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RESEARCH ON CHEMICAL INTERMEDIATES · 2013 ·Vol. 40 ·期 4 ·1575-1581 · IF 0.88

Synthesis and biological evaluation of novel 2-(substituted isoxazol-4-yl)-5-arylamino-1,3,4-oxadiazoles

Liu Feng,Wang Meiyan,Teng Xinhuan,Zhang Peizhi,Jiang Lin

A series of 2-(5-methyl-3-(4-chloro/trifluoromethylphenyl)isoxazol-4-yl)-5-arylamino-1,3,4-oxadiazoles were synthesized from 4-chloro/trifluoromethyl benzaldehyde, ethyl acetoacetate, hydroxylamine hydrochloride, hydrazine hydrate, and aryl isocyanate by multi-step reactions. The structures of the target compounds were elucidated by IR, 1 H NMR, MS, and elemental analysis. All these compounds were tested for in vitro antifungal activities against Botrytis cinerea and Rhizoctonia cerealis by the mycelium growth rate method, and the results indicated that some compounds displayed high antifungal activity against Botrytis cinerea.

研究领域: 有机化学 · 植物病理学 · 药物化学
✓ 已验证 DOI 高影响因子
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Journal of Saudi Chemical Society · 2017 · IF 2.887

Antimicrobial activities of pyridinium-tailored pyrazoles bearing 1,3,4-oxadiazole scaffolds

Lei Zhou,Pei-Yi Wang,Jian Zhou,Wu-Bin Shao,He-Shu Fang,Zhi-Bing Wu,Song Yang

Herein, a series of pyridinium-tailored 5-trifluoromethylpyrazoles containing 1,3,4-oxadiazole moieties were constructed through coupling key pharmaceutical fragments of pyridinium, pyrazole, and 1,3,4-oxadiazole scaffolds in single molecular architecture. Antimicrobial results suggested that this kind of compounds exhibited significant activities against three types of pathogenic bacteria and six fungal strains in vitro . The minimal EC 50 values of designed compounds against Xanthomonas oryzae pv . oryzae , Ralstonia solanacearum , and Xanthomonas axonopodis pv . citri could reach to 0.467, 1.04, and 0.600   μg/mL, respectively, through tuning and optimizing N -substituents, bridging atom, and alkyl length of the tailor. Antifungal assays revealed that all title molecules possessed considerable activity against Botrytis cinerea with the minimal EC 50 value up to 2.71   μg/mL; and compounds I-8 , I-10 , I-12 , II-12 , and IV-12 showed the strongest growth suppression toward Rhizoctonia solani with EC 50 values ranging from 10.2 to 24.0   μg/mL. Given the above results, this kind of compounds could serve as new lead compounds in the research of antimicrobial chemotherapy.

研究领域: 药理学 · 微生物学 · 有机化学
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JOURNAL OF HETEROCYCLIC CHEMISTRY · 2022 ·Vol. 60 ·期 1 ·145-155 · IF 2.035

Structural design and insecticidal activity of 1,3,4-oxadiazole-ring containing pyridylpyrazole-4-carboxamides

Abdalla Khallaf,Ping Wang,Shuping Zhuo,Hongjun Zhu,Hui Liu

The insecticidal activity of 1,3,4-oxadiazole-ring containing pyridylpyrazole-4-carboxamides against diamondback ( Plutella xylostella ) and noctuid ( Spodoptera frugiperda ) moths were evaluated. Only substitutions on the 1,3,4-oxadiazole moiety dictated bioreactivity, with 8q2 m -CF 3 Ph being the most effective against Plutella xylostella, showing 80%–93% mortality at a concentration of 0.5–500 μg ml −1 while the others remained inactive or less active (highest mortality being 63%). The larvicidal activity against Spodoptera frugiperda was inferior compared with that of Plutella xylostella , with the highest mortality being 33%. A crystal of 8q5 was obtained and analyzed, revealing the effects of intramolecular H-bonds and intermolecular π  π interactions.

研究领域: 昆虫学 · 有机化学 · 农药科学
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ANALYTICAL AND BIOANALYTICAL CHEMISTRY · 2022 ·Vol. 415 ·期 18 ·4221-4232 · IF 4.478

Spectrally tunable humic acid–based carbon dots: a simple platform for metronidazole and ornidazole sensing in multiple real samples

He Ziguo,Liu Jiaxu,Zhang Cheng,Sun Yudie,Chen Qian,Zhang Jian,Liu Shengjun,Yue Caibo,Ye Mingfu,Zhang Kui

Humic acid–based carbon dots (HACDs) have excellent properties and are widely used in environmental detection, bioimaging, and optoelectronic materials. Herein, we investigated the structure–activity relationship between the morphology and optical properties of HACDs, and reported on a novel strategy for metronidazole (MNZ) and ornidazole (ONZ) sensing in multiple real samples. It was found that the average particle size decreased from 3.28 to 2.44 nm, optimal emission wavelength was blue-shifted from 500 to 440 nm, and the quantum yield (QY) improved from 5 to 23% with the temperature increasing from 110 to 400 °C. Under the oxidation of hydrogen peroxide (H 2 O 2 ) and potassium permanganate (KMnO 4 ), the UV–vis spectra of HACD aqueous solution showed time-dependent behavior, and the fluorescence emission of HACDs achieved spectrally tunable multi-color luminescence in the temporal dimension. The surface of HACDs contained a large number of hydroxyl (–OH) and carboxyl (–COOH) fluorophores, resulting in excellent pH sensing. Meanwhile, the synthesized HACDs revealed sensitive response to MNZ and ONZ with the limit of detection (LOD) of 60 nM and 50 nM in aqueous solutions, which had also been successfully applied in various actual samples such as lake water, honey, eggs, and milk with satisfactory results because of the inner filter effect (IFE). Our research is advantageous to enhance the potential applications of HACDs in advanced analytical systems. Graphical abstract

研究领域: 分析化学 · 环境科学 · 生物医学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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JOURNAL OF HAZARDOUS MATERIALS · 2022 · IF 14.224

Carbazole and polyhalogenated carbazoles in the marine environment around the Zhoushan Archipelago: Distribution characteristics, environmental behavior, and sources

Zhaochao Deng,Songtao Hu,Leiming Tang,Lingbo Jiang,Junyu He,Keyu Shen,Yongjiu Xu,Rijin Jiang,Tiejun Li,Chunlei Chen,Bairu Chen,Hanghai Zhou,Dongdong Zhang,Jiawang Chen,Chunfang Zhang

The distribution characteristics and drivers of carbazole (CZ) and polyhalogenated carbazoles are still poorly understood. In this study, 96 samples were collected around the Zhoushan Archipelago, and their distribution characteristics were assessed. The results showed that CZ, 36-CCZ, and 36-BCZ were the top three abundant congeners in most collected samples. The bioaccumulation analysis revealed that marine plants prefer to accumulate CZ and bromocarbazoles rather than chlorocarbazoles. Both the mean concentrations of total carbazole and its derivants (ΣCZDs), as well as individual congeners, are the highest in sediments around the berthing areas of cargo ships and oil tankers . Meanwhile, ΣCZDs of these sediments are significantly influenced by the geo-weighted displacement of ships ( r  = 0.61; p  < 0.05), indicating the ballast water from these ships as potential contributor for marine CZDs. Moreover, the accumulation of CZ in plankton, planktonic origin of sedimentary organic matter, and relationship between CZ and C/N ratio ( p  < 0.05) in sediments support the scenario that plankton absorbs and takes CZ into the sediments. These findings will promote the understanding of the sources, environmental behaviors, and fates of marine CZDs.

CAS / MDL: 2051-24-3
研究领域: 海洋生态学 · 环境科学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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LIQUID CRYSTALS · 2013 · IF 1.959

Synthesis and mesomorphic properties of 2-(4′-alkoxybiphenyl-4-yl)-1H-benzimidazole derivatives

Lina Zhang,Xinbing Chen,Fengqi Zhao,Xuezhong Fan,Pei Chen,Zhongwei An

Three series of 2-(4′-alkoxybiphenyl-4-yl)-1H-benzimidazole derivatives (nM-x), which possessed 5-nitrobenzimidazole (nM-N series), benzimidazole (nM-H series) or 5-methylbenzimidazole (nM-M series) units at the end of the molecule, were synthesised and characterised by infrared, 1H- and 13C-nuclear magnetic resonance spectra, electrospray ionisation-mass spectrometry and elemental analysis. Their phase transition behaviour was investigated by differential scanning calorimetry, polarising optical microscopy and X-ray diffraction. All the compounds exhibited enantiotropic smectic mesophases with wide temperature domains for a carbon number in the alkoxy chain from 6 to 16, where the mesophase ranges were 14–91°C and 17–99°C during heating and cooling processes for the nM-N compounds, 7–25°C and 8–49°C for the nM-H compounds and 48–81°C and 52–85°C for the nM-M compounds, respectively. The effect of the length of alkoxy chain on mesomorphic properties was discussed. The nM-N and nM-M exhibited a much wider mesophase range whether during heating or cooling process than the corresponding nM-H series, especially for the longer terminal chain (n > 8), which indicated that the substituent in the benzimidazole moiety was helpful in increasing the mesophase stability.

研究领域: 有机化学 · 材料科学
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Frontiers in Pharmacology · 2025 · IF 4.8

UPLC-MS/MS method for simultaneous determination of pyrantel, praziquantel, febantel, fenbendazole and oxfendazole in dog plasma and its application to a bioequivalence study

Fengyichi Zhang,Fanxi Guo,Xinyu Zhao,Chongyang Li,Junli Wang,Mengyun Wang,Ruixia Ma,Baochang Chen,Qiangqiang Miao,Yimeng Wang,Zihan Wang,Di Cao,Zugong Yu

A rapid, sensitive and reliable ultra–performance liquid chromatography–tandem mass spectrometry (UPLC–MS/MS) was developed and validated for the simultaneous quantitation of pyrantel (PYR), praziquantel (PRA), febantel (FBT) and its active metabolites, fenbendazole (FEN) and oxfendazole (OXF) in dog plasma. Fenbendazole–D3 (FEN–D3) was used as an internal standard (IS). The analytes and IS were prepared using simple protein precipitation (PP) combined with liquid–liquid extraction (LLE). Chromatographic analysis was performed on UPLC BEH C18 column using acetonitrile–0.1% formic acid in water for gradient elution. Detection was carried out in multiple reaction monitoring (MRM) mode under positive electrospray ionization. The standard curves were linear through the concentration range of 4–240 ng/mL for PYR and OXF, 15–900 ng/mL for PRA, 2–120 ng/mL for FBT and 10–600 ng/mL for FEN with all correlation coefficients >0.99. The intra–and inter–batch precision was 1.08%–14.26% and accuracy was from 90.66% to 110.28%. The mean extraction recoveries for the analytes and IS were >90%. The total run time was 9.0 min. The developed method was successfully applied to a bioequivalence study after oral administration of compound febantel tablets in 38 healthy dogs.

CAS / MDL: 1336-21-6
研究领域: 兽医学 · 分析化学
✓ 已验证 产品关联 DOI PubMed 高影响因子
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CHINESE CHEMICAL LETTERS · 2016 · IF 1.947

Synthesis and bioactivities of novel 2-(thioether/sulfone)-5-pyrazolyl-1,3,4-oxadiazole derivatives

Yu-Tao Zheng,Teng-Teng Zhang,Pei-Yi Wang,Zhi-Bing Wu,Lei Zhou,Yi-Qiang Ye,Xiang Zhou,Ming He,Song Yang

By introducing the pyrazole moiety into the 5-position of 1,3,4-oxadiazole, a series of novel 2-(thioether/sulfone)-5-pyrazolyl-1,3,4-oxadiazole derivatives were synthesized. Preliminary bioassays suggested that target compounds exhibited appreciable activity against pathogenic bacteria Xanthomonas oryzae pv. oryzae ( Xoo ) and five phytopathogenic fungi in vitro . Among them, the half-maximal effective concentration (EC 50 ) values of 6c , 7a , 7b and 7c against Xoo were within 16.6   μg/mL and 65.7   μg/mL, which were better than those of commercial agricultural antibacterial bismerthiazol (92.6   μg/mL) and thiodiazole copper (121.8   μg/mL). While compounds 7a , 7b , and 7c exerted comprehensive antifungal activity toward five plant fungi, which were comparable with that of hymexazol. The results demonstrated that this kind of compounds can be further studied and developed as promising antifungal and antibacterial agents.

研究领域: 农药化学 · 植物病理学
✓ 已验证 DOI 高影响因子
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Asian Journal of Organic Chemistry · 2018 ·Vol. 7 ·期 8 ·1626-1634 · IF 2.496

Palladium-Catalyzed C−H Benzylation of (Benzo)oxazoles with Benzylic Quaternary Ammonium Triflates

Wen-Jing Pan,Zhong-Xia Wang

Graphical Cut my bonds into pieces : The C−H benzylation of oxazoles and benzoxazoles with benzyl trimethylammonium triflates was performed under mild conditions via Pd-catalyzed C−H/C−N cleavage. The method exhibits a wide scope of substrates and good compatibility of functional groups. The C−H benzylation of oxazoles and benzoxazoles with benzylic ammonium triflates was performed in reasonable to good yields via Pd-catalyzed C−H/C−N cleavage. The method exhibits a wide scope of azoles and benzylic ammonium triflates. A range of functional groups including F, CF 3 , COOEt, C(O)NMe 2 , OMe, OPh, pyridyl and thienyl groups can be tolerated.

CAS / MDL: 23743-26-2
研究领域: 有机化学 · 药物化学
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MONATSHEFTE FUR CHEMIE · 2018 ·Vol. 149 ·期 10 ·1753-1758 · IF 1.285

Experimental and theoretical investigations of the optoelectronic properties of a 1,2,5-oxadiazolo-fused phenanthroline

Wei Ting,Zeng Yongming,Hong Liang,Zhang Hongxi,Wang Guozhen,Wang Shitao

Abstract A new phenanthroline derivative, [1,2,5]oxadiazolo[3′,4′:5,6]pyrazino[2,3- f ][1,10]phenanthroline was designed and synthesized. Its molecular structure was confirmed by single-crystal X-ray diffraction analysis. Its optoelectronic properties were systematically investigated by optical and electrochemical measurements. Thermogravimetric analysis revealed that the title compound is remarkably stable. Finally, DFT calculations further indicated that the phenanthroline derivative has potential applications in organic electronics. Graphical abstract

CAS / MDL: 75-09-2
研究领域: 有机化学 · 材料科学 · 物理化学
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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2021 · IF 5.279

Discovery of Novel Pyrazole Carboxylate Derivatives Containing Thiazole as Potential Fungicides

Dongguo Xia,Xiang Cheng,Xiaohang Liu,Chengqi Zhang,Yunxiao Wang,Qiaoyun Liu,Qi Zeng,Niqian Huang,Yao Cheng,Xianhai Lv

Inspired by commercially established fluxapyroxad as the lead compound of novel efficient antifungal ingredients, novel pyrazole carboxylate derivatives containing a flexible thiazole backbone were successfully designed, synthesized, and detected for their in vitro and in vivo biological activities against eight agricultural fungi. The antifungal bioassay results showed that compound 24 revealed excellent bioactivities against Botrytis cinerea and Sclerotinia sclerotiorum, with median effective concentrations (EC50) of 0.40 and 3.54 mg/L, respectively. Compound 15 revealed remarkable antifungal activity against Valsa mali, with an EC50 value of 0.32 mg/L. For in vivo fungicide control against B. cinerea and V. mali, compounds 3 and 24 at 25 mg/L, respectively, displayed prominent efficacy on cherry tomatoes and apple branches. Molecular docking results demonstrated that compound 15 could form an interaction with several crucial residues of succinate dehydrogenase (SDH), and the in vitro enzyme assay indicated that the target compound 15 displayed an inhibitory effect toward SDH, with an IC50 value of 82.26 μM. The experimental results indicated that phenyl pyrazole carboxylate derivatives displayed a weak antifungal property and low activity compared to the other title substituent pyrazole carboxylate derivatives. Compounds 3, 15, and 24 are promising antifungal candidates worthy of further fungicide development due to their prominent effectiveness.

研究领域: 植物保护学 · 药物化学 · 农业科学
✓ 已验证 DOI PubMed 高影响因子
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CHINESE CHEMICAL LETTERS · 2013 · IF 1.21

Synthesis, fluorescence properties and selective Cr(III) recognition of tetraaryl imidazole derivatives bearing thiazole group

Bing Zhao,Ya-Cui Zhou,Meng-Jiao Fan,Zhi-Yu Li,Li-Yan Wang,Qi-Gang Deng

Three tetraaryl imidazole derivatives 5a–5c bearing thiazole groups were synthesized in the presence of [Bmin]Br by one-pot reaction and their structures were fully characterized by the 1 H NMR, IR, MS and elemental analysis. The results of UV–vis spectra and fluorescent spectra upon metal ions complexation show that compound 5a displays high selectivity and sensitivity for Cr 3+ ions. The complexation ratio of compound 5a and Cr 3+ is 1:1.

研究领域: 有机化学 · 分析化学
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