Heterocyclic Building Block-benzofuran

Palladium-catalyzed benzylic-like nucleophilic substitution of benzofuran-, benzothiophene- and indole-based substrates by dimethyl malonate anion was written by Primault, Gaelle;Legros, Jean-Yves;Fiaud, Jean-Claude. And the article was included in Journal of Organometallic Chemistry in 2003.Synthetic Route of C10H8O4 This article mentions the following:

The palladium-catalyzed benzylic-like nucleophilic substitution of acetates derived from benzofuran, benzothiophene, and indole was investigated. Reactants prepared for this study included 2-benzofuranmethanol acetate, 5-chloro-2-benzofuranmethanol acetate, 7-methoxy-2-benzofuranmethanol acetate, α-methyl-2-benzofuranmethanol acetate, (-)-(αS)-α-methyl-2-benzofuranmethanol acetate, benzo[b]thiophene-2-methanol acetate, 1H-indole-2-methanol acetate, 1-methyl-1H-indole-2-methanol acetate. The asym. substitution on racemic α-methyl-2-benzofuranmethanol acetate gave disappointing results, but the substitution product was obtained in 98% enantiomeric excess from (-)-(αS)-α-methyl-2-benzofuranmethanol acetate with overall retention of configuration. The reaction product was (-)-[(1S)-1-(2-benzofuranyl)ethyl]propanedioic acid di-Me ester. In the experiment, the researchers used many compounds, for example, 7-Methoxybenzofuran-2-carboxylic acid (cas: 4790-79-8Synthetic Route of C10H8O4).

7-Methoxybenzofuran-2-carboxylic acid (cas: 4790-79-8) 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 C10H8O4

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Tumor-derived exosomes reversing TMZ resistance by synergistic drug delivery for glioma-targeting treatment was written by Wang, Ruoning;Liang, Qifan;Zhang, Xinru;Di, Zhenning;Wang, Xiaohong;Di, Liuqing. And the article was included in Colloids and Surfaces, B: Biointerfaces in 2022.Name: 2,2′,2”,2”’-(((3′,6′-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-2′,7′-diyl)bis(methylene))bis(azanetriyl))tetraacetic acid This article mentions the following:

Temozolomide (TMZ), as the first-line chemotherapeutic agent, relies on inducing DNA methylation of O⁶-guanine for treating glioma. However, the survival time of patients are hardly exceeded 14.5 mo, attributing to inevitable drug resistance and systematic toxicity after long-term administration. Herein, reassembly-exosomes (R-EXO) deriving from homologous glioma cells is proposed to carry TMZ and Dihydrotanshinone (DHT) for reversing drug resistance and enhancing lesions-targeted drug delivery, defined as R-EXO-TMZ/DHT (R-EXO-T/D). It is found that R-EXO-T/D share various advantages, including preferable blood-brain barrier (BBB)-penetrating ability with nanomemter size, tumor-homing accumulation with homologous effects, as well as potentiated antitumor activity with overcoming TMZ resistance and triggering immune response. This work develops a new strategy for site-specific drug delivery, showing a promising application of drug compatibility in glioma treatment. In the experiment, the researchers used many compounds, for example, 2,2′,2”,2”’-(((3′,6′-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-2′,7′-diyl)bis(methylene))bis(azanetriyl))tetraacetic acid (cas: 1461-15-0Name: 2,2′,2”,2”’-(((3′,6′-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-2′,7′-diyl)bis(methylene))bis(azanetriyl))tetraacetic acid).

2,2′,2”,2”’-(((3′,6′-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-2′,7′-diyl)bis(methylene))bis(azanetriyl))tetraacetic acid (cas: 1461-15-0) 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. They are also prone to polymerisation in the presence of concentrated mineral acids and Lewis acids.Name: 2,2′,2”,2”’-(((3′,6′-Dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-2′,7′-diyl)bis(methylene))bis(azanetriyl))tetraacetic acid

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Analysis of extractable organic compounds in water by gas chromatography mass spectrometry: applications to surface water was written by Deroux, J. M.;Gonzalez, C.;Le Cloirec, P.;Kovacsik, G.. And the article was included in Talanta in 1996.Application In Synthesis of 5-Methylisobenzofuran-1(3H)-one This article mentions the following:

Over a period of 1 yr, the surface water of a canal network (Languedoc-Roussillon area, France) was analyzed in order to identify organic compounds and to monitor its quality. Pollutants were extracted from 19 L of raw water using methylene chloride in a continuous countercurrent liquid-liquid extractor with a pulsed column. The extraction was performed at a pH above 11 and again at a pH below 2 according to U.S. Environmental Protection Agency method 625. The extract was analyzed by gas chromatog./mass spectrometry, using two ionization techniques, namely electron ionization and chem. ionization. Mass spectra obtained by electron ionization were compared with those in a database (NIST). Some natural compounds and micropollutants were identified. Their structures were confirmed by chem. ionization (methane). One hundred and ten substances, making up the broad spectrum of extractable compounds in the surface water studied, were found by this method at a nanogram per L concentration level. Among them, 13 are priority pollutants. These specific pollutants were qualified. In the experiment, the researchers used many compounds, for example, 5-Methylisobenzofuran-1(3H)-one (cas: 54120-64-8Application In Synthesis of 5-Methylisobenzofuran-1(3H)-one).

5-Methylisobenzofuran-1(3H)-one (cas: 54120-64-8) 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 antioxidant, antitubercular, antiplasmodial, insecticidal.Application In Synthesis of 5-Methylisobenzofuran-1(3H)-one

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Prucalopride might improve intestinal motility by promoting the regeneration of the enteric nervous system in diabetic rats was written by Wang, Yun;Xu, Xinyu;Lin, Lin. And the article was included in International Journal of Molecular Medicine in 2022.COA of Formula: C18H26ClN3O3 This article mentions the following:

The present study aimed to investigate whether prucalopride, as a 5-hydroxytryptamine 4 (5-HT4) receptor agonist, improved intestinal motility by promoting the regeneration of the enteric nervous system (ENS) in rats with diabetes mellitus (DM). A rat model of DM was established using an i.p. injection of streptozotocin. The rats were randomly divided into four groups of 6 rats/group: Control, DM (DM model), DM + A (5 μg/kg prucalopride) and DM + B (10 μg/kg prucalopride). The rats in the Control group were given an equal volume of citric acid solvent. After successful model establishment, high blood glucose levels were maintained for 2 wk before administration of prucalopride. The colonic transit time was measured using the glass bead discharge method. It was revealed that the colonic transit time of diabetic rats was the longest, and this was significantly shortened in the DM + B group. Subsequently, the colons were collected. The expression levels of Nestin, glial fibrillary acidic protein (GFAP), SOX10, RNA-binding protein human antigen D (HuD) and ubiquitin thiolesterase (PGP9.5) were determined via immunohistochem. anal. Immunofluorescence double staining of 5-HT4 + Nestin and Ki67 + Nestin was performed. The 5-HT level was measured using ELISA. Compared with that in the control group, Nestin expression was significantly increased in the DM and DM + A groups, and it was concentrated in columnar epithelial cells and the mesenchyme. Furthermore, the expression levels of Nestin in the DM + A group were higher than those in the DM group. No difference was observed in the expression levels of Nestin between the DM + B group and the Control group. The expression levels of 5-HT protein were highest in the Control group; however, the expression levels of 5-HT protein in the DM group, DM + A group and DM + B group exhibited an increasing trend. Similar trends in the expression of 5-HT4 and Nestin were not observed; however, similar trends in the expression of Nestin and Ki67 were observed The expression levels of GFAP, SOX10, PGP9.5 and Ki67 in the DM + A and DM + B groups were higher compared with those in the DM group. In the DM + A group, HuD expression was decreased compared with that in the Control group but it was markedly higher compared with that in the DM group. In conclusion, prucalopride may improve intestinal motility by promoting ENS regeneration in rats with DM. In the experiment, the researchers used many compounds, for example, 4-Amino-5-chloro-N-(1-(3-methoxypropyl)piperidin-4-yl)-2,3-dihydrobenzofuran-7-carboxamide (cas: 179474-81-8COA of Formula: C18H26ClN3O3).

4-Amino-5-chloro-N-(1-(3-methoxypropyl)piperidin-4-yl)-2,3-dihydrobenzofuran-7-carboxamide (cas: 179474-81-8) belongs to benzofurans derivatives. Benzofurans are only weakly aromatic in nature and they are cleaved by many oxidative and reductive conditions. They are also prone to polymerisation in the presence of concentrated mineral acids and Lewis acids.COA of Formula: C18H26ClN3O3

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Use of mycophenolate mofetil in patients with pediatric and adult primary nephrotic syndrome: information from a Japanese hospital claims database was written by Funatogawa, Takashi;Narita, Yusuke;Tamura, Aya;Mii, Kazuma;Sugitani, Yasuo;Uchida, Tomoaki. And the article was included in Clinical and Experimental Nephrology in 2022.Application of 24280-93-1 This article mentions the following:

Current treatment for frequently relapsing, steroid-dependent, or steroid-resistant nephrotic syndrome focuses on immunosuppressive therapies. Although the clin. guideline suggests the use of mycophenolate mofetil (MMF), limited information is available on patients with primary nephrotic syndrome who receive off-label treatment with MMF in Japan. The dose, treatment duration, previous treatment, and characteristics of primary nephrotic syndrome patients receiving MMF were investigated using data from a Japanese hospital claims database (Apr. 2008-Sept. 2021). Data on 424 primary nephrotic syndrome patients receiving MMF (146 patients < 18 years old; 278 patients ≥ 18 years old) were captured. The most common initial daily doses of MMF capsules (% of patients < 18 and ≥ 18 years old) were 1000 mg (31.9%, 36.8%), 1500 mg (16.0%, 23.8%), and 500 mg (23.6%, 17.3%), and the most common maximum daily doses were 1000 mg (43.8%, 32.9%), 1500 mg (23.6%, 28.9%), and 2000 mg (6.3%, 16.2%). Most patients (97.9%, 99.3%) were treated with a daily dose of 2000 mg or less. Among patients < 18 years old, the younger the patient, the lower the dose. MMF was used for more than 1 yr in 30.8% of patients < 18 years old and in 28.8% of patients ≥ 18 years old. Our study suggested that off-label use of MMF for primary nephrotic syndrome has increased since 2012 in Japan. The dose of MMF used in patients with primary nephrotic syndrome was generally within the approved dose range for lupus nephritis and transplant-related diseases in Japan. In the experiment, the researchers used many compounds, for example, (E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoic acid (cas: 24280-93-1Application of 24280-93-1).

(E)-6-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydroisobenzofuran-5-yl)-4-methylhex-4-enoic acid (cas: 24280-93-1) 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. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antioxidant, antitubercular, antiplasmodial, insecticidal.Application of 24280-93-1

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

The benzofuran series was written by Villere, G.;Grinsteins, V.. And the article was included in Latvijas Valsts Univ. Ki̅m. Fak. Zina̅tniskie Raksti in 1958.Reference of 3710-47-2 This article mentions the following:

(R in this abstract = isonicotinoyl.) 3-Oxo-2,3-dihydrobenzofuran (I) refluxed 5 hrs. with RNHNH₂ (II) and the unreacted material extracted from the mixture with Et₂O left the hydrazone, m. 187-8°. Similar treatment of I with NCCH₂CONHNH₂ (III) did not give the corresponding compound, even under pressure, and I could also not be condensed in this way with H₂NCSNHNH₂ (IV). 2-Acetylbenzofuran (V), however, could be condensed with II to the hydrazone, m. 229-30°, and III and V refluxed 5 hrs. in EtOH gave the yellowish hydrazone, m. 195-6°. If the pressure was increased so the mixture reached 140°, V and IV condensed to the thiosemicarbazone, m. 190-4°. Similarly, 3-amino-2,3-dihydrobenzofuran-HCl and NCNH₂ (VI) heated 6 hrs. at 150° in EtOH in a sealed ampul and CO₂ passed through the mixture gave 3-guanidino-2,3-dihydrobenzofuran carbonate, m. 150-1°. V, EtOH, AcOH, and NaHg at 40-50° gave 1-(2-benzofuryl)ethylamine-HCl (VII), m. 159-62°. VI and VII heated 8 hrs. in EtOH, and the mixture treated with NaOH then CO₂ yielded [1-(2-benzofuryl)ethyl]guanidine carbonate, m. 102-18° (decomposition). In the experiment, the researchers used many compounds, for example, 1-(1-Benzofuran-2-yl)-1-ethanamine hydrochloride (cas: 3710-47-2Reference of 3710-47-2).

1-(1-Benzofuran-2-yl)-1-ethanamine hydrochloride (cas: 3710-47-2) 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. They are also prone to polymerisation in the presence of concentrated mineral acids and Lewis acids.Reference of 3710-47-2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Conjugated PDT drug: photosensitizing activity and tissue distribution of PEGylated pheophorbide a was written by Rapozzi, Valentina;Zacchigna, Marina;Biffi, Stefania;Garrovo, Chiara;Cateni, Francesca;Stebel, Marco;Zorzet, Sonia;Bonora, Gian Maria;Drioli, Sara;Xodo, Luigi E.. And the article was included in Cancer Biology & Therapy in 2010.Related Products of 92557-80-7 This article mentions the following:

The design of new photosensitizers with enhanced phototoxicity and pharmacokinetic properties remains a central challenge for cancer photodynamic therapy (PDT). In this study, Pheophorbide a (Pba) has been pegylated to methoxypolyethylene glycol (mPEG-Pba) to produce a soluble photosensitizer that exhibits a higher tissue distribution than free Pba. In vitro studies have shown that mPEG-Pba promotes a fairly strong photosensitizing effect in cancer cells, as previously observed for the unpegylated mol. MPEG-Pba targets the mitochondria where, following photoactivation, ROS are produced which cause a cellular injury by lipid peroxidation The effect of pegylation on the photosensitizer biodistribution has been examined in different selected organs of female mice, at different time points after i.p. administration of the drug (50 μmol/Kg body weight). Other than free Pba, which showed a low tissue accumulation, mPEG-Pba has been detected in significant amounts (8 to 16 μg/mL) in liver, spleen, duodenum and kidney and, 3-5 h after i.p. injection, in moderate amounts (3 to 8 μg/mL) in brain and lung. In vivo optical imaging performed on living female C57/BL6 mice bearing a s.c. melanoma mass, showed that injected mPEG-Pba distributes all over the body, with an higher uptake in the tumor respect to free Pba. Our results indicate that although pegylation somewhat decreases the phototoxicity, it significantly increases the drug solubility and tissue distribution and tumor uptake of mPEG-Pba, making the conjugate an interesting photosensitizer for PDT. In the experiment, the researchers used many compounds, for example, 2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate (cas: 92557-80-7Related Products of 92557-80-7).

2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate (cas: 92557-80-7) 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. 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 92557-80-7

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Identification of methoxylated phenols as candidate tracers for atmospheric wood smoke pollution was written by Hawthorne, Steven B.;Miller, David J.;Barkley, Robert M.;Krieger, Mark S.. And the article was included in Environmental Science and Technology in 1988.Recommanded Product: 205-39-0 This article mentions the following:

More than 70 organic compounds were identified in unfractionated CH₂Cl₂ extracts of soot from residential wood stoves by a combination of capillary gas chromatog. coupled with low-resolution mass spectrometry (GC/MS), GC coupled with high-resolution mass spectrometry, and chem. ionization mass spectrometry with deuteriated methanol as the reagent gas. Thirty of the species are derivatives of guaiacol and syringol, which result from the pyrolysis of wood lignin. Soots from hardwood and pine show similar proportions of the syringol derivatives, but pine soot has much higher proportions of the guaiacol derivatives Samples collected onto filters backed up by polyurethane foam plugs in the cooled smoke plume showed that some of the methoxylated phenols were primarily in the vapor phase, whereas the majority were associated with the particulates. These species are expected to be unique to wood smoke in urban atms. and are therefore suggested as tracers for atm. wood smoke pollution. In the experiment, the researchers used many compounds, for example, Naphtho[2,1-b]benzofuran (cas: 205-39-0Recommanded Product: 205-39-0).

Naphtho[2,1-b]benzofuran (cas: 205-39-0) 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.Recommanded Product: 205-39-0

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Dendrimeric bisphosphonates for multivalent protein surface binding was written by Arendt, Markus;Sun, Wei;Thomann, Jens;Xie, Xiulan;Schrader, Thomas. And the article was included in Chemistry – An Asian Journal in 2006.Safety of 2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate This article mentions the following:

A single weak-binding event is multiplied into an efficient receptor site for protein surfaces (<10^-1 to >10⁶ M^-1 in buffered aqueous solution) in a biomimetic fashion. This has hitherto been done with natural host/guest pairs, but not with artificial receptors. The organic reaction presented is one of very few that enable chemists to fuse multiple ionic building blocks covalently in highly polar solution; this 1-pot reaction proceeds with virtually quant. yield. According to this concept, other building blocks with aldehyde groups can likewise be multiplied into monodisperse functional dendrimers. Small basic proteins are bound by octameric dendrimers in 1:1 or 1:2 complexes with millimolar to submicromolar affinities. The complexation event is studied independently in buffered aqueous solution by three different spectroscopic methods (PFG-LED, UV/Vis, and fluorescence). Potential new applications include recombinant protein purification through Arg tags on immobilized dendrimers and on/off switching of protein function by reversible active-site capping of enzymes. In the experiment, the researchers used many compounds, for example, 2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate (cas: 92557-80-7Safety of 2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate).

2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate (cas: 92557-80-7) 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. 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.Safety of 2,5-Dioxopyrrolidin-1-yl 3′,6′-dihydroxy-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-5-carboxylate

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Di-tert-butylneopentylphosphine (DTBNpP): An Efficient Ligand in the Palladium-Catalyzed α-Arylation of Ketones was written by Raders, Steven M.;Jones, Jessica M.;Semmes, Jeffrey G.;Kelley, Steven P.;Rogers, Robin D.;Shaughnessy, Kevin H.. And the article was included in European Journal of Organic Chemistry in 2014.Application of 205-39-0 This article mentions the following:

Di-tert-butylneopentylphosphine (DTBNpP) and palladium(II) acetate provide an efficient catalytic system for the α-arylation of ketones. Aryl bromides were coupled with ketones using 0.25-0.5 mol-% Pd(OAc)₂/DTBNpP in toluene at 50 °C, whereas aryl chlorides required a higher catalyst loading (0.5-2.0 mol-%) and a higher temperature (80 °C). Coupling of 2-bromophenol with ketones using the Pd/DTBNpP system provides an efficient route for the synthesis of benzofurans. In the experiment, the researchers used many compounds, for example, Naphtho[2,1-b]benzofuran (cas: 205-39-0Application of 205-39-0).

Naphtho[2,1-b]benzofuran (cas: 205-39-0) 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 antioxidant, antitubercular, antiplasmodial, insecticidal.Application of 205-39-0

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem