Synthesis of 1,3,4-oxadiazoles as promising anticoagulant agents

Iyer, Vishwanathan B.; Gurupadayya, Bannimath; Inturi, Bharathkumar; Sairam, K Venkata; Pujar, Gurubasavaraj V.

doi:10.1039/c6ra01158f

Cited by 7 publications

(4 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…[9][10][11][12] Literature searches reveal that 2,5disubstituted 1,3,4-oxadiazole derivatives commonly obtained from diacylhydrazines show antioxidant potential. This class of compounds includes sulfonamidomethane linked 1,3,4-oxadiazoles, 13 substituted bis(1,3,4-oxadiazoles), 14 1,3,4-oxadiazoles possessing benzoxazole, 15 1,3,4-oxadiazole tagged thieno [2,3-d]pyrimidines, 16 2-benzoylamino-5-hetaryl-1,3,4-oxadiazoles, 17 and 1,3,4-oxadiazoles containing 3-uoro-4methoxyphenyl moiety. 18 To the best of our knowledge, there is no available data regarding antioxidant activity of hydroxysubstituted dibenzoylhydrazines in the literature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids

et al. 2017

View full text Add to dashboard Cite

Eight 1,3,4-oxadiazole derivatives containing phenolic acid moieties (7a-h) and eight of their diacylhydrazine precursors (6a-h) were synthesized, characterized using spectroscopic methods and examined by scavenging of stable DPPH (2,2-diphenyl-1-picrylhydrazyl) radicals. The most potent phenolic 1,3,4-oxadiazoles showed better DPPH scavenging activity in comparison with their corresponding diacylhydrazine precursors as a result of participation of both aromatic rings and a 1,3,4-oxadiazole moiety in resonance stabilization of the formed phenoxyl radical. Four diacylhydrazines (6d, 6e, 6g, and 6h) and four 1,3,4-oxadiazoles (7d, 7e, 7g and 7h) with the best DPPH scavenging activity, were chosen for further evaluation of their antioxidant potential through various assays. The investigated compounds exerted pronounced ABTS radical scavenging capacity, moderate to good H 2 O 2 scavenging properties and strong ferric ion reducing capacity. Further in vitro evaluation of the antioxidant properties of the most active compounds demonstrated their protective effects in normal lung fibroblasts MRC-5 against hydrogen peroxide induced oxidative stress. Diacylhydrazine 6h increased two times the activity of glutathione peroxidase in treated cells in comparison with a control sample and did not affect the superoxide dismutase activity.

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids

et al. 2017

View full text Add to dashboard Cite

show abstract

“…2, 5-disubstituted-1, 3, 4-oxadiazole exhibits a wide spectrum of biological activities [7]. As reported earlier, many derivatives containing the 1, 3, 4-oxadiazole moiety including sulfonamidomethane [8], benzoxazole [9], pyrimidines [10] and methoxyphenyl [11] display significant antioxidant properties. Thus taking into consideration the antioxidant properties of benzoic acid and 1, 3, 4-oxadiazoles scaffold, new derivatives ( 4a–5f ) containing the 1, 3, 4-oxadiazole ring formed through cyclization of derivatives of benzoic acid synthesized in our previous study could serve as potent anticancer agents by effectively scavenging the free radical formation because of extended conjugation and stability.…”

Section: Introductionmentioning

confidence: 98%

Pharmacokinetic evaluation, molecular docking and in vitro biological evaluation of 1, 3, 4-oxadiazole derivatives as potent antioxidants and STAT3 inhibitors

Khanam

Hejazi

Shahabuddin

et al. 2019

Journal of Pharmaceutical Analysis

View full text Add to dashboard Cite

1, 3, 4-Oxadiazole derivatives (4a–5f) were previously synthesized to investigate their anticancer properties. However, studies relating to their antioxidant potential and signal transducer and activator of transcription (STAT) inhibition have not been performed. We investigated previously synthesized 1, 3, 4-oxadiazole derivatives ( 4a–5f) for various radical scavenging properties using several in vitro antioxidant assays and also for direct inhibition of STAT3 through molecular docking. The data obtained from various antioxidant assays such as 2, 2,-diphenyl-1-picrylhydrazyl radical (DPPH), nitric oxide, hydrogen peroxide, and superoxide anion radical revealed that among all the derivatives, compound 5e displayed high antioxidant activities than the standard antioxidant L -ascorbic acid. Additionally, the total reduction assay and antioxidant capacity assay further confirmed the antioxidant potential of compound 5e . Furthermore, the molecular docking studies performed for all derivatives along with the standard inhibitor STX-0119 showed that binding energy released in direct binding with the SH2 domain of STAT3 was the highest for compound 5e (-9.91kcal/mol). Through virtual screening, compound 5e was found to exhibit optimum competency in inhibiting STAT3 activity. Compound 5e decreased the activation of STAT3 as observed with Western blot. In brief, compound 5e was identified as a potent antioxidant agent and STAT3 inhibitor and effective agent for cancer treatment.

show abstract

“…[ 7–14 ] The other heterocycles like pyrimidine, furan, pyrrole, indole, oxadiazole, benzoxazole, azetidine, thiophene, coumarin, benzofuran, pyrazole, quinoline oxazole, quinazoline, pyrimidine, thiazole, quinoline, pyrazole, and isoxazole also possess various pharmacological activities. [ 8,15–30 ]…”

Section: Introductionmentioning

confidence: 99%

“…[7][8][9][10][11][12][13][14] The other heterocycles like pyrimidine, furan, pyrrole, indole, oxadiazole, benzoxazole, azetidine, thiophene, coumarin, benzofuran, pyrazole, quinoline oxazole, quinazoline, pyrimidine, thiazole, quinoline, pyrazole, and isoxazole also possess various pharmacological activities. [8,[15][16][17][18][19][20][21][22][23][24][25][26][27][28][29][30] The Food and Drug Administration (FDA)-approved drugs in recent years contain biologically active heterocycles in their structures. The drugs like remdesivir (broad-spectrum antiviral drug), [31] avaprinitib (an antitumor drug), [32] pematinib (an anticancer drug used to treat cholangiocarcinoma), [33] remimazolam (sedative drug), [34] and oliceradine (pain medication) [35] approved in 2020 (Figure 1).…”

mentioning

confidence: 99%

Oxadiazole: A highly versatile scaffold in drug discovery

Desai

Monapara

Jethawa

et al. 2022

Archiv der Pharmazie

View full text Add to dashboard Cite

As a pharmacologically important heterocycle, oxadiazole paved the way to combat the problem associated with the confluence of many commercially available drugs with different pharmacological profiles. The present review focuses on the potential applications of five-membered heterocyclic oxadiazole derivatives, especially 1,2,4-oxadiazole, 1,2,5-oxadiazole, and 1,3,4-oxadiazole, as therapeutic agents. Designing new hybrid molecules containing the oxadiazole moiety is a better solution for the development of new drug molecules. The designed molecules may accumulate a biological profile better than those of the drugs currently available on the market. The present review will guide the way for researchers in the field of medicinal chemistry to design new biologically active molecules based on the oxadiazole nucleus. Antitubercular, antimalarial, anti-inflammatory, anti-HIV, antibacterial, and anticancer activities of various oxadiazoles have been reviewed extensively here.

show abstract

Synthesis of 1,3,4-oxadiazoles as promising anticoagulant agents

Abstract: A series of 1,3,4-oxadiazoles were designed and subjected to molecular docking simulation onto the enzymes vitamin K epoxide reductase (PDB: 3KP9) and factor Xa (PDB: 1NFY) to visualize their binding affinity towards the said target proteins.

Cited by 7 publications

References 20 publications

Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids

Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids

Pharmacokinetic evaluation, molecular docking and in vitro biological evaluation of 1, 3, 4-oxadiazole derivatives as potent antioxidants and STAT3 inhibitors

Oxadiazole: A highly versatile scaffold in drug discovery

Contact Info

Product

Resources

About