Archives for Chemistry Experiments of 4265-16-1

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4265-16-1, Name is Benzo[b]furan-2-carboxaldehyde, belongs to benzofurans compound, is a common compound. Safety of Benzo[b]furan-2-carboxaldehydeIn an article, once mentioned the new application about 4265-16-1.

A facile and efficient protocol for the synthesis of novel 2-aryl-imidazo[1,2-a]pyridines has been developed via a one-pot reaction of aromatic aldehydes with 2-amino-5-chloropyridine and tert-butylisocyanide in the presence of I2 in ethanol at 70 C. The present approach offers the advantages of a clean and simple methodology, high atom-economy, mild conditions, short reaction times, wide substrate scope, low environmental impact and high yield. The Royal Society of Chemistry 2013.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1006O – PubChem

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Oxidation of furan-2-carboximidamides 8 by (dicarboxyiodo)benzenes gives N1-acyl-N1-(2-furyl)ureas 9 via rearrangement to a carbodiimide. Thermolysis of eleven ureas 9 gave the corresponding 2-acylaminofurans 10, which cannot be made from the free amines owing to their high instability. When oxidation of the corresponding benzo[b]furan derivatives 12 was investigated a new type of product was isolated, in addition to the expected ureas 14, and these were shown to be benzo[4,5]furo[2,3-d]pyrimidine derivatives 15. The mechanism of formation of these products must involve reaction of the carbodiimide intermediate with the amidine precursor and cyclisation of the resulting guanidine derivatives 19. The corresponding tetraphenylguanidine 21 was prepared and underwent thermal cyclisation but the quinazoline derivative formed 23 was shown to occur via an alternative cyclisation mechanism. The structures of cyclisation products 15 and 23 were confirmed by X-ray crystallography. N-(2-Furyl)acetamide 10a readily undergoes cycloaddition reactions with electron-deficient alkynes to give phenols after spontaneous ring opening. Observed regioselectivity is in agreement with the results of AM1 molecular orbital calculations. Reaction of the amide 10a with Lawesson’s reagent gave the thioamide 26.

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Benzofuran – Wikipedia,
Benzofuran | C8H749O – PubChem

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We previously reported the discovery of pyrimido-pyrrolo-quinoxalinedione (PPQ) inhibitors of the cystic fibrosis transmembrane conductance regulator (CFTR) chloride channel and showed their efficacy in an organ culture model of polycystic kidney disease (PKD) (J. Med. Chem. 2009, 52, 6447-6455). Here, we report related benzopyrimido-pyrrolo-oxazinedione (BPO) CFTR inhibitors. To establish structure-activity relationships and select lead compound(s) with improved potency, metabolic stability, and aqueous solubility compared to the most potent prior compound 8 (PPQ-102, IC50 ? 90 nM), we synthesized 16 PPQ analogues and 11 BPO analogues. The analogues were efficiently synthesized in 5-6 steps and 11-61% overall yield. Modification of 8 by bromine substitution at the 5-position of the furan ring, replacement of the secondary amine with an ether bridge, and carboxylation, gave 6-(5-bromofuran-2-yl)-7,9-dimethyl-8,10-dioxo-11-phenyl-7,8,9, 10-tetrahydro-6H-benzo[b]pyrimido [4?,5?:3,4]pyrrolo [1,2-d][1,4]oxazine-2-carboxylic acid 42 (BPO-27), which fully inhibited CFTR with IC50 ? 8 nM and, compared to 8, had >10-fold greater metabolic stability and much greater polarity/aqueous solubility. In an embryonic kidney culture model of PKD, 42 prevented cyst growth with IC 50 ? 100 nM. Benzopyrimido-pyrrolo-oxazinediones such as 42 are potential development candidates for antisecretory therapy of PKD.

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Benzofuran – Wikipedia,
Benzofuran | C8H1053O – PubChem

Archives for Chemistry Experiments of 4265-16-1

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1-Acylpiperidine compound of the formula I STR1 in which R1 is an optionally substituted aralkyl, aryloxyalkyl, heteroaralkyl, aroyl, heteroaroyl, cycloalkylcarbonyl, aralkanoyl, heteroarylalkanoyl, aralkoxycarbonyl or arylcarbamoyl radical or the acyl radical of an alpha-amino acid which is optionally N-substituted by lower alkanoyl or carbamoyl-lower-alkanoyl, R2 is cycloalkyl or an optionally substituted aryl or heteroaryl radical, R3 is hydrogen, alkyl, carbamoyl or an alkanoyl or alkenoyl radical which is optionally substituted by carboxyl or esterified or amidated carboxyl, R4 is an optionally substituted aryl or optionally partially hydrogenated heteroaryl radical, X1 is methylene, ethylene, a direct linkage, an optionally ketalised carbonyl group or an optionally etherified hydroxymethylene group, X2 is alkylene, carbonyl or a direct linkage, and X3 is carbonyl, oxo-lower-alkylene, oxo(aza)-lower-alkylene or an alkylene radical which is optionally substituted by phenyl, hydroxymethyl, optionally esterified or amidated carboxyl or, in higher than the alpha position, by hydroxyl, and its salts have substance-P-antagonistic properties and can be used as pharmaceutically active substances in pharmaceuticals for the treatment of disorders in whose development substance P plays an essential part.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H700O – PubChem

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A direct C(sp2)-H alkynylation of aldehyde C(O)-H bonds with hypervalent iodine alkynylation reagents provides ynones under metal-free conditions. In this method, 1-[(triisopropylsilyl)ethynyl]-1,2-benziodoxol-3(1H)-one (TIPS-EBX) constitutes an efficient alkynylation reagent for the introduction of the triple bond. The substrate scope is extended to a variety of (hetero)aromatic, aliphatic, and alpha,beta-unsaturated aldehydes.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H930O – PubChem

More research is needed about Benzo[b]furan-2-carboxaldehyde

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A novel isoindole derivative represented by general formula [1] or a salt thereof: STR1 which has an excellent antitumor activity and low toxicity.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H691O – PubChem

Properties and Exciting Facts About Benzo[b]furan-2-carboxaldehyde

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The unprecedented formation of unsymmetrical alkenes from the intermolecular reductive coupling of two different aldehydes is described. In contrast to the McMurry reaction which affords statistical product mixtures, selectivity in the reported procedure is achieved by a sequential ionic mechanism in which a first aldehyde is reacted with a phosphanylphosphonate to afford a phosphaalkene intermediate which, upon activation by hydroxide, reacts with a second aldehyde to the unsymmetrical E-alkenes. The described reaction is free of transition metals and proceeds under ambient temperature within minutes in good to excellent overall yields. It is a new methodology to use feedstock aldehydes for the direct production of C C double bond-containing products and may impact how chemists think of multistep synthetic sequences in the future.

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Benzofuran – Wikipedia,
Benzofuran | C8H810O – PubChem

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A scalable, high yielding, rapid route to access an array of nitriles from aldehydes mediated by an oxoammonium salt (4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate) and hexamethyldisilazane (HMDS) as an ammonia surrogate has been developed. The reaction likely involves two distinct chemical transformations: reversible silyl-imine formation between HMDS and an aldehyde, followed by oxidation mediated by the oxoammonium salt and desilylation to furnish a nitrile. The spent oxidant can be easily recovered and used to regenerate the oxoammonium salt oxidant.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H881O – PubChem

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Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane ((-)-BPAP), which is a highly potent and selective catecholaminergic activity enhancer (CAE) substance, are described. The synthetic approach consists of the coupling reaction of benzofuran with (R)-N-tosyl-2-propylazirizine or (R)-N-methoxy-N-methylnorvaliamide, followed by appropriate modifications of the resulting coupling products. As the results, (-)-BPAP turned out to have the R configuration, which was finally confirmed by X-ray crystallographic analysis.

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Benzofuran – Wikipedia,
Benzofuran | C8H978O – PubChem

Extended knowledge of Benzo[b]furan-2-carboxaldehyde

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Free fatty acid receptor 3 (FFA3, previously GPR41) is activated by short-chain fatty acids, mediates health effects of the gut microbiota, and is a therapeutic target for metabolic and inflammatory diseases. The shortage of well-characterized tool compounds has however impeded progress. Herein, we report structure-activity relationship of an allosteric modulator series and characterization of physicochemical and pharmacokinetic properties of selected compounds, including previous and new tools. Two representatives, 57 (TUG-1907) and 63 (TUG-2015), showed improved solubility and preserved potency. Of these, 57, with EC50 = 145 nM and a solubility of 33 muM, showed high clearance in vivo but is a preferred tool in vitro. In contrast, 63, with EC50 = 162 nM and a solubility of 9 muM, showed lower clearance and seems better suited for in vivo studies. Using 57, we demonstrate for the first time that FFA3 activation leads to calcium mobilization in murine dorsal root ganglia.

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Reference:
Benzofuran – Wikipedia,
Benzofuran | C8H1080O – PubChem