• Title/Summary/Keyword: triazole

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Synthesis of Novel D-Glucose-derived Benzyl and Alkyl 1,2,3-Triazoles as Potential Antifungal and Antibacterial Agents

  • Wei, Jin-Jian;Jin, Lei;Wan, Kun;Zhou, Cheng-He
    • Bulletin of the Korean Chemical Society
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    • v.32 no.1
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    • pp.229-238
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    • 2011
  • A series of novel glucose derived benzyl and alkyl 1,2,3-triazoles and their hydrochlorides have been synthesized via Cu(I)-catalyzed 1,3-dipolar cycloaddition. All the new compounds were characterized by MS, IR and NMR spectra. The DEPT, APT, $^1H$-$^1H$ and $^1H-^{13}C$ 2D NMR spectra for some compounds were also recorded. These compounds were evaluated for their in vitro antibacterial activities against Staphylococcus aureus ATCC 29213, Bacillus subtilis, Bacillus proteus, Pseudomonas aeruginosa, Escherichia coli ATCC 25922, and antifungal activities against Candida albicans and Aspergillus fumigatus. The bioactive data revealed that (3R,4S,5S,6S)-2-(hydroxymethyl)-6-methoxy-4,5-bis((1-octyl-1H-1,2,3-triazol-4-yl)methoxy)-tetrahydro-2H-pyran-3-ol 8a exhibited excellent antifungal activity against A. fumigatus with an MIC value of 0.055 mM compared to Fluconazole. It also showed broad inhibitory efficacy against tested bacterial strains with MIC values ranging from 0.049 mM to 0.39 mM.

Mechanism Studies of Substituted Triazol-1-yl-pyrimidine Derivatives Inhibition on Mycobacterium tuberculosis Acetohydroxyacid Synthase

  • Chien, Pham Ngoc;Jung, In-Pil;Reddy, Katta Venugopal;Yoon, Moon-Young
    • Bulletin of the Korean Chemical Society
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    • v.33 no.12
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    • pp.4074-4078
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    • 2012
  • The first step in the common pathway for the biosynthesis of branched chain amino acids is catalyzed by acetohydroxyacid synthase (AHAS). The AHAS is found in plants, fungi and bacteria. With an aim to identify new anti-tuberculosis drugs that inhibit branched chain amino acid biosynthesis, we screened a chemical library against Mycobacterium tuberculosis AHAS. The screening identified four compounds, AVS 2087, AVS 2093, AVS 2236, and AVS 2387 with $IC_{50}$ values of 0.28, 0.21, 3.88, and $0.25{\mu}M$, respectively. Moreover, these four compounds also showed strong inhibition against reconstituted AHAS with $IC_{50}$ values of 0.37, 0.26, 1.0, and $1.18{\mu}M$, respectively. The basic scaffold of the AVS group consists of 1-pyrimidin-2-yl-1H-[1,2,4]-triazole-3-sulfonamide. The most active compound, AVS 2387, showed the lowest total interaction energy -8.75 Kcal/mol and illustrates its binding mode by hydrogen bonding with $H_{\varepsilon}$ of Gln517 with the distance of $2.24{\AA}$.

Synthesis of Azole-containing Piperazine Derivatives and Evaluation of their Antibacterial, Antifungal and Cytotoxic Activities

  • Gan, Lin-Ling;Fang, Bo;Zhou, Cheng-He
    • Bulletin of the Korean Chemical Society
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    • v.31 no.12
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    • pp.3684-3692
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    • 2010
  • A series of azole-containing piperazine derivatives have been designed and synthesized. The obtained compounds were investigated in vitro for their antibacterial, antifungal and cytotoxic activities. The preliminary results showed that most compounds exhibited moderate to significant antibacterial and antifungal activities in vitro. 1-(4-((4-chlorophenyl) (phenyl)methyl)piperazin-1-yl)-2-(1H-imidazol-1-yl)ethanone and 1-(4-((4-Chlorophenyl)(phenyl)methyl)piperazin-1-yl)-2-(2-phenyl-1H-imidazol-1-yl)ethanone gave remarkable and broad-spectrum antimicrobial efficacy against all tested strains with MIC values ranging from 3.1 to $25\;{\mu}g/mL$, and exhibited comparable activities to the standard drugs chloramphenicol and fluconazole in clinic. Moreover, 2-((4-((4-chlorophenyl)(phenyl)methyl)piperazin-1-yl)methyl)-1H-benzo[d]imidazole was found to be the most effective in vitro against the PC-3 cell line, reaching growth inhibition values (36.4, 60.1 and 76.5%) for each tested concentration: $25\;{\mu}g/mL$, $50\;{\mu}g/mL$ and $100\;{\mu}g/mL$ in dose-dependent manner. The results also showed that the azole ring had noticeable effect on their antimicrobial and cytotoxic activities, and imidazole and benzimidazole moiety were much more favourable to biological activity than 1,2,4-triazole.

Synthesis and Pharmacological Evaluation of Some Novel 2-Mercapto Benzimidazole Derivatives

  • Nevade, Sidram A.;Lokapure, Sachin G.;Kalyane, Navanath V.
    • Journal of the Korean Chemical Society
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    • v.57 no.6
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    • pp.755-760
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    • 2013
  • The present study is synthesis of derivatives of N'-(4-amino-5-sulfanyl-4H-1,2,4-triazole-3-yl)-2-(1H-benzimidazole-2-ylsulfanyl) acetohydrazide (IV). Antibacterial activity tested against the E. coli and A. Substilis. Biological activities conducted by disc diffusion method. Compound $2MB_1$, $2MB_3$, $2MB_5$ inhibit the appreciable microbial growth while rest of the compound possess the moderate activities. Anti-inflammatory activity tested by reduces local edema induced in the rat paw by injection of phlogestic agent. Compound $2MB_1$, $2MB_8$, $2MB_5$, $2MB_3$ and $2MB_6$ exhibit satisfying anti-inflammatory activity while analgesic activity conducted by acetic acid induced writhing effect in mice while compound $2MB_1$, $2MB_4$ and $2MB_7$ having the good analgesic activity. The chemical structures of all newly synthesized compounds were confirmed by their IR, $^1H$ NMR and mass spectral data.

Inhibitory Effects of Allicin on TNF-${\alpha}$-induced ICAM-1 Expression is Associated with Catalase

  • Kang, Nam-Sung;Pyo, Suhk-Neung;Sohn, Eun-Hwa
    • Korean Journal of Plant Resources
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    • v.22 no.6
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    • pp.552-557
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    • 2009
  • Allicin, a garlic componente, is believed to provide protection against various diseases including inflammation. Since interactions of the cell adhesion molecules are known to play important roles in mediating inflammation, inhibiting adhesion protein upregulation is a possible therapeutic target. In this study, we demonstrate that TNF-${\alpha}$- and catalase-induced expression of ICAM-1 on human lung epithelial cells (A549) in a dose-dependent manner and catalase expression and activity were also increased in TNF-${\alpha}$-treated cells. Treatment of the TNF-${\alpha}$-treated cells with catalase inhibitor 3-amino-1,2,4-triazole resulted in a significant decreased the level of ICAM-1. These data suggest that induction of ICAM-1 expression by TNF-${\alpha}$ is associated with catalase. In addition, allicin was found to inhibit the TNF-${\alpha}$ induced expression of ICAM-1 on the A549 cells. This compound also inhibited the production of catalase induced by TNF-${\alpha}$, which suggests that the inhibition of ICAM-1 expression by allicin may be due to the modulated production of catalase.

Purification and characterization of catalase-3 of deinococcus radiophilus

  • Lee, In-Jeong;Lee, young-Nam
    • Journal of Microbiology
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    • v.33 no.3
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    • pp.239-243
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    • 1995
  • Deinococcus radiophilus, an UV resistant bacterium seemed to contain three issoenzymes of catalase. Among them, the samllest and most abundant species in cell-free extract, catalase-3 which also exhibited peroxidase activity was purified to electrophoretic homogeneity (145-fold purification) by chromatographic procedures. Its molecular weight was 155 kDa composed of four 38 kDa subunits. The $K_{m}$ value of catalase-3 for H$\_$2/O$\_$2/ was approximately 0.5 mM. This enzyme showed a typical ferric heme spectrum with maximum absorption at 405 nm. Upon binding to cyanide, the 405 nm peak shifted to 420 nm. Catalase-3 was very sensitive to inhibitors of heme proteins, such as cyanide, azide and hydroxylamine. A ratio of A$\_$405/A$\_$28O/ was 0.5 Catalase-3 was active over a wide range of pH, between pH 7 and 10. The enzyme was rather heat-labile and partially sensitive to edthanol-chloroform treatment, but resistant to 3-amino-1, 2, 4-triazole. Catalase-3 of D. radiophilus, which is a bifunction catalatic peroxidatic enzyme seemed to share certain molecular properties with the typical catalase and the catalase-[roxidase along with its own unique features.

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Influence of Inhibitors on the Corrosion of Al and Al-composites in Chloride-containing Solutions - A Review

  • Kumar, Neeraj;Srivastava, Ashok K.;Gautam, Prabhat;Manoj, M.K.
    • Korean Journal of Materials Research
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    • v.32 no.5
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    • pp.280-286
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    • 2022
  • Corrosion is a natural, inevitable process, and is one of the world's most serious problems. Losses incurred due to corrosion are extremely expensive for society. Several technological strategies have been explored and implemented to address these losses. The use of inhibitors to prevent corrosion is a common and efficient method to reduce corrosion losses. This review covers Al and Al-composite corrosion inhibitors in chloride-containing solutions, because of their popularity in a broad array of industrial applications. A vast number of studies in the literature detail the common tendency of Al and Al-composites with reinforcements to deteriorate. Accordingly, it is worthwhile to employ inhibitors to protect them, as discussed in the present work. The emphasis is on selecting the smartest corrosion inhibitor and evaluating its performance. According to the study, the most commonly used corrosion inhibitors are 1,4-naphthoquinone (NQ), 1,5-naphthalene diol, 3-amino-1,2,4-triazole-5-thiol (ATAT), ammonium tetrathiotungstate, clotrimazole, amoxicillin, antimicrobial and antifungal drugs. Electrochemical impedance spectroscopy (EIS), potentiodynamic (PDP), and weight loss were among the most commonly used modern electrochemical technologies to test inhibitors' efficacy under environmental conditions.

Investigation on the Effect of Corrosion Inhibitor on Removal Rate and Surface Characteristic of Cobalt Chemical Mechanical Polishing (부식 방지제에 따른 코발트의 화학 기계적 연마 특성 및 표면 분석)

  • Eun Su Jung;Sung Gyu Pyo
    • Journal of the Korean institute of surface engineering
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    • v.57 no.3
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    • pp.140-154
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    • 2024
  • As the trend towards miniaturization in semiconductor integration process, the limitations of interconnection metals such as copper, tungsten have become apparent, prompting research into the emergence of new materials like cobalt and emphasizing the importance of studying the corresponding process conditions. During the chemical mechanical polishing (CMP) process, corrosion inhibitors are added to the slurry, forming passivation layers on the cobalt surface, thereby playing a crucial role in controlling the dissolution rate of the metal surface, enhancing both removal rate and selectivity. This review investigates the understanding of the cobalt polishing process and examines the characteristics and behavior of corrosion inhibitors, a type of slurry additive, on the cobalt surface. Among the corrosion inhibitors examined, benzotriazole (BTA), 1,2,4-triazole (TAZ), and potassium oleate (PO) all improved surface characteristics through their interaction with cobalt. These findings provide important guidelines for selecting corrosion inhibitors to optimize CMP processes for cobalt-based semiconductor materials. Future research should explore combinations of various corrosion inhibitors and the development of new compounds to further enhance the efficiency of semiconductor processes.

Conventional and Inverted Photovoltaic Cells Fabricated Using New Conjugated Polymer Comprising Fluorinated Benzotriazole and Benzodithiophene Derivative

  • Kim, Ji-Hoon;Song, Chang Eun;Kang, In-Nam;Shin, Won Suk;Zhang, Zhi-Guo;Li, Yongfang;Hwang, Do-Hoon
    • Bulletin of the Korean Chemical Society
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    • v.35 no.5
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    • pp.1356-1364
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    • 2014
  • A new conjugated copolymer, poly{4,8-bis(triisopropylsilylethynyl)benzo[1,2-b:4,5-b']dithiophene-alt-4,7- bis(5-thiophen-2-yl)-5,6-difluoro-2-(heptadecan-9-yl)-2H-benzo[d][1,2,3]triazole} (PTIPSBDT-DFDTBTz), is synthesized by Stille coupling polycondensation. The synthesized polymer has a band gap energy of 1.9 eV, and it absorbs light in the range 300-610 nm. The hole mobility of a solution-processed organic thin-film transistor fabricated using PTIPSBDT-DFDTBTz is $3.8{\times}10^{-3}cm^2V^{-1}s^{-1}$. Bulk heterojunction photovoltaic cells are fabricated, with a conventional device structure of ITO/PEDOT:PSS/polymer:$PC_{71}BM$/Ca/Al ($PC_{71}BM$ = [6,6]-phenyl-$C_{71}$-butyric acid methyl ester); the device shows a power conversion efficiency (PCE) of 2.86% with an open-circuit voltage ($V_{oc}$) of 0.85 V, a short-circuit current density ($J_{sc}$) of 7.60 mA $cm^{-2}$, and a fill factor (FF) of 0.44. Inverted photovoltaic cells with the structure ITO/ethoxylated polyethlyenimine/ polymer:$PC_{71}BM/MoO_3$/Ag are also fabricated; the device exhibits a maximum PCE of 2.92%, with a $V_{oc}$ of 0.89 V, a $J_{sc}$ of 6.81 mA $cm^{-2}$, and an FF of 0.48.

Toxic Effects of Triazole Fungicide Difenoconazole on the Early Development of African Clawed Frog, Xenopus laevis (Triazole계 농약 Difenoconazole이 Xenopus laevis의 초기 배 발생에 미치는 독성 영향)

  • Lee, You-Hwa;Yoon, Chun-Sik;Lee, Mi-Ju;Hwang, Yong-Gi;Cheong, Seon-Woo
    • Journal of Environmental Science International
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    • v.20 no.10
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    • pp.1221-1232
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    • 2011
  • We investigated the toxic effects of difenoconazole on the development in the African clawed frog, Xenopus laevis. To test the toxic effects, frog embryo teratogenesis assays using Xenopus were performed. Embryos were exposed to various concentrations of difenoconazole (0-30 ${\mu}M$). $LC_{100}$ for difenoconazole was 30 ${\mu}M$, and the $LC_{50}$ determined by probit analysis was 27.19 ${\mu}M$. Exposure to difenoconazole concentrations ${\geq}$5 ${\mu}M$ resulted in 10 different types of severe external malformation. Histological examinations revealed dysplasia of the eye, heart, liver, somatic muscle, and swelling of the pronephric ducts. The tissue-specific toxic effects were investigated with an animal cap assay. Blood cells were normally induced at a high frequency by mSCF and activin A. However, the induction of blood cells was strongly inhibited by the addition of difenoconazole. Electron micrographs of tested embryos showed the degeneration of somatic muscle and the shrinkage of microvilli on pronephric duct. The gene expression of cultivated animal cap explants was investigated by reverse transcriptase-polymerase chain reaction (RT-PCR). It revealed that the expression of the blood-specific marker(${\beta}$-globin II) and muscle-specific marker (XMA) were more strongly inhibited than the neural-specific marker(XEn2) by the addition of difenoconazole.