Heterocyclic Building Block-benzofuran

Investigation of the interactions between flavonoids and human organic anion transporting polypeptide 1B1 using fluorescent substrate and 3D-QSAR analysis was written by Xiang, Yiqun;Liu, Shuai;Yang, Jingjie;Wang, Zhongmin;Zhang, Hongjian;Gui, Chunshan. And the article was included in Biochimica et Biophysica Acta, Biomembranes in 2020.Name: 2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one This article mentions the following:

Organic anion transporting polypeptide 1B1 (OATP1B1) is a key hepatic uptake transporter whose inhibition could lead to adverse drug-drug and drug-food interactions. Flavonoids are widely distributed in food and beverages and thus our bodies are frequently exposed to them. Therefore, investigation of the interactions between OATP1B1 and flavonoids could be of great significance. In the present study, 25 common flavonoids were investigated for their interactions with OATP1B1 using the fluorescent substrate 2′,7′-dichlorofluorescein (DCF) and three-dimensional quant. structure-activity relationship (3D-QSAR) anal. Kinetic study showed that OATP1B1-mediated DCF uptake exhibited a monophasic saturation kinetics with a K_m value of 9.7 ± 2.4 μM. Inhibition assay for flavonoids on OATP1B1-mediated DCF uptake was performed and their IC₅₀ values were determined upon which reliable and predictive CoMFA (q² = 0.604, r² = 0.841) and CoMSIA (q² = 0.534, r² = 0.807) models were developed. Our exptl. and computational results showed that flavonoid aglycons interacted with OATP1B1 much stronger than their glycosides such as 3-O- and 7-O-glycosides as bulky hydrophilic and hydrogen-bond forming substituents at C-3 and C-7 positions on rings A and C were unfavorable for their binding. On the other hand, the presence of hydrogen-bond forming groups on ring B was beneficial as long as the number of hydroxyl groups was not >2. Our results also indicated that flavones usually interacted with OATP1B1 much stronger than their 3-hydroxyflavone counterparts (flavonols). The obtained information and 3D-QSAR models could be useful for elucidating and predicting the interactions between flavonoids and human OATP1B1. 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: 76-54-0Name: 2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one).

2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 76-54-0) belongs to benzofurans derivatives. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. Substituted benzofurans find applications such as fluorescent sensors, oxidants, in drug discovery, and in another field of chemistry and agriculture.Name: 2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Simultaneous determination of 16 sulfonamide residues in beef by high performance liquid chromatography-fluorescence detection with online post-column derivatization was written by Xu, Xu;Xiao, Yuancan;Geng, Dandan;Pi, Li;Dong, Qi;Hu, Fengzu. And the article was included in Sepu in 2016.Category: benzofurans This article mentions the following:

In this study, we investigated the effects of the four kinds of derivatization reagents, including fluorescamine, o-phthaladehyde, fluorescein isothiocyanate isomer and 2,3-naphthalenedicarboxaldehyde. A high performance liquid chromatog. with fluorescence detection method for the rapid determination of 16 sulfonamide residues in beef was developed by using improved QuEChERS method for sample pretreatment and fluorescamine for online post-column derivatization. The beef samples were extracted with acetonitrile containing 1% (volume/volume) acetic acid, cleaned-up by QuEChERS method, injected for online post-column derivatization with fluorescamine, and then analyzed with fluorescence detection. Under the optimized conditions of QuEChERS and chromatog., the 16 sulfonamide residues showed good linearities in the range of 0.024-2.533 mg/L with the correlation coefficients (γ) higher than 0.992. The limits of detection of the method were 1.6 to 8.2 μg/kg. The average recoveries of the 16 sulfonamide residues were in the range of 66.6%-109.5% with the relative standard deviations from 0.9% to 9.9%. The method has the advantages of rapidity, simplicity, high sensitivity and better purification effect. It is suitable for the rapid determination of the sulfonamide residues in beef. In the experiment, the researchers used many compounds, for example, 4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9Category: benzofurans).

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. Substituted benzofurans find applications such as fluorescent sensors, oxidants, in drug discovery, and in another field of chemistry and agriculture.Category: benzofurans

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Dual-Channel Theranostic System for Quantitative Self-Indication and Low-Temperature Synergistic Therapy of Cancer was written by Wang, Cheng;Chen, Shaoqing;Yu, Fangying;Lv, Jianghong;Zhao, Rui;Hu, Fuqiang;Yuan, Hong. And the article was included in Small in 2021.Synthetic Route of C20H10Cl2O5 This article mentions the following:

A conventional theranostic system usually employs a single fluorescence channel to show the pharmacokinetic events, which usually fails to quant. reveal the true cumulative drug release and with low accuracy. Herein, indocyanine green (ICG) and chlorins e6 (Ce6) are selected not only as conventional photothermal/photodynamic agents, but also to offer two independent fluorescence channels to cross validate the authenticity of pharmacokinetic events and to quant. reveal cumulative drug release in tumor tissues in a “turn on” manner. Employing the Ca2+ of amorphous calcium carbonate as a reversible linker, the photosensitivity and fluorescence of Ce6 are phys. quenched by ICG during circulation to reduce the side effect of photodynamic therapy (PDT) while being readily restored in tumor tissue to reveal the quant. drug release. Most importantly, the combination of photothermal therapy (PTT) and PDT allows low-temperature synergistic therapy of cancer through the controlled expression of heat shock protein in cells and mild hyperthermia enhanced reactive oxygen species diffusion/penetration among cells. This work not only develops a facile approach to fabricate a dual-channel theranostic system to precisely indicate the accumulation and quant. drug release in tumor tissue, but also presents a unique low-temperature synergistic strategy to destroy tumor in an effective and minimally invasive manner. 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: 76-54-0Synthetic Route of C20H10Cl2O5).

2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 76-54-0) 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. 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.Synthetic Route of C20H10Cl2O5

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Dietary supplementation with curcumin-loaded nanocapsules in lambs: Nanotechnology as a new tool for nutrition was written by Marcon, Hiam;Griss, Luiz G.;Molosse, Vitor L.;Cecere, Bruno G. O.;Alba, Davi F.;Leal, Karoline W.;Galli, Gabriela M.;Souza, Carine F.;Baldissera, Matheus D.;Gundel, Samanta;de A. Bassotto, Vitoria;Ourique, Aline F.;Vedovatto, Marcelo;Da Silva, Aleksandro S.. And the article was included in Animal Nutrition in 2021.Category: benzofurans This article mentions the following:

Curcumin-containing nanocapsule powder formulations have not been used in ruminant feed to date, despite the fact that curcumin is known to be a functional food additive. The objective of this study was to determine whether Et polymethacrylate (Eudragit L-100) nanocapsules loaded with curcumin (N-CU) would improve health and growth of lambs. Thirty-two male Lacaune lambs (body weight [BW] = 16 ± 0.99 kg; 45 d of age) were randomly assigned to 1 of 4 treatments: T0, T1, T2 and T4, representing supplementation of curcumin at 0, 1, 2, and 4 mg/kg concentrate, resp. The animals in each treatment were allocated in 4 pens of 2 lambs each (8 lambs per treatment). The experiment lasted 17 d, with samples and measurements collected on d 0, 7, 12, and 17. The T2 lambs had greater average daily gain than T0 lambs. Regression anal. showed that the ideal dose of N-CU to enhance weight gain was 1.89 mg/kg concentrate There were significant interactions (P < 0.05) between treatments x time for hematol. variables, particularly for increases in erythrocytes (T2) and reductions in counts of leukocytes, neutrophils, and lymphocytes in T1 and T2. There were significant interactions between treatment x time for total protein, globulin, urea, and triglyceride levels. Stimulation of the antioxidant system was also observed There were increased levels of non-protein thiols (NPSH), as well as increased activities of superoxide dismutase (SOD) and glutathione S-transferase (GST) in the supplemented animals. Levels of reactive oxygen species (ROS) were lower in the serum of supplemented lambs. In general, the 4 mg/kg dose had no pos. effects on growth or health. This was an unexpected result, given the known properties of curcumin. Taken together, these findings suggest that addition of low concentrations of nanoencapsulated curcumin (T1 and T2) in lamb feed improves health, minimizing oxidative stress and generates anti-inflammatory effects that may have contributed indirectly to greater weight gain. Nanocapsules potentiate the effects of curcumin and may emerge as a new tool in animal nutrition. 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: 76-54-0Category: benzofurans).

2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 76-54-0) 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.Category: benzofurans

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Direct Alkoxycarbonylation of Heteroarenes via Cu-Mediated Trichloromethylation and In Situ Alcoholysis was written by Luo, Wenkun;Jiang, Kai;Li, Yingwei;Jiang, Huanfeng;Yin, Biaolin. And the article was included in Organic Letters in 2020.SDS of cas: 1646-27-1 This article mentions the following:

An efficient approach for direct alkoxycarbonylation of furans I (R¹ = iso-Pr, cyclopentyl, benzyl, etc.) as well as other heteroarenes, e.g., thiazole via a one-step copper-mediated reaction of three components (i.e., heteroarene, alc., and CHCl₃) was reported. The copper additive was confirmed to simultaneously promote the reaction in three pathways: oxidant cracking, single electron transfer, and alcoholysis. By means of this protocol, various functionalized furancarboxylates II (R² = Me, cyclopentyl, etc) and other heteroarenecarboxylates, e.g., Me benzo[d]thiazole-2-carboxylate were facilely obtained in moderate to good yields. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1SDS of cas: 1646-27-1).

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. They are also prone to polymerisation in the presence of concentrated mineral acids and Lewis acids.SDS of cas: 1646-27-1

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Syntheses of biscationic, trypanocidal 1-benzofuran compounds was written by Dann, Otto;Char, Helmut;Griessmeier, Helmut. And the article was included in Liebigs Annalen der Chemie in 1982.Synthetic Route of C10H7BrO2 This article mentions the following:

Benzofurans I [R = CN, H₂N, C(:NH)NH₂ (Am), 2-imidazolidinyl, NHC(:NH)NH₂, NHCH:NMe₂, R¹ = NH₂, NHC(:NH)NH₂, NHCH:NMe₂, Br, CN, Am, 2-imidazolidinyl] were prepared by substitution of 2,5-(OH)RC₆H₃CHO with 4-R¹C₆H₄CH₂X (X = Cl, Br) followed by intramol. cyclocondensation. Addnl. obtained were II (R² = CO₂H, Ac, CO₂Et, CO₂Me, CHO, CH₂OH, CH₂Br, CH₂CN, CH₂CO₂H, R³ = Br, CN), II (R² = CONHC₆H₄R¹-4), and III [R = CN, Am, C(OEt):NH, X = NNHAm, NNHCSNH₂, NNHC₆H₄CN-4, NNHC₆H₄Am-4, O] and a number of alkenylene and alkylene bis(benzofurans). Arylated formamidine derivatives were prepared by reacting amine hydrochlorides with DMF in the presence of cyanamide. Selected derivatives had trypanosomicidal activity. In the experiment, the researchers used many compounds, for example, 1-(5-Bromobenzofuran-2-yl)ethanone (cas: 38220-75-6Synthetic Route of 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. They are also prone to polymerisation in the presence of concentrated mineral acids and Lewis acids.Synthetic Route of C10H7BrO2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Synthesis and antimicrobial activity of fused isatin and diazepine derivatives derived from 2-acetyl benzofuran was written by Kenchappa, R.;Bodke, Y. D.;Telkar, S.;Nagaraja, O.. And the article was included in Russian Journal of General Chemistry in 2017.Formula: C10H7BrO2 This article mentions the following:

Acetyl benzofurans reacted with isatins in the presence of pyridine to give corresponding 3-[2-(1-benzofuran-2-yl)-2-oxoethyl]-3-hydroxy-1,3-dihydro-2H-indol-2-one derivatives I [R = H, Br; R¹ = H, Cl, MeO, etc.]. Dehydration of the latter in acidic media led to the corresponding α,β-unsaturated ketones II. The structures of newly synthesized compounds I and II were established on the basis of anal. and spectral data. The synthesized benzofuranyl(phenyl)dihydrospiro[1,4-diazepine]indolones III were screened for their antibacterial and antifungal activities. Compounds III [R = R¹ = Br; R = Br, R¹ = Cl; R = Br, R¹ = O₂N] displayed excellent antimicrobial activity. The synthesized compounds III were studied for docking on the enzyme glucosamine-6-phosphate synthase. 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 derivatives have shown many biological activities, including antifungal and antimicrobial properties, and acting as antagonists of H3 receptors and angiotensin II. 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.Formula: C10H7BrO2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

A convenient, bio-inspired approach to the synthesis of multi-functional, stable fluorescent silica nanoparticles using poly(ethylene-imine) was written by Bauer, Christina A.;Chi, Gregory;Likens, Olivia Q.;Brown, Sandra M.. And the article was included in Nanoscale in 2017.Synthetic Route of C17H10O4 This article mentions the following:

Branched poly(ethylene-imine) can be tagged with luminescent dyes (e.g., fluorescein isothiocyanate and tetramethylrhodamine isothiocyanate) and used to precipitate spherical silica particles from 10s-to-100s of nm diameter size under mild conditions. These dye-PEI/SiO₂ nanoparticles are highly compatible with polar solvents to give bright fluorescent suspensions, and detailed photophys. characterization reveals well-separated dye moieties with an approx. homogeneous dispersion of dye-PEI conjugate throughout the SiO₂ matrix. Reaction of PEI amine groups incorporated at the particle surface affords a simple method for post-synthesis functionalization of these materials, and the formation of FITC/Eosin-Y fluorescence resonance energy transfer pair-tagged particles and SiO₂@Au core-shell nanocomposites using this strategy is demonstrated. This bio-inspired approach to multi-functional SiO₂ nanoparticles provides a range of potential advantages over traditional “inorganic” syntheses of similar materials, as it proceeds through a scalable, single-step reaction using inexpensive reagents, enables efficient incorporation of luminescent species into the resulting particles with very limited dye aggregation, and provides nanoparticles that do not require post-synthesis modification for further conjugation with species of interest. The method offers a simple means to generate complex nanocomposites, whereby a host of desired species can be incorporated both inside and on the surface of biocompatible SiO₂ nanoparticles. 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 have shown many biological activities, including antifungal and antimicrobial properties, and acting as antagonists of H3 receptors and angiotensin II. 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.Synthetic Route of C17H10O4

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Structure, antioxidant property and protection on PC12 of a polysaccharide isolated and screened from Abelmoschus esculentus L.Moench (okra) was written by Pan, Li-Chao;Sun, Yang-Yang;Zhang, Xiao-Ling;Zhu, Zhen-Yuan;Liu, Chun-Yu;Sun, Hui-Qing;Geng, Xue-Qing;Jiang, Wei;Wang, Jia-He. And the article was included in Natural Product Research in 2022.HPLC of Formula: 76-54-0 This article mentions the following:

AeP-P-2, a pectic polysaccharide, was extracted from the fruit pod of okra. It composed of rhamnose (Rha), arabinose (Ara), glucose (Glc), galactose (Gal) and galacturonic acid (GalA) with the ratio of 4.75:2.01:1.00:4.91:7.24. The main structural feature of AeP-P-2 are 1,4-linked galacturonan units (homogalacturonan backbone) and (1 → 2) and (1 → 2,4) linked Rha (rhamnogalacturonan I region). And the other side chains contained →1-linked Ara, (1 → 5)-linked Ara, (1 → 4)-linked Glc, (1 → 6)-linked Gal, (1 → 4)-linked Rha, (1 → 2,4)-linked Rha, →1-linked Ara and →1-linked Gal. When the concentration of AeP-P-2 was 3.2 mg/mL, the scavenging rates on DPPH·, ABTS, O2-· and ·OH reached to 61.88%, 87.10%, 52.17% and 60.32%, resp. AeP-P-2 also could protect PC12 cells from the damage of H2O2 and reduce apoptosis caused by oxidative damage by decreasing the level of ROS. The findings indicated that okra was a functional vegetable and AeP-P-2 was worth studying and developing into antioxidant component. 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: 76-54-0HPLC of Formula: 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 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.HPLC of Formula: 76-54-0

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Design, synthesis and antiproliferative activity against human cancer cell lines of novel benzo-, benzofuro-, azolo- and thieno-1,3-thiazinone resorcinol hybrids was written by Matysiak, Joanna;Karpinska, Monika M.;Skrzypek, Alicja;Wietrzyk, Joanna;Klopotowska, Dagmara;Niewiadomy, Andrzej;Paw, Beata;Juszczak, Malgorzata;Rzeski, Wojciech. And the article was included in Arabian Journal of Chemistry in 2019.Product Details of 54802-10-7 This article mentions the following:

The design and synthesis of novel derivatives of the 4H-3,1-benzothiazinone type and heterocyclic analogs, i.e. benzofuro-, azolo- and thieno-1,3-thiazin-4-ones possessing 2,4-dihydroxyphenyl substituent is reported. The compounds were obtained by the one-step reaction of aminobenzamides or heterocyclic aminocarboxamides with aryl-modified sulfinylbis[(2,4-dihydroxyphenyl)methanethione]. Evaluation of their antiproliferative potency against human cancer cell lines showed that the activity of some analogs was similar to that of cisplatin. The highest activity and low toxicity were found for 6-tert-butyl-2-(5-chloro-2,4-dihydroxyphenyl)-4H-thieno[3,2-d][1,3]thiazin-4-one. The structure-activity elucidation reveals that the most active compounds are those with a thienothiazin-4-one and benzofuro[3,2-d][1,3]thiazin-4-one skeleton and the presence of the hydrophobic substituent (Et, Cl) in the benzenediol moiety increases their antiproliferative potency. The ADMET properties of selected compounds including metabolic stability and toxicity profile were estimated in silico. In the experiment, the researchers used many compounds, for example, 3-Aminobenzofuran-2-carboxamide (cas: 54802-10-7Product Details of 54802-10-7).

3-Aminobenzofuran-2-carboxamide (cas: 54802-10-7) belongs to benzofurans derivatives. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. In nature, benzofurans have occupied an important role among the plant phenols & several pharmacologically active compounds.Product Details of 54802-10-7

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem