Heterocyclic Building Block-benzofuran

Hou, Zhen-Lin published the artcileSilver-promoted cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides by palladium catalysis, Synthetic Route of 69626-75-1, the publication is Tetrahedron Letters (2018), 59(52), 4557-4561, database is CAplus.

A ligand-free Pd-catalyzed cross-coupling of substituted allyl(trimethyl)silanes with aryl iodides enabled by silver salts was developed [e.g., trimethyl(2-phenylallyl)silane + Me 4-iodobenzoate → Me 4-(2-phenylallyl)benzoate (79%) in presence of Pd(OAc)₂ and Ag₂CO₃ in DCE]. This reaction delivered allylic arenes chemoselectively and regioselectively. The study suggested that the reaction might proceed through oxidative addition of ArI to Pd(0) followed by halide abstraction to give an electrophilic complex ArPdX, which further reacted with allyl(trimethyl)silanes via electrophilic addition/desilylation/reductive elimination to afford the allyl-aryl coupling products.

Tetrahedron Letters published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C8H5IO, Synthetic Route of 69626-75-1.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Jing, Wanghui published the artcileA practical strategy for chemical profiling of herbal medicines using ultra-high performance liquid chromatography coupled with hybrid triple quadrupole-linear ion trap mass spectrometry: a case study of Mori Cortex, Formula: C14H10O4, the publication is Analytical Methods (2015), 7(2), 443-457, database is CAplus.

Herbal medicines (HMs) are believed to produce holistic action through the synergistic effects of many major and minor components. In the current study, a practical strategy was designed to comprehensively characterize the chem. constituents in HMs. Mori Cortex (MC), which contains diverse chem. constituents and consequently exhibits a broad spectrum of pharmacol. activities, was chosen as a model case. The workflow included three steps: first, a thorough literature review was performed to summarize the available information about the phytochem. and the biosynthetic pathways for the genus Morus; second, seven compounds, namely morin (polyhydroxyflavonoid), morusin (prenylflavone), mulberroside A and oxyresveratrol (stilbenes), mulberroside C (2-arylbenzofuran derivative), sanggenon C and kuwanon G (DA-type adducts), were selected to propose mass fragmentation pathways for the primary chem. types in MC; and third, a set of parent-to-parent ion transitions was constructed using quasi-mol. and sodium adduct ions of the identified compounds and their potential derivatives, and the multiple ion monitoring-information dependent acquiring-enhanced product ion (MIM-IDA-EPI) method was thereby used to detect and identify the constituents. As a result, a total of 140 components were detected with 133 identified in the MC extract, including 10 polyhydroxyflavonoids, 4 stilbenes, 16 2-arylbenzofuran derivatives, 60 prenylflavones, and 43 DA type adducts, while the identities of 7 components could not be elucidated due to insufficient structural information. Collectively, the strategy was demonstrated to be efficient, reliable and sensitive for global chem. profiling of HMs.

Analytical Methods published new progress about 56317-21-6. 56317-21-6 belongs to benzofurans, auxiliary class Metabolic Enzyme,PDE,Natural product, name is 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, and the molecular formula is C14H10O4, Formula: C14H10O4.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Kato, Harutoshi published the artcilePrecise prediction of activators for the human constitutive androstane receptor using structure-based three-dimensional quantitative structure-activity relationship methods, Recommanded Product: 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one, the publication is Drug Metabolism and Pharmacokinetics (2017), 32(3), 179-188, database is CAplus and MEDLINE.

The constitutive androstane receptor (CAR, NR1I3) regulates the expression of numerous drug-metabolizing enzymes and transporters. The upregulation of various enzymes, including CYP2B6, by CAR activators is a critical problem leading to clin. severe drug-drug interactions (DDIs). To date, however, few effective computational approaches for identifying CAR activators exist. In this study, we aimed to develop three-dimensional quant. structure-activity relationship (3D-QSAR) models to predict the CAR activating potency of compounds emerging in the drug-discovery process. Models were constructed using comparative mol. field anal. (CoMFA) based on the mol. alignments of ligands binding to CAR, which were obtained from ensemble ligand-docking using 28 compounds as a training set. The CoMFA model, modified by adding a lipophilic parameter with calculated logD_7.4 (S+logD_7.4), demonstrated statistically good predictive ability (r² = 0.99, q² = 0.74). We also confirmed the excellent predictability of the 3D-QSAR model for CAR activation (r²_pred = 0.71) using seven compounds as a test set for external validation. Collectively, our results indicate that the 3D-QSAR model developed in this study provides precise prediction of CAR activating potency and, thus, should be useful for selecting drug candidates with minimized DDI risk related to enzyme-induction in the early drug-discovery stage.

Drug Metabolism and Pharmacokinetics published new progress about 596-01-0. 596-01-0 belongs to benzofurans, auxiliary class Benzofuran,Naphthalene,Alcohol,Ester, name is 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one, and the molecular formula is C28H18O4, Recommanded Product: 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Haito, Akira published the artcileRu₃(CO)₁₂-Catalyzed Carbonylation of C-H Bonds by Triazole-Directed C-H Activation, Quality Control of 69626-75-1, the publication is Asian Journal of Organic Chemistry (2018), 7(7), 1315-1318, database is CAplus.

The Ru-catalyzed carbonylation of C-H bonds directed by a triazole ring is reported. The reaction involves a three-component coupling reaction of a C-H bond, carbon monoxide (CO), and ethylene, leading to the production of a ketone as the carbonylation product.

Asian Journal of Organic Chemistry published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C8H5IO, Quality Control of 69626-75-1.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Matsuo, Shigeru published the artcileSynthesis and characterization of new fluorescent poly(arylene ether)s, Application of 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one, the publication is Journal of Polymer Science, Part A: Polymer Chemistry (1994), 32(6), 1071-6, database is CAplus.

The poly(arylene ether)s were prepared by the nucleophilic aromatic substitution polymerization of phenolphthalin and its derivatives with activated aromatic difluorides. The polymers had glass transition temperatures of 210-240°. Though the monomers have no fluorescence, the resulting polymers fluoresced with a light green color in solid and solution states. The maximum excitation and emission wavelengths are 420 nm and 247 nm, resp. In the polymer solutions, the fluorescence intensity decreased gradually, but the intensity was recovered by heating the polymer at 220° for a few minutes. The fluorescent polymer had a stable radical. A model compound having the same repeating unit as the polymer was also prepared The fluorescence properties of this model were almost the same as those of the polymers.

Journal of Polymer Science, Part A: Polymer Chemistry published new progress about 596-01-0. 596-01-0 belongs to benzofurans, auxiliary class Benzofuran,Naphthalene,Alcohol,Ester, name is 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one, and the molecular formula is C28H18O4, Application of 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Zheng, Zong-Ping published the artcileCharacterization of Antiproliferative Activity Constituents from Artocarpus heterophyllus, Category: benzofurans, the publication is Journal of Agricultural and Food Chemistry (2014), 62(24), 5519-5527, database is CAplus and MEDLINE.

Artocarpus heterophyllus is an evergreen fruit tree cultivated in many tropical regions. Previous studies have shown that some of its compositions exhibited potential tyrosinase inhibition activities. This study identified 8 new phenolic compounds, artoheterophyllins E-J (1-6), 4-geranyl-2′,3,4′,5-tetrahydroxy-cis-stilbene (7), and 5-methoxymorican M (8) and 2 new natural compounds (9 and 10), 2,3-dihydro-5,7-dihydroxy-2-(2-hydroxy-4-methoxyphenyl)-4H-benzopyran-4-one and 6-[(1S,2S)-1,2-dihydroxy-3-methylbutyl]-2-(2,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-3-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one, together with 23 known compounds (11-33), from the ethanol extract of the wood of A. heterophyllus. The structures of the eight new compounds (1-8) and two new natural compounds were established by extensive 1D- and 2D-NMR experiments The anticancer effects of the isolated compounds were examined in MCF-7, H460, and SMMC-7721 human cancer cell lines by MTT assay. Compounds 5, 11, 12, and 30 significantly reduced the cell viabilities of these cell lines. Especially, compounds 11 and 30 resulted in more potent cytotoxicity than the pos. control, 5-fluorouracil (5-Fu), in SMMC-7721 cell line, with IC₅₀ values of 15.85 and 12.06 μM, whereas compound 30 exhibited more potent cytotoxicity than 5-Fu in NCI-H460 cell line, with an IC₅₀ value of 5.19 μM. In addition, this study suggests that compounds 11 and 30 from the wood of A. heterophyllus have anticancer potential via MAPK pathways.

Journal of Agricultural and Food Chemistry published new progress about 56317-21-6. 56317-21-6 belongs to benzofurans, auxiliary class Metabolic Enzyme,PDE,Natural product, name is 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, and the molecular formula is C14H10O4S2, Category: benzofurans.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Arias, Leire published the artcileRegioselective Preparation of Benzo[b]furans from Phenols and α-Bromoketones, Related Products of benzofurans, the publication is Journal of Organic Chemistry (2012), 77(1), 266-275, database is CAplus and MEDLINE.

A fully regiocontrolled synthesis of either 2- and 3-substituted benzo[b]furans is described. Direct reaction between phenols and α-bromoacetophenones in the presence of neutral alumina yields 2-substituted benzo[b]furans with complete regiocontrol. When a basic salt such as potassium carbonate is used, the corresponding 2-oxoether is obtained. Cyclization of these latter compounds promoted by neutral alumina yields the corresponding 3-substituted benzo[b]furans. Using the former method, Moracin M and other analogs can be obtained from com. sources in two preparative steps. DFT calculations provide reasonable reaction paths to understand the formation of 2-substituted benzo[b]furans.

Journal of Organic Chemistry published new progress about 56317-21-6. 56317-21-6 belongs to benzofurans, auxiliary class Metabolic Enzyme,PDE,Natural product, name is 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, and the molecular formula is C14H10O4, Related Products of benzofurans.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Naka, Hiroshi published the artcileAn Aluminum Ate Base: Its Design, Structure, Function, and Reaction Mechanism, HPLC of Formula: 69626-75-1, the publication is Journal of the American Chemical Society (2007), 129(7), 1921-1930, database is CAplus and MEDLINE.

An Al ate base, i-Bu₃Al(TMP)Li, was designed and developed for regio- and chemoselective direct generation of functionalized aromatic Al compounds Direct alumination followed by electrophilic trapping with I₂, Cu/Pd-catalyzed C-C bond formation, or direct oxidation with mol. O₂ proved to be a powerful tool for the preparation of 1,2-di- or 1,2,3-trisubstituted aromatic compounds This deprotonative alumination using i-Bu₃Al(TMP)Li is effective in aliphatic chem. as well, enabling regio- and chemoselective addition of functionalized allylic ethers and carbamates to aliphatic and aromatic aldehydes. A combined multinuclear NMR spectroscopy, x-ray crystallog., and theor. study showed that the Al ate base is a Li/Al bimetallic complex bridged by the N atom of TMP and the α-C of an i-Bu ligand and that the Li exclusively serves as a recognition point for electroneg. functional groups or coordinative solvents. The mechanism of directed ortho alumination reaction of functionalized aromatic compounds was studied by NMR and in situ FTIR spectroscopy, x-ray anal., and DFT calculation The reaction proceeds with facile formation of an initial adduct of the base and aromatic, followed by deprotonative formation of the functionalized aromatic Al compound Deprotonation by the TMP ligand rather than the iso-Bu ligand was suggested and reasoned by spectroscopic and theor. study. The remarkable regioselectivity of the ortho alumination reaction was explained by a coordinative approximation effect between the functional groups and the counter Li⁺ ion, enabling stable initial complex formation and creation of a less strained transition state structure.

Journal of the American Chemical Society published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C8H5IO, HPLC of Formula: 69626-75-1.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Xu, Bin published the artcilePhotocatalyzed Diastereoselective Isomerization of Cinnamyl Chlorides to Cyclopropanes, Formula: C8H5IO, the publication is Journal of the American Chemical Society (2020), 142(13), 6206-6215, database is CAplus and MEDLINE.

Endergonic isomerizations are thermodynamically unfavored processes that are difficult to realize under thermal conditions. A photocatalytic and diastereoselective isomerization of acyclic cinnamyl chlorides to strained cyclopropanes is reported. Quantum mech. calculations (uM06-2X and DLPNO), including TD-DFT calculations, and exptl. studies provide evidence for the energy transfer from an iridium photocatalyst to the allylic chloride substrate followed by C-Cl homolytic cleavage. Subsequent Cl^• radical migration forms a localized triplet 1,3-diradical intermediate that, after intersystem crossing, undergoes ring-closing to form the desired product. The mild reaction conditions are compatible with a broad range of functional groups to generate chlorocyclopropanes in high yields and diastereoselectivities. A more efficient process is developed by addition of a catalytic amount of a nickel complex, and we propose a novel role for this cocatalyst to recycle an allyl chloride byproduct generated in the course of the reaction. The reaction is also shown to be stereoconvergent, as an E/Z mixture of cinnamyl chlorides furnish the anti-chlorocyclopropane product in high diastereoselectivity. The use of a visible light activated photocatalyst to transform substrates in combination with a transition metal catalyst to recycle byproducts back into the catalytic cycle will provide unique opportunities for the discovery of new reactivity is anticipated.

Journal of the American Chemical Society published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C15H12O6, Formula: C8H5IO.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Gawlik, Maciej published the artcileIdentification and characterization of citalopram new metabolites with the use of UHPLC-Q-TOF technique: In silico toxicity assessment of the identified transformation products, Product Details of C20H19FN2O2, the publication is Journal of Pharmaceutical and Biomedical Analysis (2020), 113299, database is CAplus and MEDLINE.

In this study the metabolite profiling of citalopram with the use of human liver microsomes as well as the complementary photocatalytic method were established. This strategy allowed the detection of five metabolites of citalopram including 3-hydroxycitalopram and 3-oxocitalopram which were found as a new and not previously described metabolites of this drug The photocatalytic simulation of metabolism was carried out using tungsten (VI) oxide nanopowders with the different particle sizes, which allowed to examine the effect of this photocatalyst parameter on the mapping of metabolic processes. The accurate characterization of all observed structures was possible due to the use of ultra-high-pressure liquid chromatog. and high-resolution mass spectrometry combined system as a highly useful technique in drug metabolism studies. In order to perform the toxicity prediction of citalopram and its metabolites, the acute toxicity to rodents, as well as genotoxicity, carcinogenicity, developmental toxicity and receptor-mediated toxicity was calculated basing on the in silico tools.

Journal of Pharmaceutical and Biomedical Analysis published new progress about 372941-54-3. 372941-54-3 belongs to benzofurans, auxiliary class Other Aliphatic Heterocyclic,Fluoride,Nitrile,Amine,Benzene,Ester, name is 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, and the molecular formula is C20H19FN2O2, Product Details of C20H19FN2O2.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem