Heterocyclic Building Block-benzofuran

Kapche, Deccaux W. F. G. published the artcileAryl benzofuran derivatives from the stem bark of Calpocalyx dinklagei attenuate inflammation, HPLC of Formula: 56317-21-6, the publication is Phytochemistry (Elsevier) (2017), 70-79, database is CAplus and MEDLINE.

Calpocalyx dinklagei Harms (Fabaceae) is a tropical medicinal tree, which is indigenous to Western Africa. A phytochem. study of this local plant species from its stem bark has led to the isolation of two previously undescribed aryl benzofuran derivatives, named dinklagein A (I) and B (II), together with eight known compounds Their chem. structures were elucidated by use of extensive spectroscopic methods (IR, HREI-MS and 1D and 2D NMR). Among all isolates, dinklagein A displayed remarkably potent inhibitory activity against the production of nitric oxide (NO) in the lipopolysaccharide (LPS) induced RAW264.7 macrophages. SAR and mol. docking investigations on iNOS and previously undescribed compounds (dinklagein A and B) supported exptl. data. Furthermore, dinklagein A dose dependently suppressed the LPS-stimulated iNOS expression at both mRNA and protein level. It also attenuated IL-1β release, mRNA expressions of IL-1β and COX-2 at low doses. These results suggest that dinklagein A can be developed as natural, multi-target agent against several inflammatory diseases.

Phytochemistry (Elsevier) 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, HPLC of Formula: 56317-21-6.

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

Ndungu, J. Maina published the artcileDevelopment of an Anomalous Heck Reaction: Skeletal Rearrangement of Divinyl and Enyne Carbinols, COA of Formula: C8H5IO, the publication is Organic Letters (2005), 7(26), 5845-5848, database is CAplus and MEDLINE.

A general set of conditions that achieves the union of aryl halides and divinyl or enyne carbinols to afford tri- or tetrasubstituted olefins in good yields (up to 83%) is described. E.g., reaction of BrPh and CH₂:CHCH(OH)CMe:CH₂ in presence of PdCl₂(PPh₃)₂, i-Pr₂NEt, and Et₄NCl gave olefin I. The mechanism by which this proceeds is believed to involve the intermediacy of a cyclopropanol, followed by a novel skeletal reorganization. The ability to suppress β-hydride elimination of organopalladium intermediates appears to be critical to the success of these processes.

Organic 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, COA of Formula: C8H5IO.

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

Zhang, Haiming published the artcileSynthesis of β- and γ-Carbolines by the Palladium/Copper-Catalyzed Coupling and Cyclization of Terminal Acetylenes, Safety of 2-Iodobenzofuran, the publication is Journal of Organic Chemistry (2002), 67(20), 7048-7056, database is CAplus and MEDLINE.

A variety of 3-substituted β- and γ-carbolines have been synthesized from N-substituted 3-iodoindole-2-carboxaldehydes and 2-bromoindole-3-carboxaldehydes, resp. The coupling of these aldehydes with various terminal acetylenes with PdCl₂(PPh₃)₂/CuI as the catalyst readily affords the corresponding alkynylindolecarboxaldehydes, which have subsequently been converted to the corresponding tert-butylimines and cyclized to β- and γ-carbolines by either copper-catalyzed or thermal processes.

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 C6H8N2O2, Safety of 2-Iodobenzofuran.

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

Pelletier, Guillaume published the artcileHighly Regioselective Intermolecular Arylation of 1,2,3,4-Tetrahydropyridines, Quality Control of 69626-75-1, the publication is Organic Letters (2008), 10(21), 4791-4794, database is CAplus and MEDLINE.

Using a catalytic amount of PdCl₂(dppf)·CH₂Cl₂ in combination with Ag₃PO₄ and NaOAc, a range of arylated 1,2,3,4-tetrahydropyridines, e.g., I, are synthesized in good yields and with complete selectivity at the β-position. The reaction is compatible with a variety of electron-donating and electron-withdrawing aryl iodides as well as with heteroaryl iodides. The application of these tetrahydropyridines toward the synthesis of polysubstituted piperidines is also demonstrated.

Organic 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, Quality Control of 69626-75-1.

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

Chaita, Eliza published the artcileAnti-melanogenic properties of Greek plants. A novel depigmenting agent from Morus alba wood, Application In Synthesis of 56317-21-6, the publication is Molecules (2017), 22(4), 514/1-514/14, database is CAplus and MEDLINE.

In therapeutic interventions associated with melanin hyperpigmentation, tyrosinase is regarded as a target enzyme as it catalyzes the rate-limiting steps in mammalian melanogenesis. Since many known agents have been proven to be toxic, there has been increasing impetus to identify alternative tyrosinase inhibitors, especially from natural sources. In this study, we investigated 900 extracts from Greek plants for potential tyrosinase inhibitive properties. Among the five most potent extracts, the methanol extract of Morus alba wood (MAM) demonstrated a significant reduction in intracellular tyrosinase and melanin content in B16F10 melanoma cells. Bioassay-guided isolation led to the acquisition of twelve compounds: oxyresveratrol (1), kuwanon C (2), mulberroside A (3), resorcinol (4), dihydrooxyresveratol (5), trans-dihydromorin (6), 2,4,3′-trihydroxydihydrostilbene (7), kuwanon H (8), 2,4-dihydroxybenzaldehyde (9), morusin (10), moracin M (11) and kuwanon G (12). Among these, 2,4,3′-trihydroxydihydrostilbene (7) is isolated for the first time from Morus alba and constitutes a novel potent tyrosinase inhibitor (IC50 0.8 ± 0.15). We report here for the first time dihydrooxyresveratrol (5) as a potent natural tyrosinase inhibitor (IC50 0.3 ± 0.05). Computational docking anal. indicated the binding modes of six tyrosinase inhibitors with the aminoacids of the active center of tyrosinase. Finally, we found both MAM extract and compounds 1, 6 and 7 to significantly suppress in vivo melanogenesis during zebrafish embryogenesis.

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

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

Degnan, Andrew P. published the artcileDiscovery of Orally Active Isofuranones as Potent, Selective Inhibitors of Hematopoetic Progenitor Kinase 1, COA of Formula: C24H22N6O4, the publication is ACS Medicinal Chemistry Letters (2021), 12(3), 443-450, database is CAplus and MEDLINE.

While the discovery of immune checkpoint inhibitors has led to robust, durable responses in a range of cancers, many patients do not respond to currently available therapeutics. Therefore, an urgent need exists to identify alternative mechanisms to augment the immune-mediated clearance of tumors. Hematopoetic progenitor kinase 1 (HPK1) is a serine-threonine kinase that acts as a neg. regulator of T-cell receptor (TCR) signaling, to dampen the immune response. Herein we describe the structure-based discovery of isofuranones as inhibitors of HPK1. Optimization of the chemotype led to improvements in potency, selectivity, plasma protein binding, and metabolic stability, culminating in the identification of compound 24 (I). Oral administration of 24, in combination with an anti-PD1 antibody, demonstrated robust enhancement of anti-PD1 efficacy in a syngeneic tumor model of colorectal cancer.

ACS Medicinal Chemistry Letters published new progress about 2320462-65-3. 2320462-65-3 belongs to benzofurans, auxiliary class MAPK/ERK Pathway,HPK1, name is (S)-5-((4-((2-Hydroxy-1-phenylethyl)amino)-5-(1,3,4-oxadiazol-2-yl)pyrimidin-2-yl)amino)-3,3-dimethylisobenzofuran-1(3H)-one, and the molecular formula is C24H22N6O4, COA of Formula: C24H22N6O4.

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

Riviere, Celine published the artcilePolyphenols from the stems of Morus alba and their inhibitory activity against nitric oxide production by lipopolysaccharide-activated microglia, Computed Properties of 56317-21-6, the publication is Fitoterapia (2014), 253-260, database is CAplus and MEDLINE.

Neuroinflammatory processes are involved in the pathogenesis of many neurodegenerative disorders. Microglial cells, the main immune cells of the central nervous system, represent a target of interest to search for naturally occurring anti-inflammatory products. In this study, we evaluated the anti-inflammatory properties of polyphenols obtained from the stems of Morus alba. This edible species, known as white mulberry, is frequently studied because of its traditional use in Asian medicine and its richness in different types of polyphenols, some of which are known to be phytoalexins. One new coumarin glycoside, isoscopoletin 6-(6-O-β-apiofuranosyl-β-glucopyranoside) (1) was mainly isolated by CPC (centrifugal partition chromatog.) from this plant, together with seven known polyphenols (2-8). Their structures were established on the basis of spectroscopic analyses including extensive 2D NMR studies. The eight isolated compounds were evaluated for their inhibitory activities on nitric oxide (NO) production in lipopolysaccharide (LPS)-induced BV-2 microglial cells. The absence of cell toxicity is checked by a MTT assay.

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 C14H10O4, Computed Properties of 56317-21-6.

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

Nassra, Merian published the artcileInhibitory activity of plant stilbenoids against nitric oxide production by lipopolysaccharide-activated microglia, Category: benzofurans, the publication is Planta Medica (2013), 79(11), 966-970, database is CAplus and MEDLINE.

Microglia-driven inflammatory processes are thought to play an important role in ageing and several neurol. disorders. Since consumption of a diet rich in polyphenols has been associated with anti-inflammatory and neuroprotective effects, we studied the effects of twenty-five stilbenoids isolated from Milicia excelsa, Morus alba, Gnetum africanum, and Vitis vinifera. These compounds were tested at 5 and 10 μM on BV-2 microglial cells stimulated with bacterial lipopolysaccharide. Ten stilbenoids reduced lipopolysaccharide-induced nitric oxide production at 5 and/or 10 μM. Two tetramers, E-vitisin A and E-vitisin B, were the most effective mols. Moreover, they attenuated the expression of the inducible NO synthase protein and gene.

Planta Medica 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, Category: benzofurans.

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

Horsing, Maritha published the artcileFate of citalopram during water treatment with O₃, ClO₂, UV and fenton oxidation, Application of 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, the publication is Chemosphere (2012), 89(2), 129-135, database is CAplus and MEDLINE.

In the present study we investigate the fate of citalopram (CIT) at neutral pH using advanced water treatment technologies that include O₃, ClO₂ oxidation, UV irradiation and Fenton oxidation The ozonation resulted in 80% reduction after 30 min treatment. Oxidation with ClO₂ removed >90% CIT at a dosage of 0.1 mg L^-1. During UV irradiation 85% reduction was achieved after 5 min, while Fenton with addition of 14 mg L^-1 (Fe²⁺) resulted in 90% reduction of CIT. During these treatment experiments transformation products (TPs) were formed from CIT, where five compounds were identified by using high resolution and tandem mass spectrometry. Among these desmethyl-citalopram and citalopram N-oxide have been previously identified as human metabolites, while three are novel and published here for the first time. The three TPs are a hydroxylated dimethylamino-side chain derivative, a butyrolactone derivative and a defluorinated derivative of CIT.

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, Application 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

Amao, Yutaka published the artcileRapid responsible optical CO₂ sensor of the combination of colorimetric change of α-naphtholphthalein in poly(trimethylsiliylpropyne) layer and internal reference fluorescent porphyrin in polystyrene layer, Name: 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one, the publication is Reactive & Functional Polymers (2005), 63(1), 35-41, database is CAplus.

An optical CO₂ sensor based on the overlay of the CO₂ induced absorbance change of pH indicator dye α-naphtholphthalein in poly(trimethylsilyl-propyne) (poly(TMSP))layer with the fluorescence of tetraphenylporphyrin (TPP) in polystyrene layer is developed. The observed luminescence intensity from TPP at 655 nm increased with increasing the CO₂ concentration The ratio I₁₀₀/I₀ value of the sensing film, where I₀ and I₁₀₀ represent the detected luminescence intensities from a layer exposed to 100% argon and 100% CO₂, resp., that the sensitivity of the sensor, is 10.3. The response and recovery times of the sensing film are <3.0 s for switching from argon to CO₂, and for switching from CO₂ to argon. The signal changes are fully reversible and no hysteresis is observed during the measurements. The highly sensitive and fast responsible optical CO₂ sensor based on fluorescence intensity changes of TPP due to the absorption change of α-naphtholphthalein with CO₂ is achieved using poly(TMSP) film.

Reactive & Functional Polymers 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