Benzotriazole Derivatives Research Articles

Unprecedented formation of benzo[ d][1,2,3,6]oxatriazocine derivatives via diazo-oxygen bond formation and synthesis of enantiomerically pure 1-alkyl benzotriazole derivatives

A series of amino acid-derived enantiomerically pure substituted benzo[ d][1,2,3,6]oxatriazocine derivatives and 1-alkyl substituted benzotriazoles has been prepared by the diazotization of amino acid-derived benzo-fused alicycles. The first unprecedented diazo-oxygen bond formation in acidic medium led to an entirely new kind of substituted benzo[ d][1,2,3,6]oxatriazocine heterocycles.

ChemInform Abstract: Conventional and Microwave Assisted Synthesis of 2‐Oxo‐4‐Substituted Aryl‐Azetidine Derivatives of Benzotriazole: A New Class of Biological Compounds.

AbstractAll synthesized compounds are screened for their antitubercular and antimicrobial activities as well as for their cytotoxicity.

Conventional as well as Eco-Friendly Microwave Irridiated Synthesis and Antimicrobial Evaluation of Some New Benzotriazole Derivatives

Conventional as well as Eco-Friendly Microwave Irridiated Synthesis and Antimicrobial Evaluation of Some New Benzotriazole Derivatives

Analysis of NO and its metabolites by mass spectrometry. Comment on ‘Detection of nitric oxide in tissue samples by ESI-MS’ by Z. Shen, A. Webster, K. J. Welham, C. E. Dyer, J. Greenman and S. J. Haswell

Recently, Shen et al. (Analyst, 2010, 135, 302) reported on a flow injection analysis (FIA) ESI-MS/MS approach for the determination of the short-lived gaseous nitric oxide (NO) in biological samples. This method is based on the reaction of NO, and presumably of other NO-derived oxides such as N(2)O(3), with the vicinal amino groups of methylpiperazinobenzendiamine to form a benzotriazole derivative. Under MS/MS conditions, the protonated derivative loses molecular nitrogen (N(2)) from the triazole ring and the product ion formed is utilized for quantitative analyses. This seems to be the first ESI-MS/MS method for authentic NO detection and quantification. However, the ESI-MS/MS method reported by Shen et al. deserves some critical discussion.

Benzotriazole derivatives as long wavelength photosensitizers for diaryliodonium salt initiators

AbstractTwo benzotriazole derivative dyes 4,7‐bis(2,3‐dihydrothieno[3,4‐b][1,4]dioxin‐5‐yl)‐2‐dodecyl‐2H‐benzo[1,2,3]triazole, and 2‐dodecyl‐4,7‐bis(4‐hexylthiophen‐2‐yl)‐2H‐benzo[d][1,2,3]triazole are shown to work as efficient photosensitizers for a diphenyliodonium salt initiator in cationic photopolymerization of epoxide and vinyl monomers. Substituted thienyl groups are attached to benzotriazole backbone to extend conjugation and enhance electron density of the molecules. Thereby, it was possible to initiate polymerizations at room temperature using long wavelength UV and visible light. The progress of photopolymerizations was monitored using optical pyrometry. The photopolymerization of an epoxide monomer using solar irradiation was also demonstrated. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2011

Multichromic polymers of benzotriazole derivatives: Effect of benzyl substitution

Two electroactive monomers 1-benzyl-4,7-di(thiophen-2-yl))-2H-benzo[d][1,2,3]triazole (BBTA) and 2-benzyl-4,7-di(thiophen-2-yl))-2H-benzo[d][1,2,3]triazole (BBTS) were synthesized with satisfactory yields. The effect of substitution site on electrochemical and optical properties was investigated with cyclic voltammetry and spectroelectrochemical studies. Results showed that position of pendant group alters the electronic structure of the resulting polymer causing different optical and electrochemical behaviors. Symmetrically positioned benzyl unit on benzotriazole moiety resulted in a neutral state red polymer, PBBTS, having multi-colored property in its different oxidized and reduced states. Its analogue PBBTA exhibited maximum absorption at 390nm in its neutral state and also revealed multicolored electrochromic property upon stepwise oxidation. Very different optical band gap values were calculated: 1.55eV and 2.25eV for PBBTS and PBBTA, respectively.

Synthesis and anti-mycobacterial activities of triazoloquinolones

A number of quinolone derivatives have been reported to possess anti-mycobacterial activity. Generally. Mycobacterium tuberculosis isolates expressing resistance to both isoniazid and rifampin are susceptible to fluoroquinolones. Benzotriazole is a hetero-bicyclic aromatic ring endowed with interesting chemical and biological properties and pharmacological activities. In a preliminary study we have recently reported the activity of triazolo[4,5-h]quinolone-carboxylic acids, a new class of benzotriazole derivatives active against multi-drug resistant M. tuberculosis (MDR-Mtb). In this study we confirm that this novel class of quinolones is endowed with a selective anti-mycobacterial activity, coupled with absence of cytotoxicity.The SAR analysis of the new derivatives in comparison with the previous series shows that the methyl group is the most effective substituent in both N-3 and N-9 positions of the ring system.

Inhibition of RNA Helicases of ssRNA(+) Virus Belonging to Flaviviridae, Coronaviridae and Picornaviridae Families.

Many viral pathogens encode the motor proteins named RNA helicases which display various functions in genome replication. General strategies to design specific and selective drugs targeting helicase for the treatment of viral infections could act via one or more of the following mechanisms: inhibition of the NTPase activity, by interferences with ATP binding and therefore by limiting the energy required for the unwinding and translocation, or by allosteric mechanism and therefore by stabilizing the conformation of the enzyme in low helicase activity state; inhibition of nucleic acids binding to the helicase; inhibition of coupling of ATP hydrolysis to unwinding; inhibition of unwinding by sterically blocking helicase translocation. Recently, by in vitro screening studies, it has been reported that several benzotriazole, imidazole, imidazodiazepine, phenothiazine, quinoline, anthracycline, triphenylmethane, tropolone, pyrrole, acridone, small peptide, and Bananin derivatives are endowed with helicase inhibition of pathogen viruses belonging to Flaviviridae, Coronaviridae, and Picornaviridae families.

ChemInform Abstract: Facile Synthesis of Novel Benzotriazole Derivatives and Their Antibacterial Activities.

AbstractSome of the title compounds, e.g. (IIIa)‐(IIIe) and (Va), exhibit potent antibacterial activities.

Conventional and microwave assisted synthesis of 2-oxo-4-substituted aryl-azetidine derivatives of benzotriazole: A new class of biological compounds

We report herein the synthesis and biological activity of a new kind of azetidinone derivatives of benzotriazole. The reaction was carried out by both conventional and microwave methods. The chemical structures of all the synthesized compounds were deduced according to FTIR, 1H NMR, 13C NMR and FAB-mass spectral along with microanalytical data. All the synthesized compounds of series 5a–i were evaluated for their antitubercular activity against Mycobacterium tuberculosis H37RV and antimicrobial activity against some selected microorganism. Unexpectedly, some azetidinone derivatives of benzotriazole displayed better activities.

Electrochemical and optical studies of furan and thieno[3,2‐b]thiophene end capped benzotriazole derivatives

AbstractTwo new 2‐dodecyl benzotriazole (BTz) based donor‐acceptor‐donor (DAD) type polymers were synthesized and characterized in terms of their electrochemical and spectral properties. These DAD type polymers were synthesized electrochemically from furan or thieno[3,2‐b]thiophene (TT) end‐capped BTz monomers. Furan based and thieno[3,2‐b]thiophene based monomers showed monomer oxidations at 1.15 and 1.25 V, respectively, which eased the formation of conducting polymer films without overoxidation. Cyclic voltammetry and spectroelectrochemistry studies showed that both materials are multicolored electrochromic polymers. Results and comparison with properties of other BTz based DAD type polymers are highlighted in detail. © 2010 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2010

ChemInform Abstract: Synthesis and Biological Screening of Some Novel Amidocarbamate Derivatives of Ketoprofen.

A series of novel ketoprofen derivatives 4a-j bearing both amide and carbamate functionalities were prepared using benzotriazole. Selective reduction of ketoprofen produced hydroxy derivative 2, which reacts with one or 2 mol of 1-benzotriazole carboxylic acid chloride (1) gave benzotriazole derivatives 3a and 3b respectively. Antioxidative screenings revealed that the prepared compounds 3b and 4a-j possess excellent lipid peroxidation inhibition at 0.1 mM concentration. Two of the compounds 3b and 4 g also showed high soybean lipoxygenase inhibition activity, where as the amidocarbamate derivatives of ketoprofen showed only weak reducing activity against 1,1-diphenyl-2-picrylhydrazyl radicals. No selective antiviral effects were noted for the tested compounds against a broad variety of DNA and RNA viruses.

Synthesis of New 2-(2´-Hydroxyaryl)benzotriazoles and Evaluation of Their Photochemical Behavior as Potential UV-Filters

Two new 2-(2´-hydroxyaryl)benzotriazole derivatives were synthesized and studied by photophysical and photochemical techniques in order to assess their ability to act as UV-filters. The absorption and emission properties of both compounds were determined in solvents of different polarity. In non polar solvent, a photoinduced excited state intramolecular proton transfer was established leading to efficient non radiative dissipation of UV-energy. In addition, the compounds considered were photostable under irradiation with simulated sunlight.

ChemInform Abstract: The Chemistry of Benzotriazole. Preparation, Characterization and Reactions of Novel Vicinal Dibenzotriazol-l-yl Derivatives of Benzotriazole and Glyoxal.

ChemInform Abstract: The Chemistry of Benzotriazole. Preparation, Characterization and Reactions of Novel Vicinal Dibenzotriazol-l-yl Derivatives of Benzotriazole and Glyoxal.

ChemInform Abstract: Benzotriazole-Assisted Synthesis of Enamines.

Abstract A new, facile preparation of enamines was achieved via a two-step sequence: (i) the ready formation of an N-(α-aminoalkyl)benzotriazole derivative from equimolar amounts of benzotriazole, an aldehyde, and a secondary amine, (ii) the elimination of benzotriazole from the derivative by sodium hydride in tetrahydrofuran (THF). The method provides enamines in good overall yields based on the quantity of amine used.

ChemInform Abstract: Sulfonyl Derivatives of Benzotriazole: Part 1. A Novel Approach to the Activation of Carboxylic Acids.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

Facile synthesis of novel benzotriazole derivatives and their antibacterial activities.

A series of benzotriazole derivatives (compounds 1–27) were synthesized, and 24 (compounds 1–5, 9–27) of which were first reported. Their chemical structures were confirmed by means of 1H NMR, IR and elemental analyses, coupled with one selected single crystal structure (compound 1). All the compounds were assayed for antibacterial activities against three Gram positive bacterial strains (Bacillus subtilis, Staphylococcus aureus and Streptococcus faecalis) and three Gram negative bacterial strains (Escherichia coli, Pseudomonas aeruginosa and Enterobacter cloacae) by MTT method. Among the compounds tested, most of them exhibited potent antibacterial activity against the six bacterial strains. Most importantly, compound 3-benzotriazol-1-yl-1-(4-bromo-phenyl)-2-[1,2,4]triazol-1-ylpropan-1-one (19) showed the most favourable antibacterial activity against B. subtilis, S. aureus, S. faecalis, P. aeruginosa, E. coli and E. cloacae with MIC of 1.56 µg/mL, 1.56 µg/mL, 1.56 µg/mL, 3.12 µg/mL, 6.25 µg/mL and 6.25 µg/mL, respectively.

RETRACTED: Synthesis and biological screening of some novel amidocarbamate derivatives of ketoprofen

A series of novel ketoprofen derivatives 4a-j bearing both amide and carbamate functionalities were prepared using benzotriazole. Selective reduction of ketoprofen produced hydroxy derivative 2, which reacts with one or 2 mol of 1-benzotriazole carboxylic acid chloride (1) gave benzotriazole derivatives 3a and 3b respectively. Antioxidative screenings revealed that the prepared compounds 3b and 4a-j possess excellent lipid peroxidation inhibition at 0.1 mM concentration. Two of the compounds 3b and 4 g also showed high soybean lipoxygenase inhibition activity, where as the amidocarbamate derivatives of ketoprofen showed only weak reducing activity against 1,1-diphenyl-2-picrylhydrazyl radicals. No selective antiviral effects were noted for the tested compounds against a broad variety of DNA and RNA viruses.

The novel amidocarbamate derivatives of ketoprofen: synthesis and biological activity

A series of novel ketoprofen derivatives 4a–j bearing both amide and carbamate functionalities were prepared using the benzotriazole method of carboxylic and hydroxy group activation. Selective reduction of ketoprofen produced hydroxy derivative 2, which in the reaction with one or two moles of 1-benzotriazole carboxylic acid chloride (1) gave benzotriazole derivatives 3a and 3b, respectively. Compounds 3a and 3b with various amines afforded amidocarbamates 4a–j. Antioxidative screenings revealed that the prepared compounds 3b and 4a–j possess excellent lipid peroxidation inhibition at 0.1 mM concentration, higher than 95% for the derivatives bearing aromatic, cycloalkyl or heterocyclic substituents. Two of the compounds, 3b and 4g, also show high soybean lipoxygenase inhibition activity (95 and 83.5%, respectively). On the other hand, the amidocarbamate derivatives of ketoprofen show only weak reducing activity against 1,1-diphenyl-2-picrylhydrazyl radicals. No selective antiviral effects were noted for the tested compounds against a broad variety of DNA and RNA viruses. Most compounds were endowed with a moderate (IC50: 10–25 μM) cytostatic activity.

Excited State Intramolecular Proton Transfer of a Chromophore Linked to Benzotriazole Derivatives

This paper presents ab initio and density functional theory(DFT) calculations on the excited state intramolecular proton transfer(ESIPT) of a chromophore linked to 2-(2-hydroxyl-phenyl)-benzotriazole: {2-hydroxyl-5-[(p-nitro-styrene)yl-oxymethylene]-phenyl}-(2H-benzotrizole)(C1) and 4′-nitro-3,4-bis-[2-hydroxyl-(2H-benzotrizole)-benzyloxy]-stilbene(C2).We undertook a comprehensive investigation on the ground state and excited state changes of the ESIPT tautomers including their bond lengths,bond angles,Mulliken charges,dipole moments,frontier orbitals,and potential surface curves.A stable keto form(K) was not obtained for C1 in the ground state and a ground state intramolecular proton transfer(GSIPT) was,therefore,impossible.The hydrogen bond strength of the keto form(K*) was higher than that of the enol form(E*) at their excited states.When excited,the negative charge of the hydrogen donor was diminished while the negative charge of the hydrogen acceptor was enhanced.For the excited state of keto from,the electron density moved from a"phenol cycle"to a protonated heterocycle because of the HOMO→LUMO electrontransition.A small energy barrier from E* to K*(ca 41 kJ.mol-1) was also observed.These results indicated that thepossibility of ESIPT occurring was high for C1.For C2,stable structures for the EK(including keto and enol(E) formssimultaneously),2K(including two keto forms simultaneously),and 2K*(the excited state of 2K) tautomers could notbe obtained because of their high energies.As a consequence,the probability of intramolecular single or double protontransfer at the ground state or excited state intramolecular double proton transfer occurring was negligible.The lowtransition energy for 2E*(the excited state of 2E)→EK*(the excited state of EK) suggested that an excited stateintramolecular single proton transfer was very possible for C2.UV-Vis absorption and fluorescence spectra werecalculated and an ESIPT fluorescence emission with a large Stoke′s shift was observed.