Heterocyclic Building Block-benzofuran

Synthesis, reactions and biological evaluation of some novel 5-bromobenzofuran-based heterocycles was written by Halawa, Ahmed Hamdy. And the article was included in World Journal of Organic Chemistry in 2014.Safety of 1-(5-Bromobenzofuran-2-yl)ethanone This article mentions the following:

Condensation of 2-acetyl-5-bromobenzofuran with Me hydrazinecarbodithioate or thiosemicarbazide afforded the corresponding hydrazone derivatives I (R = 5-bromo-2-benzofuryl; R¹ = MeS, NH₂); the product I (R¹ = MeS) was further S-alkylated with alkyl halides. Condensation of dithioester I (R¹ = MeS) with hydrazonyl halides R²C(O)C(X):NNHPh (R² = Me, X = Cl; R² = Ph, X = Br) gave 1,3,4-thiadiazoles II. Thiosemicarbazone I (R¹ = NH₂) reacted with acetic anhydride and various halogenated compounds to afford a variety of ethylidenehydrazono-substituted thiazoles and thiadiazoles, e.g. III from Et bromoacetate. The compound III underwent further condensation reactions with aromatic aldehydes, Ph isothiocyanate/chloroacetonitrile or tetracyanoethylene to give the corresponding methylidene-substituted and benzopyran-fused thiazoles. The coupling of III with DMF-DMA afforded enaminone, which on treatment with heterocyclic amines yielded the corresponding heterocycle-fused thiazoles. Some of the newly synthesized compounds showed promising antimicrobial activity. In the experiment, the researchers used many compounds, for example, 1-(5-Bromobenzofuran-2-yl)ethanone (cas: 38220-75-6Safety of 1-(5-Bromobenzofuran-2-yl)ethanone).

1-(5-Bromobenzofuran-2-yl)ethanone (cas: 38220-75-6) belongs to benzofurans derivatives. Benzofuran is the “”parent”” of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antiviral, antimicrobial, antitumor, anti-inflammatory.Safety of 1-(5-Bromobenzofuran-2-yl)ethanone

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Direct Amidation of Esters by Ball Milling was written by Nicholson, William I.;Barreteau, Fabien;Leitch, Jamie A.;Payne, Riley;Priestley, Ian;Godineau, Edouard;Battilocchio, Claudio;Browne, Duncan L.. And the article was included in Angewandte Chemie, International Edition in 2021.Name: Methyl benzofuran-2-carboxylate This article mentions the following:

The direct mechanochem. amidation of esters RC(O)OR¹ (R = Cy, Ph, pyridin-2-yl, etc.; R¹ = Me, Et) by ball milling is described. The operationally simple procedure requires an ester, amines R²NHR³ (R² = H, Me, Et; R³ = i-Pr, Ph, 2,4,6-trimethylphenyl, etc.; R²R³ = -(CH₂)₂O(CH₂)₂-, -(CH₂)₅-, -(CH₂)₆-, etc.) and 1,2,3,4-tetrahydroquinoline, and substoichiometric KOtBu, and was used to prepare a large and diverse library of 78 amide structures RC(O)N(R²)R³ and (3,4-dihydroquinolin-1(2H)-yl)(phenyl)methanone with modest to excellent efficiency. Heteroaromatic and heterocyclic components are specifically shown to be amenable to this mechanochem. protocol. This direct synthesis platform has been applied to the synthesis of active pharmaceutical ingredients (APIs) and agrochems. as well as the gram-scale synthesis of an active pharmaceutical, all in the absence of a reaction solvent. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1Name: Methyl benzofuran-2-carboxylate).

Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives. Benzofuran derivatives have shown many biological activities, including antifungal and antimicrobial properties, and acting as antagonists of H3 receptors and angiotensin II. Introduction of benzofurans in organic synthesis, particularly drug synthesis, involves generally the use of their metalated species as nucleophiles in addition reactions or in metal-catalysed cross-coupling reactions.Name: Methyl benzofuran-2-carboxylate

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Reversible energy transfer and oxetane formation in the photoreactions of carbonyl compounds with benzofurans was written by Farid, S.;Hartman, S. E.;DeBoer, C. D.. And the article was included in Journal of the American Chemical Society in 1975.COA of Formula: C10H8O3 This article mentions the following:

The photoreactions of propiophenone and acetophenone with benzofuran lead both to dimerization of the olefin and to oxetane formation. The dependency of the product ratio on the concentration of the reactants can be rationalized in terms of 2 different mechanisms. Kinetic studies gave support for the mechanism involving a reversible energy-transfer step as a reaction competing with the oxetane formation. The data implied, however, that the difference in triplet energies of propiophenone and acetophenone is much smaller than the reported values, which were derived from the phosphorescence spectra in glasses. This apparent contradiction was eliminated by establishing that both ketone triplets in benzene at room temperature are practically isoenergetic. This was concluded from a chem. kinetic study based on competing oxetane formation from both ketones with 2-methyl-2-butene. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1COA of Formula: C10H8O3).

Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives. Benzofuran derivatives are one of the most important oxygen-containing heterocycles. Substituted benzofurans find applications such as fluorescent sensors, oxidants, in drug discovery, and in another field of chemistry and agriculture.COA of Formula: C10H8O3

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Phosphonofluoresceins: Synthesis, Spectroscopy, and Applications was written by Turnbull, Joshua L.;Benlian, Brittany R.;Golden, Ryan P.;Miller, Evan W.. And the article was included in Journal of the American Chemical Society in 2021.Recommanded Product: 76-54-0 This article mentions the following:

Xanthene fluorophores, like fluorescein, have been versatile mols. across diverse fields of chem. and life sciences. Despite the ubiquity of 3-carboxy and 3-sulfonofluorescein for the last 150 years, to date, no reports of 3-phosphonofluorescein exist. Here, we report the synthesis, spectroscopic characterization, and applications of 3-phosphonofluoresceins. The absorption and emission of 3-phosphonofluoresceins remain relatively unaltered from the parent 3-carboxyfluorescein. 3-Phosphonofluoresceins show enhanced water solubility compared to 3-carboxyfluorescein and persist in an open, visible light-absorbing state even at low pH and in low dielec. media while 3-carboxyfluoresceins tend to lactonize. In contrast, the spirocyclization tendency of 3-phosphonofluoresceins can be modulated by esterification of the phosphonic acid. The bis-acetoxymethyl ester of 3-phosphonofluorescein readily enters living cells, showing excellent accumulation (>6x) and retention (>11x), resulting in a nearly 70-fold improvement in cellular brightness compared to 3-carboxyfluorescein. In a complementary fashion, the free acid form of 3-phosphonofluorescein does not cross cellular membranes, making it ideally suited for incorporation into a voltage-sensing scaffold. We develop a new synthetic route to functionalized 3-phosphonofluoresceins to enable the synthesis of phosphono-voltage sensitive fluorophores, or phosVF2.1.Cl. Phosphono-VF2.1.Cl shows excellent membrane localization, cellular brightness, and voltage sensitivity (26% ΔF/F per 100 mV), rivaling that of sulfono-based VF dyes. In summary, we develop the first synthesis of 3-phosphonofluoresceins, characterize the spectroscopic properties of this new class of xanthene dyes, and utilize these insights to show the utility of 3-phosphonofluoresceins in intracellular imaging and membrane potential sensing. In the experiment, the researchers used many compounds, for example, 2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 76-54-0Recommanded Product: 76-54-0).

2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 76-54-0) belongs to benzofurans derivatives. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. Benzofurans are stable towards alkali and readily polymerize on treatment with sulfuric acid, due to which they are useful for the preparation of low cost chemically relatively inert resins.Recommanded Product: 76-54-0

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Three-dimensional direct visualization of silica dispersion in polymer-based composites was written by Feng, Zemin;Zhong, Jinpan;Guan, Weijiang;Tian, Rui;Lu, Chao;Ding, Caifeng. And the article was included in Analyst (Cambridge, United Kingdom) in 2018.Related Products of 38183-12-9 This article mentions the following:

The uniform dispersion of silica fillers or other neutral fillers in the polymer matrix is significant for fabricating high-performance polymer-based composites. However, there is a long-standing challenge to provide a comprehensive, wide-area and real 3D distribution map to achieve direct visualization for the dispersion state of neutral silica. Herein, we propose a novel strategy for modifying silica fillers with com. fluorophores to form fluorescent fillers in a standard manner. Through fluorescence imaging technol., we successfully observed the 2D-planar and 3D-spatial dispersion states of silica fillers in the polymer matrix. This success not only provides a visualized evaluation method for the spatial dispersion of an oxide filler, but also offers great potential in the further establishment of industrialized standards for the polymer-based composite industry. In the experiment, the researchers used many compounds, for example, 4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9Related Products of 38183-12-9).

4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antiviral, antimicrobial, antitumor, anti-inflammatory.Related Products of 38183-12-9

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Synthesis and evaluation of pyridylbenzofuran, pyridylbenzothiazole and pyridylbenzoxazole derivatives as ¹⁸F-PET imaging agents for β-amyloid plaques was written by Swahn, Britt-Marie;Sandell, Johan;Pyring, David;Bergh, Margareta;Jeppsson, Fredrik;Jureus, Anders;Neelissen, Jan;Johnstroem, Peter;Schou, Magnus;Svensson, Samuel. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2012.HPLC of Formula: 551001-79-7 This article mentions the following:

The synthesis and SAR of new β-amyloid binding agents are reported. Evaluation of important properties for achieving good signal-to-background ratio is described. 2-(2-Fluoro-6-methylamino-3-pyridinyl)-6-benzofuranol (I), 2-(3-fluoro-2-methylamino-5-pyridinyl)-6-benzofuranol, and 2-(2-fluoro-3-methylamino-6-pyridinyl)-6-benzofuranol displayed desirable lipophilic and pharmacokinetic properties. I was further evaluated with autoradiog. studies in vitro on human brain tissue and in vivo in Tg2576 mice. I showed an increased signal-to-background ratio compared to flutemetamol, indicating its suitability as PET ligand for β-amyloid deposits in AD patients. The preparation of the corresponding ¹⁸F-labeled PET radioligand of I is presented. In the experiment, the researchers used many compounds, for example, (5-Methoxybenzofuran-2-yl)boronic acid (cas: 551001-79-7HPLC of Formula: 551001-79-7).

(5-Methoxybenzofuran-2-yl)boronic acid (cas: 551001-79-7) belongs to benzofurans derivatives. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. In nature, benzofurans have occupied an important role among the plant phenols & several pharmacologically active compounds.HPLC of Formula: 551001-79-7

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Functional in vitro characterization of SLCO1B1 variants and simulation of the clinical pharmacokinetic impact of impaired OATP1B1 function. was written by Kiander, Wilma;Sjostedt, Noora;Manninen, Riikka;Jaakkonen, Liina;Vellonen, Kati-Sisko;Neuvonen, Mikko;Niemi, Mikko;Auriola, Seppo;Kidron, Heidi. And the article was included in European Journal of Pharmaceutical Sciences in 2022.Safety of 2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one This article mentions the following:

Organic Anion Transporting Polypeptide 1B1 is important to the hepatic elimination and distribution of many drugs. If OATP1B1 function is decreased, it can increase plasma exposure of e.g. several statins leading to increased risk of muscle toxicity. First, we examined the impact of three naturally occurring rare variants and the frequent SLCO1B1 c.388A>G variant on in vitro transport activity with cellular uptake assay using two substrates: 2′, 7′-dichlorofluorescein (DCF) and rosuvastatin. Secondly, LC-MS/MS based quant. targeted absolute proteomics measured the OATP1B1 protein abundance in crude membrane fractions of HEK293 cells over-expressing these single nucleotide variants. Addnl., we simulated the effect of impaired OATP1B1 function on rosuvastatin pharmacokinetics to estimate the need for genotype-guided dosing. R57Q impaired DCF and rosuvastatin transport significantly yet did not change protein expression considerably, while N130D and N151S did not alter activity but increased protein expression. R253Q did not change protein expression but reduced DCF uptake and increased rosuvastatin K_m. Based on pharmacokinetic simulations, doses of 30 mg (with 50% OATP1B1 function) and 20 mg (with 0% OATP1B1 function) result in plasma exposure similar to 40 mg dose (with 100% OATP1B1 function). Therefore dose reductions might be considered to avoid increased plasma exposure caused by function-impairing OATP1B1 genetic variants, such as R57Q. In the experiment, the researchers used many compounds, for example, 2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 76-54-0Safety of 2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one).

2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 76-54-0) belongs to benzofurans derivatives.Benzofuran is one of the most significant oxygen-containing heterocycles consisting of fused benzene and furan ring, which are widely presented in various naturally occurring and synthetically active compounds. In nature, benzofurans have occupied an important role among the plant phenols & several pharmacologically active compounds.Safety of 2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Experimental and Computational Prediction of Glass Transition Temperature of Drugs was written by Alzghoul, Ahmad;Alhalaweh, Amjad;Mahlin, Denny;Bergstroem, Christel A. S.. And the article was included in Journal of Chemical Information and Modeling in 2014.Safety of 4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione This article mentions the following:

Glass transition temperature (T_g) is an important inherent property of an amorphous solid material which is usually determined exptl. In this study, the relation between T_g and melting temperature (T_m) was evaluated using a data set of 71 structurally diverse druglike compounds Further, in silico models for prediction of T_g were developed based on calculated mol. descriptors and linear (multilinear regression, partial least-squares, principal component regression) and nonlinear (neural network, support vector regression) modeling techniques. The models based on T_m predicted T_g with an RMSE of 19.5 K for the test set. Among the five computational models developed herein the support vector regression gave the best result with RMSE of 18.7 K for the test set using only four chem. descriptors. Hence, two different models that predict T_g of drug-like mols. with high accuracy were developed. If T_m is available, a simple linear regression can be used to predict T_g. However, the results also suggest that support vector regression and calculated mol. descriptors can predict T_g with equal accuracy, already before compound synthesis. In the experiment, the researchers used many compounds, for example, 4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9Safety of 4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione).

4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9) belongs to benzofurans derivatives. Benzofuran is the “”parent”” of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antioxidant, antitubercular, antiplasmodial, insecticidal.Safety of 4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Silica nanoparticles with thermally activated delayed fluorescence for live cell imaging was written by Crucho, Carina I. C.;Avo, Joao;Nobuyasu, Roberto;N. Pinto, Sandra;Fernandes, Fabio;Lima, Joao C.;Berberan-Santos, Mario N.;Dias, Fernando B.. And the article was included in Materials Science & Engineering, C: Materials for Biological Applications in 2020.Category: benzofurans This article mentions the following:

Thermally activated delayed fluorescence (TADF) has revolutionized the field of organic light emitting diodes owing to the possibility of harvesting non-emissive triplet states and converting them in emissive singlet states. Despite this strong potential, only recently TADF has emerged as a powerful tool to develop metal-free long-lived luminescent probes for imaging and sensing. The application of TADF mols. in aqueous and/or biol. media requires specific structural features that allow complexation with biomols. or enable emission in the aggregated state, in order to retain the delayed fluorescence that is characteristic of these compounds Herein we demonstrate a facile method that maintains the optical properties of solvated dyes by dispersing TADF mols. in nanoparticles. TADF dye-doped silica nanoparticles are prepared using a modified fluorescein fluorophore. However, the strategy can be used with many other TADF dyes. The covalent grafting of the TADF emitter into the inorganic matrix effectively preserves and transfers the optical properties of the free dye into the luminescent nanomaterials. Importantly, the silica matrix is efficient in shielding the dye from solvent polarity effects and increases delayed fluorescence lifetime. The prepared nanoparticles are effectively internalized by human cells, even at low incubation concentrations, localizing primarily in the cytosol, enabling fluorescence microscopy imaging at low dye concentrations In the experiment, the researchers used many compounds, for example, 2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 76-54-0Category: benzofurans).

2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 76-54-0) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antioxidant, antitubercular, antiplasmodial, insecticidal.Category: benzofurans

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Synthesis of 3-heteroaryloxindoles through t-BuOCl-mediated oxidation of 3-heteroarylindoles was written by Baroni, Marco;Lesma, Giordano;Puleio, Letizia;Sacchetti, Alessandro;Silvani, Alessandra;Zanchet, Marco. And the article was included in Synthesis in 2010.Recommanded Product: 1-(5-Bromobenzofuran-2-yl)ethanone This article mentions the following:

The oxidation of 3-heteroarylindoles, e.g., I (R = H, Cl) to the corresponding oxindoles, e.g., II (R = H, Cl; X = H, Cl), with t-Bu hypochlorite has been investigated. Under carefully adjusted conditions, desired products can be obtained on preparative scale. Two competing pathways seem to contribute to the reaction mechanism, affording 3-heteroaryloxindoles bearing hydrogen or chlorine at C3, depending on stereoelectronic factors. The present methodol. appears also generally applicable for the preparation of simple 3-aryloxindoles. In the experiment, the researchers used many compounds, for example, 1-(5-Bromobenzofuran-2-yl)ethanone (cas: 38220-75-6Recommanded Product: 1-(5-Bromobenzofuran-2-yl)ethanone).

1-(5-Bromobenzofuran-2-yl)ethanone (cas: 38220-75-6) belongs to benzofurans derivatives. Benzofurans are only weakly aromatic in nature and they are cleaved by many oxidative and reductive conditions. As benzofurans are prone to undergo ring opening of the heterocycle, examples of reduction of this type of aromatics by using dissolving metals are rather scarce.Recommanded Product: 1-(5-Bromobenzofuran-2-yl)ethanone

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem