- Hydrothermal synthesis of two Zinc coordination Polymers with 1-(1H-Tetrazol-5-ylmethyl)-1H-benzotriazole Ligands
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The direct reaction of ZnBr2 with H-1-mbtz [1-mbtz = 1- (1H-tetrazol-5-ylmethyl)-1H-benzotriazole] gives the two-dimensional complex [Zn(Br)(1-mbtz)] (1), whereas the reaction of benzotriazol-1- yl-acetonitrile with NaN3 in the presence of water and a Lewis acid (ZnBr2) affords the 2D coordination polymer [Zn2(OH)(1-mbtz)3H2O] (2). The central zinc atom in 1 is bonded to one terminal bromine atom and three different nitrogen atoms from two tetrazole ligands and one BTA group (BTA = benzotriazole), and each 1-mbtz ligand is coordi- nated to three zinc atoms forming a 2D framework. The coordination polyhedron around the metal atom in 2 is a slightly distorted trigonal bipyramid made up by one zinc atom, four nitrogen atoms as well as one oxygen atom, two of the 1-mbtz ligands coordinated to three zinc atoms and the third 1-mbtz ligand acts in a bidentate fashion, which leads to the formation of a complicated 2D network. The syntheses and solid-state structures of the two coordination polymers are reported.
- Sun, Su-Wen,Jin, Lei,Shi, Ping-Ping,Liu, Ming-Liang,Kong, Li-Hui,Ye, Qiong
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- Synthesis and anticancer activity of benzotriazole derivatives
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A series of benzotriazole (BTA) derivatives were synthesized as tyrosine protein kinase inhibitors using fragment-based design strategy. All desired compounds were synthesized with the reaction of benzotriazole, chloroacetonitrile and aromatic aldehyde using Ultrasonic-Microwave method and characterized by IR, 1H and 13C-NMR, mass spectrometry (MS) and elemental analysis. The anticancer activity of these compounds was evaluated by CCK-8 method against carcinoma VX2, lung cancer A549, stomach cancer cell lines MKN45 and MGC in vitro. The results showed that all compounds showed good antiproliferative activity. In particular, compound 2.1 showed the most prominent inhibition of VX2 cell lines with IC50 of 3.80 ± 0.75 μM. Compound 2.2 exhibited highly potent anticancer activity of stomach MGC cell lines with IC50 of 3.72 ± 0.11 μM. A549 and MKN45 cell lines were sensitive to compound 2.5 with IC50 of 5.47 ± 1.11 and 3.04 ± 0.02 μM, respectively.
- Li, Qiujing,Li, Zhulai,Liu, Guijun,Wang, Ningning,Yin, Huiyong
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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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- Synthesis and characterization of benzotriazolyl acrylonitrile analogs-based donor-acceptor molecules: Optical properties, in vitro cytotoxicity, and cellular imaging
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A series of eight new (E)-benzotriazolyl acrylonitrile derivatives were synthesized under reflux conditions via Knoevenagel condensation between acetonitrile analogs and a short series of aromatic aldehydes. X-ray diffraction analysis for one of the compounds was performed to determine the (E)-geometry of its double bond. The photoluminescent properties of all compounds in solution were also evaluated. These compounds exhibit strong blue, green and yellow emission under ultraviolet light excitation with fluorescence quantum yield in the 0.08–0.58% range. To determine the suitability of these compounds for use in cell-based analysis, cytotoxicity assays were performed on a representative molecule using a common mammalian cell line (HEK 293T cells) at different concentrations. The results showed limited toxicity (72 ± 16% viability) at the highest concentration tested (50 μM). Finally, confocal microscopy demonstrated that our compound was internalized into cells and localized to endosomes and/or lysosomes in a similar fashion to Dextran–Cascade Blue (DCB).
- Hernández-Fernández, Eugenio,Ortega-Villarreal, Ana Sofia,García-López, Ma. Concepción,Chan-Navarro, Rodrigo,Garrard, Samuel,Valdivia-Berroeta, Gabriel A.,Smith, Stacey J.,Christensen, Kenneth A.,Michaelis, David J.
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- Benzotriazole-Assisted Preparations of 2-(Substituted amino)pyridines and Pyrid-2-ones
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Base-promoted reactions of benzotriazolyl-containing acetic acid derivatives, 2-(benzotriazol-1-yl)acetonitrile (7a), 2-(benzotriazol-1-yl)acetamide (7b), and (±)-2-(benzotriazol-1-yl)propionamide (7c), with α,β-unsaturated ketones 8 give efficient and regioselective access to previously difficult to attain 3-unsubstituted pyridine derivatives: the 2-(substituted amino)pyridines 14a-k and the 4,6-substituted pyrid-2-ones 15a-h. The pyridine rings result from tandem [3 + 3] annulations involving a Michael addition followed by cyclization.
- Katritzky, Alan R.,Belyakov, Sergei A.,Sorochinsky, Alexander E.,Henderson, Scott A.,Chen, Jie
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- Synthesis, crystal structure and photo- and electro-luminescence of the coumarin derivatives with benzotriazole moiety
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Two new coumarin derivatives containing an electron-transporting moiety (benzotriazole), 7-N,N-diethylamino-3-(benzotriazol-1-yl)coumarin (DABTC-1) and 7-N,N-diethylamino-3-(benzotriazol-2-yl)coumarin (DABTC-2), were synthesized and characterized by element analysis, 1H NMR, FT-IR and UV-vis absorption spectra. Their structures were determined by X-ray crystallography single crystal analysis. The photoluminescent behaviors of the compounds in both solution and solid states were observed, they exhibit strong blue and blue-green emissions under ultraviolet light excitation, respectively. The energy levels of the HOMO and LUMO of the compounds have been calculated with density functional theory (DFT) and time-dependent density functional theory (TD-DFT) at B3LYP/6-31G(d) level. The electroluminescent devices with the compounds as the emitters were fabricated.
- Yu, Tianzhi,Zhang, Peng,Zhao, Yuling,Zhang, Hui,Meng, Jing,Fan, Duowang,Chen, Lili,Qiu, Yongqing
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- Synthesis and antiproliferative activity of 3-aryl-2-[1H(2H)-benzotriazol- 1(2)-yl]acrylonitriles variously substituted: Part 4
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A new series of variously substituted 3-aryl-2-[1H(2H)-benzotriazol-1(2)- yl]acrylonitriles was synthesized and tested for antiproliferative and antitubercular activity as part of our continuing research program in the antimicrobial and antitumor fields. The most cytotoxic derivatives (5a,g,i,j,l and 7b) (CC50 3.0 μM against MT-4 cells) were evaluated against a panel of human cell lines derived from hematological and solid tumors, using 6-mercaptopurine (6-MP) and etoposide as reference drugs. In particular, E-2-(5,6-dimethyl-1H-benzotriazol-1-yl)-3-(3-nitrophenyl)acrylonitrile (5g) resulted more potent than 6-MP on all cell lines, even if 2-14-fold less potent than etoposide. In the antitubercular screening, the derivatives 5i,j and 7e showed moderate activity against some resistant strains of Mycobacterium tested.
- Carta, Antonio,Palomba, Michele,Boatto, Gianpiero,Busonera, Bernardetta,Murreddu, Marta,Loddo, Roberta
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- Perfluorobutyl iodide-assisted direct cyanomethylation of azoles and phenols with acetonitrile
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A perfluorobutyl iodide-assisted transition-metal-free cyanomethylation of azoles and phenols with acetonitrile in the presence of NaH has been developed. The reaction proceeded smoothly under mild reaction conditions to give the cyanomethylated products in moderate to high yields. A mechanism involving the cyanomethyl radical through C-H bond cleavage in acetonitrile was proposed. This journal is
- Zhang, Juan,Wu, Wei,Ji, Xinfei,Cao, Song
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p. 20562 - 20565
(2015/03/30)
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- Effects of positional and geometrical isomerism on the biological activity of some novel oxazolidinones
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Some novel oxazolidinone derivatives have been synthesized and tested for antibacterial activity. Compound 13 was found to be active against Gram-positive pathogens whereas compound 14 was less active. Either less active or inactive molecules were obtained, when benzotriazole was replaced with benzimidazole, benzthiazole, or benzoxazole. However, thioacetamide analogue of 13 produced a potent molecule similar to linezolid in vitro. Some novel oxazolidinone derivatives with benzotriazole as pendant have been synthesized and tested for antibacterial activity. Linearly attached benzotriazole derivative showed more potency compared to angular one in vitro. Out of E/Z-isomers of angularly attached derivatives E-isomer was found to be more potent than Z-isomer. Either less active or inactive molecules were obtained, when benzotriazole was replaced with benzimidazole, benzthiazole, or benzoxazole. Finally, thioacetamide analogue of linear compound gave a lead having activity similar to linezolid in vitro.
- Das, Jagattaran,Rao, C.V. Laxman,Sastry,Roshaiah,Sankar, P. Gowri,Khadeer, Abdul,Kumar, M. Sitaram,Mallik, Arundhuti,Selvakumar,Iqbal, Javed,Trehan, Sanjay
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p. 337 - 343
(2007/10/03)
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- Synthesis of polynuclear nonfused azoles
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Polynuclear blocks consisting of nonfused heterocycles of the azole series, connected through methylene bridges, were synthesized by successive addition of azole units via cycloaddition of organic azides to the triple bond of N-(2-propynyl)azoles, as well
- Verkhozina,Kizhnyaev,Vereshchagin,Rokhin,Smirnov
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p. 1792 - 1796
(2007/10/03)
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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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- Synthesis and antiparasitic activities of amidinic azolated derivatives
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A set of heterocyclic N-acetamidinium hydrochlorides were prepared from the corresponding N-acetonitriles. The antiparasitic screening showed that, while all amidines are practically inactive, some nitriles present leishmanicide properties.
- Danan,Charon,Kirkiacharian,Bories,Loiseau
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p. 227 - 229
(2007/10/03)
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- The Chemistry of N-Substituted Benzotriazoles. Part 1. 1-(Chloromethyl)-benzotriazole
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The N-chloromethyl group of 1-(chloromethyl)benzotriazole undergoes nucleophilic substitution by carbon, nitrogen, phosphorus, oxygen, and sulphur nucleophiles. α-Lithiation was achieved in high yield in 1-phenylthiomethyl-, 1-phenylsulphinylmethyl-, and 1-(phenylsulphonylmethyl)benzotriazoles and the lithio derivatives reacted with a variety of electrophiles.New benzotriazolium salts were prepared by quaternization of the N-3 nitrogen with methyl iodide.
- Katritzky, Alan R.,Rachwal, Stanislaw,Caster, Kenneth C.,Mahni, Fatma,Law, Kam Wah,Rubio, Olga
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p. 781 - 790
(2007/10/02)
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