Synthesis and Antioxidant Activity of a Variety of Sulfonamidomethane Linked 1,3,4-Oxadiazoles and Thiadiazoles

Swapna, M.; Reddy, S.; Padmaja, A.; Padmavathi, V.

doi:10.1248/cpb.c12-00997

Cited by 8 publications

(3 citation statements)

References 21 publications

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“…[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

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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.

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Section: Introductionmentioning

confidence: 99%

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

et al. 2017

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“…Derivatives of 1,3,4-thiadiazole represent a relatively new class of compounds that demonstrate a broad array of biological activities, making them of significant interest to various fields in medicinal chemistry and pharmacology worldwide (Gowramma et al, 2018;Kaviarasan et al, 2020;Upadhyay & Mishra, 2017;Yusuf et al, 2008). 1,3,4-Thiadiazole derivatives exhibit many biological properties, such as antimicrobial (Li et al, 2014;Chen et al, 2019), antituberculosis (Foroumadi et al, 2004;Kolavi et al, 2006), antioxidant (Jakovljevic ´et al, 2017;Swapna et al, 2013), anticancer (Altıntop et al, 2018;Aliabadi, 2016), herbicidal (Wang et al, 2011) and antifungal (Chen et al, 2007;Karaburun et al, 2018) activities. In addition, a limited number of studies mention the utilization of diverse thiadiazoles as ligands in the synthesis of biologically active metal complexes (Huxel et al, 2015;Chandra et al, 2015;Hangan et al, 2015).…”

Section: Chemical Contextmentioning

confidence: 99%

Synthesis, crystal structure and Hirshfeld surface analysis of bromidotetrakis[5-(prop-2-en-1-ylsulfanyl)-1,3,4-thiadiazol-2-amine-κN ³]copper(II) bromide

Atashov,

Azamova,

Ziyatov

et al. 2024

Acta Cryst E

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A novel cationic complex, bromidotetrakis[5-(prop-2-en-1-ylsulfanyl)-1,3,4-thiadiazol-2-amine-κN 3]copper(II) bromide, [CuBr](C5H7N3S2)4Br, was synthesized. The complex crystallizes with fourfold molecular symmetry in the tetragonal space group P4/n. The CuII atom exhibits a square-pyramidal coordination geometry. The Cu atom is located centrally within the complex, being coordinated by four nitrogen atoms from four AAT molecules, while a bromine anion is located at the apex of the pyramid. The amino H atoms of AAT interact with bromine from the inner and outer spheres, forming a two-dimensional network in the [100] and [010] directions. Hirshfeld surface analysis reveals that 33.7% of the intermolecular interactions are from H...H contacts, 21.2% are from S...H/H...S contacts, 13.4% are from S...S contacts and 11.0% are from C...H/H...C, while other contributions are from Br...H/H...Br and N...H/H...N contacts.

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“…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

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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.

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Synthesis and Antioxidant Activity of a Variety of Sulfonamidomethane Linked 1,3,4-Oxadiazoles and Thiadiazoles

Abstract: A variety of sulfonamidomethane linked 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were prepared and tested for antioxidant activity. The methyl substituted arylsulfonylaminomethyl-1,3,4-oxadiazole 9b showed excellent antioxidant activity.

Cited by 8 publications

References 21 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

Synthesis, crystal structure and Hirshfeld surface analysis of bromidotetrakis[5-(prop-2-en-1-ylsulfanyl)-1,3,4-thiadiazol-2-amine-κN ³]copper(II) bromide

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

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Synthesis and Antioxidant Activity of a Variety of Sulfonamidomethane Linked 1,3,4-Oxadiazoles and Thiadiazoles

Abstract: A variety of sulfonamidomethane linked 1,3,4-oxadiazoles and 1,3,4-thiadiazoles were prepared and tested for antioxidant activity. The methyl substituted arylsulfonylaminomethyl-1,3,4-oxadiazole 9b showed excellent antioxidant activity.

Cited by 8 publications

References 21 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

Synthesis, crystal structure and Hirshfeld surface analysis of bromidotetrakis[5-(prop-2-en-1-ylsulfanyl)-1,3,4-thiadiazol-2-amine-κN 3]copper(II) bromide

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

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Synthesis, crystal structure and Hirshfeld surface analysis of bromidotetrakis[5-(prop-2-en-1-ylsulfanyl)-1,3,4-thiadiazol-2-amine-κN ³]copper(II) bromide