Heterocyclic Building Block-benzofuran

Zheng, Zong-Ping published the artcileChemical components and tyrosinase inhibitors from the twigs of Artocarpus heterophyllus, Application In Synthesis of 56317-21-6, the publication is Journal of Agricultural and Food Chemistry (2009), 57(15), 6649-6655, database is CAplus and MEDLINE.

An HPLC method was developed and validated to compare the chem. profiles and tyrosinase inhibitors in the woods, twigs, roots, and leaves of Artocarpus heterophyllus. Five active tyrosinase inhibitors including dihydromorin, steppogenin, norartocarpetin, artocarpanone, and artocarpesin were used as marker compounds in this HPLC method. It was discovered that the chem. profiles of A. heterophyllus twigs and woods are quite different. Systematic chromatog. methods were further applied to purify the chems. in the twigs of A. heterophyllus. Four new phenolic compounds, including one isoprenylated 2-arylbenzofuran derivative, artoheterophyllin A (1), and three isoprenylated flavonoids, artoheterophyllin B (2), artoheterophyllin C (3), and artoheterophyllin D (4), together with 16 known compounds, were isolated from the ethanol extract of the twigs of A. heterophyllus. The structures of compounds 1-4 were elucidated by spectroscopic anal. However, the four new compounds did not show significant inhibitory activities against mushroom tyrosinase compared to kojic acid. It was found that similar compounds, such as norartocarpetin and artocarpesin in the twigs and woods of A. heterophyllus, contributed to their tyrosinase inhibitory activity.

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 C3H5BN2O2, Application In Synthesis of 56317-21-6.

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

Zhao, Peng published the artcileThe molecular basis for the inhibition of phosphodiesterase-4D by three natural resveratrol analogs. Isolation, molecular docking, molecular dynamics simulations, binding free energy, and bioassay, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, the publication is Biochimica et Biophysica Acta, Proteins and Proteomics (2013), 1834(10), 2089-2096, database is CAplus and MEDLINE.

The phosphodiesterase-4 (PDE4) enzyme is a promising therapeutic target for several diseases. Our previous studies found resveratrol and moracin M to be natural PDE4 inhibitors. In the present study, three natural resveratrol analogs [pterostilbene, (E)-2′,3,5′,5-tetrahydroxystilbene (THSB), and oxyresveratrol] are structurally related to resveratrol and moracin M, but their inhibition and mechanism against PDE4 are still unclear. A combined method consisting of mol. docking, mol. dynamics (MD) simulations, binding free energy, and bioassay was performed to better understand their inhibitory mechanism. The binding pattern of pterostilbene demonstrates that it involves hydrophobic/aromatic interactions with Phe340 and Phe372, and forms hydrogen bond(s) with His160 and Gln369 in the active site pocket. The present work also reveals that oxyresveratrol and THSB can bind to PDE4D and exhibits less neg. predicted binding free energies than pterostilbene, which was qual. validated by bioassay (IC₅₀ = 96.6, 36.1, and 27.0 μM, resp.). Addnl., a linear correlation (R² = 0.953) is achieved for five PDE4D/ligand complexes between the predicted binding free energies and the exptl. counterparts approx. estimated from their IC₅₀ values (≈RT ln IC₅₀). Our results imply that hydrophobic/aromatic forces are the primary factors in explaining the mechanism of inhibition by the three products. Results of the study help to understand the inhibitory mechanism of the three natural products, and thus help the discovery of novel PDE4 inhibitors from resveratrol, moracin M, and other natural products.

Biochimica et Biophysica Acta, Proteins and Proteomics 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 C6H20Cl2N4, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol.

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

Zhang, Mi published the artcileIn vivo hypoglycemic effects of phenolics from the root bark of Morus alba, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, the publication is Fitoterapia (2009), 80(8), 475-477, database is CAplus and MEDLINE.

Moracin M (1), Steppogenin-4′-O-β-D-glucoside (2), Mullberroside A (3) were isolated from the root bark of Morus alba L. and identified by spectral evidence. Compounds 1, 2 and 3 were studied in hypoglycemic effects on alloxan-diabetic mice. The results showed that compounds 1, 2 and 3 all produced hypoglycemic effects. The compound 2 in a dose of 50 mg/kg exerted significant effect (p < 0.05), 2 and 3 in a dose of 100 mg/kg exerted obviously effect (p < 0.01). Meantime, the compound 1 in a dose of 100 mg/kg can make the fasting blood glucose level have decreasing tendency.

Fitoterapia 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 C4H8Cl2S2, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol.

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

Zhang, Mi published the artcileChemical constituents of Chinese medicine Cortex Mori (II), Quality Control of 56317-21-6, the publication is Zhongguo Zhongyao Zazhi (2009), 34(12), 1601-1602, database is CAplus.

The chem. constituents of Chinese medicine Cortex Mori, the root bark of Morus alba, was isolated and purified with silica gel and gel column chromatog., and obtained compounds were identified by physico-chem. properties and spectroscopic data. 11 Compounds were isolated and identified, including moracin C (1), moracin M (2), moracin M-3′-O-β-D-glucopyranoside (3), moracin O (4), kuwanon S (5), kuwanon T (6), 5,7-dihydroxychromone (7), 5,7,2′-trihydroxyflavanone-4′-O-β-D-glucoside (steppogenin-4′-O-β-D-glucoside) (8), 7-hydroxycoumarin (9), 5,7-dihydroxycoumarin-7-O-β-D-glucopyranoside (10), and mullberroside C (11). Compound (8) was firstly isolated from this genus, and compounds 2, 4, 6 were firstly isolated from this plant.

Zhongguo Zhongyao Zazhi 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 C12H15ClO3, Quality Control of 56317-21-6.

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

He, Xi-xin published the artcileResearch on chemical ingredients of heartwood of root of morus atpropurpurea, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, the publication is Tianran Chanwu Yanjiu Yu Kaifa (2014), 26(2), 193-196, database is CAplus.

Eight known compounds, including Moracin C(1), Moracin M(2), Dihydromorin(3), Oxyresveratrol(4), 2,4-Dihydroxy benzaldehyde(5), 7-Hydroxy coumarin(6), Daucosterol(7) and 3-Hydroxy-2-piperidinone(8) have been isolated from EtOH extract of heartwood of root of Morus atpropurpurea. Compounds 1, 3-6 and 8 were isolated from Morus atpropurpurea for the first time. Compound 8 was also isolated from Morus plant for the first time. Their antioxidant and neuroprotective activity were test by DPPH, MTT methods. Polyphenolic compounds 1-4 exhibited antioxidative and neuroprotective activities. Compound 2 showed significant neuroprotective activity at 20 μM.

Tianran Chanwu Yanjiu Yu Kaifa 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

Osawa, Rodrigo A. published the artcileTransformation products of citalopram: Identification and in-silico toxicological assessment, Safety of 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, the publication is Chemosphere (2019), 858-868, database is CAplus and MEDLINE.

The objective of this study was to identify transformation products (TPs) of citalopram (CIT), an antidepressant drug, in laboratory experiments Moreover, toxicity predictions and analyzes in wastewater samples were performed. For the formation of TPs, raw water was used for the processes of hydrolysis; photodegradation under UV irradiation and chlorination. The toxicities were predicted by computational toxicity assessment. The TPs were identified by liquid chromatog. quadrupole time-of-flight mass spectrometry (LC-QTOF/MS) in broadband collision induced dissociation (bbCID) acquisition mode and product ion scan mode (MS/MS). The probable structures of the TPs under study were established based on accurate mass, fragmentations observed in the MS spectra and prediction tools software. The experiments resulted in seventeen possible identified TPs and their stability and formation was monitored over time in the experiments Two of these TPs were identified in wastewater samples It was also observed that most of TPs formed were either less toxic then CIT or had a similar toxicity.

Chemosphere 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, Safety of 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile.

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

Perez de Vargas-Sansalvador, I. M. published the artcilePhosphorescent sensing of carbon dioxide based on secondary inner-filter quenching, Recommanded Product: 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one, the publication is Analytica Chimica Acta (2009), 655(1-2), 66-74, database is CAplus and MEDLINE.

A study of different strategies to prepare phosphorescence-based sensors for gaseous CO₂ determination was performed. It includes the characterization of different configurations tested, a discussion of the results obtained and possibilities for the future. The optical sensor for gaseous CO₂ is based on changes in the phosphorescence intensity of the platinum octaethylporphyrin (PtOEP) complex trapped both on oxygen-insensitive poly(vinylidene chloride-co-vinyl chloride) (PVCD) membranes and PVCD microparticles, due to the displacement of the α-naphtholphthalein acid-base equilibrium with CO₂ concentration A secondary inner-filter mechanism was tested for the sensor and a full range linearized calibration was obtained by plotting (I₁₀₀-I₀)/(I-I ₀) vs. the inverse of the CO₂ concentration, where I₀ and I₁₀₀ are the detected luminescence intensities from a membrane exposed to 100% nitrogen and 100% CO₂, resp., and I at a defined CO₂ concentration The different configurations tested included the use of membranes containing luminophore and pH-sensitive dye placed on two opposite sides of a transparent support to prevent the observed degradation of the PtOEP complex in the presence of the tetraoctylammonium hydroxide (TOAOH) phase transfer agent, which produced better results regarding stability and sensitivity. The CO₂ gas sensor based on PtOEP homogeneous membranes presented better properties in terms of response time and sensitivity than that based on PtOEP microparticles. With a detection limit of 0.02%, the response time (10-90% maximum signal) is 9 s and the recovery time (90-10%) is 115 s. The lifetime of the membranes for CO₂ sensing preserved in a 94% RH atm. and dark conditions is longer than at least 4 mo.

Analytica Chimica Acta 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

Aguayo-Lopez, M. L. published the artcileOptical sensor for carbon dioxide gas determination, characterization and improvements, Quality Control of 596-01-0, the publication is Talanta (2014), 196-201, database is CAplus and MEDLINE.

A study of different alternatives to improve the stability and lifetime of sensors for the determination of gaseous CO₂ was performed. It includes the characterization of different sensing membranes, a discussion of the results obtained and possibilities for the future. The solid sensor membrane for gaseous CO₂ based on changes in the luminescence of a luminophore immobilized on O₂-insensitive film, concurrent with the displacement of a pH indicator, has some drawbacks, such as the loss of efficiency over time and the need to maintain the sensor in special atm. conditions. As a solution to these drawbacks, two alternatives were tested, the 1st alternative was replacing the newly proposed tetraoctyl ammonium hydroxide (TOAOH ) phase transfer agent with other basic agents that did not undergo a Hoffman degradation reaction, and the 2nd alternative was the use of hydrophilic polymers that could retain water needed for CO₂ sensing more efficiently. The different membranes tested indicated that the use of tetra-Me ammonium (TMAOH) instead of TOAOH as the phase transfer agent produced better results regarding stability and sensitivity. Replacing the membrane polymer with hydrophilic polymers improved the sensing characteristics in terms of response time and stability over hydrophobic polymers. With a detection limit of 0.006%, the response time is 19 s and the recovery time is 100 s. The lifetime of the sensing membranes, which do not need to be held in any special atm. other than darkness, is longer than at least 300 days for membranes with TMAOH in hydrophilic polymer and 515 days for membranes with TMAOH in Et cellulose.

Talanta 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, Quality Control of 596-01-0.

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

Zhang, Ling published the artcileDeconstructive Reorganization: De Novo Synthesis of Hydroxylated Benzofuran, Application of 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, the publication is Angewandte Chemie, International Edition (2020), 59(12), 4670-4677, database is CAplus and MEDLINE.

An unprecedented deconstructive reorganization strategy for the de novo synthesis of hydroxylated benzofurans I [R = H, OH; R¹ = t-Bu, 3-thienyl, Ph, etc.; R² = H, OH, Me, OMe, 4-MeOC₆H₄S; R³ = H, OH, Ph, etc.] from kojic acid- or maltol-derived alkynes was reported. In this reaction, both the benzene and furan rings were simultaneously constructed, whereas the pyrone moiety of the kojic acid or maltol was deconstructed and then reorganized into the benzene ring as a six-carbon component. Through this strategy, at least one free hydroxyl group was introduced into the benzene ring in a substitution-pattern tunable fashion without protection-deprotection and redox adjustment. With this method, a large number of hydroxylated benzofuran derivatives with different substitution-patterns were prepared efficiently. This methodol. was shown as the key step in a collective total synthesis of hydroxylated benzofuran-containing natural products.

Angewandte Chemie, International Edition 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 C34H33ClN6O7, Application of 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol.

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

Fernandez-Sanchez, J. F. published the artcileOptical CO₂-sensing layers for clinical application based on pH-sensitive indicators incorporated into nanoscopic metal-oxide supports, Synthetic Route of 596-01-0, the publication is Sensors and Actuators, B: Chemical (2007), 128(1), 145-153, database is CAplus.

We describe CO₂-selective films designed for clin. application based on the co-incorporation of different phenol dyes, α-naphtholphthalein (NAF), naphthol blue black (NBB) and Calmagite (CMG), with a phase-transfer agent, tetraoctylammonium hydroxide (TONOH), into metal-oxide nanoporous matrixes. The metal-oxide coatings consist of aluminum (AlOOH), silicon (SiO₂) and zirconium (ZrO₂) oxides. The chem. reaction principle and preparation of these new sensing layers are described in detail. We have investigated the effect of the type and concentration of the pH-indicator and TONOH together with that of the composition and morphol. characteristics of the nanostructured material. The influence of external parameters such as flow-rate, humidity and interfering gases (NO, CO, NO₂ and SO₂) were also looked into. The sensing films responded to CO₂ concentrations in the gas phase between 0.25% and 40% CO₂ (volume/volume) for NAF-TONOH, 4.1% and 30% CO₂ for NBB-TONOH and 0.6% and 40% CO₂ for CMG-TONOH, with detection limits of 0.25%, 4.1% and 0.6% CO₂ (volume/volume) for NAF-TONOH, NBB-TONOH and CMG-TONOH, resp. The nanoporous membranes provided higher dispersion and accessibility of the dye, and thus a quick response time, lower probability of aggregation, the possibility of sterilization by gamma radiation, insulation from reactive chems. and higher ambient stability.

Sensors and Actuators, B: Chemical 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, Synthetic Route of 596-01-0.

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