Month: November 2022

Wu, Xuewei published the artcileTwo new 2-arylbenzofuran derivatives from the leaves of Morus alba, Safety of 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, the publication is Natural Product Research (2019), 33(2), 204-211, database is CAplus and MEDLINE.

Two new 2-arylbenzofuran derivatives, moracinfurol A and B (1-2), and 10 known compounds (3-12) were isolated from the leaves of M. alba. Their structures were determined on the basis of spectroscopic anal. including 1D and 2D NMR and HR-ESI-MS. All of the 2-arylbenzofuran derivatives were evaluated for cytotoxicity against A549 cells with compounds 2, 4, 6-8, and 12 exhibiting moderate activity. Some cytotoxic 2-arylbenzofuran derivatives might induce autophagy characterized by the accumulation of LC-3 II.

Natural Product Research 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 C8H8O3, Safety of 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol.

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

Gao, Zhumei published the artcileAcidity determination of oxidation solution from phenol production with 1- naphtholphthalein as indicator, Recommanded Product: 3,3-Bis(4-hydroxynaphthalen-1-yl)isobenzofuran-1(3H)-one, the publication is Shihua Jishu Yu Yingyong (2010), 28(1), 56-57, database is CAplus.

The acidity of oxidation solution from phenol production was determined with 1-naphtholphthalein as indicator instead of phenolphthalein, and the accuracy was investigated. The results showed that when 1-naphtholphthalein was used as indicator, the pH value at end point was 8.69, similar with the theor. pH value at end point 8.70. The determination results of organic acid samples whose acidity was known as 288mg/kg indicated that the deviation for 1-naphtholphthalein was 3 mg/kg, while 102mg/kg for phenolphthalein.

Shihua Jishu Yu Yingyong 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

Snegaroff, Katia published the artcileDeprotonative Metalation of Functionalized Aromatics Using Mixed Lithium-Cadmium, Lithium-Indium, and Lithium-Zinc Species, Recommanded Product: 2-Iodobenzofuran, the publication is Chemistry – A European Journal (2009), 15(39), 10280-10290, S10280/1-S10280/16, database is CAplus and MEDLINE.

In situ mixtures of CdCl₂.TMEDA (0.5 equiv; TMEDA = N,N,N’,N’-tetramethylethylenediamine) or InCl₃ (0.33 equiv) with [Li(tmp)] (tmp = 2,2,6,6-tetramethylpiperidino; 1.5 or 1.3 equiv, resp.) were compared with the previously described mixture of ZnCl₂.TMEDA (0.5 equiv) and [Li(tmp)] (1.5 equiv) for their ability to deprotonate anisole, benzothiazole, and pyrimidine. [(Tmp)₃CdLi] proved to be the best base when used in THF at room temperature, as demonstrated by subsequent trapping with iodine. The Cd-Li base then proved suitable for the metalation of a large range of aromatics including benzenes bearing reactive functional groups (CONEt₂, CO₂Me, CN, COPh) or heavy halogens (Br, I), and heterocycles (from the furan, thiophene, pyrrole, oxazole, thiazole, pyridine, and diazine series). Five-membered heterocycles benefiting from doubly activated positions were similarly dideprotonated at room temperature The aromatic lithium cadmates thus obtained were involved in palladium-catalyzed cross-coupling reactions or simply quenched with acid chlorides.

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 C8H11BrN2, Recommanded Product: 2-Iodobenzofuran.

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

Liu, Xi-Hai published the artcileCopper-mediated aerobic iodination and perfluoroalkylation of boronic acids with (CF₃)₂CFI at room temperature, Synthetic Route of 69626-75-1, the publication is Journal of Fluorine Chemistry (2016), 59-67, database is CAplus.

The copper-mediated aerobic reactions between the branched (CF₃)₂CFI and boronic acids (R-B(OH)₂) are described. Different from the linear perfluoroalkyl analogs CF₃(CF₂)_nI (n = 2, 3, 5, 7), (CF₃)₂CFI reacting with R-B(OH)₂ at room temperature under air in the presence of catalytic Cu powder provided exclusively the corresponding iodides (R-I), while the aerobic reactions of arylboronic acids with (CF₃)₂CFI at room temperature in the presence of Cu(OAc)₂ gave the perfluoroalkylation products (R-CF(CF₃)₂) in acceptable to moderate yields. The iodination reaction could be further promoted by hydroquinone, the addition of which improved the oxidation ability of (CF₃)₂CFI and provided the ipso-iodination products in high yields. The perfluoroalkylation was facilitated by the copper carboxylates since the addition of these salts into the reaction mixtures could successfully give rise to Ar-CF(CF₃)₂.

Journal of Fluorine 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, Synthetic Route of 69626-75-1.

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

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