Final Thoughts on Chemistry for Benzo[b]furan-2-carboxaldehyde

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Trifluoromethylation of Secondary Nitroalkanes

Using a commercially available Umemoto’s reagent, the metal-free trifluoromethylation of nitroalkanes is now possible. This method provides a general, high-yielding synthesis of alpha-(trifluoromethyl)nitroalkanes. The quaternary alpha-(trifluoromethyl)nitroalkanes obtained from this transformation can be elaborated to a variety of complex nitrogen-containing molecules, including alpha-(trifluoromethyl)amines.

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Benzofuran – Wikipedia,
Benzofuran | C8H828O – PubChem

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Novel Terminal Bipheny-Based Diapophytoene Desaturases (CrtN) Inhibitors as Anti-MRSA/VISR/LRSA Agents with Reduced hERG Activity

CrtN has been identified as an attractive and druggable target for treating pigmented Staphylococcus aureus infections. More than 100 new compounds were synthesized, which target the overwhelming the defects of the CrtN inhibitor 1. Analogues 23a and 23b demonstrated a significant activity against pigmented S. aureus Newman and 13 MRSA strains (IC50 = 0.02-10.5 nM), along with lower hERG inhibition (IC50 > 30 muM, ?10-fold decrease in comparison with 1). Furthermore, 23a and 23b were confirmed to reduce the staphylococcal load in the kidney and heart in a mouse model with normal treatment deeper than pretreatment ones, comparable even with vancomycin and linezolid. Remarkably, 23a could strongly block the pigment biosynthesis of these nine multidrug-resistant MRSA strains, including excellent activity against LRSA strains and VISA strains in vivo, and all of which demonstrated that 23a has a huge potential against intractable MRSA, VISA, and LRSA issues as a therapeutic drug.

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Benzofuran – Wikipedia,
Benzofuran | C8H916O – PubChem

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Synthesis and SAR study of novel amidino 2-substituted benzimidazoles as potential antibacterial agents

A series of novel 2-substituted benzimidazole derivatives were synthesized and their antibacterial activity was assessed against selected Gram-positive and Gram-negative bacteria. The specific moiety at the 2-position of the benzimidazole was extensively modified with several fused heterocyclic functional groups containing nitrogen and sulfur heteroatoms. In addition, the influence of different amidino groups at the position 5 of benzimidazole scaffold was evaluated. The values of clogP (a partition coefficient) and clogD7.5 (calculated distribution coefficient, pH 7.5) were determined and the lipophilic character of compounds has been found to be important parameter for the observed activity of the tested benzimidazole derivatives against Moraxella catarrhalis. The indolo 2-substituted benzimidazole 13a demonstrated solid activity against Staphylococcus aureus (MICs 16 mug/mL) and Moraxella catarralis (MICs 2 mug/mL) and represents promising lead molecule for further optimization.

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Benzofuran – Wikipedia,
Benzofuran | C8H999O – PubChem

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Synthesis of benzofuro[3,2-f]phthalazine derivatives

The reaction of hydrazine with dibenzofuran-1,2-dicarboxylic anhydrides followed by treatment with acetic acid resulted in the formation of 1,4-dioxo-1,2,3,4-tetrahydrobenzofuro[3,2-f]phthalazines. Dibenzofuran-1,2-dicarboxylic anhydrides were prepared by the Diels-Alder reaction of 2-alkenyl benzofurans and maleic anhydride followed by oxidative aromatization. Chlorination of 1,4-dioxo-1,2,3,4-tetrahydrobenzofuro[3,2-f]phthalazines and subsequent nucleophilic substitution afforded 1,4-dialkoxybenzofuro[3,2-f]phthalazines. These compounds were subjected to cytotoxicity assay against L1210 mice leukemia as analogues of methoxyellipticines.

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Benzofuran – Wikipedia,
Benzofuran | C8H910O – PubChem

The important role of Benzo[b]furan-2-carboxaldehyde

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Catalytic Redox Chain Ring Opening of Lactones with Quinones to Synthesize Quinone-Containing Carboxylic Acids

Catalytic ring opening of five- to eight-membered lactones with quinones is achieved through a redox chain mechanism. With low loading of a simple metal triflate Lewis acid catalyst and a chain initiator, C-H bonds of many quinones were efficiently functionalized with carboxylic acid-containing side chains. This method also features 100% atom economy and wide substrate scope. A novel route to the anti-asthma drug Seratrodast was developed. Mechanism study suggests that the redox chain reaction likely undergoes a carbocation intermediate.

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Benzofuran – Wikipedia,
Benzofuran | C8H1114O – PubChem

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P(i-PrNCH2CH2)3N: an efficient catalyst for TMS-1,3-dithiane addition to aldehydes

Herein we report the use of commercially available P(i-PrNCH2CH2)3N (1a) as an efficient catalyst for 2-trimethylsilyl-1,3-dithiane (TMS-dithiane) addition to aldehydes at room temperature. The catalyst loading required for these reactions (5 mol %) is the lowest recorded in the literature, and the majority of the reaction times for this transformation are the shortest thus far reported. A variety of functional groups are tolerated on the aryl aldehyde substrates.

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Benzofuran – Wikipedia,
Benzofuran | C8H1093O – PubChem

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Novel heterocyclic toxicity is high-efficient agricultural chemicals and its preparation method and application (by machine translation)

The invention relates to a novel heterocyclic toxicity is high-efficient agricultural chemicals and its preparation method and application, the novel heterocyclic toxicity is high-efficient method of preparing pesticide, comprises the following steps: (1) the 2 – thio hydantoin, benzofuran – 2 – formaldehyde, piperidine with anhydrous ethanol after mixing, heating to reflux temperature of the reaction 2 – 3 hours later, water to terminate the reaction, filtration, the filter residue are isopropyl alcohol, ethanol, water washing, obtained by vacuum drying the solid; (2) the step (1) in the obtained solid dissolved in methanol, adding sodium methoxide, iodomethane, heating to reflux temperature of the reaction 3 – 5 hours, adding water to terminate the reaction, filtration, the filter residue is washed, obtained by vacuum drying the solid, that is the type I structure of the heterocyclic compounds. (by machine translation)

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Benzofuran – Wikipedia,
Benzofuran | C8H651O – PubChem

Discovery of Benzo[b]furan-2-carboxaldehyde

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Synthesis of a fluorous ligand and its application for asymmetric addition of dimethylzinc to aldehydes

A new fluorous ligand was synthesized from the acetonide of dimethyl tartarate, which showed excellent asymmetric induction on the addition of dimethylzinc to aldehydes. This ligand will be useful for synthesis of bioactive compounds with a methyl carbinol moiety. It could be recycled without using a fluorous solvent or a fluorous column.

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Benzofuran – Wikipedia,
Benzofuran | C8H1054O – PubChem

Brief introduction of Benzo[b]furan-2-carboxaldehyde

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Discovery of a novel selective PPARgamma modulator from (-)-Cercosporamide derivatives

In an investigation of (-)-Cercosporamide derivatives with a plasma glucose-lowering effect, we found that N-benzylcarboxamide derivative 4 was a partial agonist of PPARgamma. A SAR study of the substituents on carboxamide nitrogen afforded the N-(1-naphthyl)methylcarboxamide derivative 23 as the most potent selective PPARgamma modulator. An X-ray crystallography study revealed that compound 23 bounded to the PPARgamma ligand binding domain in a unique way without any interaction with helix12. Compound 23 displayed a potent plasma glucose-lowering effect in db/db mice without the undesirable increase in body fluid and heart weight that is typically observed when PPARgamma full agonists are administrated.

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Benzofuran – Wikipedia,
Benzofuran | C8H823O – PubChem

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Synthesis and Derivatization of 1,1-[18F]Difluorinated Alkenes

A general method for the synthesis of 1,1-[18F]difluorinated alkenes from [18F]fluoride is reported. This transformation is highly regioselective giving the desired 18F-fluoroalkenes with radiochemical purities of up to 77 % within 20 minutes and a molar activity (Am) of 1 GBq mumol?1. The transformations are operationally simple to perform and were readily translated onto a commercial automated synthesis unit. The resultant 1,1-[18F]difluorinated alkene motif is prevalent in numerous drug molecules, and this is the first general method to synthesize this motif with fluorine-18. 18F-fluorinated alkenes are excellent building blocks and participate in a number of post-labeling transformations to access a range of 18F-perfluorinated functional groups that have never before been radiolabeled with non-carrier-added [18F]fluoride. This method considerably expands the range of 18F-motifs accessible to radiochemists.

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Benzofuran – Wikipedia,
Benzofuran | C8H821O – PubChem