November 2022 | Page 5 of 45 | Heterocyclic Building Block-benzofuran

Ali, Farrah et al. published their research in European Journal of Pharmacology in 2016 | CAS: 524-12-9

1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9) 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. 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.Category: benzofurans

Wedelolactone mitigates UVB induced oxidative stress, inflammation and early tumor promotion events in murine skin: plausible role of NFkB pathway was written by Ali, Farrah;Khan, Bilal Azhar;Sultana, Sarwat. And the article was included in European Journal of Pharmacology in 2016.Category: benzofurans The following contents are mentioned in the article:

UVB (Ultra-violet B) radiation is one of the major etiol. factors in various dermal pathol. viz. dermatitis, actinic folliculitis, solar urticaria, psoriasis and cancer among many others. UVB causes toxic manifestation in tissues by inciting inflammatory and tumor promoting events. We have designed this study to assess the anti-inflammatory and anti-tumor promotion effect of Wedelolactone (WDL) a specific IKK inhibitor. Results indicate significant restoration of anti-oxidative enzymes due to WDL treatments. We also found that WDL was effective in mitigating inflammatory markers consisting of MPO (myeloperoxidase), Mast cells trafficking, Langerhans cells suppression and COX 2 expression up regulation due to UVB exposure. We also deduce that WDL presented a promising intervention in attenuating early tumor promotion events caused by UVB exposure as indicated by the results of ODC (Ornithine Decarboxylase), Thymidine assay, Vimentin and VEGF (Vascular-endothelial growth factor) expression. This study was able to provide substantial cues for the therapeutic ability of Wedelolactone against inflammatory and tumor promoting events in murine skin depicting plausible role of NFkB pathway. This study involved multiple reactions and reactants, such as 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9Category: benzofurans).

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Atre, B. N. et al. published their research in International Journal of Research in Pharmaceutical Sciences in 2021 | CAS: 524-12-9

1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. In nature, benzofurans have occupied an important role among the plant phenols & several pharmacologically active compounds.Application In Synthesis of 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one

Formulation of wedelolactone enriched extract with enhanced potential to inhibit cytokines in experimental arthritis was written by Atre, B. N.;Arulmozhi, S.;Sathiyanarayanan, L.;Dhapte-Pawar, V. V.;Mahadik, K. R.. And the article was included in International Journal of Research in Pharmaceutical Sciences in 2021.Application In Synthesis of 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one The following contents are mentioned in the article:

Eclipta alba Linn. (Asteraceae) is traditionally claimed and reported to possess antarthritic and anti-inflammatory activity. Wedelolactone, an active constituent of Eclipta alba Linn responsible for its therapeutic effectiveness, is poorly water soluble and less bioavailable. Hence in the present study, we proposed a SNEDDS formulation of wedelolactone rich extracts of Eclipta alba Linn. (EAF) and evaluated its effect in Freund’s complete adjuvant (FCA) induced arthritis in rats. EAF reduced increase in paw volume and hyperalgesia in 50, 100 and 200 mg/kg doses significantly. It restored all cytokines (Tumor Necrosis Factor- α , Interleukin-1β and Interleukin-6); hematol. and biochem. parameters altered due to FCA induction. The histopathol. further supported the potential of EAF in arresting the progress of the disease. It protected cartilage destruction and exudation of inflammatory cells dose dependently. In conclusion, the EAF exhibited potent antarthritic potential due to the increased bioavailability of wedelolactone and other constituents. The mechanism of action is mainly mediated through inhibition of cytokines, anti-inflammatory and antioxidant potential of wedelolactone. This study involved multiple reactions and reactants, such as 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9Application In Synthesis of 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one).

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Wang, Chun-ming et al. published their research in International Journal of Biological Sciences in 2021 | CAS: 524-12-9

1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9) belongs to benzofurans derivatives. Benzofurans are only weakly aromatic in nature and they are cleaved by many oxidative and reductive conditions. 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.SDS of cas: 524-12-9

Ailanthus altissima-derived ailanthone enhances gastric cancer cell apoptosis by inducing the repression of base excision repair by downregulating p23 expression was written by Wang, Chun-ming;Li, Hua-fu;Wang, Xiao-kun;Li, Wu-guo;Su, Qiao;Xiao, Xing;Hao, Teng-fei;Chen, Wei;Zhang, Ya-wei;Zhang, Hai-yong;Wu, Wang;Hu, Zhen-ran;Zhao, Guang-yin;Huo, Ming-yu;He, Yu-long;Zhang, Chang-hua. And the article was included in International Journal of Biological Sciences in 2021.SDS of cas: 524-12-9 The following contents are mentioned in the article:

Chemotherapy plays an irreplaceable role in the treatment of GC, but currently available chemotherapeutic drugs are not ideal. The application of medicinal plants is an important direction for new drug discovery. Through drug screening of GC organoids, we determined that ailanthone has an anticancer effect on GC cells in vitro and in vivo. We also found that AIL can induce DNA damage and apoptosis in GC cells. Further transcriptome sequencing of PDX tissue indicated that AIL inhibited the expression of XRCC1, which plays an important role in DNA damage repair, and the results were also confirmed by western blotting. In addition, we found that AIL inhibited the expression of P23 and that inhibition of P23 decreased the expression of XRCC1, indicating that AIL can regulate XRCC1 via P23. The results of coimmunoprecipitation showed that AIL can inhibit the binding of P23 and XRCC1 to HSP90. These findings indicate that AIL can induce DNA damage and apoptosis in GC cells. Meanwhile, AIL can decrease XRCC1 activity by downregulating P23 expression to inhibit DNA damage repair. The present study sheds light on the potential application of new drugs isolated from natural medicinal plants for GC therapy. This study involved multiple reactions and reactants, such as 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9SDS of cas: 524-12-9).

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Maciel, Geveraldo et al. published their research in Plant Cell, Tissue and Organ Culture in 2022 | CAS: 524-12-9

1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9) 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 have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antioxidant, antitubercular, antiplasmodial, insecticidal.Name: 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one

Jasmonates promote enhanced production of bioactive caffeoylquinic acid derivative in Eclipta prostrata (L.) L. hairy roots was written by Maciel, Geveraldo;Lopes, Adriana Aparecida;Cantrell, Charles L.;de Castro Franca, Suzelei;Bertoni, Bianca Waleria;Lourenco, Miriam Verginia. And the article was included in Plant Cell, Tissue and Organ Culture in 2022.Name: 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one The following contents are mentioned in the article:

Eclipta prostrata (L.) L. is widely used in traditional medicine for treatment of hepatitis, poisoning from snake bites and viral infections. Pharmacol. studies confirmed its antioxidant, anti-inflammatory and anticancer activities. The efficacy of E. prostrata (L.) L. extracts has been correlated to phenylpropanoids such as flavonoids, coumestans and caffeoylquinic acid derivatives In this work, the production of wedelolactone, demethylwedelolactone and 3,5-di–caffeoylquinic acid (3,5-diCQA) in hairy root cultures of E. prostrata (L.) L. C19 clone was increased after addition of eliciting agents jasmonic acid (JA) or Me jasmonate (MeJA) at multiple concentrations Cultures elicited with 100μM of JA saw a 5.2 fold increase in wedelolactone (from 0.72 to 3.72 mg/g d.w.), a 1.6 fold increase in demethylwedelolactone (from 5.54 to 9.04 mg/g d.w.) and a 2.47 fold increase in 3,5-diCQA (from 18.08 to 44.71 mg/g d.w.). Obtained data validate the potential of E. prostrata (L.) L. hairy root cultures as a production system of wedelolactone, demethylwedelolactone and especially 3,5-diCQA, which has recently been reported to possess activity against coronavirus disease (Covid-19) by in silico computational studies. This study involved multiple reactions and reactants, such as 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9Name: 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one).

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Lin, Te-Yueh et al. published their research in Journal of Molecular Endocrinology in 2021 | CAS: 524-12-9

1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9) 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. 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.Recommanded Product: 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one

Unraveling mechanisms of pentraxin 3 secretion in adipocytes during inflammation was written by Lin, Te-Yueh;Guo, Hong;Chen, Xiaoli. And the article was included in Journal of Molecular Endocrinology in 2021.Recommanded Product: 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one The following contents are mentioned in the article:

Pentraxin 3 (PTX3) is a soluble pattern recognition receptor playing an important role in immune response and inflammation. Lipopolysaccharide (LPS) stimulation can significantly induce PTX3 expression and secretion in adipocytes. Appropriate regulation of PTX3 secretion is critical for inflammatory homeostasis. Using chem. inhibitors of conventional and unconventional protein secretion, we explored the mechanisms that control LPS-stimulated PTX3 secretion in 3T3-L1 adipocytes. Inhibiting the conventional protein secretion blocked LPS-stimulated PTX3 secretion, resulting in cellular PTX3 accumulation in adipocytes. We also detected PTX3 in exosomes from LPS-treated adipocytes; inhibiting exosome trafficking attenuated PTX3 secretion. However, only 4.3% of secreted PTX3 was detected in exosomes compared to 95.7% in the non-exosomal fractions. The fractionation of isolated exosomes by the iodixanol d. gradient centrifugation confirmed that a small portion of secreted PTX3 overlapped with exosomal markers in small extracellular-vesicle fractions. We conclude that PTX3 is secreted mainly through conventional protein secretion, and a small percentage of PTX3 is released in exosomes from LPS-stimulated adipocytes. This study involved multiple reactions and reactants, such as 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9Recommanded Product: 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one).

1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9) 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. 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.Recommanded Product: 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

He, Jiahong’s team published research in Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands) in 102 | CAS: 56317-21-6

Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands) published new progress about 56317-21-6. 56317-21-6 belongs to benzofurans, auxiliary class Metabolic Enzyme,PDE,Natural product, name is 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, and the molecular formula is C14H10O4, Computed Properties of 56317-21-6.

He, Jiahong published the artcileInsight into the corrosion inhibition property of Artocarpus heterophyllus Lam leaves extract, Computed Properties of 56317-21-6, the publication is Journal of Industrial and Engineering Chemistry (Amsterdam, Netherlands) (2021), 260-270, database is CAplus.

In this work, the method (water extraction way) was uesd to acquire Artocarpus heterophyllus Lam leaves extract (AHLLE). We refer to the relevant references on the composition of Artocarpus heterophyllus Lam leaves and perform Fourier IR spectroscopy anal. for AHLLE. It can be concluded that AHLLE contains 2-(2,4-dihydroxyphenyl)-5,7-dihydroxy-4H-chromen-4-one (DPD), (2R,3R)-2-(2,4-dihydroxyphenyl)-3 ,5,7-trihydroxychroman-4-one (DPT), 3-(4-hydroxyphenyl)acrylic acid (HPT), and 5-(6-hydroxybenzofuran-2-yl)benzene-1,3-diol (HBB). Quantum chem. calculations (QCC) data and mol. dynamics (MD) simulations results show that DPD, DPT, HPT, and HBB all have the potential of excellent corrosion inhibitors. Scanning electron microscope (SEM) results and at. force microscope (AFM) test results show that after adding AHLLE to H2SO4 environment, the copper surface is still correspondingly flat. In addition, the results of electrochem. experiments indicate that the AHLLE is 500 ppm, the anti-corrosion efficiency obtained from electrochem. impedance spectroscopy data can reach 97.3%. With the temperature augments to 313 K, the corrosion inhibition nature of AHLLE can still be maintained to 97%. AHLLE is adsorbed onto the Cu surface and belongs to Langmuir monolayer adsorption.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Wang, Ping’s team published research in Zhongguo Zhongyao Zazhi in 38 | CAS: 56317-21-6

Zhongguo Zhongyao Zazhi published new progress about 56317-21-6. 56317-21-6 belongs to benzofurans, auxiliary class Metabolic Enzyme,PDE,Natural product, name is 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, and the molecular formula is C9H8O4, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol.

Wang, Ping published the artcilePhenylpropanoids and diphenylethene compounds from roots and rhizomes of Smilax scobinicaulis, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, the publication is Zhongguo Zhongyao Zazhi (2013), 38(10), 1531-1535, database is CAplus and MEDLINE.

The chem. constituents were separated and purified from the roots and rhizomes of Smilax scobinicaulis by various chromatog. methods including silica gel, Sephadex LH-20. Their structures were obtained and identified as resveratrol-3-O-β-D-glucopyranosyl-(1->3)-β-D-glucopyranoside(1), resveratrol(2), δ-viniferin(3), Et caffeate(4), 1-O-caffeoyl glycerol(5), 1-O-p-coumaroyl glycerol(6), 1-O-feruloyl glycerol(7), grossamide(8), moracin M(9) on the anal. of spectroscopic data. Compound 1 was a new compound and compounds 3-5, 8, 9 were separated from this plant for the first time.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Negishi, Ei-ichi’s team published research in Heterocycles in 46 | CAS: 69626-75-1

Heterocycles published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C8H5IO, Computed Properties of 69626-75-1.

Negishi, Ei-ichi published the artcileDirect synthesis of heteroarylethynes via palladium-catalyzed coupling of heteroaryl halides with ethynylzinc halides. Its application to an efficient synthesis of a thiophenelactone from Chamaemelum nobile L, Computed Properties of 69626-75-1, the publication is Heterocycles (1997), 209-214, database is CAplus.

A variety of terminal alkynes containing a heteroaryl group can be directly and selectively synthesized by the Pd-catalyzed coupling of heteroaryl iodides or bromides with ethynylzinc halides. Various compounds of this class containing furan, thiophene, and pyridine have been prepared, and the procedure has been applied to an efficient and selective synthesis of a thiophenelactone from Chamaemelum nobile L.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Zhang, Fuyi’s team published research in Carbohydrate Research in 417 | CAS: 69626-75-1

Carbohydrate Research published new progress about 69626-75-1. 69626-75-1 belongs to benzofurans, auxiliary class Iodide,Benzofuran, name is 2-Iodobenzofuran, and the molecular formula is C10H16Br3N, HPLC of Formula: 69626-75-1.

Zhang, Fuyi published the artcileGeneral and efficient one-pot synthesis of novel sugar/heterocyclic(aryl) 1,2-diketones from sugar terminal alkynes by Sonogashira/tetra-n-butylammonium permanganate oxidation, HPLC of Formula: 69626-75-1, the publication is Carbohydrate Research (2015), 41-51, database is CAplus and MEDLINE.

A new approach for one-pot synthesis of novel sugar/heterocyclic(aryl) 1,2-diketones has been achieved by the reaction of various sugar terminal alkynes with heterocyclic(aryl) iodides at room temperature This one-pot protocol includes Sonogashira coupling and mild n-Bu₄NMnO₄ oxidation reaction. This method is mild, general and efficient. Fifty-six examples have been given and the sugar/heterocyclic(aryl) 1,2-diketones were obtained in 71-94% yields. The sugar terminal alkynes include 9 structurally different sugars in pyranose, furanose, and acyclic form which have various protecting groups, sensitive groups, and sterically bulky substituents. The heterocyclic(aryl) iodides include sterically bulky heterocyclic compounds and iodobenzenes with electron-donating, electron-neutral, and electron-withdrawing substituents.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem

Wu, Kai’s team published research in Angewandte Chemie, International Edition in 59 | CAS: 56317-21-6

Angewandte Chemie, International Edition published new progress about 56317-21-6. 56317-21-6 belongs to benzofurans, auxiliary class Metabolic Enzyme,PDE,Natural product, name is 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, and the molecular formula is C7H8FNO2S, Name: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol.

Wu, Kai published the artcileTransition-Metal-Free C(sp²)-C(sp²) Cross-Coupling of Diazo Quinones with Catechol Boronic Esters, Name: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, the publication is Angewandte Chemie, International Edition (2020), 59(37), 16202-16208, database is CAplus and MEDLINE.

A transition-metal-free C(sp²)-C(sp²) bond formation reaction by the cross-coupling of diazo quinones with catechol boronic esters was developed. With this protocol, a variety of biaryls and alkenyl phenols were obtained in good to high yields under mild conditions [e.g., ortho-diazo quinone I + catechol boronic ester II → III (94%) using K₂CO₃ as base and MeCN/DCM mixed solvent]. The reaction tolerates various functionalities and is applicable to the derivatization of pharmaceuticals and natural products. The synthetic utility of the method was demonstrated by the short synthesis of multi-substituted triphenylenes and three bioactive natural products, honokiol, moracin M, and stemofuran A. Mechanistic studies and d. functional theory (DFT) calculations revealed that the reaction involves attack of the boronic ester by a singlet quinone carbene followed by a 1,2-rearrangement through a stepwise mechanism. Safety: diazo quinones are potentially explosive.

Referemce:
https://en.wikipedia.org/wiki/Benzofuran,
Benzofuran | C8H6O – PubChem