- A novel 1,2,3-benzotriazolium based ionic liquid monomer for preparation of MMT/poly ionic liquid (PIL) pH-sensitive positive charge nanocomposites
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Abstract : In this work, a new ionic liquid (IL) with two acidic and vinylic functional groups based on 1,2,3-benzotriazolium cation was synthesized. This IL monomer was intercalated into the montmorillonite (MMT) layers by the ion exchange reaction and subsequently copolymerized with the IL monomer and methacrylic acid in order to obtain positive charge pH-sensitive nanocomposites. The structure of the IL monomer was characterized by FT-IR and 1H -NMR spectroscopy, and the structure of the nanocomposites was studied and confirmed by the FT-IR, XRD, TGA, SEM, and EDX data. These pH-sensitive nanocarriers were used to load and in vitro release of the anticancer drug, methotrexate (MTX) in pH?= 4 and pH?= 7.4. The results showed that the release is pH dependent and more effective in acidic pH; therefore, these nanocarriers have potential to be used for cancer therapy. Graphical abstract : SYNOPSIS Synthesis and characterization of a new dual functional ionic liquid monomer and use of it to prepare positive charge pH-sensitive nanocomposites for anti-cancer drug delivery application. Results showed that use of only this monomer in the structure of nanocomposite is more effective to the delivery of negatively charged drugs. [Figure not available: see fulltext.].
- Jahed, Fatemeh Soghra,Galehassadi, Mohammad,Davaran, Soodabeh
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- Cycloaddition reactions of N-benzotriazolylketene as a heteroarylketene: A practical approach to the synthesis of novel azetidinones
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A series of novel functionalized azetidinones containing the benzotriazole moiety were synthesized stereoselectively by a ?reaction of benzotriazolylacetic acid, aromatic amines, and ?Mukaiyama's reagent in the presence of triethylamine in dichloromethane at ambient temperature. This transformation generates a four-membered lactam and presumably proceeds via in situ generation of benzotriazolylketene as a heteroarylketene. In contrast to the products obtained from the reaction of pyrrolylketene with imines in which cis-azetidinones were formed as major products, the generated benzotriazolylyketene reacted with imines forming the trans-lactams as major products. Georg Thieme Verlag Stuttgart New York.
- Zigheimat, Fatemeh,Islami, Mohammad Reza,Nourmohammadian, Farahnaz
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- Visible-Light-Promoted Site-Selective N1-Alkylation of Benzotriazoles with α-Diazoacetates
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A visible-light-promoted highly site-selective N1-alkylation of benzotriazoles with diazo compounds has been achieved under mild and metal-free conditions. Using cheap, readily available p-benzoquinone (PBQ) as a catalyst, a wide range of benzotriazoles and diazo compounds are reacted, providing N1-alkylated benzotriazoles in moderate to excellent yields with excellent N1-selectivities. Preliminary mechanistic studies suggest that a radical process accounts for the exclusive site-selectivity of this transformation.
- Duan, Jiaokui,Ma, Ben,Wang, Ganggang,Wu, Chengqi,Xiao, Jianliang,Yang, Jingya,Zhou, Hongyan
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- Enhanced proton conductivity of Nafion-azolebisphosphonate membranes for PEM fuel cells
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Fuel cells are among the cleaner alternatives of sustainable energy technologies, where their proton exchange membranes continue to be a key component with many challenges and opportunities ahead. In this study, different indazole-and benzotriazolebisphosphonic acids were prepared and incorporated into new Nafion-doped membranes up to a 5 wt% loading. The new membranes were characterised, and their proton conductivities were evaluated using electrochemical impedance spectroscopy. Membranes with a 1 wt% loading showed better proton conductivities than Nafion N-115 at all temperature and under relative humidity conditions studied. In these conditions, the best value was observed for the membrane doped with [hydroxy(1H-indazol-3-yl)methanediyl]bis(phosphonic acid) (BP2), with a proton conductivity of 98 mS cm-1. Activation energy (Ea) values suggests that both Grotthuss and vehicular mechanisms are involved in the proton conduction across the membrane.
- Teixeira, Fátima C.,De Sá, Ana I.,Teixeira, António P. S.,Rangel
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- Fundamental structure-activity relationships associated with a new structural class of respiratory syncytial virus inhibitor
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Structure-activity relationships surrounding the dialkylamino side chain of a series of benzotriazole-derived inhibitors of respiratory syncytial virus fusion based on the screening lead 1a were examined. The results indicate that the topology of the side chain is important but the terminus element offers considerable latitude to modulate physical properties.
- Yu, Kuo-Long,Zhang, Yi,Civiello, Rita L.,Kadow, Kathleen F.,Cianci, Christopher,Krystal, Mark,Meanwell, Nicholas A.
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- Water-soluble benzo triazole imidazoline extreme pressure anti-wear agent and its preparation method
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The invention relates to a synthetic process of a benzotriazole derivative containing an imidazole group. By taking benzotriazole as a raw material, the synthetic process comprises the steps of reacting benzotriazole with chloroacetic acid to obtain benzotriazole acetic acid; and sequentially reacting benzotriazole acetic acid with diethylenetriamine, N-hydroxy ethanediamine, ethanediamine, triethylene tetramine and tetraethylenepentamine, wherein dimethylbenzene or toluene is used as a water carrying agent, the molar ratio of benzotriazole acetic acid to the amine including diethylenetriamine and N-hydroxy ethanediamine is 1 to 1.1, the reaction temperatures are 130-160 DEG C and 180-220 DEG C, and the reaction time is about 4 hours and about 2 hours. The synthetic process is simple to operate and high in yield, and reaction conditions are easy to control. The product, namely the benzotriazole imidazoline derivative, can be applied to water-based lubricating liquid, a copper corrosion inhibitor, an anti-rust agent and the like.
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Paragraph 0009; 0020-0022
(2019/07/04)
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- Benzotriazole imidazoline derivative, and preparation method and application thereof
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The invention discloses an imidazoline group-containing benzotriazole derivative, and a synthesis process and application thereof. The synthesis process comprises the following steps: taking benzotriazole as a raw material, and reacting with sodium monochloroacetate/ethyl chloroacetate/ethyl bromoacetate (wherein the reacting yield of the sodium monochloroacetate is highest) to form benzotriazole acetic acid, and performing dehydration and cyclization reaction with diethylenetriamine/triethylenetetramine/tetraethylenepentamine to generate the benzotriazole imidazoline derivative. The reaction conditions are easy to control; and the yield is high. The benzotriazole imidazoline derivative has a good corrosion inhibiting effect on YG8 hard alloy and Q235 low-carbon steel in an acidic water environment.
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Paragraph 0047; 0048; 0049
(2017/10/25)
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- NITROGEN SUBSTITUTED AROMATIC TRIAZOLES AS CORROSION CONTROL AGENTS
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Compositions and methods for inhibiting corrosion of metallic surfaces in contact with an aqueous medium such as copper, copper alloy, and steel surfaces of an open recirculating cooling water system. In certain embodiments, an aromatic triazole having an anionic substituent bonded to a nitrogen atom of the triazole (ANST) is used as the corrosion inhibitor. In other embodiments, the corrosion inhibitor is a reaction product of an aromatic triazole and an aldehyde (ATA).
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Paragraph 0043
(2017/12/01)
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- Design and Synthesis of Alanine Triazole Ligands and Application in Promotion of Hydration, Allene Synthesis and Borrowing Hydrogen Reactions
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A new type of alanine triazole (ATA) ligand was found to be an efficient partner for the stabilization of gold(III), thus rendering improved stability and high catalytic activities in allene synthesis and hydration reactions through the 3,3′-arrangement of propargyl esters and propargyl alcohols. In addition to Au(I), ATA-gold(III) was also proven to be an effective catalyst in promoting the formation of allenes with high yields. Furthermore, alanine triazole ruthenium has exhibited excellent potential as a means to catalyze borrowing hydrogen of alcohols and amines, ketones and alcohols.
- Yang, Yongchun,Qin, Anni,Zhao, Keyan,Wang, Dawei,Shi, Xiaodong
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supporting information
p. 1433 - 1439
(2016/05/19)
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- Targeting zoonotic viruses: Structure-based inhibition of the 3C-like protease from bat coronavirus HKU4 - The likely reservoir host to the human coronavirus that causes Middle East Respiratory Syndrome (MERS)
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The bat coronavirus HKU4 belongs to the same 2c lineage as that of the deadly Middle East Respiratory Syndrome coronavirus (MERS-CoV) and shows high sequence similarity, therefore potentiating a threat to the human population through a zoonotic shift or 'spill over' event. To date, there are no effective vaccines or antiviral treatments available that are capable of limiting the pathogenesis of any human coronaviral infection. An attractive target for the development of anti-coronaviral therapeutics is the 3C-like protease (3CLpro), which is essential for the progression of the coronaviral life cycle. Herein, we report the screening results of a small, 230-member peptidomimetic library against HKU4-CoV 3CLpro and the identification of 43 peptidomimetic compounds showing good to excellent inhibitory potency of HKU4-CoV 3CLpro with IC50 values ranging from low micromolar to sub-micromolar. We established structure-activity relationships (SARs) describing the important ligand-based features required for potent HKU4-CoV 3CLpro inhibition and identified a seemingly favored peptidic backbone for HKU4-CoV 3CLpro inhibition. To investigate this, a molecular sub-structural analysis of the most potent HKU4-CoV 3CLpro inhibitor was accomplished by the synthesis and testing of the lead peptidomimetic inhibitor's sub-structural components, confirming the activity of the favored backbone (22A) identified via SAR analysis. In order to elucidate the structural reasons for such potent HKU4-CoV 3CLpro inhibition by the peptidomimetics having the 22A backbone, we determined the X-ray structures of HKU4-CoV 3CLpro in complex with three peptidomimetic inhibitors. Sequence alignment of HKU4-CoV 3CLpro, and two other lineage C Betacoronaviruses 3CLpro's, HKU5-CoV and MERS-CoV 3CLpro, show that the active site residues of HKU4-CoV 3CLpro that participate in inhibitor binding are conserved in HKU5-CoV and MERS-CoV 3CLpro. Furthermore, we assayed our most potent HKU4-CoV 3CLpro inhibitor for inhibition of HKU5-CoV 3CLpro and found it to have sub-micromolar inhibitory activity (IC50 = 0.54 ± 0.03 μM). The X-ray structures and SAR analysis reveal critical insights into the structure and inhibition of HKU4-CoV 3CLpro, providing fundamental knowledge that may be exploited in the development of anti-coronaviral therapeutics for coronaviruses emerging from zoonotic reservoirs.
- St. John, Sarah E.,Tomar, Sakshi,Stauffer, Shaun R.,Mesecar, Andrew D.
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p. 6036 - 6048
(2015/11/10)
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- Synthesis of some novel 3-Alkyl/aryl-6-((1H-benzo[d][1,2,3]triazol-1-yl) methyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles
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(Chemical Equation Presented) A series of 3-alkyl/aryl substituted-6-((1H- benzo[d][1,2,3]triazol-1-yl)methyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadizoles 4a-m are prepared by the condensation of 3-alkyl/aryl substituted-4-amino-5- mercapto-1,2,4-triazoles 2a-m with benzotriazole-1-yl acetic acid 3 through a single step reaction. The structures of all newly synthesized compounds are established on the basis of their IR, 1H NMR, and elemental analyses data. Two selected compounds 4l and 4m are investigated for their analgesic and anti-inflammatory activities; they showed weak anti-inflammatory activity and no analgesic activity.
- Chen, Xiqing,Liu, Chenjiang,Wang, Jide,Li, Yanping
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experimental part
p. 1225 - 1229
(2010/11/18)
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- Synthesis and cytotoxic activity of coumarin derivatives containing benzotriazole moieties
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Three coumarin derivatives containing benzotriazole moieties, 3-(1-benzotriazolyl)-4-methyl-coumarin (BMC), 3-(1-benzotriazolyl)-4-methyl- benzo[7,8]coumarin (BMBC), and 3-(4-methyl-1-benzotriazolyl)-4-methyl-benzo[7,8] coumarin (MBMBC), were synthesized. Among them, 3-(4-methyl-1-benzotriazolyl)-4- methyl-benzo[7,8]coumarin has been structurally characterized by X-ray crystallography. The cytotoxic effect by Sulforhodamine B (SRB) assay with these compounds against the human hepatocellular carcinoma cell lines (HepG-2) was carried out in vitro. The preliminary results showed that all compounds inhibit HepG-2 growth effectively. Taylor & Francis Group, LLC.
- Yu, Tianzhi,Zhang, Peng,Zhao, Yuling,Zhang, Hui,Fan, Duowang,Dong, Wenkui,Ding, Lan
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experimental part
p. 2655 - 2663
(2010/04/05)
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- Synthesis, crystal structure and photoluminescence of 3-(1-benzotriazole)-4-methyl-coumarin
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A novel coumarin derivative containing an electron-transporting moiety (benzotriazole), 3-(1-benzotriazole)-4-methyl-coumarin (BMC), was synthesized from starting substances, i.e. benzotriazole and 2-hydroxyacetophenone. The compound structure was verified by FT-IR, 1H NMR, element analysis and single crystal X-ray crystallography. Crystallographic data reveal a dihedral angle of 108° between the coumarin and benzotriazole rings, which is attributed to the spatial hindrance of a 4-positioned methyl group. The fluorescence and UV-vis absorption of BMC were discussed. The compound exhibits a strong UV emission peak at 385 nm under 360 nm excitation. The molecular structure of BMC was optimized using density functional theory (DFT) at B3LYP/6-31G(d) level, showing that the optimized geometric parameters are in good agreement with experimental data. In addition, the HOMO and LUMO levels of BMC were deduced.
- Yu, Tianzhi,Zhao, Yuling,Fan, Duowang
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- Ramoplanin derivatives possessing antibacterial activity
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Novel ramoplanin derivatives are disclosed. These ramoplanin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against gram positive bacteria, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.
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Page/Page column 64
(2010/11/23)
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- Synthesis and antitubercular activity of 3-aryl substituted-2-(1H(2H) benzotriazol-1(2)-yl)acrylonitriles
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A series of 223-aryl substituted-2-(1H(2H)-benzotriazol-1(2)- yl)acrylonitriles was synthesized for a preliminary in vitro evaluation of antitubercular activity according to an international program with the Tuberculosis Antimicrobial Acquisition and Coordinating Facility (TAACF). This work reports the synthetic approach and analytical and spectroscopic characterization (UV, IR, 1H- and 13C-NMR) of all compounds synthesized. Several compounds showed an interesting activity in the preliminary screening with a percent growth inhibition of the virulent Mycobacterium tuberculosis between 40 and 99% at the concentration of 12.5 μg/mL. The most effective derivatives E-5a and E-5e were also tested against M. avium in vitro. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
- Sanna, Paolo,Carta, Antonio,Nikookar, Mohammad E. Rahbar
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p. 535 - 543
(2007/10/03)
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- Studies on fused β-lactams: Synthesis, stereochemistry and antimicrobial activity of some new cepham analogues
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β-Lactam ring has been conveniently grafted onto 2-phenyl-5,6-dihydro-1,3-thiazine 1 by annelating it with in situ prepared ketenes to furnish cepham analogues 6-9. A variety of acids such as menthoxy acetic acid 2, butylthioacetic acid 3, chloroacetic acid 4 and benzotriazole acetic acid 5 have been used as mixed sulphonic acid anhydrides for the cycloaddition reaction. All the compounds have been screened for their antibacterial activities.
- Sharma,Saluja,Bhaduri
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p. 156 - 159
(2007/10/03)
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- Syntheses and transformations of substituted benzazolyl- and tetrazolyl(benzotriazol-1-yl)methanes
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Condensation reactions of o-hydroxy- and o-mercaptoanilines, and o-phenylenediamine with (benzotriazol-1-yl)acetic acid result in (1,3-benzazol-2-yl)(benzotriazol-1-yl)methanes. Cycloaddition of sodium azide to (benzotriazol-1-yl)acetonitrile leads to (1,2,3,4-tetrazol-5-yl)(benzotriazol-1-yl)methane. The diazolo-substituted benzotriazolylmethanes thus obtained were mono- and di-alkylated at the methylene group and the displacement of the benzotriazole group by nucleophiles was investigated.
- Katritzky, Alan R.,Aslan, Diana,Shcherbakova, Irina V.,Chen, Jie,Belyakov, Sergei A.
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p. 1107 - 1114
(2007/10/03)
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- Synthesis of N-substituted mono- and bi-heterocycles as antiinflammatory, anticonvulsant and anthelmintic agents
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Various N-substituted carbazoles (3a-f) and 1-methylpiperazines (4a-f) containing benzotriazole-, phenothiazine or diphenylaminoacetyl/propionyl moiety have been synthesized by appropriate methods.All the compounds have been screened for their antiinflammatory activity against the carrageenan-induced rat paw oedema in albino rats, anticonvulsant activity against pentylenetetrazole induced convulsions in mice and anthelmintic activity against the experimental infection of Ancyclostoma ceylanicum and Hymenolepsis nana in rats.Some of the compounds exhibit appreciable activity.
- Shukla, Yogendra K.,Srivastava, Savitri D.
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p. 397 - 399
(2007/10/02)
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- A Novel Selective Route to 1-Substituted Benzotriazoles via Lithiation of Simple 1-Alkylbenzotriazoles
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1-Methylbenzotriazole (2a) is lithiated readily with butyllithium or LDA at the methyl group to 4 and the subsequent reaction with various electrophiles provides 1-substituted benzotriazoles 5.Other 1-(n-alkyl)benzotriazoles 2 also undergo lithiation with LDA, the carbanions can be trapped with alkyl halides giving benzotriazoles 6 bearing secondary alkyl groups on the N-1 atom.On standing in the absence of electrophiles, all the lithium derivatives decompose to afford complex mixtures. - Key Words: Benzotriazoles, 1-alkyl / Lithiation / Haloalkanes
- Katritzky, Alan R.,Wu, Jing,Kuzmierkiewicz, Wojciech,Rachwal, Stanislaw
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- The Preparation and Some Reactions of a Benztriazole Substituted Vinamidium Salt
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A three step synthesis of a novel 2-(1-benzotriazolyl)-vinamidium salt is described along with its direct conversion to a series of unusual 5-(1-benzotriazolyl)pyrimidines, 4-(1-benzotriazolyl)-pyrazoles, and 4-(1-benzotriazolyl)pyrroles.
- Gupton, John T.,Hicks, Fred A.,Smith, Stanton Q.,Main, A. Denise,Petrich, Scott A.,et al.
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p. 10205 - 10218
(2007/10/02)
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