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This work highlights the literature of one of the most valuable moieties in the field of organic chemistry. In this review, the chemistry of tetronic acid as a simple precursor to privileged heterocyclic motifs is described. The synthetic procedures of different fused heterocycles incorporating a furan moiety are described. Fused heterocycles are classified as bicyclic, tricyclic, tetracyclic and spiro-fused pyran derivatives.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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A new series of novel Podophyllotoxin-like benzo[b]furo[3,4-e][1,4]diazepin-1-ones possessing structural elements of 4-aza-2,3-didehydropodophyllotoxins with central diazepine ring was designed and synthesized as anti-cancer agents. In initial assessment, the cytotoxic activity of the synthesized compounds was evaluated against three cancer cell lines including MCF-7, PC3 and B16-F10 employing the MTT assay. Some of compounds (12h, 13a, 13c and 14b) showed significant cytotoxic activity. So, we investigated the cytotoxicity of compounds 12h, 13a, 13c and 14b, along with podophyllotoxin as the reference drug in different cancer cell lines including A549, A2780, DU145, HeLa, and normal Huvec cell line. Among these four compounds, 13c showed promising antiproliferative activity against all cancer cells stronger than the other compounds and comparable to reference drug podophyllotoxin in some cancer cells. All these four compounds did not show significant cytotoxicity on normal Huvec cell line. The flow cytometry analysis of the MCF-7, PC3 and A2780 human cancer cell lines treated with 13c showed that 13c, induced apoptosis in the MCF-7, PC3 and A2780 human cancer cell lines, which is in good agreement to its cytotoxic activity as well. Compound 13c did not show significant influence on tubulin assembly and exert its cytotoxic effects via induction of apoptosis and has potent and selective cytotoxic effects in cancer cells.

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Tetrahydrofuran – Wikipedia,
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Synthesis of mono-trifluoromethylated saturated cycles has emerged as an important research area that has previously received little attention in reviews. This review illustrates a variety of reagents available for direct trifluoromethylation of non-fluorinated cycles, and various CF3-containing synthetic building blocks that may be incorporated into the cyclic compounds. Direct trifluoromethylation has been dominated by the use of TFMTMS on cyclic ketones and lactones because of its simplicity. The more widely applicable approach is that of converting readily available simple trifluoromethylated compounds into a variety of cycles. Here, the Diels-Alder reactions and 1,3- dipolar cycloadditions of the trifluoromethylated alkenes are of significant value. Many mono-trifluoromethylated saturated cycles are accessible from trifluoromethylated carbonyl compounds by a number of multiple-step synthetic routes. It is hoped that this Report will help guide synthetic chemists who are not organo-fluorine specialists to develop synthetic routes to trifluoromethylsubstituted saturated cycles.

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Tetrahydrofuran – Wikipedia,
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equation presented A convergent method has been found to prepare 4-aza-2,3-didehydropodophyllotoxin and derivatives in a one-pot procedure. The mechanism of the reaction between tetronic acid, anilines, and benzaldehydes is discussed.

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Tetrahydrofuran – Wikipedia,
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(S,S)- or (R,R)-Naph-diPIM-dioxo-i-Pr-CpRu(II) complex with a Bronsted acid catalyzes dehydrative intermolecular C-allylation with high enantio- and regioselectivity. The new soft Ru/hard H+ combined catalyst can also be used for intramolecular C-, N-, and O-allylations, giving nearly enantiomerically pure alpha-alkenyl-substituted cyclic compounds. As water is only the co-product, the synthetic process can be readily scaled up. Georg Thieme Verlag Stuttgart New York.

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A series of 3-oxo-C12-HSL, tetramic acid, and tetronic acid analogues were synthesized to gain insights into the structural requirements for quorum sensing inhibition in Staphylococcus aureus. Compounds active against agr were noncompetitive inhibitors of the autoinducing peptide (AIP) activated AgrC receptor, by altering the activation efficacy of the cognate AIP-1. They appeared to act as negative allosteric modulators and are exemplified by 3-tetradecanoyltetronic acid 17, which reduced nasal cell colonization and arthritis in a murine infection model.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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The aim of this study was the synthesis and lead structure selection of a best anti-leukemic agent from a library of aza-podophyllotoxin analogues (APTs). To this end, we report a scalable, modified multicomponent reaction using a “sacrificial” aniline partner as a more general route to rapidly construct the pivotal library of 50 APT analogues. Our preliminary structure activity relationship studies for anti-leukemic activity also address the innate toxicity of these compounds against non-malignant cells. As a result, we identified 2 novel compounds 2ca? and 2jc? more potent than etoposide 1 (25-60 fold) having high selectivity against the human THP-1 leukemia cell line and a minimal toxicity (IC50 of 9.3 ± 0.8 and 19.6 ± 1.4 nM respectively) which represent the best candidates for further pharmacological optimization.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Abstract: An enviro-economic protocol has been described for the synthesis of bis-tetronic acids by pseudo-three-component condensation between aldehydes/isatins and tetronic acid using sulfamic acid as a solid acid catalyst. Easy commercial availability of the catalyst at extremely low cost, excellent yields and avoidance of conventional purification procedures are the main merits of this energy efficient protocol. Graphical Abstract: [Figure not available: see fulltext.]

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Pyridine-functionalized MCM-41 catalyzed reactions between tetracyanoethylene and various activated CH-acid compounds are described. These reactions afford the corresponding pyran annulated heterocyclic ring systems in high yields at room temperature within a few minutes. The work-up procedure is very simple and the products do not require further purification. The catalyst can be recycled and reused for several times without observable loss of performance.

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Tetrahydrofuran – Wikipedia,
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In the last years, the honeybee population is facing growing threats such as expansion of pathogens, incorrect use of phytosanitary products and environmental contaminants, loss or fragmentation of habitat, invasive species and climate change. The citrus cropping by Integrated Pest Management (IPM) in Spain combines strategies to reduce pest populations preventing environmental problems and reducing levels of damage by using chemicals only when it is strictly necessary. The goal of this study is to develop a simple analytical method to evaluate pesticide residue levels in honeybees and corbicular pollen when honeybees are exposed to plant protection products (PPPs) used in integrated pest management citrus orchards. The proposed method is based in an ultrasound assisted extraction procedure followed by a dispersive solid phase extraction (d-SPE) clean-up with alumina and LC-MS/MS pesticides determination. The method was validated in samples of honeybee and corbicular pollen for 10 pesticides commonly used in citrus orchards under IPM. This procedure was compared with QuEChERS methodologies for these matrices. The developed method was applied to determine pesticides in both matrices in a two -year study in citrus orchards.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem