benzofurans and carbazole

Fluorene and its three heteroatomic analogs, dibenzofuran, dibenzothiophene, and carbazole, are environmental contaminants in areas impacted by spills of creosote. In addition, dibenzofuran has been used as an insecticide, and it is formed from the photolysis of chlorinated biphenyl ethers. Many biodegradation studies of dibenzofuran have considered it as a model for chlorinated dibenzofurans, which are of greater environmental concern. This paper reviews the bacterial degradation of fluorene and its analogs. These compounds are susceptible to three different modes of initial oxidation: (i) the naphthalene-like attack, in which one of the aromatic rings is oxidized to a dihydrodiol; (ii) an angular dioxygenase attack, in which the carbon bonded to the methylene group in fluorene or to the heteroatoms in the analogs, and the adjacent carbon in the aromatic ring are both oxidized; and (iii) the five-membered ring attack, in which the methylene carbon atom in fluorene or the sulfur atom in dibenzothiophene is oxidized. The metabolites, enzymology, and genetics of these transformation are summarized. Literature data are presented, indicating that the electronegativity of the atom connecting the two aromatic rings influences the attack of the angular dioxygenase. In dibenzofuran and carbazole, the connecting atoms, O and N respectively, have high electronegativities, and these compounds serve as substrates for angular dioxygenases. In contrast, the connecting atoms in dibenzothiophene and fluorene, S and C respectively, have lower electronegativities, and these atoms must be oxidized before the angular dioxygenases attack these compounds.

Topics: Bacteria; Benzofurans; Biodegradation, Environmental; Carbazoles; Fluorenes; Thiophenes

Herein described the design, synthesis and antitubercular evaluation of novel series of dibenzofuran, dibenzothiophene and N-methyl carbazole tethered 2-aminothiazoles and their cinnamamide analogs. One pot condensation of N-methyl carbazole, dibenzofuran and dibenzothiophene methyl ketones with thiourea in the presence of Iodine and CuO gave respective 2-aminothiazoles 4-6 in very good yields. Aminothiazoles were further coupled with substituted cinnamic acids using acid-amine coupling conditions to give desired cinnamamide analogs 8a-e, 9a-e and 10a-e. All the newly synthesized compounds were fully characterized by their NMR and mass spectral analysis. In vitro screening of new derivatives against Mycobacterium tuberculosis H37Rv (Mtb) resulted 8c, 10d and 10e (MIC: 0.78 µg/mL) and 2-aminothiazoles 5 and 6 (MIC: 1.56 µg/mL) as potent compounds with lower cytotoxicity profile.

Topics: Anti-Bacterial Agents; Benzofurans; Carbazoles; Cell Survival; Cinnamates; Dose-Response Relationship, Drug; HEK293 Cells; Humans; Microbial Sensitivity Tests; Molecular Structure; Mycobacterium tuberculosis; Structure-Activity Relationship; Thiazoles; Thiophenes

Magnetically immobilized cells of Comamonas sp. JB coupling with electrode reaction was developed to enhance the treatment efficiency of coking wastewater containing phenol, carbazole (CA), dibenzofuran (DBF), and dibenzothiophene (DBT). The pair of graphite plate-stainless iron mesh electrodes was chosen as the most suitable electrodes. Magnetically immobilized cells coupling with graphite plate-stainless iron mesh electrodes (coupling system) exhibited high degradation activity for all the compounds, which were significantly higher than the sum by single magnetically immobilized cells and electrode reaction at the optimal voltage. Recycling experiments demonstrated that the degradation activity of coupling system increased gradually during eight recycles, indicating that there was a coupling effect between the biodegradation and electrode reaction. Phenol hydroxylase and qPCR assays confirmed that appropriate electrical stimulation could improve phenol hydroxylase activity and promote cells growth. Toxicity assessment suggested the treatment of the coking wastewater by coupling system led to less toxicity than untreated wastewater.

Topics: Benzofurans; Biodegradation, Environmental; Carbazoles; Cells, Immobilized; Coke; Comamonas; Electrodes; Graphite; Iron; Magnetics; Mixed Function Oxygenases; Phenol; Thiophenes; Waste Disposal, Fluid; Wastewater

A naphthalene-utilizing bacterium, Arthrobacter sp. W1, was used to investigate the cometabolic degradation of carbazole (CA), dibenzofuran (DBF) and dibenzothiophene (DBT) using naphthalene as the primary substrate. Both the growing and washed cells of strain W1 could degrade CA, DBF, DBT, and naphthalene simultaneously and quickly. Inhibition kinetics confirmed that the presence of CA, DBF and DBT in the growing system would inhibit the cells growth and biodegradability of strain W1. The relationship between ln(C/C0) and time, and specific degradation rate and CA, DBF and DBT concentration could be described well by First-order and Michaelis-Menten kinetics. The treatment of real coking wastewater containing high concentration of phenol, naphthalene, CA, DBF, DBT and NH3-N was shown to be highly efficient by naphthalene-grown W1 coupling with activation zeolite. Toxicity assessment indicated the treatment of the coking wastewater by strain W1 coupling with activation led to less toxicity than untreated wastewater.

Topics: Arthrobacter; Benzofurans; Biodegradation, Environmental; Carbazoles; Coke; Kinetics; Naphthalenes; Thiophenes; Time Factors; Toxicity Tests; Vibrio; Wastewater; Water Pollutants, Chemical

In this study, the cometabolic degradation of carbazole (CA), dibenzofuran (DBF), and dibenzothiophene (DBT) by immobilized Arthrobacter sp. W1 cells pregrown with naphthalene was investigated. Four kinds of polymers were evaluated as immobilization supports for strain W1. After comparison with agar, alginate, and κ-carrageenan, gellan gum was selected as the optimal immobilization support. Furthermore, magnetic Fe₃O₄ nanoparticle was selected as most suitable nanoparticle for immobilization and the optimal concentration was 80 mg/L. The relationship between specific degradation rate and the initial concentration of CA, DBF and DBT was described well by Michaelis-Menten kinetics. The recycling experiments demonstrated that the magnetically immobilized cells coupling with activation zeolite showed highly bioremediation activity on the coking wastewater containing high concentration of phenol, naphthalene, CA, DBF and DBT during seven recycles. Toxicity assessment indicated the treatment of the coking wastewater by magnetically immobilized cells with activation zeolite led to less toxicity than untreated wastewater.

Topics: Arthrobacter; Benzofurans; Biodegradation, Environmental; Carbazoles; Cells, Immobilized; Coke; Kinetics; Nanoparticles; Polysaccharides, Bacterial; Thiophenes; Waste Disposal, Fluid; Wastewater; Water Pollutants, Chemical

An efficient three-step approach was developed to assemble indole- or benzofuran-fused benzocarbazole-1,4-diones in 42-53% overall yield. This approach includes AgOAc-promoted oxidative cyclization of 2,6-di-bromocyclohexene-1,4-dione with indol-3-ylpropanoid acid, condensation of the resulting bromocarbazole intermediates with phenols or anilines, followed by Pd(OAc)-catalyzed cyclization. Such convenient synthetic protocol and the novelty of the corresponding products will largely assist our drug design and development program.

Topics: Benzofurans; Carbazoles; Catalysis; Cyclization; Indoles

A combination of multireference CASSCF/CASPT2 and time-dependent DFT (TD-B3P86) theoretical treatments was employed to test their predictions against recently proposed assignments of the vacuum-UV spectra of fluorene and its three heteroanalogues-dibenzofuran, carbazole, and dibenzothiophene-up to the ionization threshold. For the low-lying transitions, the theoretically based assignments are generally not problematic because of the well-resolved bands, although, even in this region, the two methods yield some opposing predictions. Further on toward the vacuum region, the assignments prove increasingly challenging because of predicted crowding of transitions, many of which exhibit significant intensity. Some of the transitions in this region and beyond-toward the ionization thresholds-are thus necessarily assigned only tentatively. Overall, the two methods are frequently found to complement each other well, and equivalent transitions usually appear as bracketed from the high- (CASPT2) and low- (TD-B3P86) energy sides.

Topics: Benzofurans; Carbazoles; Electrons; Fluorenes; Quantum Theory; Thiophenes; Time Factors

A carbazole-utilizing bacterium was isolated by enrichment from petroleum-contaminated soil. The isolate, designated Sphingomonas sp. strain XLDN2-5, could utilize carbazole (CA) as the sole source of carbon, nitrogen, and energy. Washed cells of strain XLDN2-5 were shown to be capable of degrading dibenzofuran (DBF) and dibenzothiophene (DBT). Examination of metabolites suggested that XLDN2-5 degraded DBF to 2-hydroxy-6-(2-hydroxyphenyl)-6-oxo-2,4-hexadienic acid and subsequently to salicylic acid through the angular dioxygenation pathway. In contrast to DBF, strain XLDN2-5 could transform DBT through the ring cleavage and sulfoxidation pathways. Sphingomonas sp. strain XLDN2-5 could cometabolically degrade DBF and DBT in the growing system using CA as a substrate. After 40 h of incubation, 90% of DBT was transformed, and CA and DBF were completely removed. These results suggested that strain XLDN2-5 might be useful in the bioremediation of environments contaminated by these compounds.

Topics: Base Sequence; Benzofurans; Biodegradation, Environmental; Carbazoles; Chromatography, High Pressure Liquid; Environmental Pollutants; Mass Spectrometry; Molecular Sequence Data; RNA, Ribosomal, 16S; Sequence Analysis, DNA; Spectrophotometry, Ultraviolet; Sphingomonas; Thiophenes

Pseudomonas sp. strain C3211 was isolated from a temperate climate soil contaminated with creosote. This strain was able to degrade carbazole, dibenzothiophene and dibenzofuran at 10 degrees C with acetone as a co-substrate. When dibenzothiophene was degraded by strain C3211, an orange compound, which absorbed at 472 nm, accumulated in the medium. Degradation of dibenzofuran was followed by accumulation of a yellowish compound, absorbing at 462 nm. The temperature optimum of strain C3211 for degradation of dibenzothiophene and dibenzofuran was at 20 to 21 degrees C, while the maximum temperature for degradation was at 27 degrees C. Both compounds were degraded at 4 degrees C. Degradation at 10 degrees C was faster than degradation at 25 degrees C. This indicates that strain C3211 is adapted to life at low temperatures.

Topics: Benzofurans; Biodegradation, Environmental; Carbazoles; Carcinogens; Molecular Structure; Pseudomonas; Temperature; Thiophenes; Time Factors

Bacterial samples were collected from three marine beaches in coastal Newfoundland, Canada, and enriched by growth on 1-methylnaphthalene. The most prominent bacterial cell type for each consortium was isolated in a serial dilutions test, and a substrate utilization profile was obtained for each using the Biolog MicroStation System. Each bacterial community was tested for its ability to co-metabolize sulfur heterocycles (benzothiophene: BT, 3-methylbenzothiophene: 3-MBT, and dibenzothiphene: DBT), a nitrogen heterocycle (carbazole: CARB), and an oxygen heterocycle (dibenzofuran: DBF). Co-metabolism of the starting material was determined using gas chromatography-mass spectroscopy (GC-MS), and formation of products was investigated by GC-MS and Fourier transform infrared (FTIR) spectroscopy. Bacterial growth was monitored turbidimetrically to determine the dry weight (microgram) of cells/ml. The 2-ringed heterocycles were co-metabolized faster and to a greater extent than the 3-ringed compounds. Co-metabolism of BT was not statistically different from that for 3-MBT and, likewise, a comparison of the 3-ringed heterocycles showed no significant differences in degradation rates. Statistical examination showed that no one culture demonstrated a significantly greater ability to co-metabolize the heterocycles studied. This study represents the first comprehensive investigation of the ability of local bacteria to co-metabolize a range of aromatic compounds and provides a preliminary understanding of their fate in sediments should contamination by these compounds occur.

Topics: Aerobiosis; Benzofurans; Biodegradation, Environmental; Carbazoles; Ecosystem; Gas Chromatography-Mass Spectrometry; Gram-Negative Bacteria; Heterocyclic Compounds; Newfoundland and Labrador; Nitrogen; Oxygen; Seawater; Spectroscopy, Fourier Transform Infrared; Sulfur; Thiophenes

The UV absorption spectra structures of carbazole, fluorene and dibenzofurane are studied using the atom monopole-dipole interaction (AMDI) model and atomic dipolar polarisabilities and effective charge given by Fraga. The absorption spectra corresponding to these molecules and their self-associations are presented. The original obtained results are discussed and compared to previous works.

Topics: Benzofurans; Carbazoles; Fluorenes; Molecular Structure; Spectrophotometry, Ultraviolet

A method for bioremediation of chlorinated dibenzo-p-dioxins (CDDs) and dibenzofurans (CDFs) by a carbazole-utilizing bacterium, Pseudomonas sp. strain CA10, was developed. CA10 cells transferred to carbon- and nitrogen-free mineral medium supplemented with 1 mg carbazole (CAR)/ml grew rapidly during the first 2 days; and the cells at the end of this rapid growth period showed the highest 2,3-dichlorodibenzo-p-dioxin (2,3-Cl2DD)-degrading activity. The CA10 cells pregrown for 2 days efficiently degraded 2,3-Cl2DD in aqueous solution at either 1 ppm or 10 ppm. The effect of inoculum density on the efficiency of 2,3-Cl2DD degradation was investigated in a soil slurry microcosm [ratio of soil:water = 1:5 (w/v)]. The results showed that a single inoculation with CA10 cells at densities of 10(7) CFU/g soil and 10(9) CFU/g soil degraded 46% and 80% of 2,3-Cl2DD, respectively, during the 7-day incubation. The rate of degradation of each CDD congener, 2-ClDD, 2,3-Cl2DD, and 1,2,3-Cl3DD (1 ppm each) by strain CA10 in the soil slurry system was not significantly influenced by the coexistence of the other congeners. Using this soil slurry system, we tried an experimental bioremediation of the actual dioxin-contaminated soil, which contained mainly tetra- to octochlorinated dioxins. Although the degradation rate of total CDD and CDF congeners by a single inoculation with CA10 cells was 8.3% after a 7-day incubation, it was shown that strain CA10 had a potential to degrade tetra- to hepta-chlorinated congeners including the most toxic compound, 2,3,7,8-tetrachlorinated dibenzo-p-dioxin.

Topics: Benzofurans; Biodegradation, Environmental; Biotechnology; Carbazoles; Culture Media; Dioxins; Pseudomonas; Soil Pollutants

The solubilizing effect of humic acids on fluorene and its NSO analogues carbazole, dibenzofuran and dibenzothiophene has been studied. The interaction between these substances and humic acids was found to depend significantly on the actual humic acid concentration. A pronounced decrease in the interaction constant, as well as in the water-organic matter partitioning coefficient was observed with increasing humic acid concentration. The effects are discussed in terms of concentration dependent macromolecular structural changes in the humic acids. A linear free energy relation for the interaction is suggested.

Topics: Benzofurans; Carbazoles; Carbon; Chemical Phenomena; Chemistry, Physical; Fluorenes; Fresh Water; Humic Substances; Solubility; Thiophenes; Water Supply