Design, Synthesis and Biological Evaluation of New <i>N</i>‐Acyl Hydrazones with a Methyl Sulfonyl Moiety as Selective COX‐2 Inhibitors

Osmaniye, Derya; Sağlık, Begüm Nurpelin; Levent, Serkan; Özkay, Yusuf; Kaplancıklı, Zafer Asım

doi:10.1002/cbdv.202100521

Cited by 14 publications

(9 citation statements)

References 22 publications

(33 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The evaluation was based on the detection of an intermediate product produced by COX enzyme which is known as prostaglandin G2. The in vitro COX inhibition test was performed using the available fluorometric method, and the percentages and IC 50 values of obtained compounds were calculated as previously described by our research group 29,30 …”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of new compounds bearing methyl sulfonyl pharmacophore as selectiveCOX‐2 inhibitor

Almarsoomi,

Osmaniye,

Sağlık

et al. 2023

J of Molecular Recognition

Self Cite

View full text Add to dashboard Cite

Cyclooxygenase, also known as prostaglandin H2 synthase (PGH2), is one of the most important enzymes in pharmacology because inhibition of COX is the mechanism of action of most nonsteroidal anti-inflammatory drugs. In this study, ten thiazole derivative compounds had synthesized. The analysis of the obtained compounds was performed by 1 H NMR and 13 C NMR methods. By this method, the obtained compounds could be elucidated. The inhibitory effect of the obtained compounds on cyclooxygenase (COX) enzymes was investigated. The encoded compounds 5a, 5b, and 5c were found to be the most potent compared to the reference compounds ibuprofen (IC 50 = 5.589 ± 0.278 μM), celecoxib (IC 50 = 0.132 ± 0.004 μM), and nimesulide (IC 50 = 1.692 ± 0.077 μM)against COX-2 isoenzyme. The inhibitory activity of 5a, 5b, and 5c is approximate, but the 5a derivative proved to be the most active in the series with an IC 50 value of 0.180 ± 0.002 μM. The most potent COXs inhibitor was 5a, which was further investigated for its potential binding mode by a molecular docking study. Compound 5a was found to be localized at the active site of the enzyme, like celecoxib, which has a remarkable effect on COXs enzymes.

show abstract

Section: Methodsmentioning

confidence: 99%

“…The in vitro COX inhibition test was performed using the available fluorometric method, and the percentages and IC 50 values of obtained compounds were calculated as previously described by our research group. 29,30…”

Section: In Vitro Cox-1 and Cox-2 Inhibition Assaymentioning

confidence: 99%

Synthesis of new compounds bearing methyl sulfonyl pharmacophore as selectiveCOX‐2 inhibitor

Almarsoomi,

Osmaniye,

Sağlık

et al. 2023

J of Molecular Recognition

Self Cite

View full text Add to dashboard Cite

show abstract

“…[13][14][15][16][17][18][19] Several studies on the chemistry and bioactivity of N-acylhydrazone lead scaffold have been published recently. This topic has gained significance over time for the development of novel, therapeutically effective bioactive N-acylhydrazone candidates as anticancer, [20][21][22][23] anti-inflammatory, [24][25][26][27][28][29][30][31] anti-Alzheimer, [32][33][34][35] antimicrobial agents, [36][37][38][39][40] and more. N-Acylhydrazones continue to be a prominent topic in therapeutic research, especially when it comes to the treatment of cancer.…”

Section: Researchers In Medicinal Chemistry Have Paid Interest Tomentioning

confidence: 99%

Anticancer agents incorporating the N‐acylhydrazone scaffold: Progress from 2017 to present

Kassab

2023

Archiv der Pharmazie

View full text Add to dashboard Cite

The N-acylhydrazone motif has been shown to be particularly adaptable and promising in the area of medicinal chemistry and drug development, due to its significant biological and pharmacological characteristics. Moreover, N-acylhydrazones are appealing synthetic and biological tools because of their simple and straightforward synthesis. This scaffold has emerged as a fundamental building block for the synthesis of bioactive compounds.Particularly, the N-acylhydrazone scaffold served as a base for the synthesis of a number of potent anticancer agents acting via different mechanisms. An updated summary of the anticancer activity of N-acylhydrazone derivatives described in the literature (from 2017 to 2022) is provided in the current review. It discusses the structure-activity relationship (SAR) of N-acylhydrazone derivatives exhibiting anticancer potential, which could be helpful in designing and developing new derivatives as effective antiproliferative candidates in the future.

show abstract

“…Therefore, the introduction of functional groups containing hydrogen bond donors or acceptors into molecules is a common strategy in drug design . Oxime, hydrazone structures can be used as hydrogen bond acceptors and donors at the same time. − Their introduction can enhance the interaction between drugs and proteins, thus improving the biological activity of drug molecules. − …”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Bioactivity of Aldisine Derivatives Containing Oxime and Hydrazine Moieties Based on Hydrogen Bonds

Yang

Liu

et al. 2023

J. Agric. Food Chem.

View full text Add to dashboard Cite

Marine natural products have attracted more and more attention in drug research and development due to their unique structure, diverse biological activities, and novel mode of action. Using antiviral alkaloid aldisine as the lead compound and drawing on the hydrogen bond effect widely used in drug design, derivatives containing oxime and hydrazone moieties were designed and synthesized by introducing functional groups with hydrogen-bond receptors or donors into molecules. The configuration of derivatives was systematically studied through nuclear Overhauser effect (NOE) spectroscopy and single crystal analysis. The antiviral activity test result showed that most derivatives had antiviral activity against tobacco mosaic virus (TMV), and some compounds had better activity than the commercial antiviral drug ribavirin, especially compounds 2 and 24, which had comparable activity to the most effective commercial antiviral drug ningnanmycin. Preliminary mode of action studies showed that compound 2 could affect the assembly of rod-shaped TMVs by promoting the aggregation and fragmentation of TMV coat proteins. Molecular docking experiments demonstrated that the introduction of oxime and hydrazone moieties could indeed increase the hydrogen bond between molecules and target proteins. In addition, we conducted fungicidal and larvicidal activities study of these derivatives. Most of these derivatives had good larvicidal activities against Mythimna separata and Plutella xylostella and showed broad-spectrum fungicidal activities.

show abstract

Design, Synthesis and Biological Evaluation of New N‐Acyl Hydrazones with a Methyl Sulfonyl Moiety as Selective COX‐2 Inhibitors

Cited by 14 publications

References 22 publications

Synthesis of new compounds bearing methyl sulfonyl pharmacophore as selectiveCOX‐2 inhibitor

Synthesis of new compounds bearing methyl sulfonyl pharmacophore as selectiveCOX‐2 inhibitor

Anticancer agents incorporating the N‐acylhydrazone scaffold: Progress from 2017 to present

Design, Synthesis, and Bioactivity of Aldisine Derivatives Containing Oxime and Hydrazine Moieties Based on Hydrogen Bonds

Contact Info

Product

Resources

About