Heterocyclic Building Block-benzofuran

Scaffold hopping and optimisation of 3′,4′-dihydroxyphenyl- containing thienopyrimidinones: synthesis of quinazolinone derivatives as novel allosteric inhibitors of HIV-1 reverse transcriptase-associated ribonuclease H was written by Tocco, Graziella;Esposito, Francesca;Caboni, Pierluigi;Laus, Antonio;Beutler, John A.;Wilson, Jennifer A.;Corona, Angela;Le Grice, Stuart F. J.;Tramontano, Enzo. And the article was included in Journal of Enzyme Inhibition and Medicinal Chemistry in 2020.Application In Synthesis of 3-Aminobenzofuran-2-carboxamide This article mentions the following:

Bioisosteric replacement and scaffold hopping are powerful strategies in drug design useful for rationally modifying a hit compound towards novel lead therapeutic agents. Recently, we reported a series of thienopyrimidinones that compromise dynamics at the p66/p51 HIV-1 reverse transcriptase (RT)-associated RNase H (RNase H) dimer interface, thereby allosterically interrupting catalysis by altering the active site geometry. Although they exhibited good submicromolar activity, the isosteric replacement of the thiophene ring, a potential toxicophore, is warranted. Thus, in this article, the most active 2-(3,4-dihydroxyphenyl)-5,6-dimethylthieno[2,3-d]pyrimidin-4(3H)-one was selected as the hit scaffold and several isosteric substitutions of the thiophene ring were performed. A novel series of highly active RNase H allosteric quinazolinone inhibitors was thus obtained. To determine their target selectivity, they were tested against RT-associated RNA-dependent DNA polymerase (RDDP) and integrase (IN). Interestingly, none of the compounds were particularly active on (RDDP) but many displayed micromolar to submicromolar activity against IN. In the experiment, the researchers used many compounds, for example, 3-Aminobenzofuran-2-carboxamide (cas: 54802-10-7Application In Synthesis of 3-Aminobenzofuran-2-carboxamide).

3-Aminobenzofuran-2-carboxamide (cas: 54802-10-7) belongs to benzofurans derivatives.Benzofuran is one of the most significant oxygen-containing heterocycles consisting of fused benzene and furan ring, which are widely presented in various naturally occurring and synthetically active compounds. Benzofurans are stable towards alkali and readily polymerize on treatment with sulfuric acid, due to which they are useful for the preparation of low cost chemically relatively inert resins.Application In Synthesis of 3-Aminobenzofuran-2-carboxamide

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Kinetics of bromination of benzofurans by phenyltrimethylammonium tribromide was written by Suryawanshi, V. S.. And the article was included in Journal of Chemical and Pharmaceutical Research in 2017.Formula: C10H7BrO2 This article mentions the following:

The kinetics of the reaction between different 2-acetyl benzofuran (BF) and phenyltrimethylammonium tribromide (PTT) has been studied spectrophotometrically in acetic acid under varying conditions. The results indicate first order kinetic with respect to 2-acetyl benzofurans (BF) and inverse first order due to phenyltrimethylammonium tribromide (PTT). Effect of ionic strength and dielec. constant on reaction rate was observed The rates of reaction are measured at different temperature and activation parameters have been calculated The products of the bromination are the corresponding 2-bromoacetyl benzofurans. In the experiment, the researchers used many compounds, for example, 1-(5-Bromobenzofuran-2-yl)ethanone (cas: 38220-75-6Formula: C10H7BrO2).

1-(5-Bromobenzofuran-2-yl)ethanone (cas: 38220-75-6) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. Introduction of benzofurans in organic synthesis, particularly drug synthesis, involves generally the use of their metalated species as nucleophiles in addition reactions or in metal-catalysed cross-coupling reactions.Formula: C10H7BrO2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Ligand-Promoted Nickel-Catalyzed para-Selective Carboxylation of Anisoles was written by Tu, Guangliang;Ju, Guodong;Ji, Shun-Jun;Zhao, Yingsheng. And the article was included in Organic Letters in 2022.Category: benzofurans This article mentions the following:

It has always been a challenge in free radical chem. to control site selectivity during the reaction of free radicals with aromatic rings. Herein, the site-selective carboxylation of anisoles through the direct reaction of the bromoform radical with a benzene ring at the para position under the assistance of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline with nickel(II) as the catalyst is reported. A wide variety of anisoles were compatible, leading to para-carboxylated products in moderate to good yields. A preliminary mechanistic study suggested that the Ni(II) complex coordinates with the methoxyl group of the aromatic ring, which may have increased the steric hindrance at the ortho and meta positions, while this weak interaction reduces the aromaticity of the aromatic ring, affording an activated Ph ring, thereby leading to highly para-selective carboxylation. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1Category: benzofurans).

Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives. Benzofurans are only weakly aromatic in nature and they are cleaved by many oxidative and reductive conditions. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antiviral, antimicrobial, antitumor, anti-inflammatory.Category: benzofurans

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Rapid and selective determination of multi-sulfonamides by high-performance thin layer chromatography coupled to fluorescent densitometry and electrospray ionization mass detection was written by Chen, Yisheng;Schwack, Wolfgang. And the article was included in Journal of Chromatography A in 2014.COA of Formula: C17H10O4 This article mentions the following:

Sulfonamides are widely used in animal husbandry and monitoring their residues in edible animal tissues is important for food safety and quality control. A simple and efficient high-performance thin-layer chromatog. (HPTLC) anal. method for rapid screening of 12 veterinary sulfonamide drugs was developed. Sample acetonitrile extracts were 10-fold concentrated and applied to HPTLC without any further cleanup. Following separation and fluram derivatization, sensitive and selective quantitation of the analytes was readily accomplished with fluorescence densitometry. Limits of detection and quantitation were 15-40 and 35-70 μg/kg, resp. Confirmative detection by HPTLC-electrospray ionization mass spectrometry (HPTLC-ESI/MS) was optimized for straightforward identification of target TLC zones to decrease the risk of potential false pos. findings. The method was validated for different matrix complexities (cow milk, pork liver and kidney). In the experiment, the researchers used many compounds, for example, 4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9COA of Formula: C17H10O4).

4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9) belongs to benzofurans derivatives.Benzofuran is one of the most significant oxygen-containing heterocycles consisting of fused benzene and furan ring, which are widely presented in various naturally occurring and synthetically active compounds. Introduction of benzofurans in organic synthesis, particularly drug synthesis, involves generally the use of their metalated species as nucleophiles in addition reactions or in metal-catalysed cross-coupling reactions.COA of Formula: C17H10O4

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Development of a dual luciferase activity and fluorescamine protein assay adapted to a 384 micro-well plate format: Reducing variability in human luciferase transactivation cell lines aimed at endocrine active substances was written by Brennan, Jennifer C.;Tillitt, Donald E.. And the article was included in Toxicology In Vitro in 2018.SDS of cas: 38183-12-9 This article mentions the following:

There is a need to adapt cell bioassays to 384-well and 1536-well formats instead of the traditional 96-well format as high-throughput screening (HTS) demands increase. However, the sensitivity and performance of the bioassay must be re-verified in these higher micro-well plates, and verification of cell health must also be HT (high-throughput). We have adapted two commonly used human breast luciferase transactivation cell bioassays, the recently re-named estrogen agonist/antagonist screening VM7Luc4E2 cell bioassay (previously designated BG1Luc4E2) and the androgen/glucocorticoid screening MDA-kb2 cell bioassay, to 384-well formats for HTS of endocrine-active substances (EASs). This cost-saving adaptation includes a fast, accurate, and easy measurement of protein amount in each well via the fluorescamine assay with which to normalize luciferase activity of cell lysates without requiring any transfer of the cell lysates. Here we demonstrate that by accounting for protein amount in the cell lysates, antagonistic agents can easily be distinguished from cytotoxic agents in the MDA-kb2 and VM7Luc4E2 cell bioassays. Addnl., we demonstrate via the fluorescamine assay improved interpretation of luciferase activity in wells along the edge of the plate (the so-called “edge effect”), thereby increasing usable wells to the entire plate, not just interior wells. In the experiment, the researchers used many compounds, for example, 4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9SDS of cas: 38183-12-9).

4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9) belongs to benzofurans derivatives. Many natural or synthetic compounds containing benzofuran skeletons have been found to possess remarkable activity as agrochemicals and pharmaceuticals. As benzofurans are prone to undergo ring opening of the heterocycle, examples of reduction of this type of aromatics by using dissolving metals are rather scarce.SDS of cas: 38183-12-9

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

The CHD6 chromatin remodeler is an oxidative DNA damage response factor was written by Moore, Shaun;Berger, N. Daniel;Luijsterburg, Martijn S.;Piett, Cortt G.;Stanley, Fintan K. T.;Schrader, Christoph U.;Fang, Shujuan;Chan, Jennifer A.;Schriemer, David C.;Nagel, Zachary D.;van Attikum, Haico;Goodarzi, Aaron A.. And the article was included in Nature Communications in 2019.Related Products of 76-54-0 This article mentions the following:

Cell survival after oxidative DNA damage requires signaling, repair and transcriptional events often enabled by nucleosome displacement, exchange or removal by chromatin remodeling enzymes. Here, we show that Chromodomain Helicase DNA-binding protein 6 (CHD6), distinct to other CHD enzymes, is stabilized during oxidative stress via reduced degradation CHD6 relocates rapidly to DNA damage in a manner dependent upon oxidative lesions and a conserved N-terminal poly(ADP-ribose)-dependent recruitment motif, with later retention requiring the double chromodomain and central core. CHD6 ablation increases reactive oxygen species persistence and impairs anti-oxidant transcriptional responses, leading to elevated DNA breakage and poly(ADP-ribose) induction that cannot be rescued by catalytic or double chromodomain mutants. Despite no overt epigenetic or DNA repair abnormalities, CHD6 loss leads to impaired cell survival after chronic oxidative stress, abnormal chromatin relaxation, amplified DNA damage signaling and checkpoint hypersensitivity. We suggest that CHD6 is a key regulator of the oxidative DNA damage response. In the experiment, the researchers used many compounds, for example, 2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 76-54-0Related Products of 76-54-0).

2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 76-54-0) belongs to benzofurans derivatives. Benzofuran derivatives have shown many biological activities, including antifungal and antimicrobial properties, and acting as antagonists of H3 receptors and angiotensin II. Substituted benzofurans find applications such as fluorescent sensors, oxidants, in drug discovery, and in another field of chemistry and agriculture.Related Products of 76-54-0

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

A novel ¹⁸F-labeled pyridyl benzofuran derivative for imaging of β-amyloid plaques in Alzheimer’s brains was written by Cheng, Yan;Ono, Masahiro;Kimura, Hiroyuki;Kagawa, Shinya;Nishii, Ryuichi;Saji, Hideo. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Recommanded Product: (5-Methoxybenzofuran-2-yl)boronic acid This article mentions the following:

A potential probe for PET targeting β-amyloid plaques in Alzheimer’s disease (AD) brain, FPYBF-1 (5-(5-(2-(2-(2-fluoroethoxy)ethoxy)ethoxy)benzofuran-2-yl)-N,N-dimethylpyridin-2-amine), was synthesized and evaluated. In experiments in vitro, FPYBF-1 displayed high affinity for Aβ(1-42) aggregates (K _i = 0.9 nM), and substantial labeling of β-amyloid plaques in sections of postmortem AD brains but not control brains. In experiments in vivo, [¹⁸F]FPYBF-1 displayed good initial uptake (5.16%ID/g at 2 min postinjection) and rapid washout from the brain (2.44%ID/g at 60 min postinjection) in normal mice, and excellent binding to β-amyloid plaques in a murine model of AD. Furthermore, the specific labeling of plaques labeling was observed in autoradiographs of autopsied AD brain sections. [¹⁸F]FPYBF-1 may be a useful probe for imaging β-amyloid plaques in living brain tissue. In the experiment, the researchers used many compounds, for example, (5-Methoxybenzofuran-2-yl)boronic acid (cas: 551001-79-7Recommanded Product: (5-Methoxybenzofuran-2-yl)boronic acid).

(5-Methoxybenzofuran-2-yl)boronic acid (cas: 551001-79-7) belongs to benzofurans derivatives. Benzofuran is the “”parent”” of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants. Introduction of benzofurans in organic synthesis, particularly drug synthesis, involves generally the use of their metalated species as nucleophiles in addition reactions or in metal-catalysed cross-coupling reactions.Recommanded Product: (5-Methoxybenzofuran-2-yl)boronic acid

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Quinoxalines. Part 13: Synthesis and mass spectrometric study of aryloxymethylquinoxalines and benzo[b]furylquinoxalines was written by Starke, Ines;Sarodnick, Gerhard;Ovcharenko, Vladimir V.;Pihlaja, Kalevi;Kleinpeter, Erich. And the article was included in Tetrahedron in 2004.COA of Formula: C10H7BrO2 This article mentions the following:

A series of new aryloxymethylquinoxalines, benzo[b]- and naphtho[2,1-b]furylquinoxalines, possessing potential biol. activity, was prepared, characterized by IR and NMR spectroscopy and their electron ionization (EI) mass spectra studied in detail. The aryloxymethylquinoxalines were obtained by reacting halogenomethylquinoxalines with bifunctional O-nucleophiles. The benzo[b]furylquinoxalines and naphtho[2,1-b]furylquinoxalines were prepared via two routes, which differed in the order of the two cyclization steps involved in the syntheses. The composition of the ions obtained by EI mass spectrometry were determined by accurate mass measurements and the fragmentation pathways clarified by B/E linked scans and collision induced dissociation The mass spectrometric behavior of the compounds studied as to the possible loss of OH^• radicals proved to be very characteristic. In the experiment, the researchers used many compounds, for example, 1-(5-Bromobenzofuran-2-yl)ethanone (cas: 38220-75-6COA of Formula: C10H7BrO2).

1-(5-Bromobenzofuran-2-yl)ethanone (cas: 38220-75-6) belongs to benzofurans derivatives.Benzofuran is one of the most significant oxygen-containing heterocycles consisting of fused benzene and furan ring, which are widely presented in various naturally occurring and synthetically active compounds. As benzofurans are prone to undergo ring opening of the heterocycle, examples of reduction of this type of aromatics by using dissolving metals are rather scarce.COA of Formula: C10H7BrO2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

1-(5-Bromo-1-benzofuran-2-yl)ethanone was written by Fun, Hoong-Kun;Quah, Ching Kheng;Abdel-Aziz, Hatem A.. And the article was included in Acta Crystallographica, Section E: Structure Reports Online in 2012.Related Products of 38220-75-6 This article mentions the following:

The title compound, C₁₀H₇BrO₂, is approx. planar (r.m.s. deviation = 0.057 Å for the 13 non-H atoms). In the crystal, mols. are linked via C-H···O hydrogen bonds into C(5) chains propagating in [100]. Crystallog. data are given. In the experiment, the researchers used many compounds, for example, 1-(5-Bromobenzofuran-2-yl)ethanone (cas: 38220-75-6Related Products of 38220-75-6).

1-(5-Bromobenzofuran-2-yl)ethanone (cas: 38220-75-6) belongs to benzofurans derivatives. Benzofuran derivatives are one of the most important oxygen-containing heterocycles. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antiviral, antimicrobial, antitumor, anti-inflammatory.Related Products of 38220-75-6

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

A new cyano-substituted fluorescamine superior to its original form as a fluorescent probe for amino acid detection was written by Motoyoshiya, Jiro;Tomioka, Satoshi;Kobayashi, Daigo;Fujimoto, Tetsuya. And the article was included in Tetrahedron Letters in 2018.Synthetic Route of C17H10O4 This article mentions the following:

Synthesis and spectral study of two new cyano-substituted fluorescamine as the fluorescent probes for amino acid detection have been carried out comparing with the original fluorescamine. Of the three compounds, the derivative with a cyano group at the meta-position on the 4-Ph group was superior to the original one in the reactivity toward some amino acids as well as the fluorescence intensity of the adducts. The fluorescent amino acid adducts were also applied to the peroxyoxalate chemiluminescence system as the fluorophores, in which the derivative described above was more effective also in chemiluminescence than the original one. In the experiment, the researchers used many compounds, for example, 4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9Synthetic Route of C17H10O4).

4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9) belongs to benzofurans derivatives. Benzofuran derivatives are one of the most important oxygen-containing heterocycles. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antiviral, antimicrobial, antitumor, anti-inflammatory.Synthetic Route of C17H10O4

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem