- Synthesis, local anesthetic activity and QSAR studies for a set of N-[2-(alkylamino)ethyl]benzotriazol-x-yl acetamides
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A set of N-[2-(alkylamino)ethyl]benzotriazol-x-yl acetamides were synthesized and tested for local anesthetic activity. The compounds were designed by varying independently the hydrophobicity and size of the side chains. Anesthetic activity was assessed by different tests using lidocaine as a reference: rabbit corneal and mouse tail anesthesia. These two anesthetic activities were correlated with calculated log P values and significant linear dependences were observed. The three most potent compounds of the series were evaluated in the rat sciatic nerve block assay and their acute toxicity in mice was also assessed. Compound 4b(N-[2-(diethylamino)ethyl]benzotriazol-2-yl acetamide), which has an anesthetic activity comparable to that of lidocaine, was also characterized by a more favorable therapeutic index.
- Caliendo,Di Carlo,Greco,Grieco,Meli,Novellino,Perissutti,Santagada
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Read Online
- B(C6F5)3-Catalyzed site-selective N1-alkylation of benzotriazoles with diazoalkanes
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Alkylation of benzotriazoles is synthetically challenging, often leading to mixtures of N1 and N2 alkylation. Herein, metal-free catalytic site-selective N1-alkylation of benzotriazoles with diazoalkanes is described in the presence of 10 mol% of B(C6F5)3. These reactions provide N1-alkylated benzotriazoles in good to excellent yields and this protocol is successfully adapted to gram-scale syntheses as well as a derivative with antimicrobial activity.
- Guo, Jing,Mandal, Dipendu,Stephan, Douglas W.,Wu, Yile,Zhao, Yunbo
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supporting information
p. 7758 - 7761
(2021/08/13)
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- A “turn-on” small molecule fluorescent sensor for the determination of Al3+ion in real samples: theoretical calculations, and photophysical and electrochemical properties
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Aluminum, one of the most plentiful metal ions on Earth, demonstrates toxic effects after excessive accumulation in the environment and human bodies because it is a non-essential element for living organisms. Therefore, strict limits on Al3+intake by humans have been proposed by the EPA and WHO. In the current study, ultrasound sonication was used for the green synthesis of the naphthalene-based acetohydrazide derivative (3), and it was used as a fluorescent sensor in order to determine the levels of Al3+ions in real samples. Theoretical calculations were carried out and the photophysical and electrochemical properties of3were deeply investigatedviaDFT; steady-state fluorescence, UV-vis absorption, time-resolved fluorescence, and 3D-fluorescence spectroscopy; excitation-emission matrix (EEM) analysis; and CV and SWV measurements. The fluorescent sensor investigations demonstrated that3can sensitively and selectively detect Al3+ionsviaa “turn-on” fluorescence response, which is based on the inhibition of PET and ESIPT processes with a synergistic effect from CHEF. The optimal conditions with regards to the initial sensor concentration, pH, selectivity, and interaction time were determined for the detection of Al3+ions. The linear working range and detection limit for Al3+ions were calculated to be 1.00-20.00 μmol L?1and 0.34 μmol L?1, respectively. Method validation was examinedviathe analysis of a certified reference material (CRM-TMDW-500), and spike/recovery testing and spectrofluorimetric analysis of Al3+ions in drinking water, seawater, and urine samples were successfully carried out using3. Importantly,3-capped paper-based test strips were developed for the practical analysis and monitoring of Al3+ions in the field. According to the obtained results, the presented detection technique, which is based on a “turn-on” fluorescence response change of3, can be applied to the highly sensitive, facile, reliable, and fast determination of Al3+ions in real samples.
- ?enocak, Ahmet,Mermer, Arif,Tümay, Süreyya O?uz
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p. 18400 - 18411
(2021/10/19)
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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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supporting information
p. 7284 - 7289
(2020/10/12)
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- Synthesis and characterization of ethyl benzotriazolyl acrylate-based D-π-A fluorophores for live cell-based imaging applications
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A series of eight new ethyl (Z)-benzotriazolyl acrylates 6a-d and 7a-d have been synthesized by conventional heating and microwave irradiation from ethyl benzotriazolyl acetates 3 and 4 with the corresponding aromatic aldehydes. This work reports the synthetic approach and spectroscopic characterization (1H, 13C-NMR, HRMS) of all the synthesized compounds. X-ray diffraction analyses were performed for molecules 6a, 7a and 7d. Photophysical properties of compounds were evaluated. Finally, compound 6a was tested in a human cell line and showed low to no cytotoxicity at relevant concentrations. Initial testing demonstrates its potential use as a fluid-phase fluorescent marker for live cell imaging.
- Ortega-Villarreal, Ana Sofia,Hernández-Fernández, Eugenio,Jensen, Christopher,Valdivia-Berroeta, Gabriel A.,Garrard, Samuel,López, Israel,Smith, Stacey J.,Christensen, Kenneth A.,Reyes-González, Miguel A.,Michaelis, David J.
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p. 8759 - 8767
(2019/03/28)
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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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p. 15249 - 15257
(2019/10/08)
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- Synthesis of coumarin-benzotriazole hybrids and evaluation of their anti-tubercular activity
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Background: Tuberculosis is one of the top ranked airborne infectious diseases caused by the bacillus Mycobacterium tuberculosis with high mortality rate from a single infectious agent. In the present article, we aimed to synthesize oxadiazole-coumarin-triazole based small molecules and evaluate for their possible anti-mycobacterial activity. Method: Herein, we describe the facile synthesis of 5-((1H-benzo[d][1, 2, 3]triazol-1-yl)methyl)-1, 3, 4- oxadiazole-2-thiol-tethered substituted 4-(bromomethyl)-7-methyl-2H-chromen-2-one derivatives and evaluated for their anti-mycobacterial activity against H37Rv strain of M. tuberculosis. We also evaluated the cytotoxic effect of new compounds on normal cells. Results: Among the 14 novel oxadiazole-coumarin-triazole derivatives, 4-((5-((1H-benzo[d][1, 2, 3]triazol-1- yl)methyl)-1, 3, 4-oxadiazol-2-ylthio)methyl)-6-methoxy-2H-chromen-2-one (5f) displayed good antimycobacterial activity towards M. tuberculosis with an MIC value of 15.5 μM. Pyrazinamide was used as reference drug. Our investigation also revealed that, 5f is not cytotoxic to normal cells. Conclusion: In summary, the findings suggested that novel 1, 3, 4-oxadiazole coumarin-triazole hybrids are promising antimycobacterial agents against M. tuberculosis.
- Ambekar, Sachin P.,Mohan, Chakrabhavi Dhananjaya,Shirahatti, Arunkumar,Kumar, Mahesh K.,Rangappa, Shobith,Mohan, Surender,Basappa,Kotresh, Obelannavar,Rangappa, Kanchugarakoppal S.
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- Novel benzotriazole N-acylarylhydrazone hybrids: Design, synthesis, anticancer activity, effects on cell cycle profile, caspase-3 mediated apoptosis and FAK inhibition
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A series of novel benzotriazole N-acylarylhydrazone hybrids was synthesized according fragment-based design strategy. All the synthesized compounds were evaluated for their anticancer activity against 60 human tumor cell lines by NCI (USA). Five compounds: 3d, 3e, 3f, 3o and 3q exhibited significant to potent anticancer activity at low concentrations. Compound 3q showed the most prominent broad-spectrum anticancer activity against 34 tumor cell lines, with mean growth inhibition percent of 45.80%. It exerted the highest potency against colon HT-29 cell line, with cell growth inhibition 86.86%. All leukemia cell lines were highly sensitive to compound 3q. Additionally, compound 3q demonstrated lethal activity to MDA-MB-435 belonging melanoma. Compound 3e exhibited the highest anticancer activity against leukemic CCRF-CEM and HL-60(TB) cell lines, with cell growth inhibition 86.69% and 86.42%, respectively. Moreover, it exerted marked potency against ovarian OVCAR-3 cancer cell line, with cell growth inhibition 78.24%. Four compounds: 3d, 3e, 3f and 3q were further studied through determination of IC50 values against the most sensitive cancer cell lines. The four compounds exhibited highly potent anticancer activity against ovarian cancer OVCAR-3 and leukemia HL-60 (TB) cell lines, with IC50 values in nano-molar range between 25 and 130 nM. They showed 18–2.3 folds more potent anticancer activity than doxorubicin. The most prominent compound was 3e, (IC50 values 29 and 25 nM against OVCAR-3 and HL-60 (TB) cell lines, respectively), representing 10 and 18 folds more potency than doxorubicin. The anti-proliferative activity of these four compounds appeared to correlate well with their ability to inhibit FAK at nano-molar range between 44.6 and 80.75 nM. Compound 3e was a potent, inhibitor of FAK and Pyk2 activity with IC50 values of 44.6 and 70.19 nM, respectively. It was 1.6 fold less potent for Pyk2 than FAK. Additionally, it displayed inhibition in cell based assay measuring phosphorylated-FAK (IC50 = 32.72 nM). Inhibition of FAK enzyme led to a significant increase in the level of active caspase-3, compared to control (11.35 folds), accumulation of cells in pre-G1 phase and annexin-V and propidium iodide staining in addition to cell cycle arrest at G2/M phase indicating that cell death proceeded through an apoptotic mechanism.
- Kassab, Asmaa E.,Hassan, Rasha A.
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p. 531 - 544
(2018/07/25)
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- Synthesis and antimicrobial and antioxidant activities of hybrid molecules containing benzotriazole and 1,2,4-triazole
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Eleven novel 1,2,4-triazolylbenzotriazoles have been prepared using 1-(hydrazinylcarbonylmethyl)-1 H -benzotriazole (3) as a potent intermediate. Compound 3, however, was obtained from benzotriazole in two steps. All synthesized compounds were characteriz
- Chand, Mahesh,Kaushik, Reena,Chand Jain, Subhash
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p. 1663 - 1677
(2019/01/03)
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- Stereoselective synthesis and spectral studies of some benzotriazolylacetyl hydrazones of 3–alkyl–2,6–diarylpiperidin–4–ones
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An effort to include biologically potent benzotriazole nucleus into piperidine ring is achieved through hydrazone formation. The characterization of the synthesized compounds was carried out using FT-IR, 1H &13C NMR, 1H–1H COSY, 1H–13C COSY, NOESY spectral techniques and GC-Mass spectrum. The spectral assignments were done without ambiguity using 2D-NMR techniques. The conformational preference of the piperidine ring deduced from the spectral studies is ‘chair’. The diastereotopic nature of the methylene protons/methyl groups present in the molecules is revealed clearly in their spectral pattern observed.
- Pillai, M. Velayutham,Rajeswari,Kumar, C. Udhaya,Krishnan, K. Gokula,Mahendran,Ramalingan,Nagarajan,Vidhyasagar
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p. 558 - 565
(2017/09/19)
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- 1-H phenyltheophylline and the three kinds of the nitrogen production method of [...] ester
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The invention discloses a production method of 1-H benzotriazole acetate. The method comprises the steps of synthesizing ethyl chloroacetate and synthesizing 1-H benzotriazole ethyl acetate; firstly adding trichloromethane and a catalyst namely triethylamine, dropping a trichloromethane solution containing chloroacetyl chloride, removing triethylamine hydrochloride by filtration, and evaporating filtrate to dryness by using a rotary evaporator, thereby obtaining a residue namely ethyl chloroacetate; adding absolute ethyl alcohol, benzotriazole and sodium hydroxide, filtering an ethanol solution containing ethyl chloroacetate to obtain a generated inorganic salt, concentrating the filtrate, precipitating crystals, and filtering to obtain a product. Compared with conventional production methods, the method disclosed by the invention can be used for greatly shortening the production time and greatly improving the production efficiency; 1-H benzotriazole acetate produced by using the method has good thermal stability and oil solubility, can be used for significantly improving the extreme pressure property of liquid paraffin under an appropriate additive amount and improving the bearing capacity of liquid paraffin, and can reach a yield of more than 90%.
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Paragraph 0025; 0027
(2017/02/17)
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- 1,3,4-Oxadiazole derivatives as potential antitumor agents: Discovery, optimization and biological activity valuation
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Recent studies have proved that focal adhesion kinase (FAK) is a new potential therapeutic target in cancer therapy. In this study, a virtual screening was conducted to discover potential candidates for FAK inhibitors. Based on the results, a series of novel oxadiazole derivatives (5a-5q) bearing the benzotriazole group were designed and synthesized for FAK inhibitory evaluation. Among the compounds, 5h, which has an ortho methoxy group on the benzene ring, exhibited the most potent inhibitory activity for cancer cell growth with an IC50 value of 11 μM and 0.250 μM against Hela cells and FAK, respectively. Further, the apoptosis assay indicated that compound 5h induced the apoptosis of HeLa cells, and docking simulation showed that 5h could bind to the FAK protein catalytic region. Taking these together, 5h could be a lead for discovering novel FAK inhibitors.
- Luo, Yin,Liu, Zhi-Jun,Chen, Guo,Shi, Jing,Li, Jing-Ran,Zhu, Hai-Liang
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p. 263 - 271
(2016/03/01)
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- Cycloadditions of azides with arynes via photolysis of phthaloyl peroxide derivatives
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Photolysis of phthaloyl peroxides yields arynes, which undergo [3 + 2] cycloadditions with azides. This reaction tolerates a variety of organic azides and phthaloyl peroxides and affords the corresponding benzotriazoles in moderate to good yields at room
- Chang, Denghu,Zhu, Dan,Shi, Lei
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p. 5928 - 5933
(2015/06/16)
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- A photoinduced, benzyne click reaction
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The [3 + 2] cycloaddition of azides and alkynes has proven invaluable across numerous scientific disciplines for imaging, cross-linking, and site-specific labeling among many other applications. We have developed a photoinitiated, benzyne-based [3 + 2] cycloaddition that is tolerant of a variety of functional groups as well as polar, protic solvents. The reaction is complete on the minute time scale using a single equivalent of partner azide, and the benzyne photoprecursor is stable for months under ambient light at room tempurature. Herein we report the optimization and scope of the photoinitiated reaction as well as characterization of the cycloaddition products.
- Gann, Adam W.,Amoroso, Jon W.,Einck, Vincent J.,Rice, Walter P.,Chambers, James J.,Schnarr, Nathan A.
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p. 2003 - 2005
(2014/05/06)
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- Synthesis and antimicrobial of some new substituted tetrazolomethylbenzo[d] -[1,2,3]triazole derivatives using 1H-benzo[d][1,2,3]triazole as starting material
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A series of tetrazolomethylbenzo[d][1,2,3]triazole derivatives (2-14) have been synthesized and evaluated as antimicrobial agents from 1H-benzo[d][1,2,3] triazole (1) as starting material. The reaction of benzotriazole 1 with chloroacetonitrile afforded 2-(1H-benzo[d][1,2,3]-triazol-1-yl)acetonitrile 2, which was reacted with sodium azide to give tetrazole derivative 3. Esterification of benzotriazole 1 with ethyl bromoacetate in the presence of anhydrous potassium carbonate afforded ester 4, which was treated with hydrazine hydrate to afford the corresponding hydrazide 5. Reaction of 3 with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide afforded the nitro-glycoside derivative 6, which was deacetylated using methanolic ammonia to deprotected nitroglycoside 7. The hydrazide 5 was reacted with 4,5,6,7-tetrachlorophthalic anhydride or 1,2,4,5-benzenetetracarboxylic dianhydride in refluxing glacial acetic acid to give the corresponding imides 8 and 9, respectively. Also, the hydrazide 5 was reacted with carbon disulphide in ethanol to give potassium salt 10, which was reacted with hydrazine hydrate to afford aminotriazole derivative 11. The latter compound was reacted with carbon disulphide to afford thiadiazole derivative 12, which was treated with 2,3,4,6-tetra-O-acetyl-α-d-glucopyranosyl bromide to give the thioglycoside derivative 13. Deacetylation of the thioglycoside 13 using methanolic ammonia solution at room temperature afforded the deprotected thioglycoside 14. The antimicrobial screening of some synthesized compounds showed that many of these compounds have good antimicrobial activities comparable to streptomycin and fusidic acid as reference drugs.
- Ali, Omar M.,Amr, Abd El-Galil E.,Mostafa, Elsayed E.
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p. 1545 - 1556
(2014/05/06)
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- MW assisted synthesis of some pyrazoles containing benzotriazole moiety: An environmentally benign approach
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MW assisted synthesis of pyrazoles containing benzotriazole moieties 4a-n has been achieved by cyclocondensation of substituted chalcones 3a-n with hydrazide of benzotriazole 2 in presence of glacial acetic acid (GAA). Thus, synthesized compounds 4a-n have been characterized by their spectral data and evaluated for their antibacterial and antifungal activities against various microbes.
- Tiwari, Urvashi,Ameta, Chetna,Rawal, Manish K.,Ameta, Rakshit,Punjabi, Pinki B.
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p. 432 - 439
(2013/05/08)
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- Synthesis, biological evaluation, and molecular docking studies of novel 1,3,4-oxadiazole derivatives possessing benzotriazole moiety as FAK inhibitors with anticancer activity
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1,3,4-Oxadiazole derivatives have drawn continuing interest over the years because of their varied biological activities. In order to search for novel anticancer agents, we designed and synthesized a series of new 1,3,4-oxadiazole derivatives containing benzotriazole moiety as potential focal adhesion kinase (FAK) inhibitors. All the synthesized compounds were firstly reported. Among the compounds, compound 4 shows the most potent inhibitory activity against MCF-7 and HT29 cell lines with IC50 values of 5.68 μg/ml and 10.21 μg/ml, respectively. Besides, all the compounds were assayed for FAK inhibitory activity using the TRAP-PCR-ELISA assay. The results showed compound 4 exhibited the most potent FAK inhibitory activity with IC50 values of 1.2 ± 0.3 μM. Docking simulation by positioning compound 4 into the FAK structure active site was performed to explore the possible binding mode. Apoptosis which was analyzed by flow cytometry, demonstrated that compound 4 induced apoptosis against MCF-7 cells. Therefore, compound 4 may be a potential anticancer agent against MCF-7 cancer cell.
- Zhang, Shuai,Luo, Yin,He, Liang-Qiang,Liu, Zhi-Jun,Jiang, Ai-Qin,Yang, Yong-Hua,Zhu, Hai-Liang
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p. 3723 - 3729
(2013/07/19)
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- A New class of anticonvulsants possessing 6 hz psychomotor seizure test activity: 2-(1H-benzotriazol-1-yl)-N'-[substituted] acetohydrazides
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A series of 2-(1H-Benzotriazol-1-yl)-N'-[substituted]acetohydrazides was designed and synthesized keeping in view the structural requirement of pharmacophore and evaluated for anticonvulsant activity and neurotoxicity. The new compounds were characterized using FT-IR, 1H NMR, mass spectral data and elemental analysis. The anticonvulsant activity of the titled compounds was assessed using the 6 Hz psychomotor seizure test. The neurotoxicity was assessed using the rotarod method. The most active compound of the series was N'-[4-(1,3-Benzodioxol-5-yloxy)benzylidene]-2-(1Hbenzotriazol-1-yl) acetohydrazide (BTA 9), which showed good activity with 75 % protection (3/4, 0.5 h) at a dose of 100 mg/kg in mice. None of the compounds exhibited neurotoxicity. A computational study was carried out for the calculation of pharmacophore pattern and prediction of pharmacokinetic properties. Titled compounds have also exhibited good binding properties with epilepsy molecular targets such as glutamate, GABA (A) delta, GABA (A) alpha-1 receptors and Na/H exchanger, in Lamarckian genetic algorithm based flexible docking studies.
- Kumar, Praveen,Tripathi, Laxmi
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experimental part
p. 337 - 348
(2012/08/28)
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- Substituted [1,3,4]-oxadiazole, [1,3,4]-thiadiazole and [1,2,4]-triazole; synthesis, characterization and antimicrobial study
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Series of compounds 5-(benzotriazol-1-yl-methyl)-2-aryl/alkyl-amino-[1,3,4] -oxadiazoles, 5-(benzotriazol-1-yl-methyl)-2-aryl/alkyl-amino-[1,3,4]- thiadiazoles and 5-(benzotriazol-1-yl-methyl)-3-mercapto-4-aryl/alkyl-4H-[1,2,4] -triazoles have been synthesized by the oxidative cyclization of 2-benzotriazol-1-yl-N-aryl/alkyl thiocarbamido-acetamides using alkaline ethanolic solution of iodine containing potassium iodide, ortho-phosphoric acid and aqueous potassium hydroxide solution respectively. These compounds on acetylation afforded acetyl derivatives, on benzoylation afforded benzoyl derivatives and on reaction with ethyl iodide afforded ethylmercapto derivatives. These compounds have been assayed for their antimicrobial activity against Gram-positive as well as Gram-negative microorganisms.
- Deohate, Pradip P.
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p. 253 - 259
(2012/11/06)
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- Substituted [1,2,4,5]-dithiadiazines and [1,3,4]-thiadiazolidines; synthesis, characterization and antimicrobial study
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Series of compounds 2-benzotriazol-1-yl-1-(3-phenylimino-6-aryl/alkylimino- [1,2,4,5]-dithiadiazinan-4-yl)-ethanones and 2-benzotriazol-1-yl-1-(2- phenylimino-5-aryl/alkylimino-[1,3,4]-thiadiazolidin-3-yl)-ethanones have been synthesized by the interaction of 2-benzotriazol-1-yl-N-aryl/alkyl thiocarbamido-acetamides with N-phenyl-S-chloro isothiocarbamoyl chloride and N-phenyl isocyanodichloride respectively. These compounds on acetylation afforded acetyl derivatives. The title compounds have been assayed for their antimicrobial activity against Gram-positive as well as Gram-negative microorganisms.
- Deohate, Pradip P.
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p. 1705 - 1710
(2013/08/24)
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- Synthesis and biological activity test of some new five membered heterocycles
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A new series of 1,3,4-oxadiazoles, 1,2,4-triazoles, 1,3,4-thiadiazoles were synthesized using alkylhydrazides as the starting materials, and then 1,2,4-triazoles were used to synthesize [1,2,4]triazolo[3,4-b][1,3,4] thiadiazoles. All the compounds were evaluated for in vitro antibacterial activity and antitumor activity. A new series of five membered heterocyclic compounds were synthesized using alkylhydrazides as the starting materials. All the compounds were evaluated for in vitro antibacterial activity and antitumor activity.
- Xia, Qingchun,Xu, Dongfang,He, Qizhuang,Li, Xingyu,Sun, Dazhi
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body text
p. 2433 - 2440
(2011/10/05)
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- Benzyne click chemistry: Synthesis of benzotriazoles from benzynes and azides
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(Chemical Equation Presented) A variety of substituted benzotriazoles have been prepared by the [3 + 2] cycloaddition of azides to benzynes. The reaction scope is quite general, affording a rapid and easy entry to substituted, functionalized benzotriazoles under mild conditions.
- Shi, Feng,Waldo, Jesse P.,Chen, Yu,Larock, Richard C.
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supporting information; experimental part
p. 2409 - 2412
(2009/05/11)
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- Copper-free 'click': 1,3-dipolar cycloaddition of azides and arynes
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Arynes formed through fluoride-promoted ortho-elimination of o-(trimethylsilyl)aryl triflates can undergo [3 + 2] cycloaddition with various azides to form substituted benzotriazoles. The rapid reaction times and mild conditions make this an attractive variation of the classical 'click' reaction of azides and alkynes.
- Campbell-Verduyn, Lachlan,Elsinga, Philip H.,Mirfeizi, Leila,Dierckx, Rudi A.,Feringa, Ben L.
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supporting information; experimental part
p. 3461 - 3463
(2009/02/05)
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- Synthesis of some new 5-[2-{(1,2,3-benzotriazole)-1- Yl-methyl}-1′- (4′-substituted aryl-3′-chloro-2′-oxo azetidine)]-amino-1,3,4- thiadiazoles: Antifungal and antibacterial agents
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As a part of systematic investigation of synthesis and biological activity, several new 5-[2-(1,2,3-benzotriazole)-1-yl-methyl]-arylidene hydrazino-1,3,4-thiadiazoles 7 and 5-[2-{(1,2,3-benzotriazole)-1-yl-methyl}- 1′-(4′-substituted aryl-3′-chloro-2′-oxo
- Shukla,Srivastava
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p. 463 - 469
(2008/09/20)
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- Synthesis of some new 3-(1,2,3-benzotriazolylmethyl)-4-(3-chloro-4- substituted aryl-2-oxo-azetidine)-5-mercapto-1,2,4-triazoles: Antifungal and antibacterial agents
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1,2,3-Benzotriazole on treatment with ethyl chloroacetate gave ethyl 1,2,3-benzotriazole-1-acetate 1 which on amination with hydrazine hydrate afforded 1,2,3-benzotriazole-1-acetic acid hydrazide 2. The compound 2 on cyclisation with CS2-KOH yi
- Nema,Srivastava
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p. 1037 - 1041
(2008/09/20)
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- Synthesis and characterization of some alkoxyphthalimide derivatives of benzotriazolylthiadiazoles and benzotriazolylthiazolidinones
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In the present investigation newer and simple synthetic methods of 5-(1,2,3-benzotriazol-1-yl-methyl)-N-alkoxyphthalimido-1,3,4-thiadiazol-2- amines 5a-b and 2-[(1,2,3-benzo-triazolyl)acetohydrazido]-3-N-alkoxyphthalimido- 5-arylidene-1,3-thiazolidin-4-on
- Ojha, Swati,Ameta, Usha,Dhakar, Neelam,Talesara
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p. 860 - 865
(2008/09/18)
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- Synthesis of 5-arylidene-2-aryl-3-(benzotriazoloacetamidyl)-1,3- thiazolidin-4-ones as analegesic and antimicrobial agents
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Benzotriazole on reaction with ethyl chloroacetate affords 1, which on treatment with hydrazine hydrate yields 2. Condensation of N 1(acetohydrazido)benzotriazole 2 with various carbonyls gives arylidene acetohydrazido benzotriazoles 3 which on
- Asati,Srivastava,Srivastava
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p. 526 - 531
(2007/10/03)
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- Organic reactions in ionic liquids: A simple highly regioselective or regiospecific substitutions of benzotriazole
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In the absence of any added base in ionic liquids [Bmim][BF4], benzotriazole replaces the halogen atom of an α-halogenated ketone or α-halogenated carboxylic ester to give the corresponding N-1-substituted benzotriazole as the only isomer, and
- Le, Zhang-Gao,Chen, Zhen-Chu,Hu, Yi,Zheng, Qin-Guo
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p. 1077 - 1081
(2007/10/03)
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- Organic reactions in ionic liquids: An efficient method for the N-alkylation of benzotriazole
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The N-alkylation of benzotriazole with alkyl halides proceeds efficiently in the presence of potassium hydroxide in ionic liquid 1-butyl-3- methylimidazolium tetrafluoroborate ([Bmim][BF4]).
- Le, Zhang-Gao,Chen, Zhen-Chu,Hu, Yi,Zheng, Qin-Guo
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p. 344 - 346
(2007/10/03)
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- Aqueous micellar medium in organic synthesis: Alkylations and Michael reactions of benzotriazole
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The feasibility of aqueous micelles of cetyltrimethylammonium bromide in catalyzing C-N bond formation has been studied with respect to N-alkylations of benzotriazole (Bt). Alkylations with various alkylating agents and the addition of Bt across activated double bonds in the Michael fashion occurred successfully in fair-to-good yields in the aqueous micellar regime. These reactions provided a mixture of N-1 and N-2 alkylated products, with a marked preference for N-1 over N-2 isomers. Micellar catalysis has been evaluated experimentally to indicate over a 50% micellar contribution to these alkylations in contrast to their aqueous counterparts. Since, N-alkyl benzotriazoles are of potential biological interest, the present micellar procedure offers a convenient alternative to other available methods.
- Mashraqui, Sabir Hussain,Kumar, Sukeerthi,Mudaliar, Chandrasekhar Dayal
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p. 2133 - 2138
(2007/10/03)
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- Synthesis of new benzotriazole derivatives: Antimicrobial and anticonvulsant agents
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Several 2-arylidenylamino-5-(N1-benzotriazolomethyl)-1, 3, 4- thiadiazoles 4 and 1-[5'-(N1-benzotriazolomethyl)-1, 3, 4-thiadiazol-2'- yl]4-(substituted phenyl)-3-chloro-2-oxo-azetidines 5 have been synthesized and tested for their a
- Srivastava,Rawat
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p. 623 - 627
(2007/10/03)
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- Synthesis of 5-arylidene-2-aryl-3-(phenothiazino/benzotriazoloacetamidyl)-1,3-thiazolidine-4-ones as antiimflammatory, anticonvulsant, analgesic and antimicrobial agents
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Condensation of N10(acetohydrazido) phenothiazine/benzotriazole 5, 6 with various carbonyls give arylidene acetohydrazido phenothiazines/benzotriazoles 7, 8 which on cycloaddition with mercapto acetic acid yield the corresponding 4-thiazolidino
- Mishra, Seema,Srivastava, S. K.,Srivastava, S. D.
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p. 826 - 830
(2007/10/03)
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- Preparation and local anaesthetic activity of N-[2-(tert-amino)ethyl]- and N-(lupinyl)-benzotriazol-1/2-ylacetamides
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Two sets of N-[2-(tert-amino)ethyl]- and N-[(quinolizidin-1α- yl)methyl]-benzotriazol-2-ylacetamides, bearing substituents on position 5 or 5 and 6, were prepared and tested for local anaesthetic activity in comparison with lidocaine. Most of the prepared compounds exhibited a fairly good activity comparable or superior to that of lidocaine. The introduction of substituents on the benzene ring and the replacement of the usual tert- amino alkyl chains with the quinolizidin-1α-ylmethyl (lupinyl) moiety were quite profitable for both the intensity and duration of activity. One selected compound was subjected to a large pharmacological screening and found endowed with a good level of the purported antiarrhythmic activity without any other disturbing activity.
- Vazzana,Boido,Sparatore,Di Carlo,Raso,Pacilio
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p. 131 - 139
(2007/10/03)
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- SYNTHESIS AND CHARACTERIZATION OF METAL COMPLEXES DERIVED FROM POTASSIUM 3-(BENZOTRIAZOLE-1-CARBONYLMETHYL)-DITHIOCARBAZATE
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The preparation and characterization of some dipositive metal ion complexes derived from potassium 3-(benzotriazole-1-carbonylmethyl)-dithiocarbazate (BCDHK) is reported.The solid complexes of the composition ML*nH2O (M=Mn(II), Ni(II), Cu(II), Cd(II), Zn(II) and Co(II), n=0,1) and ML2*2H2O (M=Pb(II), UO2(VI)), have been characterized on the basis of elemental analyses, IR, UV and TGA.IR spectral data indicate that BCDHK behaves as either a mononegative or binegative ligand and coordinates in a tridentate or bridging tetradentate manner.
- Xu, Peng-Fei,Liu, Zhang-Lu,Wu, Shao-Zu
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p. 579 - 584
(2007/10/02)
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- A simple, versatile synthetic route to N-1-aryl-, -heteroaryl-, -acylmethyl-, -carboxymethyl- and -alkyl-benzotriazoles via regiospecific or highly regioselective substitutions of benzotriazole
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In the absence of any added base in refluxing benzene or toluene, benzotriazole replaces the halogen atom of an α-halogenated ketone or a carboxylic ester to give the corresponding N-1-substituted benzotriazole as the only isomer. 2-Bromopyridine and 1-chloro-2,4-dinitrobenzene reacted similarly with benzotriazole to afford the corresponding N-1-substituted benzotriazole derivatives in quantitative yields. Alkyl halides reacted regioselectively to afford the N-1-alkylbenzotriazoles in ratios of more than 10 to 1 over the N-2 isomers. An α-(benzotriazol-1-yl)carboxylic ester was hydrolyzed into the corresponding carboxylic acid, which upon heating underwent smooth decarboxylation into the corresponding 1-alkylbenzotriazole.
- Katritzky,Wu
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p. 597 - 600
(2007/10/02)
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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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- An improved method for the N-alkylation of benzotriazole and 1,2,4-triazole
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The N-alkylation of benzotriazole and 1,2,4-triazole with alkyl halides proceeds efficiently in the presence of sodium hydroxide in N,N-dimethylformamide.
- Katritzky, Alan R.,Kuzmierkiewiecz, Wojciech,Greenhill, John V.
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p. 369 - 373
(2007/10/02)
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