Awesome Chemistry Experiments For 6-Fluoroisobenzofuran-1(3H)-one

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3-Nitroindenoisoquinoline human topoisomerase IB (Top1) poisons have potent antiproliferative effects on cancer cells. The undesirable nitro toxicophore could hypothetically be replaced by other functional groups that would retain the desired biological activities and minimize potential safety risks. Eleven series of indenoisoquinolines bearing 3-nitro bioisosteres were synthesized. The molecules were evaluated in the Top1-mediated DNA cleavage assay and in the National Cancer Institute’s 60 cell line cytotoxicity assay. The data reveal that fluorine and chlorine may substitute for the 3-nitro group with minimal loss of Top1 poisoning activity. The new information gained from these efforts can be used to design novel indenoisoquinolines with improved safety.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1525O – PubChem

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A series of 11-[4-(cinnamyl)-1-piperazinyl]-6,11-dihydrodibenz[b,e]oxepins and related compounds were synthesized and evaluated for their protective activities against complete ischemia, normobaric hypoxia, lipidperoxidation and convulsion. Structure-activity relationship studies of this series led to the finding of (E)-1-(3-fluoro-6,11-dihydrodibenz[b,e]oxepin-11-yl)-4-(3-phenyl-2-prop enyl)piperazine dimaleate (50), AJ-3941 with the most appropriate property for combined pharmacological activities. Compound 50 also shows an inhibitory effect against cerebral edema as well when orally given to rats.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1532O – PubChem

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A new catalytic system that employs water as an environmentally friendly solvent for the dehydrogenative oxidation of alcohols and lactonization of diols has been developed. In this catalytic system, a water-soluble dicationic iridium complex having a functional ligand that comprises alpha-hydroxypyridine and 4,5-dihydro-1H-imidazol-2-yl moieties exhibits high catalytic performance. For example, the catalytic dehydrogenative oxidation of 1-phenylethanol in the presence of 0.25 mol % of the iridium catalyst and base under reflux in water proceeded to give acetophenone in 92% yield. Additionally, under similar reaction conditions, the iridium-catalyzed dehydrogenative lactonization of 1,2-benzenedimethanol gave phthalide in 98% yield.

Sometimes chemists are able to propose two or more mechanisms that are consistent with the available data. Application In Synthesis of 6-Fluoroisobenzofuran-1(3H)-one, If a proposed mechanism predicts the wrong experimental rate law, however, the mechanism must be incorrect.Welcome to check out more blogs about 23932-84-5, in my other articles.

Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1539O – PubChem

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DC-SIGN is a cell-surface receptor for several pathogenic threats, such as HIV, Ebola virus, or Mycobacterium tuberculosis. Multiple attempts to develop inhibitors of the underlying carbohydrate?protein interactions have been undertaken in the past fifteen years. Still, drug-like DC-SIGN ligands are sparse, which is most likely due to its hydrophilic, solvent-exposed carbohydrate-binding site. Herein, we report on a parallel fragment screening against DC-SIGN applying SPR and a reporter displacement assay, which complements previous screenings using 19F NMR spectroscopy and chemical fragment microarrays. Hit validation by SPR and 1H?15N HSQC NMR spectroscopy revealed that although no fragment bound in the primary carbohydrate site, five secondary sites are available to harbor drug-like molecules. Building on key interactions of the reported fragment hits, these pockets will be targeted in future approaches to accelerate the development of DC-SIGN inhibitors.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1524O – PubChem

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The direct carboxylation of benzoxasiloles with carbon dioxide proceeded smoothly under mild conditions using copper iodide as a catalyst to afford phthalides after an acid work-up. Broad substrate scope and application of this methodology for the synthesis of natural products highlight the synthetic utility of this protocol.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1533O – PubChem

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A HIGH-YIELDING SYNTHESIS OF 3-CYANOPHTHALIDES

Dehydration, with dicyclohexylcarbodiimide, of the cyanohydrins derived from the ring open tautomers of the 3-hydroxyphthalides (4) provides an efficient synthesis of 3-cyanophthalides (8a) and its derivatives (8b-f).

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H1535O – PubChem

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Site-Selective Functionalization of (sp3)C?H Bonds Catalyzed by Artificial Metalloenzymes Containing an Iridium-Porphyrin Cofactor

The selective functionalization of one C?H bond over others in nearly identical steric and electronic environments can facilitate the construction of complex molecules. We report site-selective functionalizations of C?H bonds, differentiated solely by remote substituents, catalyzed by artificial metalloenzymes (ArMs) that are generated from the combination of an evolvable P450 scaffold and an iridium-porphyrin cofactor. The generated systems catalyze the insertion of carbenes into the C?H bonds of a range of phthalan derivatives containing substituents that render the two methylene positions in each phthalan inequivalent. These reactions occur with site-selectivity ratios of up to 17.8:1 and, in most cases, with pairs of enzyme mutants that preferentially form each of the two constitutional isomers. This study demonstrates the potential of abiotic reactions catalyzed by metalloenzymes to functionalize C?H bonds with site selectivity that is difficult to achieve with small-molecule catalysts.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H1528O – PubChem

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Synthesis of chiral 3-substituted phthalides by a sequential organocatalytic enantioselective aldol-lactonization reaction. Three-step synthesis of (S)-(-)-3-butylphthalide

(Chemical Equation Presented) The development of efficient methods for the facile construction of important molecular frameworks is an important goal in organic synthesis. Chiral 3-substituted phthalides are widely distributed in a large collection of natural products with broad, potent, and potentially path-pointing biological activities. In this investigation, we have uncovered an unprecedented organocatalytic asymmetric aldol-lactonization reaction of 2-formylbenzoic esters with ketones/aldehydes for convenient construction of the enantioenriched “privileged” scaffold. As a result of the sensitive nature of substrate structures of an organocatalytic enantioselective aldol reaction, after extensive optimization of reaction conditions, catalyst L-prolinamide alcohol IV is identified as the best promoter. Interestingly, it is found that in this reaction, addition of an acid additive PhCO2H can significantly enhance reaction efficiency with use of only as low as 2.5 mol % IV for the process. Moreover, due to the sensitivity of reaction conditions toward a sequential aldol-lactonization process without affecting enantioselectivity and racemization, it is essential to remove the catalyst for the subsequent facile lactonization reaction in the presence of K 2CO3. The aldol-lactonization processes serve as a powerful approach to the preparation of synthetically and biologically important 3-substitued phthalides with a high level of enantioselectivities. A 3-step catalytic asymmetric synthesis of the natural product of 3-butylphthalide is reported.

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Reference£º
Benzofuran – Wikipedia,
Benzofuran | C8H1540O – PubChem