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7-Iodo-5-aza-7-deazaguanine ribonucleoside: crystal structure, physical properties, base-pair stability and functionalization

The positional change of nitrogen-7 of the RNA constituent guanosine to the bridgehead position-5 leads to the base-modified nucleoside 5-aza-7-deaza-guanosine. Contrary to guanosine, this molecule cannot form Hoogsteen base pairs and the Watson-Crick proton donor site N3-H becomes a proton-acceptor site. This causes changes in nucleobase recognition in nucleic acids and has been used to construct stable ‘all-purine’ DNA and DNA with silver-mediated base pairs. The present work reports the single-crystal X-ray structure of 7-iodo-5-aza-7-deazaguanosine, C10H12IN5O5 (1). The iodinated nucleoside shows an anti conformation at the glycosylic bond and an N conformation (O4′-endo) for the ribose moiety, with an antiperiplanar orientation of the 5′-hydroxy group. Crystal packing is controlled by interactions between nucleobase and sugar moieties. The 7-iodo substituent forms a contact to oxygen-2′ of the ribose moiety. Self-pairing of the nucleobases does not take place. A Hirshfeld surface analysis of 1 highlights the contacts of the nucleobase and sugar moiety (O-H center dot center dot center dot O and N-H center dot center dot center dot O). The concept of pK-value differences to evaluate base-pair stability was applied to purine-purine base pairing and stable base pairs were predicted for the construction of ‘all-purine’ RNA. Furthermore, the 7-iodo substituent of 1 was functionalized with benzofuran to detect motional constraints by fluorescence spectroscopy.

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

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

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

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Organocatalytic Gram-Scale Synthesis and Alkylation of Heteroaryl and Electron-Rich Aryl alpha-Substituted gamma-Lactones

The synthesis of gamma-lactones alpha-substituted with heterocycles and electron-rich aromatic rings is described. The method, based on a sequence involving an organocatalytic addition of boronic acid to the 5-hydroxyfuran-2(5H)-one, followed by reduction and lactonization, gives access to broad range of gamma-lactones on a gram scale. Among these, gamma-lactones bearing a benzofuran, a benzothiophene, and an indole ring were alkylated in mild catalytic conditions to construct alpha-quaternary stereocenters. Interesting mild oxidation reaction, using molecular oxygen, was also highlighted during this study.

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