Category: benzofurans

Moir, James published the artcileColor and chemical constitution. XX. Some residual problems, Related Products of benzofurans, the publication is Transactions of the Royal Society of South Africa (1926), 131-8, database is CAplus.

cf. C. A. 19, 988. Locations of absorption bands are given for a considerable number of naphtholphthaleins, azo dyes, hydrazones, S compounds, and miscellaneous organic compounds Com. α-naphtholphthalein was shown to consist chiefly of a white substance (I) together with a small quantity of a brown substance (II). Apparently I is mostly the p,p’-isomer, with a little o,p (as with com. phenolphthalein); II is the o,o’-isomer, m. 234°.

Transactions of the Royal Society of South Africa 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, Related Products of benzofurans.

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

Murata, Kazuya published the artcileChemical Diversity of β-Secretase Inhibitors From Natural Resources, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, the publication is Natural Product Communications (2019), 14(12), 1934578X19894819, database is CAplus.

A review. Reports on β-secretase inhibitors of natural origin are listed in order to reveal their chem. diversity. Various types of compounds were found to inhibit β-secretase, and natural resources included a wide spectrum of biol. species. Among them, some triterpenes and moracin derivatives, which are nonpeptidic compounds, were determined to be competitive inhibitors. In addition, no peptide compounds were reported from natural resources. These points will be clarified in future studies.

Natural Product Communications 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, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol.

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

Novikova, E. N. published the artcileEffect of the inhibitors on the formation of peroxides in α-pinene, Recommanded Product: 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one, the publication is Vestsi Akademii Navuk BSSR, Seryya Fizika-Tekhnichnykh Navuk (1957), 47-55, database is CAplus.

To a 25 mL. glass tube was added 4 mL. freshly distilled α-pinene (I), d₂₀ 0.8573, n²⁰_D 1.4665, b. 155-6°, containing 4 m mol inhibitor/100 mL. I, and the tube placed in an oil bath at 110° for air oxidation during 2 h. The amount of peroxides (II) formed was then determined iodometrically and calculated as ml. 0.1N hyposulfite solution/l. oxidized I. Secondary aromatic amines: dinaphthylphenylenediamine, p-H₂NC₆H₄NHPh, 2,4 – (H₂N)₂C₆H₃NHPh, 1,4 – diphenylenediamine, and p-HOC₆H₄NHPh caused total inhibition of the formation of II. Other equally effective inhibitors were p-hydroxyphenyl-β-naphthylamine, ο-, and p-aminophenol. The following aromatic compounds showed a much smaller inhibitory effect (in the decreasing order of the inhibitory efficiency): α-naphthol, phenyl-α-naphthylamine, nitrosodimethylamine, dihydroxynaphthalene, α-naphtholphthalein, hydroxyquinoline, phenyl-β-naphthylamine (III), and “aldol-α-naphthylamine” (titration values 1.5-10.1 mL. vs. 51.2-57.8 mL. for the controls), and hydroquinone (IV), pyrocatechol, pyrogallol, β-naphthol, β-naphthylamine, dianisidine, α-naphthylamine, phloroglucinol, resorcinol, Azatol A, p-toluidine, p-anisidine, nitroresorcinol, orcinol, m-tolylenediamine, ο-anthranilic acid, m-anthranilic acid, m-aminophenol, naphthalene, benzidine, ο-tolidine, hydroxyquinoline, and biphenyl (titration values from 11.8 to 50.4 mL.). Primary amines showed the lower inhibition. Naphthols were more effective than naphthylamines. ο- and p-Isomers of phenols and aminophenols inhibited formation of II more than did m-isomers. In another experiment, conducted on I and dipentene (fraction of turpentine, d₂₀ 0.8486, n²⁰_D 1.474, b. 174-5°), by using a dry O oxidation in a semivacuum at 80° 4 h., it was shown that the inhibitors are equally effective against formation of I in dry O as in the air. Addition of 0.005% Mn (as Mn stearate) to I did not increase the inhibitory effects of III and IV as found by the determinations of II and the O absorption by I. Triphenylphosphine and IV were found to be strong inhibitors against oxidation of terpenes. The inhibitory effects of the aromatic compounds against formation of II in I is discussed in the light of the chem. and structural nature of the inhibitors.

Vestsi Akademii Navuk BSSR, Seryya Fizika-Tekhnichnykh Navuk 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

Novikova, E. N. published the artcileEffect of substituents in molecules of inhibitors on their protective action in autoxidation of α-pinene, Name: 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one, the publication is Zhurnal Obshchei Khimii (1958), 1993-7, database is CAplus.

The effect of various inhibitors on autoxidation and formation of peroxides in α-pinene was studied in scattered light at 18-20°. The inhibitors were added in 0.01 millimolar amount to 1 mole of pinene, and the reaction was permitted to occur in contact with air at room temperature for up to 150 days. Peroxide formation is hindered by pyrocatechol, pyrogallol, o- and p-aminophenols, p-hydroxydiphenylamine, dinaphthylphenylenediamine, 1,4-diphenylphenylenediamine, p-aminodiphenylamine, 1-naphthol, and p-hydroxypheyl-2-naphthylamine. Derivatives of phenols were weak inhibitors. Fe palmitate is an initiator for peroxidation of pinene. The activity of the inhibitor is determined both by the polarity of the substance and the mobility of available H atoms.

Zhurnal Obshchei Khimii 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, Name: 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

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

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

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

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

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