Piperazine and piperidine‐substituted 7‐hydroxy coumarins for the development of anti‐inflammatory agents

Buran, Kerem; Reıs, Rengin; Sipahi, Hande; Bayram, F Esra Önen

doi:10.1002/ardp.202000354

Cited by 12 publications

(7 citation statements)

References 20 publications

(25 reference statements)

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“…NO release through its stable metabolite, nitrite level, was assessed by the similar method of Buran and colleagues (2021) [60] . Briefly, collected cell supernatants were mixed with equal amount of Griess reagent containing sulfanilamide (Sigma–Aldrich, CAT No.…”

Section: Methodsmentioning

confidence: 99%

“…NO release through its stable metabolite, nitrite level, was assessed by the similar method of Buran and colleagues (2021). [60] Briefly, collected cell supernatants were mixed with equal amount of Griess reagent containing sulfanilamide (Sigma-Aldrich, CAT No. S9251, USA), o-phosphoric acid and N-(1naphtyl)ethylenediamine at room temperature and incubated for an additional 5 min.…”

Section: Nitrite Levelmentioning

confidence: 99%

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Alpha‐Lipoic Acid Modulates the Oxidative and Inflammatory Responses Induced by Traditional and Novel Tobacco Products in Human Liver Epithelial Cells

Reıs

Kolci

Bahcivan

et al. 2023

Chemistry & Biodiversity

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Smoking has been associated with NAFLD recently, thus might be a contributing factor for liver disease progression. In this study, we identified the modulative action of α-lipoic acid (α-LA), an organosulphur compound, towards heated tobacco product (HTP) and cigarette smoke extract (CSE)-induced oxidative stress and inflammation in human liver HepG2 cells. The cells were pre-treated with α-LA and exposed to tobacco extracts, and cytotoxicity, oxidative response (SOD, CAT activities and GSH, MDA levels), inflammation (nitrite, IL-6, AhR levels), and liver function (AST/ALT) were assessed. According to the results, a notable increase in oxidative response was observed with CSE, whereas GSH depletion and decreased SOD activity were the key toxicological events induced by HTP (p < 0.05). The oxidative and inflammatory responses were ameliorated with α-LA treatment, particularly through GSH restoration and IL-6 modulation. To conclude, these findings on α-LA might contribute to the design of novel adjuvant therapies for people exposed to tobacco smoke.

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Section: Methodsmentioning

confidence: 99%

Section: Nitrite Levelmentioning

confidence: 99%

Alpha‐Lipoic Acid Modulates the Oxidative and Inflammatory Responses Induced by Traditional and Novel Tobacco Products in Human Liver Epithelial Cells

Reıs

Kolci

Bahcivan

et al. 2023

Chemistry & Biodiversity

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“…Anti‐inflammatory activity of the compounds was evaluated by measuring the stable NO metabolite, nitrite, with Griess assay. [ 31 ] Briefly, RAW‐264.7 cells were plated in a 48‐well plate and incubated for 24 h at 37°C in 5% CO 2 . Plated cells were pretreated with the same concentrations in cell viability assay for 2 h and then stimulated with 1 µg/ml of LPS for additional 22 h. The culture supernatant (50 µl) was mixed with Griess reagent (1% sulfanilamide and 0.1% N ‐(1‐naphthyl)ethylenediamine dihydrochloride in 5% phosphoric acid Mettler]) and incubated at room temperature for 10 min.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, and molecular docking of novel 3,5‐disubstituted‐1,3,4‐oxadiazole derivatives as iNOS inhibitors

Koksal

Dedeoglu-Erdogan

Bader

et al. 2021

Archiv der Pharmazie

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To obtain new anti‐inflammatory agents, recent studies have aimed to replace the carboxylate functionality of nonsteroidal anti‐inflammatory drugs with less acidic heterocyclic bioisosteres like 1,3,4‐oxadiazole to protect the gastric mucosa from free carboxylate moieties. In view of these observations, we designed and synthesized a series of 3,5‐disubstituted‐1,3,4‐oxadiazole derivatives as inhibitors of prostaglandin E2 (PGE2) and NO production with an improved activity profile. As initial screening, and to examine the anti‐inflammatory activities of the compounds, the inhibitions of the productions of lipopolysaccharide‐induced NO and PGE2 in RAW 264.7 macrophages were evaluated. The biological assays showed that, compared with indomethacin, compounds 5a, 5g, and 5h significantly inhibited NO production with 12.61 ± 1.16, 12.61 ± 1.16, and 18.95 ± 3.57 µM, respectively. Consequently, the three compounds were evaluated for their in vivo anti‐inflammatory activities. Compounds 5a, 5g, and 5h showed a potent anti‐inflammatory activity profile almost equivalent to indomethacin at the same dose in the carrageenan‐induced paw edema test. Moreover, the treatment with 40 mg/kg of 5h produced significant anti‐inflammatory activity data. Furthermore, docking studies were performed to reveal possible interactions with the inducible nitric oxide synthase enzyme. Docking results were able to rationalize the biological activity data of the studied inhibitors. In summary, our data suggest that compound 5h is identified as a promising candidate for further anti‐inflammatory drug development with an extended safety profile.

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“…[55] Piperazine-linked coumarin hybrids synthesized by Karem et al, Compound 7 displayed good anti-inflammatory activity with IC 50 of 25 μg better than reference drug indomethacin with IC 50 of 100 μg. [56] Zhi-ping et al synthesized piperazine linked to oxadiazole and dioxane hybrids and evaluated them for anti-inflammatory activity. Compared to the reference drug diclofenac's swelling degree of 6.51 mg with 52 % inhibition, Compound 8 showed a powerful swelling degree of 4.34 mg with 68.02 % inhibition.…”

Section: Anti-inflammatory and Antioxidant Agentsmentioning

confidence: 99%

Versatile Therapeutic Values of N‐Containing Heterocycles Benzimidazole, Piperazine and Piperidine Hybrids

Zala,

Kumari

2023

ChemistrySelect

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Nitrogen‐containing benzimidazole, piperazine, and piperidine are significant pharmacophores in medicinal chemistry and drug development. Many medications, lead compounds, and various reagents have these N‐containing scaffolds. This review concentrated on the development of novel therapeutic agents as well as the broad range of pharmacological actions demonstrated by benzimidazole, piperazine, and piperidine hybrids. The review emphasizes these hybrids′ potential, range, and medical significance. The review also discusses the structural criteria for benzimidazole, piperazine, and piperidine hybrids created by diverse chemists to be physiologically effective against a variety of disorders.

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Piperazine and piperidine‐substituted 7‐hydroxy coumarins for the development of anti‐inflammatory agents

Cited by 12 publications

References 20 publications

Alpha‐Lipoic Acid Modulates the Oxidative and Inflammatory Responses Induced by Traditional and Novel Tobacco Products in Human Liver Epithelial Cells

Alpha‐Lipoic Acid Modulates the Oxidative and Inflammatory Responses Induced by Traditional and Novel Tobacco Products in Human Liver Epithelial Cells

Design, synthesis, and molecular docking of novel 3,5‐disubstituted‐1,3,4‐oxadiazole derivatives as iNOS inhibitors

Versatile Therapeutic Values of N‐Containing Heterocycles Benzimidazole, Piperazine and Piperidine Hybrids

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