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One-pot access to 2-amino-3-arylbenzofurans: direct entry to polyheterocyclic chemical space

As a means to make new benzofuran-embedded polycyclic structures, we established two efficient one-pot sequential coupling routes to 2-amino-3-arylbenzofurans and 2-amino-3-arylnaphtho[2,1-b]furans. Further ring formation (six- and seven-membered rings) with the resulting amine moiety at the C2 position of benzofurans was realized, leading to further expansion of benzofuran-based chemical space.

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Benzofuran – Wikipedia,
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Organocatalytic asymmetric [4+1] annulation of in situ generated ortho-quinomethanes with 4-halo pyrazolones: straightforward access to chiral spiro-benzofuran pyrazolones

A highly straightforward route to enantiomerically enriched spiro-benzofuran pyrazolones has been achieved via chiral amine squaramide catalyzed [4 + 1] annulation of in situ generated ortho-quinomethanes with the novel C1 synthons of 4-halo pyrazolones. In oil-water biphases, high yields (up to 95%) and high to excellent stereoselectivities (up to 99 : 1 dr, 99% ee) of the resulting 4-spiropyrazolones with a wide substrate scope could be achieved. Furthermore, the present protocol provided an arbitrary access to all four possible stereoisomers of the spiro-benzofuran pyrazolones via an appropriate choice of C1 synthons and chiral catalysts.

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Benzofuran – Wikipedia,
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Synthesis and biological activity of new bisbenzofuran-imidazolium salts

A series of novel bisbenzofuran-imidazolium salts were designed and prepared. The in vitro antitumor activity of these derivatives was evaluated against a panel of human tumor cell lines (A549, HL-60, MCF-7, SMMC-7721 and SW480). Results demonstrated that 2-methyl-benzimidazole ring and substitution of the imidazolyl 3 po sition with a 4-methoxyphenacyl or 2-naphthylacyl substituent were important for promoting cytotoxic activity. Notably, compound 23 was found to be the most potent compound with IC50 values of 0.64-1.47 mu M against five human tumor cell lines, and exhibited higher selectivity to MCF-7 and SW-480 cell lines with IC50 values 15.3-fold and 9.1-fold lower than DDP.

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Reference:
Benzofuran – Wikipedia,
,Benzofuran | C8H6O – PubChem

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Discovery of Potent, Selective, and Orally Bioavailable Inhibitors of USP7 with In Vivo Antitumor Activity

USP7 is a promising target for cancer therapy as its inhibition is expected to decrease function of oncogenes, increase tumor suppressor function, and enhance immune function. Using a structure-based drug design strategy, a new class of reversible USP7 inhibitors has been identified that is highly potent in biochemical and cellular assays and extremely selective for USP7 over other deubiquitinases. The succinimide was identified as a key potency-driving motif, forming two strong hydrogen bonds to the allosteric pocket of USP7. Redesign of an initial benzofuran-amide scaffold yielded a simplified ether series of inhibitors, utilizing acyclic conformational control to achieve proper amine placement. Further improvements were realized upon replacing the etherlinked amines with carbon-linked morpholines, a modification motivated by free energy perturbation (FEP+) calculations. This led to the discovery of compound 41, a highly potent, selective, and orally bioavailable USP7 inhibitor. In xenograft studies, compound 41 demonstrated tumor growth inhibition in both p53 wildtype and p53 mutant cancer cell lines, demonstrating that USP7 inhibitors can suppress tumor growth through multiple different pathways.

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Reference:
Benzofuran – Wikipedia,
,Benzofuran | C8H6O – PubChem

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Chemo-enzymatic cascade processes are invaluable due to their ability to rapidly construct high-value products from available feedstock chemicals in a one-pot relay manner. In an article, author is Lichitsky, Boris V., once mentioned the application of 66357-35-5, Name is Ranitidine, molecular formula is C13H22N4O3S, molecular weight is 314.4038, MDL number is MFCD00081180, category is benzofurans. Now introduce a scientific discovery about this category, Quality Control of Ranitidine.

Photochemical synthesis of novel naphtho[1,2-b]benzofuran derivatives from 2,3-disubstituted benzofurans

A novel approach to the synthesis of naphtho[1,2-b]benzofuran derivatives based on the photochemical reaction of 2,3-disubstituted benzofurans was developed. The studied process includes the photocyclization of the hexatriene system and subsequent aromatization of benzene ring via elimination of water molecule. The starting terarylenes were prepared via a new three-component condensation of phenols, arylglyoxals, and cyclic 1,3-diketones.

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Benzofuran – Wikipedia,
,Benzofuran | C8H6O – PubChem

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Chemistry, like all the natural sciences, COA of Formula: C13H22N4O3S, begins with the direct observation of nature¡ª in this case, of matter.66357-35-5, Name is Ranitidine, SMILES is O=[N+]([O-])/C=C(NCCSCC1=CC=C(O1)CN(C)C)NC, belongs to benzofurans compound. In a document, author is Zhao, Guode, introduce the new discover.

The structure-based virtual screening of non-benzofuran inhibitors against M. tuberculosis Pks13-TE for anti-tuberculosis phenotypic discovery

Tuberculosis is the most infectious disease worldwide, primarily because of its increasing resistance to first-line anti-TB drugs. Therefore, development of new drugs with novel mechanisms of action is the solution to the growing problem of drug resistance. The thioesterase domain (TE) of polyketide synthase Pks13 is crucial for the biosynthesis of mycolic acids, which are the essential components of the cell wall of Mycobacterium tuberculosis. However, all the inhibitors of Pks13-TE just share the same benzofuran scaffold, which restricts the further development of Pks13-TE inhibitors. Hence, in order to search for new inhibitors with novel scaffolds and in vitro anti-tuberculosis activity, a structure-based virtual screening method was established to screen the FDA database against pks13-TE. The hit drugs were purchased and tested for anti-tubercular activity against the selectable marker-free autoluminescent Mycobacterium tuberculosis H37Ra (UAlRa). Interestingly, three old drugs approved by FDA, namely, carvedilol (32 mu g ml(-1)), celecoxib (64 mu g ml(-1)), and quinacrine (64 mu g ml(-1)) were discovered to possess in vitro anti-tubercular activity. The complexes of Pks13-TE with the hits showed a similar binding stability and interaction mode with Pks13-TE/co-crystal ligand Tam16, which were validated by the 100 ns molecular dynamics simulations, the binding free energy calculations and alanine scanning mutagenesis analysis. The rest of the chiral isomers for carvedilol and quinacrine were also researched by the same computational strategies. The results of the calculations proved that the S-configuration of carvedilol had a stronger binding affinity with Pks13-TE than the R-configuration of carvedilol, and S and R configurations of quinacrine displayed an equivalent binding affinity with the protein. As the three hit compounds have already been on the market for decades, these compounds possess good enough druggability and definite toxicity and side effects, which were consistent with the prediction results. Our work shows the successful application of computational strategies for the discovery of Pks13-TE non-benzofuran inhibitors with in vitro anti-tubercular activities. These discoveries would further promote the development of Pks13-TE inhibitors and anti-tubercular agents.

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Reference:
Benzofuran – Wikipedia,
,Benzofuran | C8H6O – PubChem

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Reactions catalyzed within inorganic and organic materials and at electrochemical interfaces commonly occur at high coverage and in condensed media, causing turnover rates to depend strongly on interfacial structure and composition, 66357-35-5, Name is Ranitidine, SMILES is O=[N+]([O-])/C=C(NCCSCC1=CC=C(O1)CN(C)C)NC, in an article , author is Zheng, Suhua, once mentioned of 66357-35-5, Recommanded Product: Ranitidine.

Reductive 3-Silylation of Benzofuran Derivatives via Coupling Reaction with Chlorotrialkylsilane

Reductive silylation of benzofurans with an electron-withdrawing group by a magnesium metal and the subsequent oxidative rearomatization by DDQ gave the selective formation of less reported 3-silylated benzofurans in moderate to good yields under mild reaction conditions with wide substituent scope. The silyl group introduced on the five-membered ring by the reductive coupling could survive with no elimination throughout the oxidation process. The silylated heteroaromatic skeleton is useful as an intermediate in organic synthesis, and its practical utility was also demonstrated by several transformation reactions.

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Benzofuran – Wikipedia,
,Benzofuran | C8H6O – PubChem

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Strongly fluorescing silver(I) complex of a new thiadiazole ligand: X-ray crystallography, close anagostic interactions and TD-DFT emissive states

A new thiadiazole ligand, N-ethyl-5- (benzo[b]thien-2-yl-)-1,3,4-thiadiazol-2-amine (BTH), was prepared from 3-methyl-1-benzofuran-2-carboxylic acid and N-ethylhydrazinecarbothioamide precursors. Corresponding silver(I) complex, tetrakis(N-ethyl-5-(benzo[b]thien-2-yl-)-1,3,4-thiadiazol-2-amine)silver(I) nitrate [Ag-2(BTH)(4)](NO3)(2) (1), was prepared. The structures of BTH and 1 were characterized by H-1-NMR, C-13-NMR, FT-IR, elemental analysis and HR-MS techniques. Furthermore, molecular structure of 1 was illuminated by X-ray crystallography. Owing to strong anagsotic interaction, crystal structure of the complex revealed an intriguing asymmetric monomer unit even with two same ligands in 2:1 metal-to-ligand stoichiometry. Photoluminescence properties of the complex were investigated by solid and solution media emission measurements. Excited and emissive state behavior of the complex was further analyzed by quantum chemical TD-DFT calculations and natural transition orbital (NTO) analyses.

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Reference:
Benzofuran – Wikipedia,
,Benzofuran | C8H6O – PubChem

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Synthesis, in vitro urease inhibitory potential and molecular docking study of benzofuran-based-thiazoldinone analogues

In continuation of our work on enzyme inhibition, the benzofuran-based-thiazoldinone analogues (1-14) were synthesized, characterized by HREI-MS, H-1 and (CNMR)-C-13 and evaluated for urease inhibition. Compounds 1-14 exhibited a varying degree of urease inhibitory activity with IC50 values between 1.2 +/- 0.01 to 23.50 +/- 0.70 mu M when compared with standard drug thiourea having IC50 value 21.40 +/- 0.21 mu M. Compound 1, 3, 5 and 8 showed significant inhibitory effects with IC50 values 1.2 +/- 0.01, 2.20 +/- 0.01, 1.40 +/- 0.01 and 2.90 +/- 0.01 mu M respectively, better than the rest of the series. A structure activity relationship (SAR) of this series has been established based on electronic effects and position of different substituents present on phenyl ring. Molecular docking studies were performed to understand the binding interaction of the compounds.

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Reference:
Benzofuran – Wikipedia,
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Pd-catalyzed C-H bond activation of Indoles for Suzuki reaction

We present a practical method for Suzuki coupling by which unprotected or N-protected indoles may be selectively arylated in the C2-position through direct C-H bond activation by electrophilic Pd(TFA)2 catalyst. The protocol is operationally simple as it is carried out in dioxane/water mixture, and air as the sole oxidant at room temperature. Various 2-arylated indoles were obtained in good yields. The protocol works for benzofuran, pyrrole and thiophene also. Graphic abstract Selective C-2 arylation of heterocycles using Pd(II) catalyst via C-H activation was performed under ambient condition. C3-C2 migration of organopalladium intermediate controls the reaction pathway.Computed Properties of C13H22N4O3S.

Reference:
Benzofuran – Wikipedia,
,Benzofuran | C8H6O – PubChem