Synthesis, characterization and antioxidant activity studies of new coumarin tethered 1,3,4-oxadiazole analogues

Basappa, Vagish Channa; Penubolu, Sudeep; Achutha, Dileep Kumar; Kariyappa, Ajay Kumar

doi:10.1007/s12039-021-01914-5

Cited by 11 publications

(7 citation statements)

References 27 publications

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“…Moreover, it was reported that 1,3,4-oxadiazole scaffold has been found to be a potent antioxidant pharmacophore, and chemical modulation of the conventional drugs with this scaffold resulted in a synergistic effect, enhancing the antioxidant efficiency of the parent drug [47,49,50,83,84]. In our research, the presence of 1,3,4-oxadiazole scaffold significantly enhanced antioxidant activity for the majority of the NO-IND-OXDs.…”

Section: In Vitro Radical Scavenging Assaysupporting

confidence: 51%

Design, Synthesis, In Silico and In Vitro Studies for New Nitric Oxide-Releasing Indomethacin Derivatives with 1,3,4-Oxadiazole-2-thiol Scaffold

Sava

Buron

Routier

et al. 2021

IJMS

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Starting from indomethacin (IND), one of the most prescribed non-steroidal anti-inflammatory drugs (NSAIDs), new nitric oxide-releasing indomethacin derivatives with 1,3,4-oxadiazole-2-thiol scaffold (NO-IND-OXDs, 8a-p) have been developed as a safer and more efficient multitarget therapeutic strategy. The successful synthesis of designed compounds (intermediaries and finals) was proved by complete spectroscopic analyses. In order to study the in silico interaction of NO-IND-OXDs with cyclooxygenase isoenzymes, a molecular docking study, using AutoDock 4.2.6 software, was performed. Moreover, their biological characterization, based on in vitro assays, in terms of thermal denaturation of serum proteins, antioxidant effects and the NO releasing capacity, was also performed. Based on docking results, 8k, 8l and 8m proved to be the best interaction for the COX-2 (cyclooxygense-2) target site, with an improved docking score compared with celecoxib. Referring to the thermal denaturation of serum proteins and antioxidant effects, all the tested compounds were more active than IND and aspirin, used as references. In addition, the compounds 8c, 8h, 8i, 8m, 8n and 8o showed increased capacity to release NO, which means they are safer in terms of gastrointestinal side effects.

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Section: In Vitro Radical Scavenging Assaysupporting

confidence: 51%

Design, Synthesis, In Silico and In Vitro Studies for New Nitric Oxide-Releasing Indomethacin Derivatives with 1,3,4-Oxadiazole-2-thiol Scaffold

Sava

Buron

Routier

et al. 2021

IJMS

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“…The excellent DPPH and hydroxyl radical scavenging activity shown by compounds 25a and 25e are comparable with the respective standards and also with the reported structurally related compounds. [ 40 ]…”

Section: Overview Of the Diverse Derivatives And Their Activitiesmentioning

confidence: 99%

“…In the DPPH assay, it was observed that some compounds of the series showed positive radical scavenging are comparable with the respective standards and also with the reported structurally related compounds. [40] Farshori et al reported a series of 1,3,5-oxadiazole compounds developed by one-pot synthesis under conventional and microwave conditions without any solvent (solvent-free synthesis). Using the conventional method, 2,5-disubstituted-1,3,4-oxadiazoles were formed by the reaction of phosphorus oxychloride (5 mL) and a mixture of substituted carboxylic acid (0.01 mol) and fatty acid hydrazide (0.01 mol) without the use of any solvent.…”

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confidence: 99%

Unveiling the chemistry of 1,3,4‐oxadiazoles and thiadiazols: A comprehensive review

Gour,

Yahya,

Shahar Yar

2023

Archiv der Pharmazie

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Oxadiazoles and thiadiazoles are malleable heterocycles that have recently generated major interest in the field of medicinal chemistry. Compounds based on these moieties have versatile biological applications such as anticonvulsant, anticancer, antidiabetic, and antioxidant agents. Due to the versatile nature and stability of the oxadiazole and thiadiazole nucleus, medicinal chemists have changed the structural elements of the ring in numerous ways. These compounds have shown significant anticonvulsant effects, demonstrating their potential in the management of epileptic disorders. In this review, we have covered numerous biological pathways and in silico targeted proteins of oxadiazole and thiadiazole derivatives for treating various biological disorders. The data compiled in this article will be helpful for researchers, research scientists, and research chemists who work in the field of drug discovery and drug development.

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“…Coumarins are regarded to be the most versatile chemical rings for development and discovery of anticancer drug. Coumarins have attracted the attentions of scientists due to the fact that they have a variety of pharmacological properties, such as antiviral [6,7], antibacterial [8,9], antimicrobial [10], anticancer [11][12][13], anti-SARS-CoV-2-agents [14], antioxidant [15], anti-in ammatory and anti-HIV [16,17]. On the other side, thiazole derivatives are found in nature as penicillin, thiamine (vitamin-B1) and luciferin [18].…”

Section: Introductionmentioning

confidence: 99%

Greener synthesis and antimicrobial activity of some coumarin analogues

Abdel‐Aziem

Baaiu

2023

Preprint

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Herein, a rapid, clean, less expensive and environmental friendly route to a novel series of coumarins bearing thiazoles or 1,3,4- H thiadiazoles was developed via grinding method. Thus, 6-bromo-3-(2-bromoacetyl)-2-chromen-2-one was treated with cyanothioacetamide to produce thiazole-2-acetonitrile derivative 2, which was then transformed to iminocoumarins by reacting with hydroxyaldehydes. Hydrolysis of iminocoumarins by Conc. HCl furnished coumarins. Furthermore, treatment of compound 2 with phenylisothiocyanate produced thioanilide. Reaction of the latter with hydrazonoyl halide and / or α-halocarbonyl compounds afforded 1, 3, 4-thiadiazole and thiophene derivative, consequently. All the newly prepared coumarins were screened against six pathogenic microorganisms. The results indicated that compounds 7 and 12 were the most effective against B. pumilis, while compound 4b was highly active against S. faecalis. Also, compound 5b was highly active against E. cloacae. Compounds 2 and 7 were higher active compared with reference drug ketoconazole against fungi S. cerevisiae.

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Synthesis, characterization and antioxidant activity studies of new coumarin tethered 1,3,4-oxadiazole analogues

Cited by 11 publications

References 27 publications

Design, Synthesis, In Silico and In Vitro Studies for New Nitric Oxide-Releasing Indomethacin Derivatives with 1,3,4-Oxadiazole-2-thiol Scaffold

Design, Synthesis, In Silico and In Vitro Studies for New Nitric Oxide-Releasing Indomethacin Derivatives with 1,3,4-Oxadiazole-2-thiol Scaffold

Unveiling the chemistry of 1,3,4‐oxadiazoles and thiadiazols: A comprehensive review

Greener synthesis and antimicrobial activity of some coumarin analogues

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