Tag: M.W=200-250

Rao, Maddali L. N. published the artcileFunctional group manoeuvering for tuning stability and reactivity: synthesis of cicerfuran, moracins (D, E, M) and chromene-fused benzofuran-based natural products, Computed Properties of 56317-21-6, the publication is Organic & Biomolecular Chemistry (2017), 15(44), 9415-9423, database is CAplus and MEDLINE.

The protecting group maneuvering as a strategy was applied for tuning the stability and reactivity of 4-(2,2-dibromovinyl)benzene-1,3-diol and 6-(2,2-dibromovinyl)-2,2-dimethylchroman-7-ol in the domino synthesis of benzofuran-based natural products. The functional group demands and their impact on the reactivity driven by electronic effects were successfully managed by varying the protecting groups with substituted gem-dibromovinylphenols in domino couplings and triarylbismuth reagents under palladium-catalyzed conditions. This approach paved the way for the synthesis of moracin M and cicerfuran, and the first time synthesis of moracin D and moracin E along with chromene-fused benzofuran-based natural products in overall good yields.

Organic & Biomolecular 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, Computed Properties of 56317-21-6.

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

Sichaem, Jirapast published the artcileChemical Constituents of the Leaves of Artocarpus integer, HPLC of Formula: 56317-21-6, the publication is Chemistry of Natural Compounds (2022), 58(3), 538-540, database is CAplus.

During our recent chem. investigation, 11 compounds, epiafzelechin (1) , (+)-epicatechin (2), 3β-hydroxy-7α-methoxy-24β-ethylcholest-5-ene (3) , isobavachalcone (4), kuwanon J (5), moracin M (6), morachalcone A (7) ,apigenin (8) , scopoletin (9), ferulic acid (10), and luteolin (11) were isolated from the leaves of A. integer. Their structures were identified by interpretation of their spectroscopic data and comparison with those reported in the literature. Among these compounds, compounds 2, 6, and 11 exhibited potent antioxidant activity in DPPH radical scavenging with IC50 values of 20.59 ± 0.56, 54.17 ± 1.84, and 26.43 ± 0.17 μg/mL, resp.

Chemistry of Natural Compounds 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 C17H18N2O6, HPLC of Formula: 56317-21-6.

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

Mokhtari Brikci-Nigassa, Nahida published the artcileFunctionalization of 9-thioxanthone at the 1-position: From arylamino derivatives to [1]benzo(thio)pyrano[4,3,2-de]benzothieno[2,3-b]quinolines of biological interest, HPLC of Formula: 69626-75-1, the publication is Bioorganic Chemistry (2020), 103347, database is CAplus and MEDLINE.

Original 1-amino substituted thioxanthone derivatives were easily prepared from the bare heterocycle by a deprotometalation-iodolysis-copper-catalyzed C-N bond formation sequence. This last reaction delivered mono- or/and diarylated products I (R = 4-FC₆H₄, 1-naphthyl, 3-aminopyridin-2-yl, etc.) and II (R = 4-CH₃C₆H₄, 4-CH₃OC₆H₄) depending on the anilines RNH₂ involved. 1-Amino-9-thioxanthone was also prepared and reacted with 2-iodoheterocycles R¹I (R¹ = 2-thienyl, 1-benzothiophen-2-yl, 1-benzofuran-2-yl). Interestingly, while 1-(arylamino)-9-thioxanthones like 1-(2-thienylamino)-9-thioxanthone and 1-(2-benzothienylamino)-9-thioxanthone could be isolated, their subsequent cyclization was found to deliver original hexacyclic derivatives like [1]benzothiopyrano[4,3,2-de]benzothieno[2,3-b]quinoline and [1]benzothiopyrano[4,3,2-de]benzofuro[2,3-b]quinoline of helicoidal nature. Evaluation of their photophys. properties revealed high fluorescence in polar media, indicating potential applications for biol. imaging. These compounds being able to inhibit PIM1 kinase, their putative binding mode was examined through mol. modeling experiments Altogether, these results tend to suggest the discovery of a new family of fluorescent PIM inhibitors and pave the way for their future rational optimization.

Bioorganic 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, HPLC of Formula: 69626-75-1.

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

Lee, Ju Hee published the artcileMoracin M inhibits airway inflammation by interrupting the JNK/c-Jun and NF-κB pathways in vitro and in vivo, Safety of 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, the publication is European Journal of Pharmacology (2016), 64-72, database is CAplus and MEDLINE.

The therapeutic effectiveness of moracins as 2-arylbenzofuran derivatives against airway inflammation was examined Moracin M, O, and R were isolated from the root barks of Morus alba, and they inhibited interleukin (IL)-6 production from IL-1β-treated lung epithelial cells (A549) at 101-00 μM. Among them, moracin M showed the strongest inhibitory effect (IC₅₀=8.1 μM). Downregulation of IL-6 expression by moracin M was mediated by interrupting the c-Jun N-terminal kinase (JNK)/c-Jun pathway. Moracin derivatives inhibited inducible nitric oxide synthase (iNOS)-catalyzed NO production from lipopolysaccharide (LPS)-treated alveolar macrophages (MH-S) at 50-100 μM. In particular, moracin M inhibited NO production by downregulating iNOS. When orally administered, moracin M (20-60 mg/kg) showed comparable inhibitory action with dexamethasone (30 mg/kg) against LPS-induced lung inflammation, acute lung injury, in mice with that of dexamethasone (30 mg/kg). The action mechanism included interfering with the activation of nuclear transcription factor-κB in inflamed lungs. Therefore, it is concluded that moracin M inhibited airway inflammation in vitro and in vivo, and it has therapeutic potential for treating lung inflammatory disorders.

European Journal of Pharmacology 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, Safety of 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol.

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

Snegaroff, Katia published the artcileDeprotonative Metalation of Substituted Benzenes and Heteroaromatics Using Amino/Alkyl Mixed Lithium-Zinc Combinations, Formula: C8H5IO, the publication is Chemistry – A European Journal (2010), 16(27), 8191-8201, S8191/1-S8191/50, database is CAplus and MEDLINE.

Various homoleptic and heteroleptic lithium-zinc combinations were prepared, and structural elements obtained on the basis of NMR spectroscopic experiments and DFT calculations In light of their ability to metalate anisole, pathways were proposed to justify the synergy observed for some mixtures The best basic mixtures were obtained either by combining ZnCl₂·TMEDA (TMEDA = N,N,N’,N’-tetramethylethylenediamine) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidine; 3 equiv) or by replacing one of the tmp in the precedent mixture with an alkyl group. The reactivity of the aromatic lithium zincates supposedly formed was next studied, and proved to be substrate-, base-, and electrophile-dependent. The aromatic lithium zincates were finally involved in palladium-catalyzed cross-coupling reactions with aromatic chlorides and bromides.

Chemistry – A European Journal 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 C7H13NO2, Formula: C8H5IO.

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

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

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

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

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