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

Nevena Mihailovi?; Violeta Markovi?; Ivana Z. Mati?; Nemanja S. Stanisavljevi?; ?ivko S. Jovanovi?; Sne?ana Trifunovi?; Ljubinka Joksovi?

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

机译：酚酸衍生的1,3,4-恶二唑及其二酰基肼前体的合成及抗氧化活性

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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 H₂O₂ 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.

机译：合成了八种含酚酸部分（7a–h）的1,3,4-恶二唑衍生物和八种其二酰基肼前体（6a–h），使用分光光度法进行了表征，并通过清除稳定的DPPH（2,2-二苯基- 1-picllhydrazyl）自由基。与它们相应的二酰基肼前体相比，最有效的酚类1,3,4-恶二唑表现出更好的DPPH清除活性，这是由于芳环和1,3,4-恶二唑部分均参与了形成的苯氧基自由基的共振稳定化。选择了四种具有最佳DPPH清除能力的二酰基肼（6d，6e，6g和6h）和四种1,3,4-恶二唑（7d，7e，7g和7h），用于通过各种测定进一步评估其抗氧化能力。所研究的化合物具有明显的ABTS自由基清除能力，中等至良好的H _{2 O _{2 清除性能和强铁离子还原能力。对大多数活性化合物的抗氧化性能的进一步体外评估表明，它们在正常肺成纤维细胞MRC-5中具有抗过氧化氢诱导的氧化应激的保护作用。与对照样品相比，二酰基肼6h将处理过的细胞中的谷胱甘肽过氧化物酶的活性提高了两倍，并且不影响超氧化物歧化酶的活性。}} 展开▼

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《RSC Advances》 |2017年第14期|共11页

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Nevena Mihailovi?; Violeta Markovi?; Ivana Z. Mati?; Nemanja S. Stanisavljevi?; ?ivko S. Jovanovi?; Sne?ana Trifunovi?; Ljubinka Joksovi?;
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1. Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids [J] . Nevena Mihailovi?, Violeta Markovi?, Ivana Z. Mati?, RSC Advances . 2017,第14期

机译：酚酸衍生的1,3,4-恶二唑及其二酰基肼前体的合成及抗氧化活性

2. A convenient synthesis of 1,3,4-thiadiazole and 1,3,4-oxadiazole based peptidomimetics employing diacylhydrazines derived from amino acids [J] . G. Nagendra, Ravi S. Lamani, N. Narendra Tetrahedron letters: The International Journal for the Rapid Publication of Preliminary Communications in Organic Chemistry . 2010,第48期

机译：使用衍生自氨基酸的二酰基肼方便地合成1,3,4-噻二唑和1,3,4-恶二唑类拟肽

3. Synthesis, antioxidant and antiproliferative activities of 1,3,4-thiadiazoles derived from phenolic acids [J] . Katarina Jakovljevi?, Ivana Z. Mati?, Tatjana Stanojkovi?, Bioorganic and Medicinal Chemistry Letters . 2017,第16期

机译：酚酸衍生1,3,4-噻二唑的合成，抗氧化剂和抗增殖活性

4. Synthesis, characterization of some new l,3-oxazine-4-one derivatives containing 1,3,4-oxadiazole and 1,3,4-thiadiazole moiety with screening some of their biological activity. [C] . Raneen Hashim Rida, Maysoon Tariq Tawfiq International Scientific Conference on Pure Sciences, Brilliant Creativity and Renewed Building . 2019

机译：合成，表征一些含有1,3,4-二唑和1,3,4-噻二唑部分的一些新的L，3-氧嗪-4-一种衍生物，其具有筛选其一些生物活性。

5. Part I: 1,3,4-oxadiazoles in tandem Diels-Alder, 1,3-dipolar cycloaddition reactions: A rapid synthesis of vinca alkaloid motifs. Part II: Exceptionally potent inhibitors of fatty acid amide hydrolase [D] . Wilkie, Gordon David 2002

机译：第一部分：串联Diels-Alder中的1,3,4-恶二唑，1,3-偶极环加成反应：长春花生物碱基序的快速合成。第二部分：脂肪酸酰胺水解酶的超强抑制剂

6. Dynamic Changes of Ascorbic Acid Phenolics Biosynthesis and Antioxidant Activities in Mung Beans (Vigna radiata) until Maturation [O] . Yanyan Lu, Xiaoxiao Chang, Xinbo Guo 2019

机译：直至成熟的绿豆中抗坏血酸酚类生物合成和抗氧化活性的动态变化

7. Synthesis and antioxidant activity of 1,3,4-oxadiazoles and their diacylhydrazine precursors derived from phenolic acids [O] . Nevena Mihailović, Violeta Marković, Ivana Z. Matić, 2017

机译：1,3,4-二唑的合成和抗氧化活性及其衍生自酚酸的二酰肼前体

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2. 1—取代酰基—4—磷酰基氨基硫脲及其1,3,4—恶二唑杂环衍生物的合成 [J] . 卢水明 ,陈茹玉 . 有机化学 . 1999,第004期

3. 2-取代苯氧乙硫基-5-吡唑基-1,3,4-恶二唑和1,ω-二(5-吡唑基-1,3,4-恶二唑-2-硫代)烷烃的合成及生物活性 [J] . 陈寒松 ,李正名 ,王忠文 . 合成化学 . 1999,第002期

4. 2,5—二取代—1,3—4—恶二唑和N,N‘—二酰基肼化合物的合成与生物活性 [J] . 张荣 ,钱旭红 . 应用化学 . 1996,第005期

5. 2,5—二取代基—1,3,4—恶二唑及恶二唑啉类化合物的合成 [J] . 刘方明 ,陈耀祖 . 有机化学 . 1999,第003期

6. 含5-甲基异恶唑基的氨基硫脲,1,3,4-噻二唑,1,3,3-恶二唑及1,2,4-三唑衍生物的合成及抗菌活性研究 [C] . 张林梅 ,惠新平 ,许鹏飞 . 第八届全国有机合成学术会议 . 2000

7. 串联环化反应合成2--酰基苯并噻唑衍生物和1,3,4--恶二唑衍生物的研究 [A] . 张珊珊 . 2021

1. 由二氧化碳、芳香肼与多聚甲醛电合成1,3,4-噁二唑-2(3H)-酮衍生物的方法 [P] . 中国专利： CN106245053B . 2018.06.22

2. 由二氧化碳、芳香肼与多聚甲醛电合成1,3,4‑噁二唑‑2(3H)‑酮衍生物的方法 [P] . 中国专利： CN106245053A . 2016-12-21

3. 2,5-DIARYL-1,3,4-OXADIAZOLE HYDROXY ACIDS AND ACETOXY ACIDS,¹PROCESS FOR THEIR SYNTHESIS [P] . 外国专利： IE920319A1 . 1992-07-29

机译：2,5-DIARYL-1,3,4-恶二唑羟基酸和乙醛，¹合成方法

4. The 4-nitro have herbicidal activity - substituted N- ( tetrazol-5-yl ) aryl carboxylic acid amides , 4-nitro - substituted N- ( triazol -5-yl ) aryl carboxylic acid amides and 4-nitro - N -substituted - ( 1,3,4-oxadiazole -2-yl ) aryl carboxylic acid amides [P] . 外国专利： JP2015508769A . 2015-03-23

机译：4-硝基具有除草活性-取代的N-（四唑-5-基）芳基羧酸酰胺，4-硝基取代的N-（三唑-5-基）芳基羧酸酰胺和4-硝基-N取代的- （1,3,4-恶二唑-2-基）芳基羧酸酰胺

5. 2,5-DIARYL-1,3,4-OXADIAZOLE HYDROXYESTER, HYDROXYACID AND ACETOXYACID AND SYNTHESIS THEREOF [P] . 外国专利： JPH06107615A . 1994-04-19

机译：2,5-二芳基-1,3,4-氧杂唑羟基酯，羟基乙酸和乙酰氧基乙酸及其合成

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

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