Heterocyclic Building Block-benzofuran

L’Helgoual’ch, Jean-Martial published the artcileDeprotonative metalation of five-membered aromatic heterocycles using mixed lithium-zinc species, HPLC of Formula: 69626-75-1, the publication is Journal of Organic Chemistry (2008), 73(1), 177-183, database is CAplus and MEDLINE.

Deprotonation of benzoxazole, benzothiazole, benzo[b]thiophene, benzofuran, N-Boc-protected indole and pyrrole, and N-phenylpyrazole using an in situ mixture of ZnCl₂·TMEDA (0.5 equiv) and lithium 2,2,6,6-tetramethylpiperidide LiTMP (1.5 equiv) in THF at room temperature gave 2-zincated or 5-zincated (for 1-phenylpyrazole) derivatives, which were trapped by iodine to give the corresponding 2-iodo- or 5-iodo-substituted heterocycles in 52-73% yields; thiazole in the studied conditions gave mixture of 2- and 2,5-diiodothiazoles. One-pot palladium dichloride-catalyzed cross-coupling reactions of 2-metalated benzo[b]thiophene and benzofuran with 2-chloropyridine and 2,4-dichloropyrimidine gave 2-(2-pyridinyl)benzo[b]thiophene (18) and 2(2-chloro-4-pyrimidinyl)benzofuran (19), resp. A reaction pathway where the lithium amide and zinc diamide present in solution behave synergically was proposed for the deprotonation reaction, taking account of NMR and DFT studies carried out on the basic mixture

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, HPLC of Formula: 69626-75-1.

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

Theveau, Laure published the artcileSynthesis and orthogonal functionalization of oxazolo[5′,4′:4,5]pyrano[2,3-b]pyridine by intra- and intermolecular Pd-catalyzed direct C-H bond heteroarylation, Formula: C8H5IO, the publication is Organic & Biomolecular Chemistry (2016), 14(13), 3459-3468, database is CAplus and MEDLINE.

The construction and subsequent orthogonal functionalization of a hitherto unknown oxazolo[5′,4′:4,5]pyrano[2,3-b]pyridines was reported. A palladium-catalyzed direct C-H bond functionalization methodol. was used to build the tricyclic scaffold as well as to achieve the subsequent C-H bond functionalization at the C-2 position of the oxazole unit with various (hetero)aryl iodides. Remarkably, selective C-H construction and functionalization procedures preserved the chorine atom on the pyridine moiety offering a late-stage substitution site to progress drug design.

Organic & Biomolecular 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 C8H6N2O3, Formula: C8H5IO.

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

Jimenez-Holgado, Cristina published the artcilePhototransformation of three psychoactive drugs in presence of sedimental water extractable organic matter, Recommanded Product: 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, the publication is Molecules (2021), 26(9), 2466, database is CAplus and MEDLINE.

Psychoactive drugs are classified as contaminants of emerging concern but there is limited information on their fate in surface waters. Here, we studied the photodegradation of three psychoactive drugs (sertraline, clozapine, and citalopram) in the presence of organic matter (WEOM) extracted under mild conditions from sediment of Lake Pamvotis, Greece. Spectral characterization of WEOM confirmed its humic-like nature. Preliminary experiments using chem. probes showed that WEOM was able to produce oxidant triplet excited state (3WEOM*), singlet oxygen (1O2), and hydroxyl radicals under irradiation with simulated solar light. Then, WEOM at 5 mgC L^-1 was irradiated in the presence of the three drugs. It enhanced their phototransformation by a factor of 2, 4.2, and 16 for sertraline, clozapine, and citalopram, resp. The drastic inhibiting effect of 2-propanol (5 x 10^-3 M) on the reactions demonstrated that hydroxyl radical was the key intermediate responsible for drugs photodegradation A series of photoproducts were identified by ultra-high performance liquid chromatog. (UHPLC) coupled to high resolution mass spectrometry (HR-MS). The photodegradation of the three drugs proceeded through several pathways, in particular oxidations of the rings with or without O atom inclusion, N elimination, and substitution of the halogen by OH. The formation of halogenated aromatics was observed for sertraline. To conclude, sedimental natural organic matter can significantly phototransform the studied antidepressant drugs and these reactions need to be more investigated. Finally, ecotoxicity was estimated for the three target analytes and their photoproducts, using the Ecol. Structure Activity Relationships (ECOSAR) computer program.

Molecules 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, Recommanded Product: 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile.

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

Jeong, Seong Hun published the artcileTyrosinase Inhibitory Polyphenols from Roots of Morus lhou, Application In Synthesis of 56317-21-6, the publication is Journal of Agricultural and Food Chemistry (2009), 57(4), 1195-1203, database is CAplus and MEDLINE.

Twelve polyphenols (1-12) possessing tyrosinase inhibitory properties were isolated from the methanol (95%) extract of Morus lhou. The isolated compounds consisted of four flavanones (1-4), four flavones (5-8), and four phenylbenzofurans (9-12). Moracin derivative 12 proved to be new a compound which was fully characterized. Compounds 1-12 were evaluated for both monophenolase and diphenolase (the two steps catalyzed by tyrosinase) inhibition to identify the structural characteristics required for mushroom tyrosinase inhibition. We observed that all parent compounds (1, 5, and 9) possessing an unsubstituted resorcinol group were highly effective inhibitors of monophenolase activity (IC₅₀ values of 1.3, 1.2, and 7.4 μM). The potency of the inhibitors diminished with alkyl substitution on either the aromatic ring or the hydroxyl functions. Interestingly, flavone 5 was shown to possess only monophenolase inhibitory activity, but flavanone 1 and phenylbenzofuran 9 inhibited diphenolase as well as monophenolase significantly. The inhibitory mode of these species was also dependent upon the skeleton: phenylbenzofuran 9 manifested a simple competitive inhibition mode for monophenolase and diphenolase; on the other hand flavanone 1 (monophenolase, k₃ = 0.1966 min^-1 μM^-1, k₄ = 0.0082 min^-1, and K_i^app = 0.0468 μM; diphenolase, k₃ = 0.0014 min^-1 μM^-1, k₄ = 0.0013 min^-1, and K_i^app = 0.8996 μM) and flavone 5 both showed time-dependent inhibition against monophenolase. Compound 1 operated according to the simple reversible slow binding model whereas compound 5 operated under the enzyme isomerization model.

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 C14H10O4, Application In Synthesis of 56317-21-6.

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

Boonyaketgoson, Sirada published the artcileDeoxybenzoin and flavan derivatives from the twigs of Artocarpus lakoocha, Category: benzofurans, the publication is Phytochemistry Letters (2019), 96-100, database is CAplus.

One new deoxybenzoin, named lakoochanoside A (1), and one new flavan, named lakoochanoside B (2), along with 17 known compounds were isolated and identified from the twigs of Artocarpus lakoocha. The structures of isolated compounds were elucidated by spectroscopic methods, especially 1D and 2D NMR spectroscopy. Cycloartocarpin (14) exhibited strong antibacterial activities against Staphylococcus aureus and methicillin-resistant S. aureus with the same MIC values of 2 μg/mL. It also displayed antimalarial activity against Plasmodium falciparum K1 with an IC₅₀ value of 2.66 μM.

Phytochemistry Letters 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

Boonyaketgoson, Sirada published the artcileCytotoxic arylbenzofuran and stilbene derivatives from the twigs of Artocarpus heterophyllus, Category: benzofurans, the publication is Tetrahedron Letters (2017), 58(16), 1585-1589, database is CAplus.

Four new natural products, including three arylbenzofurans named heterophyllenes A-C (I-3), and one stilbene named heterophyllene D (II), together with twenty-one known compounds were isolated from the twigs of Artocarpus heterophyllus and their structures elucidated by spectroscopic methods, mainly 1D and 2D NMR spectroscopy. The cytotoxic activity of selected compounds against KB, MCF-7 and NCI-H187 cell lines was evaluated. Heterophyllene C (3) exhibited cytotoxicity against the MCF-7 cell line with an IC₅₀ value of 12.56 μM. Addnl., the known compounds norartocarpin and artocarpin showed cytotoxic activity against MCF-7 and KB cell lines with IC₅₀ values of 10.04 and 13.57 μM, resp. Both compounds also displayed cytotoxicity against the NCI-H187 cell line with values of 14.78 and 14.21 μM, resp.

Tetrahedron Letters 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

Royer, Mariana published the artcileEfficacy of Bagassa guianensis Aubl. extract against wood decay and human pathogenic fungi, Product Details of C14H10O4, the publication is International Biodeterioration & Biodegradation (2012), 55-59, database is CAplus.

Extractives that provide natural resistance to Bagassa guianensis Aubl. heartwood were examined Soil-bed tests showed that the B. guianensis heartwood resistance was significantly reduced after Et acetate extraction, whereas methanol and especially water extractions improved the resistance. The Et acetate extract was submitted to a bioguided fractionation, and fractions were tested against one wood-destroying fungal strain (Pycnoporus sanguineus) and two human pathogenic fungal strains (Candida glabrata (yeast) and Trichophyton rubrum (filamentous dermatophyte)). Fraction F7, which exhibited the strongest antifungal activity, was subsequently fractionated by high performance liquid chromatog. (HPLC). Six previously described compounds were isolated. Although the two moracins, 6-O-methyl-moracin N (3) and moracin N (4) were the most active against fungal strains with MIC values between 4 and 16 μg ml^-1, the isolated compounds showed less or equivalent antifungal activity than the initial fraction. Possible synergism between compounds 3 and 4 and other secondary metabolites have been hypothesized. Our study demonstrated that this extract as a whole might be used as a wood preservation or antimycotic product.

International Biodeterioration & Biodegradation 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, Product Details of C14H10O4.

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

Ishfaq, Muhammad published the artcileInsight into potent TLR2 inhibitors for the treatment of disease caused by Mycoplasma pneumoniae based on machine learning approaches, Computed Properties of 56317-21-6, the publication is Molecular Diversity, database is CAplus and MEDLINE.

Mycoplasma pneumoniae (MP) is one of the most common pathogens that causes acute respiratory tract infections. Children experiencing MP infection often suffer severe complications, lung injury, and even death. Previous studies have demonstrated that Toll-like receptor 2 (TLR2) is a potential therapeutic target for treating the MP-induced inflammatory response. However, the screening of natural compounds has received more attention for the treatment of bacterial infections to reduce the likelihood of bacterial resistance. Herein, we screened compounds by combining mol. docking and machine learning approaches to find potential lead compounds for treating MP infection. First, all compounds were docked with the TLR2 receptor protein to screen for potential candidates. To predict drug bioactivity, a machine learning model (random forest) was trained for TLR2 inhibitors to obtain the predictive model. The model achieved significant squared correlation coefficient (R2) values for the training set (0.85) and validation set (0.84) of compounds The developed machine learning model was then used to predict the pIC50 values of the top 50 candidates from the Traditional Chinese compounds and Discovery Diversity sets of compounds As a result, these compounds are capable of inhibiting the inflammatory response induced by MP. However, prior to bringing these compounds to market, it is necessary to verify these results with addnl. biol. testing, including preclin. and clin. studies. Moreover, the present study provides a theor. basis for the use of natural compounds as potential candidates to treat pneumonia caused by MP.

Molecular Diversity 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

Perry, Gregory J. P. published the artcileTransition-metal-free decarboxylative iodination: New routes for decarboxylative oxidative cross-couplings, Related Products of benzofurans, the publication is Journal of the American Chemical Society (2017), 139(33), 11527-11536, database is CAplus and MEDLINE.

Constructing products of high synthetic value from inexpensive and abundant starting materials is of great importance. Aryl iodides are essential building blocks for the synthesis of functional mols., and efficient methods for their synthesis from chem. feedstocks are highly sought after. Here we report a low-cost decarboxylative iodination that occurs simply from readily available benzoic acids and I₂. The reaction is scalable and the scope and robustness of the reaction is thoroughly examined Mechanistic studies suggest that this reaction does not proceed via a radical mechanism, which is in contrast to classical Hunsdiecker-type decarboxylative halogenations. In addition, DFT studies allow comparisons to be made between our procedure and current transition-metal-catalyzed decarboxylations. The utility of this procedure is demonstrated in its application to oxidative cross-couplings of aromatics via decarboxylative/C-H or double decarboxylative activations that use I₂ as the terminal oxidant. This strategy allows the preparation of biaryls previously inaccessible via decarboxylative methods and holds other advantages over existing decarboxylative oxidative couplings, as stoichiometric transition metals are avoided.

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, Related Products of benzofurans.

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

Chen, Hong-Bin published the artcileAccessing 2-Arylbenzofurans by Cu^I₂(pip)₂-Catalyzed Tandem Coupling/Cyclization Reaction: Mechanistic Studies and Application to the Synthesis of Stemofuran A and Moracin M, Product Details of C14H10O4, the publication is Asian Journal of Organic Chemistry (2016), 5(11), 1345-1352, database is CAplus.

An asym. dinuclear copper(I) complex, Cu^I2(pip)₂ (pip = (2-picolyliminomethyl)pyrrole anion), was utilized to catalyze the tandem coupling/cyclization reaction of o-iodophenols and terminal alkynes, which led to the formation of valuable 2-arylbenzofurans I (R¹ = Ph, 4-EtC₆H₄, 1-naphthyl, etc.; R² = H, 4-MeO, 4-t-Bu, 4-Ph, 4-F, 4-Br) in good yields. DFT calculations showed that the two proximate copper atoms play cooperative roles throughout the catalytic cycle. Using this catalytic protocol, bioactive natural products stemofuran A and moracin M were concisely synthesized.

Asian 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, Product Details of C14H10O4.

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