- Discovery of benzotriazole-azo-phenol/aniline derivatives as antifungal agents
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A series of benzotriazole-azo-phenol/aniline derivatives were prepared and evaluated for their antifungal activities against six phytopathogenic fungi such as Fusarium graminearum, Fusarium solani, Alternaria alternate, Valsa mali, Botrytis cinerea, and Curvularia lunata. Among them, compounds IIf, IIn, and IIr showed a broad-spectrum of potent antifungal activities. Especially some compounds displayed 3.5–10.8 folds more potent activities than carbendazim against A. alternata and C. lunata. Notably, compounds IIc, IIm, and IIr exhibited good protective and therapeutic effects against B. cinerea at 200 μg/mL. Their structure-activity relationships were also discussed.
- Lv, Min,Ma, Jingchun,Li, Qin,Xu, Hui
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- New N-nitrosoamines 2. Transformations of tetrahydro-1,3-oxazines into nitrates of N-nitrosoamino alcohols
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The reactions of HNO3 with tetrahydro-1,3-oxazines 1a-c produced by aminomethylation of diketopiperazine, isatin, and succinimide, respectively, afforded nitrates of amino alcohols [RCH2NH2(CH 2)3ONO
- Korepin,Galkin,Perepelkina,Glushakova,Lodygina,Eremenko,Nefedov,Eremenko
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Read Online
- Synthesis of Structurally Diverse Benzotriazoles via Rapid Diazotization and Intramolecular Cyclization of 1,2-Aryldiamines
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An operationally simple method has been developed for the preparation of N-unsubstituted benzotriazoles by diazotization and intramolecular cyclization of a wide range of 1,2-aryldiamines under mild conditions, using a polymer-supported nitrite reagent and p-tosic acid. The functional group tolerance of this approach was further demonstrated with effective activation and cyclization of N-alkyl, -aryl, and -acyl ortho-aminoanilines leading to the synthesis of N1-substituted benzotriazoles. The synthetic utility of this one-pot heterocyclization process was exemplified with the preparation of a number of biologically and medicinally important benzotriazole scaffolds, including an α-amino acid analogue.
- Faggyas, Réka J.,Sloan, Nikki L.,Buijs, Ned,Sutherland, Andrew
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p. 5344 - 5353
(2019/05/21)
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- Tert -Butyl nitrite mediated nitrogen transfer reactions: Synthesis of benzotriazoles and azides at room temperature
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A conversion of o-phenylenediamines into benzotriazoles was achieved at room temperature using tert-butyl nitrite. The optimized conditions are also well suited for the transformation of sulfonyl and acyl hydrazines into corresponding azides. This protocol does not require any catalyst or acidic medium. The desired products were obtained in excellent yields in a short span of time.
- Azeez, Sadaf,Chaudhary, Priyanka,Sureshbabu, Popuri,Sabiah, Shahulhameed,Kandasamy, Jeyakumar
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supporting information
p. 6902 - 6907
(2018/10/02)
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- Synthesis of 2-(Quinoxalin-2-ylamino-benzotriazolyl) Pentanedioic Derivatives as Potential Anti-Folate Agents
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Anti-folate agents had a significant impact on therapeutic treatment plans for diseases such as cancer, and bacterial and parasitic infections, notably malaria. Quinoxaline derivatives showed in vitro anticancer activity and were able to inhibit both the dihydrofolate reductase and thymidylate synthase. Here, we decided to combine the chemical properties of quinoxalines and quinoxaline 1,4-dioxides with those of benzotriazole nucleus with the aim to evaluate the resulting biological properties. Two main new series, including more than 60 compounds, were prepared. In the first one, the benzotriazole moiety was linked through the nitrogen atoms 1, 2, or 3, to a glutaric acid substituent to simulate a glutamic moiety. In the second series, the glutaric acid was substituted with acetic acid moiety to evaluate the effects of steric hindrance. Here, we describe the multistep chemical processes to obtain all titled quinoxalines starting from commercially available diamines. The classical oxidation of selected quinoxalines was unsuccessful, and we have come to an independent synthetic pathway to obtain new derivatives linked to the benzotriazole moieties starting from synthons bearing N-oxide functionality.
- Briguglio,Piras,Corona,Pirisi,Burrai,Boatto,Gavini,Rassu
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p. 1721 - 1737
(2016/11/23)
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- Facile synthesis of benzotriazole derivatives using nanoparticles of organosilane-based nitrite ionic liquid immobilized on silica and two room-temperature nitrite ionic liquids
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Nanoparticles of organosilane-based nitrite ionic liquid immobilized on silica, 1-butyl-3-methylimidazolium nitrite, and 1-(3-trimethoxysilylpropyl)-3- methylimidazolium nitrite were used as effective reagents for the preparation of benzotriazole derivatives from 1,2-diaminobenzenes at room temperature under mild solvent-free conditions. These ionic liquids play as nitrosonium sources in this procedure.1,2-Diaminobenzene derivatives have been treated with ionic liquids to give the related diaminobenzenes in very good to excellent yields in short reaction times. Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications for the full experimental and spectral details.
- Valizadeh, Hassan,Gholipour, Hamid,Mahmoodian, Manzar
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p. 2801 - 2808
(2013/08/15)
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- Relative role of halogen bonds and hydrophobic interactions in inhibition of human protein kinase CK2α by tetrabromobenzotriazole and some C(5)-substituted analogues
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To examine the relative role of halogen bonding and hydrophobic interactions in the inhibition of human CK2α by 4,5,6,7- tetrabromobenzotriazole (TBBt), we have synthesized a series of 5-substituted benzotriazoles (Bt) and the corresponding 5-substituted 4,6,7- tribromobenzotriazoles (Br3Bt) and examined their inhibition of human CK2α relative to that of TBBt. The various C(5) substituents differ in size (H and CH3), electronegativity (NH2 and NO 2), and hydrophobicity (COOH and Cl). Some substituents were halogen bond donors (Cl, Br), while others were fluorine bond donors (F and CF 3). Most of the 5-substituted analogues of Br3Bt (with the exception of COOH and NH2) exhibited inhibitory activity comparable to that of TBBt, whereas the 5-substituted analogues of the parent Bt were only weakly active (Br, Cl, NO2, CF3) or inactive. The observed effect of the volume of a ligand molecule pointed to its predominant role in inhibitory activity, indicating that presumed halogen bonding, identified in crystal structures and by molecular modeling, is dominated by hydrophobic interactions. Extended QSAR analysis additionally pointed to the monoanion and a preference for the N(1)-H protomer of the neutral ligand as parameters crucial for prediction of inhibitory activity. This suggests that the monoanions of TBBt and its congeners are the active forms that efficiently bind to CK2α, and the binding affinity is coupled with protomeric equilibrium of the neutral ligand.
- W?sik, Romualda,?ebska, Maja,Felczak, Krzysztof,Poznański, Jaros?aw,Shugar, David
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experimental part
p. 10601 - 10611
(2011/01/03)
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- Design, synthesis and determination of antifungal activity of 5(6)-substituted benzotriazoles
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In an effort to find inhibitors that are effective against both Candida and Aspergillus spp., a series of 5(6)-(un)substituted benzotriazole analogs, represented by compounds 3a-3h and 3b′-3f′, were prepared using a crystalline oxirane intermediate 1 previously synthesized in our laboratory. All the compounds were evaluated for inhibitory activity against various species of Candida and Aspergillus. Compounds 3b′ (5,6-dimethylbenzotriazol-2-yl derivative), 3d (5-chlorobenzotriazol-1-yl derivative) and 3e′ (6-methylbenzotriazol-1-yl derivative) exhibited potent antifungal activity, with the MICs for Candida spp. and Aspergillus niger, ranging from 1.6 μg/mL to 25 μg/mL and 12.5 μg/mL to 25 μg/mL, respectively. The present work describes the design, synthesis, regioisomer characterization (through COSY and NOESY 2D-NMR spectroscopy and single molecule X-ray crystallography), antifungal evaluation, molecular docking, and structure-activity relationships of the various 5(6)-(un)substituted benzotriazole analogs.
- Patel, Pallav D.,Patel, Maulik R.,Kocsis, Bela,Kocsis, Erika,Graham, Steven M.,Warren, Andrew R.,Nicholson, Stacia M.,Billack, Blase,Fronczek, Frank R.,Talele, Tanaji T.
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supporting information; experimental part
p. 2214 - 2222
(2010/09/08)
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- 1H, 13C and 15N NMR spectroscopy and tautomerism of nitrobenzotriazoles
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Benzotriazole nitro derivatives were prepared by nitration of the corresponding benzotriazoles and by methylation or cyclization of appropriate nitro-1,2-phenylenediamines. Structures and tautomerism of the nitrobenzotriazoles were studied by multinuclear 1H, 13C, 15N, and 2D NMR spectroscopy and quantum chemistry. Copyright
- Larina, Lyudmila I.,Milata, Viktor
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experimental part
p. 142 - 148
(2009/12/26)
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- [1,2,3]Triazolo[4,5-h]quinolones. A new class of potent antitubercular agents against multidrug resistant Mycobacterium tuberculosis strains
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In this preliminary study we report the activity of 3-methyl-9-substituted-6-oxo-6,9-dihydro-3H-[1,2,3]-triazolo[4,5-h]quinolone-carboxylic acids and their esters as a new class of antiinfective agents against MDR Mycobacterium tuberculosis. In antitubercular screening against H37Rv and 11 clinically isolated strains of M. tuberculosis several derivatives (1o,3a,c,i,j,p) showed MIC90 in the range 0.5-3.2 μg/mL. 3c showed no cytotoxicity and proved to be the most potent derivative exhibiting MIC90 = 0.5 μg/mL against all M. tuberculosis strains and infected human macrophages (J774-A1) tested.
- Carta, Antonio,Palomba, Michele,Paglietti, Giuseppe,Molicotti, Paola,Paglietti, Bianca,Cannas, Sara,Zanetti, Stefania
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p. 4791 - 4794
(2008/09/19)
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- 1H,6H-Triazolo[4,5-e]benzotriazole-3-oxides and 5,5′-(Z)-diazene-1,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) derived from chloronitrobenzotriazoles and hydrazine
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Nitration of 5-chlorobenzotriazole (1) and its N1-methyl derivatives (2 and 3) produced 5-chloro-4-nitrobenzotriazole (5), 5-chloro-1-methyl-4-nitrobenzotriazole (6) and 6-chloro-1-methyl-7-nitrobenzotriazole (7) respectively. Nitration of 5-chloro-2-methylbenzotriazole (4) gave either 5-chloro-2-methyl-4-nitrobenzotriazole (8) or 5-chloro-2-methyl-4,6-dinitrobenzotriazole (9). Introduction of the nitro group activated chlorine atom that underwent nucleophilic displacement by hydrazine to give rise to a new tricyclic system 1H,6H-triazolo[4,5-e]benzotriazole-3-oxide compounds (10 and 11) in the case of 5 and 6. From 9 no linear or angular tricyclic triazolobenzotriazole was obtained but instead the 5,5′-(Z)-diazene-1,2-diylbis(2-methyl-2H-1,2,3-benzotriazole) (18).{A figure is presented}.
- Carta, Antonio,Piras, Sandra,Boatto, Gianpiero,Paglietti, Giuseppe
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p. 2471 - 2481
(2007/10/03)
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- An NMR study of the equilibria involved with benzotriazole, carbonyl compounds, and their adducts
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A 1H and 13C NMR study of the equilibrium mixtures of benzotriazole and several carbonyl compounds with their adducts, in [ 2H6]benzene and other solvents, affords the equilibrium constants for the reversible formation of N-1 (K1) and N-2 (K 2) isomeric adducts. Thermodynamic parameters have been computed. Adduct formation is generally less predominant in sterically crowded cases. In general the N-1 isomer predominates over the N-2 isomer, however, with the sterically hindered 4,7-dimethylbenzotriazole this order is reversed.
- Katritzky, Alan R.,Perumal, Subbu,Savage, G. Paul
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p. 921 - 924
(2007/10/02)
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- Kinetics of General and Specific Catalysis During Hydrolysis of 1-Benzoylbenzotriazoles
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The hydrolysis of 1-benzoylbenzotriazole is independent of pH in the range 2.0 - 7.0 and catalysed by OH(-) at pH > 7 at 25 deg C in acetonitrile-water medium (10percent, v/v) at ionic strength=0.5 mol dm-3.Based on the solvent deuterium isotope effect and structure-reactivity considerations, a mechanism involving at least two water molecules in the transition state is proposed for the pH independent hydrolysis.The results of the effect of substituents on the phenyl ring of the benzoyl group on the rate constant lead to Hammett's rho value of +1.7 and Bronsted β value of -1.7.Aquopentaamminocobaltic perchlorate catalyses the hydrolysis and the ratio of rate constants for metal complex catalysed reaction and the corresponding hydroxide ion catalysed reaction has been found to be 1.2E3 - 5.7E3 suggesting a nucleophilic attack of hydroxy group of the complex on the carbonyl of the amide.
- Yeshoda, G.,Alwar, S. Bangaru Sudarasan,Thiagarajan, V.
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p. 564 - 568
(2007/10/02)
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- SYNTHESE ET REACTIONS DE DEPLACEMENT NUCLEOPHILE DE DERIVES NITRES ET HALOGENES DU PYRIDINO BENZO-1,3a,6,6a-TETRAAZAPENTALENE.
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The reactions of pyridino benzo-1,3a,6,6a-tetraazapentalene and its nitro- or halogeno-derivatives with some electrophiles and nucleophiles are described.The directive influence of the tetraazapentalene nucleus on electrophilic and nucleophilic substitution reactions at the pyridine and the benzene rings is discussed.
- Maquestiau, A.,Flammang-Barbieux, M.,Vilain, E.
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p. 973 - 982
(2007/10/02)
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