benzofurans and furan

The collapse of the World Trade Center (WTC) on September 11, 2001 released a dust cloud containing numerous environmental contaminants, including polychlorinated dibenzo-para-dioxins and polychlorinated dibenzofurans (PCDD/Fs). PCDD/Fs are toxic and are associated with numerous adverse health outcomes including cancer, diabetes, and impaired reproductive and immunologic function. Prior studies have found adults exposed to the WTC disaster to have elevated levels of PCDD/Fs. This is the first study to assess PCDD/F levels in WTC-exposed children.. This analysis includes 110 participants, a subset of the 2014-2016 WTC Adolescent Health Study, a group of both exposed youths who lived, attended school, or were present in lower Manhattan on 9/11 recruited from the WTC Health Registry (WTCHR) and unexposed youths frequency matched on age, sex, race, ethnicity, and income. Our sample was selected to maximize the contrast in their exposure to dust from the WTC collapse. Questionnaire data, including items about chronic home dust and acute dust cloud exposure, anthropometric measures, and biologic specimens were collected during a clinic visit. Serum PCDD/F concentrations were measured according to a standardized procedure at the New York State Department of Health Organic Analytical Laboratory. We used multivariable linear regression to assess differences in PCCD/Fs between WTCHR and non-WTCHR participants. We also compared mean and median PCDD/F and toxic equivalency (TEQ) concentrations in our cohort to 2003-4 National Health and Nutrition Examination Survey (NHANES) levels for youths age 12-19.. Median PCDD/F levels were statistically significantly higher among WTCHR participants compared to non-WTCHR participants for 16 out of 17 congeners. Mean and median TEQ concentrations in WTCHR participants were >7 times those in non-WTCHR participants (72.5 vs. 10.1 and 25. 3 vs. 3.39pg/g lipid, respectively). Among WTCHR participants, median concentrations of several PCDD/Fs were higher than the NHANES 95th percentiles. After controlling for dust cloud exposure, home dust exposure was significantly associated with higher PCDD/F level.. Adolescents in lower Manhattan on the day of the WTC attack and exposed to particulate contamination from the WTC collapse had significantly elevated PCDD/F levels >12years later compared to a matched comparison group, driven by chronic home dust exposure rather than acute dust cloud exposure. PCDD/F and TEQ levels substantially exceeded those in similar-aged NHANES participants. Future studies are warranted to explore associations of PCDD/Fs with health and developmental outcomes among individuals exposed to the WTC disaster as children.

Topics: Adolescent; Benzofurans; Case-Control Studies; Dibenzofurans, Polychlorinated; Dioxins; Disasters; Dust; Female; Furans; Humans; Male; New York; Nutrition Surveys; Polychlorinated Biphenyls; Polychlorinated Dibenzodioxins; September 11 Terrorist Attacks; Young Adult

Topics: Acetamides; Benzofurans; Benzophenones; Copper; Cyclization; Furans; Oxidation-Reduction

High-accuracy molecular orbital calculation has been performed to investigate the atmospheric oxidation reaction of 2,3,7,8-tetrachlorodibenzofuran (2,3,7,8-TeCDF) initiated by the OH radical in the presence of O(2) and NO/H(2)O. The possible channels involved in the reaction are discussed, and the favorable reaction pathways are revealed. The degradation occurs easily once the OH radical initiates the reaction. Two aspects need to be mentioned: one is that H(2)O in atmosphere is a source of OH radical which will initiate a new round of degradation and improve the degradation efficiency; the other is that the furan ring of 2,3,7,8-TeCDF can be turned into dioxin ring, which may explain the experimental hypothesis that polychlorodibenzofurans can be transformed to polychlorodibenzo-p-dioxins. Rate constants of the elementary reactions are calculated over a temperature range of 250-400K. Arrhenius formulas are fitted and the atmospheric lifetimes of reaction species in the troposphere are discussed for the first time, which can be applied to the study on the model simulation and the management of the hazardous materials.

Topics: Air Pollutants; Atmosphere; Benzofurans; Computer Simulation; Dioxins; Furans; Hydroxyl Radical; Kinetics; Models, Chemical; Nitric Oxide; Oxidation-Reduction; Oxygen; Polychlorinated Dibenzodioxins; Water

Many benzo[b]furan lignans are known to be biologically active in nature. 2-(3'-Methoxy-4'-hydroxy-phenyl)-5-(3-hydroxypropyl)-7-methoxy-benzo[b]furan-3-carbaldehyde (XH-14) is found as a bioactive component isolated from the plant Salvia miltiorrhiza, commonly known as Danshen, which is a traditional Chinese medicine that is used as a cardiovascular medication. This study examined whether 3 different XH-14 derivatives can inhibit adipocyte differentiation and induction of the adipokines visfatin and resistin in 3T3-L1 adipocytes. Adipocytes were cultured and differentiated in Dulbecco's modified Eagle medium containing fetal bovine serum, 3-isobytyl-1-methylxanthine, dexamethasone, and insulin for 6-8d in the absence and presence of 1-25μM XH-14-derived benzo[b]furan derivatives. Nontoxic 2-(3'-methoxy-4'-hydroxy-phenyl)-6-(3-hydroxypropyl)-5-methoxy-benzo[b]furan (5-MBF) at ≥5μM attenuated cellular lipid accumulation and down-regulated induction of peroxisome proliferator activated receptors γ (PPARγ) and CCAAT enhancer binding protein α (C/EBPα) in a dose-dependent manner, as evidenced by Oil Red O staining and Western blot analysis. Such inhibition of PPAR( and C/EBP( by 5-MBF was achieved at transcriptional mRNA levels. However, 2-(3'-methoxy-4'-hydroxy-phenyl)-5-(3-hydroxypropyl)-7-methoxy-benzo[b]furan (7-MBF) and 2-(3'-methoxy-4'-hydroxy-phenyl)-5-(3-hydroxypropyl)-7-methoxy-benzo[b]furan (6-MBF) had minimal effects on adipogenic differentiation, suggesting a structure-activity relationship of methoxybenzo[b]furan derivatives as an inhibitor of adipogenic differentiation. Furthermore, ≥5μM 5-MBF retarded protein and mRNA expression of proinflammatory and insulin resistance-enhancing adipokines of visfatin and resistin in differentiated adipocytes. Induction of visfatin and resistin was, at least in part, mediated via adipocyte differentiation-associated activation of PPARγ signal targeting adipocyte protein 2 and stearoyl-CoA desaturase. These results demonstrate that the 2-(3'-methoxy-4'-hydroxy-phenyl)-3-hydroxypropyl benzo[b]furan lignan, with a methoxy group at the 5-position on the benzene ring, may be a promising agent for disturbance of adipogenic differentiation and for blockage of obesity-associated inflammatory and metabolic diseases.

Topics: 3T3-L1 Cells; Adipocytes; Adipogenesis; Adipokines; Animals; Benzene; Benzofurans; CCAAT-Enhancer-Binding Protein-alpha; Cell Survival; Enzyme Induction; Furans; Gene Expression Regulation, Enzymologic; Guaiacol; Inflammation; Lipid Metabolism; Mice; Nicotinamide Phosphoribosyltransferase; PPAR gamma; Resistin; Salvia miltiorrhiza; Structure-Activity Relationship

Concise diastereoselective syntheses of the marine (+/-)-panacene and terrestrial (+/-)-desbromopanacene have been achieved in a few steps based on a concept of "aromatic ring umpolung". The synthetic avenue to the (+/-)-panacene involved a novel oxymercuration strategy to produce the correct configuration of the bromoallene moiety.

Topics: Alkadienes; Benzofurans; Biological Products; Furans; Molecular Structure

A series of benzofuran-2-yl-(phenyl)-3-pyridylmethanol derivatives were prepared using an efficient 1-step procedure in good yields. In addition furan-2-yl-(phenyl)-3-pyridylmethanol derivatives were also prepared to determine the effect of the benzene ring in benzofuran with respect to inhibitory activity. The pyridylmethanol derivatives were all evaluated in vitro for inhibitory activity against aromatase (P450(AROM), CYP19), using human placental microsomes. The benzofuran-2-yl-(phenyl)-3-pyridylmethanol derivatives showed good to moderate activity (IC50 = 1.3-25.1 microM), which was either better than or comparable with aminoglutethimide (IC50 = 18.5 microM) but lower than arimidex (IC50 = 0.6 microM), with the 4-methoxyphenyl substituted derivative displaying optimum activity. Molecular modelling of the benzofuran-2-yl-(4-fluorophenyl)-3-pyridylmethanol derivative suggested activity to reside with the (S)-enantiomer. The furan-2-yl-(phenyl)-3-pyridylmethanol derivatives were devoid of activity indicating the essential role of the benzene ring of the benzofuran component for enzyme binding.

Topics: Aromatase; Aromatase Inhibitors; Benzofurans; Enzyme Inhibitors; Furans; Humans; Inhibitory Concentration 50; Magnetic Resonance Spectroscopy; Methanol; Microsomes; Models, Chemical; Models, Molecular; Placenta; Protein Binding; Protons; Software; Temperature

Topics: Acetoacetates; Alkanesulfonates; Benzofurans; Curare; Furans; Tubocurarine

Topics: Anti-Bacterial Agents; Benzofurans; Diphtheria; Diphtheria Toxin; Furans; Tetanus

Topics: Benzofurans; Furans; Lichens; Usnea

Topics: Benzofurans; Furans

Topics: Benzofurans; Furans; Humans; Virus Diseases

Topics: Anti-Bacterial Agents; Bacteria; Benzofurans; Furans; Lichens

Topics: Anti-Bacterial Agents; Bacteria; Benzofurans; Furans; Lichens; Structure-Activity Relationship

Topics: Acids; Benzofurans; Furans

Topics: Acids; Benzofurans; Furans

Topics: Acids; Anti-Bacterial Agents; Bacteria; Benzofurans; Furans

Topics: Acids; Benzofurans; Furans; Humans; Skin Diseases; Skin Diseases, Bacterial

Topics: Acids; Anti-Bacterial Agents; Bacteria; Benzofurans; Furans; Humans

Topics: Acids; Benzofurans; Furans; Humans; Lichens; Tuberculosis; Tuberculosis, Pulmonary

Topics: Anti-Bacterial Agents; Bacteria; Benzofurans; Furans; Lichens

Topics: Acids; Benzofurans; Dihydrostreptomycin Sulfate; Furans; Guinea Pigs; Streptomycin; Tuberculosis

Topics: Benzofurans; Furans; Mycobacterium tuberculosis; Tuberculosis

Topics: Bacteria; Benzofurans; Furans; In Vitro Techniques; Plants