Synthesis, modeling and biological evaluation of some pyrazolo[3,4-d]pyrimidinones and pyrazolo[4,3-e][1,2,4]triazolo[4,3-a]pyrimidinones as anti-inflammatory agents

Tageldin, Gina N.; Ibrahim, Tamer M.; Fahmy, Salwa M.; Ashour, Hayam M. A.; Khalil, M. A.; Nassra, Rasha A.; Labouta, Ibrahim M.

doi:10.1016/j.bioorg.2019.03.018

Cited by 22 publications

(7 citation statements)

References 45 publications

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“…Results obtained after conducting in vitro formalin-induced paw oedema and cotton-pellet induced granuloma assays revealed that compounds 67a – 67d displayed anti-inflammatory activity (AI = 64.3–78.6%) higher than celecoxib (AI = 46.4%) in the acute model, whereas compounds 67a and 67b possessed potent anti-inflammatory activity (AI = 43.4% and 46.9%) superior to both references (AI = 8.6% and 36.1% for celecoxib and diclofenac sodium, respectively) in the chronic model. All the tested compounds exhibited safe gastrointestinal profile, with the exception of compound 67a 82 .…”

Section: Recent Development In Anti-inflammatory Agentsmentioning

confidence: 95%

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Bian

Wu³

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Inflammation and disease are closely related. Inflammation can induce various diseases, and diseases can promote inflammatory response, and two possibly induces each other in a bidirectional loop. Inflammation is usually treated using synthetic anti-inflammatory drugs which are associated with several adverse effects hence are not safe for long-term use. Therefore, there is need for anti-inflammatory drugs which are not only effective but also safe. Several researchers have devoted to the research and development of effective anti-inflammatory drugs with little or no side effects. In this review, we studied some small molecules with reported anti-inflammatory activities and hence potential sources of anti-inflammatory agents. The information was retrieved from relevant studies published between January 2019 and May, 2021 for review. This review study was aimed to provide relevant information towards the design and development of effective and safe anti-inflammation agents.

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Section: Recent Development In Anti-inflammatory Agentsmentioning

confidence: 95%

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Bian

Wu³

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Several pyrazole-based drugs namely celecoxib, rimonabant, difenamizole and fezolamine, etc., with excellent anti-inflammatory, anti-obesity, analgesic and/or antidepressant activities have been developed and are used to treat various diseases (Figure 23) [32][33][34][35]. Pyrazole fused triazole molecules 20 were identified as anti-inflammatory agents and COX-1/COX-2 enzyme inhibitors by Tageldin and co-workers [73]. Among them, compound 20a showed promising anti-inflammatory activity with an IC 50 value of 4.33 µM against the COX-1 enzyme as compared with celecoxib (IC 50 = 5.46 µM) ( Figure 24).…”

Section: Pyrazolesmentioning

confidence: 99%

“…Furthermore, docking studies of the most active compound showed that the acetate moiety of 20a was involved in a H-bonding interaction with the Tyr385 of the COX-2 enzyme. In addition, the 1-phenyl substituent attached to the core pyrazolo [4,3- Pyrazole fused triazole molecules 20 were identified as anti-inflammatory agents and COX-1/COX-2 enzyme inhibitors by Tageldin and co-workers [73]. Among them, compound 20a showed promising anti-inflammatory activity with an IC50 value of 4.33 M against the COX-1 enzyme as compared with celecoxib (IC50 = 5.46 M) ( Figure 24).…”

Section: Pyrazolesmentioning

confidence: 99%

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

et al. 2020

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The analogs of nitrogen-based heterocycles occupy an exclusive position as a valuable source of therapeutic agents in medicinal chemistry. More than 75% of drugs approved by the FDA and currently available in the market are nitrogen-containing heterocyclic moieties. In the forthcoming decade, a much greater share of new nitrogen-based pharmaceuticals is anticipated. Many new nitrogen-based heterocycles have been designed. The number of novel N-heterocyclic moieties with significant physiological properties and promising applications in medicinal chemistry is ever-growing. In this review, we consolidate the recent advances on novel nitrogen-containing heterocycles and their distinct biological activities, reported over the past one year (2019 to early 2020). This review highlights the trends in the use of nitrogen-based moieties in drug design and the development of different potent and competent candidates against various diseases.

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“…[125] (Figure 8) Extension of the above work identified that the hydrazones (93 a, 93 b, 93 c) and the cyano acetohydrazide derivative (93 d) of pyrazolo [3,4-d] able anti-inflammatory activity both in acute and chronic model and hence can be considered as a lead. [126] Ten acid chlorides of pyrazolo [3,4-d]pyrimidine derivatives bearing alkyl and aromatic substitutions were evaluated for both in vitro and in vivo anti-inflammatory activity using celecoxib as standard. Compounds 94 a-d exhibited IC 50 of 42.1, 31.4, 34.4 and 23.8 μM respectively compared with 11.7 μM of celecoxib, also ED 50 values for the acute inflammatory model for the compounds 94 a and 94 d were found to be 8.3 and 7.6 μM respectively which was equivalent to 7.2 of celecoxib proving that compound 94 d with bulky aromatic group produces antiinflammatory activity comparable to celecoxib and branched isomers showed significant COX-2 inhibition than linear isomers.…”

Section: Pyrazolopyrimidine and Pyrazolopyrimidin-4-onementioning

confidence: 99%

Structural Insights into Pyrazoles as Agents against Anti‐inflammatory and Related Disorders

et al. 2022

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Pyrazole moiety is considered as the most important therapeutic agent for the treatment of inflammation and inflammation associated cancers. Celecoxib, Ramifenazone, Rimonabant and Lonazolac are some of the commercially available pyrazole moieties which are potent COX‐2 inhibitors and also acts in inhibiting various cancers. Recently there are numerous reviews on the biological significance of pyrazole derivatives. However, this review discusses pyrazole derivatives possessing anti‐inflammatory and anticancer activity (COX inhibition) and also illustrates the recent updates on pyrazole research emphasizing on the medicinal chemistry aspects such as the key structural fragments required for the biological activity. There are series of pyrazoles like di‐substituted, tri‐substituted, tetra‐substituted pyrazoles, pyrazole hydrazones, pyrazoles bearing various other heterocycles, bicyclic fused pyrazoles, tricyclic fused pyrazoles, and miscellaneous class of pyrazoles. All these pyrazoles are being researched as COX inhibitors, anti‐inflammatory and against related disorders like cancer.

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Synthesis, modeling and biological evaluation of some pyrazolo[3,4-d]pyrimidinones and pyrazolo[4,3-e][1,2,4]triazolo[4,3-a]pyrimidinones as anti-inflammatory agents

Cited by 22 publications

References 45 publications

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

Small molecule compounds with good anti-inflammatory activity reported in the literature from 01/2009 to 05/2021: a review

A Review on Recent Advances in Nitrogen-Containing Molecules and Their Biological Applications

Structural Insights into Pyrazoles as Agents against Anti‐inflammatory and Related Disorders

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