. A variety of chemical drugs and natural products have been found to exert therapeutic effects by modulating COX-2 levels. This paper summarizes the relationship between COX-2 and depression in terms of neuroinflammation, intestinal flora, neurotransmitters, HPA axis, mitochondrial dysfunction and hippocampal neuronal damage, which can provide a reference for further preventive control, clinical treatment and scientific research on depression.

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Section: Cyclo-oxygen-ase-2 Inhibitorsmentioning

confidence: 83%

Biology of cyclooxygenase-2: An application in depression therapeutics

Han

Liao

et al. 2022

Front. Psychiatry

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“…General method for the synthesis of compounds (9)(10)(11)(12)(13)(14)(15)(16)(17)(18) Polyacryloyl chloride (2 mmol) was dissolved in dry acetonitrile (10 ml) and pyridine (1.5 ml). Subsequently, compounds 1-8 (2 mmol) were added to the solution.…”

Section: Methodsmentioning

confidence: 99%

“…1,2,4-triazole derivatives have attracted considerable attention due to their wide range of biological activities, including insecticidal [6], antifungal [7], antimicrobial [2,8], antiviral [9], antitumor [10], and antiin ammatory properties [11]. These derivatives have found applications in various elds, such as medicine and agriculture.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Evaluation of Antibacterial and Anticorrosion Properties of 4-Azo-3,5-sustituted-1,2,4-Triazole Polymers

Hamzah,

Mhaibes

2024

Preprint

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In this study, a series of 4-azo derivatives of 1,2,4-triazole were synthesized through the reaction of melt thiocarbohydrazide with various substituted benzoic acids. Subsequently, these derivatives were coupled with different aromatic amines to obtain 4-azo derivatives of 1,2,4-triazole. The synthesized derivatives were then converted into 4-azo-3,5-substituted-1,2,4-triazole polymers using dry acetonitrile, pyridine, and poly acryloyl chloride. The physical properties, FT-IR spectra, and 1H-NMR spectra (for selected compounds) were utilized to confirm the structures of the synthesized compounds and polymers. Furthermore, the antibacterial and anticorrosion activities of the compounds and polymers were investigated.

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“…8 Notably, 1,2,4-triazole and its derivatives exhibit significant biological activities, including antioxidant capabilities demonstrated through their ability to scavenge free radicals. 8,9 An investigation conducted by Pokuri et al involved the synthesis and assessment of twenty-six 1,2,4-triazole analogs, highlighting their exceptional potential as free radical scavengers through 2,2-diphenyl-1-picrylhydrazyl (DPPH • ) assay. 10 The utilization of 2D-QSAR models correlated with the in vitro findings, elucidating the key structural attributes prevalent in the molecules that contributed to their antioxidant efficacy.…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Free Radical Scavenging Ability of Triazole-3-Thiol: A Combination of Experimental and Theoretical Approaches

Quy Huong,

Nam,

Quang

et al. 2024

ACS Omega

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An assessment of the free radical scavenging potential of 4-amino-5-phenyl-4H-1,2,4-triazole-3-thiol (AT) and 4-amino-5-(4-pyridyl)-4H-1,2,4-triazole-3-thiol (AP) involved a combination of experimental methodologies and theoretical calculations. In the 2,2-diphenyl-1-picrylhydrazyl (DPPH•) assay, AT exhibited an heightened efficacy in scavenging DPPH• radicals compared to AP. This was evidenced by the notably lower IC50DPPH value observed for AT (1.3 × 10–3 ± 0.2 × 10–3 M) in comparison to AP (2.2 × 10–3 ± 0.1 × 10–3 M). Similarly, in the 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonate) (ABTS• +) test, AT exhibited superior ability in neutralizing ABTS•+ free radical cations compared to AP, with the computed IC50ABTS values of 4.7 × 10–5 ± 0.1 × 10–5 M for AT and 5.5 × 10–5 ± 0.2 × 10–5 M for AP. Density functional theory served as the tool for evaluating the correlation between structural attributes and the antioxidant efficacy of the studied molecules. The findings highlighted the flexibility of hydrogen atoms within NH and NH2 groups to nucleophilic attacks, indicative of their pivotal role in the scavenging mechanism. Furthermore, investigations into the interactions between AT and AP with the free radical HOO• revealed predominantly the reaction via the hydrogen atom transfer mechanism. Both experimental observations and theoretical deductions collectively affirmed AT’s superior free radical scavenging ability over AP in the gas phase and ethanol.

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Design and Synthesis of Novel 1,3,4-Oxadiazole and 1,2,4-Triazole Derivatives as Cyclooxygenase-2 Inhibitors with Anti-inflammatory and Antioxidant activity in LPS-stimulated RAW264.7 Macrophages

Cited by 20 publications

References 49 publications

Biology of cyclooxygenase-2: An application in depression therapeutics

Biology of cyclooxygenase-2: An application in depression therapeutics

Synthesis, Characterization, and Evaluation of Antibacterial and Anticorrosion Properties of 4-Azo-3,5-sustituted-1,2,4-Triazole Polymers

Evaluation of Free Radical Scavenging Ability of Triazole-3-Thiol: A Combination of Experimental and Theoretical Approaches

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