November 2022 | Page 7 of 45 | Heterocyclic Building Block-benzofuran

Wang, Zhiren’s team published research in Journal of Medicinal Chemistry in 58 | CAS: 56317-21-6

Journal of Medicinal Chemistry 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 C16H12O, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol.

Wang, Zhiren published the artcileDesign, Synthesis, and Evaluation of Orally Available Clioquinol-Moracin M Hybrids as Multitarget-Directed Ligands for Cognitive Improvement in a Rat Model of Neurodegeneration in Alzheimer’s Disease, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, the publication is Journal of Medicinal Chemistry (2015), 58(21), 8616-8637, database is CAplus and MEDLINE.

A novel series of clioquinol-moracin hybrids were designed and synthesized by fusing the pharmacophores of clioquinol and moracin M, and their activities as multitarget-directed ligands against Alzheimer’s disease were evaluated. Biol. activity results demonstrated that these hybrids possessed significant inhibitory activities against phosphodiesterase 4D (PDE4D) and Aβ aggregation as well as remarkable antioxidant effects and excellent blood-brain barrier permeability. The optimal compound, I (WBQ5187), exhibited excellent PDE4D inhibitory potency (IC₅₀ = 0.32 μM), significant antioxidant effects, appropriate biometal chelating functions, and interesting properties that modulated self- and metal-induced Aβ aggregation. Two-dimensional NMR studies revealed that I had significant interactions with Aβ_1-42 at the R5, H6, H14, Q15, and F20 residues. Furthermore, this typical hybrid possessed preeminent neuroprotective effects against inflammation in microglial cells. Most importantly, oral administration of I·HCl demonstrated marked improvements in cognitive and spatial memory in a rat model of Alzheimer’s disease and protected hippocampal neurons from necrosis.

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

Minami, Hiroki’s team published research in European Journal of Organic Chemistry in 2013 | CAS: 69626-75-1

European Journal of Organic Chemistry 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, Safety of 2-Iodobenzofuran.

Minami, Hiroki published the artcileDirect C-C Bond Construction from Arylzinc Reagents and Aryl Halides without External Catalysts, Safety of 2-Iodobenzofuran, the publication is European Journal of Organic Chemistry (2013), 2013(35), 7891-7894, database is CAplus.

A direct cross-coupling between an arylzinc reagent and an aryl halide was accomplished without any external catalyst, enabling efficient and selective formation of the corresponding biaryl compound with broad functional group compatibility. An exchange reaction of (aryl)lithium compounds with zinc chloride gave the desired zinc reactants. The synthesis of the target compounds was achieved using bis(4-methylphenyl)zinc, bis[4-(trifluoromethyl)phenyl]zinc, bis(2-thienyl)zinc, bis(2-benzofuranyl)zinc, etc., as starting materials in a reaction with iodobenzene derivatives The products thus formed included 2-(4-methylphenyl)naphthalene, 2-(2,4,6-trimethylphenyl)naphthalene, 2-(2-naphthalenyl)thiophene, 2-(2-naphthalenyl)benzofuran, 4-methoxy-4′-methyl-1,1′-biphenyl, 4′-methyl[1,1′-biphenyl]-4-carbonitrile and related substances. A reaction of 1-Bromo-4-iodobenzene with bis(2-methylphenyl)zinc gave 2,2”-dimethyl-1,1′:4′,1”-terphenyl.

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

Li, Ruilin’s team published research in Phytomedicine in 92 | CAS: 56317-21-6

Phytomedicine 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, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol.

Li, Ruilin published the artcileA combined network pharmacology and molecular biology approach to investigate the active ingredients and potential mechanisms of mulberry (Morus alba L.) leaf on obesity, Recommanded Product: 5-(6-Hydroxybenzofuran-2-yl)benzene-1,3-diol, the publication is Phytomedicine (2021), 153714, database is CAplus and MEDLINE.

As one of traditional Chinese medicine, mulberry leaf is abundant in diverse active ingredients and widely used for the treatment of metabolic disease and its complications. However, there are a few of reports on its application in the prevention and treatment of obesity. And the mol. mechanism on the anti-obesity of mulberry leaf are unknown till now. The present study aimed to evaluate the potential ingredients and targets of mulberry leaf and uncover the anti-obesity mechanisms by using the network pharmacol. tactics and verify its effect by biol. experiments Active ingredients and key targets of mulberry leaf, genes related to obesity were screened through public database. Based on the results of network pharmacol., the flavonoids-enriched fraction of mulberry leaf (MLF) was extracted and composition of this fraction was identified. After that, HepG2 cells model of lipid accumulation was established for verifying the effect of MLF and related mechanisms. A total of 37 active ingredients in mulberry leaf, 192 predicted biol. targets and 8813 obesity-related targets were determined, of which 180 overlapping targets might have obvious curative effects on obesity. The networks showed that mulberry leaf might play a role through key targets, such as AKT, MAPK and IL-6, and regulated PI3K-Akt signaling pathway. Based on HPLC-ESI-QQQ-MS anal., 13 constituents of MLF were identified, including 9 flavonoids. Furthermore, HepG2 cells model of lipid accumulation was established. The results indicated that MLF treatment could down-regulate the secretion of inflammatory cytokines, as well as clearly inhibited lipid droplets formation and alleviated TC, TG, HDL-C and LDL-C levels. Pos. effect was observed on hypolipidemic efficacy due to the regulation of PI3K/Akt/Bcl-xl pathway, as indicated by the amelioration of PI3K, Akt and Bcl-xl gene and protein expression. This study firstly systematically disclose the multi-ingredients, multi-targets mechanisms of mulberry leaf on obesity by using network pharmacol. approach, and validate in HepG2 cells that the protective effect of MLF against obesity involved both inflammation response and lipid metabolism involving PI3K/Akt/Bcl-xl signaling pathway. It provides indications for further mechanistic research of mulberry leaf and also for the development as a potential candidate for the therapy for obese patients.

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

Pflieger, Aude’s team published research in PLoS One in 8 | CAS: 56317-21-6

PLoS One 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, SDS of cas: 56317-21-6.

Pflieger, Aude published the artcileNatural stilbenoids isolated from grapevine exhibiting inhibitory effects against HIV-1 integrase and eukaryote MOS1 transposase in vitro activities, SDS of cas: 56317-21-6, the publication is PLoS One (2013), 8(11), e81184/1-e81184/13, 13 pp., database is CAplus and MEDLINE.

Polynucleotidyl transferases are enzymes involved in several DNA mobility mechanisms in prokaryotes and eukaryotes. Some of them such as retroviral integrases are crucial for pathogenous processes and are therefore good candidates for therapeutic approaches. To identify new therapeutic compounds and new tools for investigating the common functional features of these proteins, we addressed the inhibition properties of natural stilbenoids deriving from resveratrol on two models: the HIV-1 integrase and the eukaryote MOS-1 transposase. Two resveratrol dimers, leachianol F and G, were isolated for the first time in Vitis along with fourteen known stilbenoids: E-resveratrol, E-piceid, E-pterostilbene, E-piceatannol, (+)- E-ε-viniferin, E-ε-viniferinglucoside, E-scirpusin A, quadragularin A, ampelopsin A, pallidol, E-miyabenol C, E-vitisin B, hopeaphenol, and isohopeaphenol and were purified from stalks of Vitis vinifera (Vitaceae), and moracin M from stem bark of Milliciaexelsa (Moraceae). These compounds were tested in in vitro and in vivo assays reproducing the activity of both enzymes. Several mols. presented significant inhibition on both systems. Some of the mols. were found to be active against both proteins while others were specific for one of the two models. Comparison of the differential effects of the mols. suggested that the compounds could target specific intermediate nucleocomplexes of the reactions. Addnl. E-pterostilbene was found active on the early lentiviral replication steps in lentiviruses transduced cells. Consequently, in addition to representing new original lead compounds for further modeling of new active agents against HIV-1 integrase, these mols. could be good tools for identifying such reaction intermediates in DNA mobility processes.

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

Vedantham, Ravindra’s team published research in Organic Process Research & Development in 17 | CAS: 372941-54-3

Organic Process Research & Development published new progress about 372941-54-3. 372941-54-3 belongs to benzofurans, auxiliary class Other Aliphatic Heterocyclic,Fluoride,Nitrile,Amine,Benzene,Ester, name is 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, and the molecular formula is C3H5F3O, Name: 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile.

Vedantham, Ravindra published the artcileImproved One-Pot Synthesis of Citalopram Diol and Its Conversion to Citalopram, Name: 1-(3-(Dimethylamino)propyl)-1-(4-fluorophenyl)-3-oxo-1,3-dihydroisobenzofuran-5-carbonitrile, the publication is Organic Process Research & Development (2013), 17(5), 798-805, database is CAplus.

An improved process is developed for the preparation of citalopram diol, I which involves two consecutive Grignard reactions in situ followed by an efficient and simple workup process with improved overall yield. Process development efforts for conversion of I·HBr into citalopram, II·HBr, and a control strategy for impurities are discussed. The present work addresses the challenges associated with the process development and scale-up of citalopram such as handling of unstable intermediates, control of various potential impurities, and process safety to achieve an economic and scalable process.

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

Chen, Qing et al. published their research in Molecules in 2019 | 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 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 antioxidant, antitubercular, antiplasmodial, insecticidal.Related Products of 524-12-9

Development and validation of an ultra-performance liquid chromatography method for the determination of wedelolactone in rat plasma and its application in a pharmacokinetic study was written by Chen, Qing;Wu, Xiaoxue;Gao, Xuemin;Song, Hua;Zhu, Xuan. And the article was included in Molecules in 2019.Related Products of 524-12-9 The following contents are mentioned in the article:

Wedelolactone is a coumarin ether with significant hepatoprotective effects. However, there are few pharmacokinetic studies of wedelolactone, which will affect the studies of its efficacy and potential toxicity. In this study, a selective ultra-performance liquid chromatog. (UPLC) method was developed to confirm the pharmacokinetic parameters of wedelolactone in rat plasma. The chromatog. separation was carried out on a Kromasil C18 UPLC column (250 × 4.6 mm; 5.0 mum) by gradient mobile phase of methanol-water containing 0.5% acetic acid (volume/volume). Perfect linearity was obtained and the samples were stable under different conditions. The intra-day and inter-day precisions (relative standard deviation, %) were within 3.81% and accuracies (relative error, %) ranged from -4.01% to 7.12%. The extraction recoveries in rat plasma ranged from 95.98% to 108.93%. This rapid method was successfully applied in the pharmacokinetic study of wedelolactone in rat plasma. Following the oral administration of 5.00 mg/kg wedelolactone, the wedelolactone was rapidly absorbed. Pharmacokinetic parameters were used to quant. describe the dynamic changes of wedelolactone in vivo, providing a theor. basis for pharmacol. research on drugs and preclin. medication. The study of wedelolactone can provide a theor. basis and quick anal. for the study of other traditional Chinese medicine. This study involved multiple reactions and reactants, such as 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9Related Products of 524-12-9).

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Lin, Hao et al. published their research in ACS Applied Materials & Interfaces in 2018 | 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.Formula: C16H10O7

Caspase-1 Specific Light-Up Probe with Aggregation-Induced Emission Characteristics for Inhibitor Screening of Coumarin-Originated Natural Products was written by Lin, Hao;Yang, Haitao;Huang, Shuai;Wang, Fujia;Wang, Dong-Mei;Liu, Bin;Tang, Yi-Da;Zhang, Chong-Jing. And the article was included in ACS Applied Materials & Interfaces in 2018.Formula: C16H10O7 The following contents are mentioned in the article:

Caspase-1 is a key player in pyroptosis and inflammation. Caspase-1 inhibition is found to be beneficial to various diseases. Coumarin-originated natural products have an anti-inflammation function, but their direct inhibition effect to caspase-1 remains unexplored. To evaluate their interactions, the widely used com. coumarin-based probe (Ac-YVAD-AMC) is not suitable, as the background signal from coumarin-originated natural products could interfere with the screening results. Therefore, fluorescent probes using a large Stokes shift could help solve this problem. In this work, we chose the fluorophore of tetraphenylethylene-thiophene (TPETH) with aggregation-induced emission characteristics and a large Stokes shift of about 200 nm to develop a mol. probe. Bioconjugation between TPETH and hydrophilic peptides (DDYVADC) through a thiol-ene reaction generated a light-up probe, C1-P3. The probe has little background signal in aqueous media and exerts a fluorescent turn-on effect in the presence of caspase-1. Moreover, when evaluating the inhibition potency of coumarin-originated natural products, the new probe could generate a true and objective result but not for the com. probe (Ac-YVAD-AMC), which is evidenced by HPLC anal. The quick light-up response and accurate screening results make C1-P3 very useful in fundamental study and inhibitor screening toward caspase-1. This study involved multiple reactions and reactants, such as 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9Formula: C16H10O7).

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Tripathi, K. Sharad et al. published their research in International Journal of Pharmaceutical Sciences and Research 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. Substituted benzofurans find applications such as fluorescent sensors, oxidants, in drug discovery, and in another field of chemistry and agriculture.Category: benzofurans

Phytochemical and antioxidant assay of Eclipta alba (L.) leaf extract was written by Tripathi, K. Sharad;Jha, Saket;Dikshit, Anupam;Kumar, Rajesh. And the article was included in International Journal of Pharmaceutical Sciences and Research in 2021.Category: benzofurans The following contents are mentioned in the article:

Currently, pharmacol. activities of Eclipta alba (L.) plant extracts and individual phytoconstituents have revealed anticancer, hepatoprotective, snake venom neutralizing, anti-inflammatory and antimicrobial properties. The role of antioxidants is increasing day by day due to their multiple roles to reduce the harmful effects of oxidative stress. Phytoconstituents like wedelolactone and ursolic and oleanolic acids as well as luteolin and apigenin can form the basis of new drugs against cancer, arthritis, gastrointestinal disorders, skin diseases, and liver disorders. Plants have all these activities due to biol. active compounds, and for this, we have analyzed phytochem. screenings and antioxidant activity through the DPPH, ABTS·+, and reducing power assay and we got maximally phenols then flavonoids and flavonols and a good natural antioxidant agent. The best-known compound in E. alba i.e., Wedelolactone. It was analyzed by TLC, and it was present as 0.52 Rf value and present in pet ether extract and acetone extract and min. in ethanol extract The antioxidant activity was assessed through DPPH, ABTS·+ free radical scavenging activity and reducing power assay, this was explained in terms of effective concentration EC50 / IC₅₀ and Anti-oxidant Radical Power (ARP) values. The maximum free radical scavenging activity was showed in pet ether compared to other extracts 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

Zhi, Deyuan et al. published their research in Journal of International Medical Research 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. Substituted benzofurans find applications such as fluorescent sensors, oxidants, in drug discovery, and in another field of chemistry and agriculture.Synthetic Route of C16H10O7

Wedelolactone improves the renal injury induced by lipopolysaccharide in HK-2 cells by upregulation of protein tyrosine phosphatase non-receptor type 2 was written by Zhi, Deyuan;Zhang, Meng;Lin, Jin;Liu, Pei;Wang, Yajun;Duan, Meili. And the article was included in Journal of International Medical Research in 2021.Synthetic Route of C16H10O7 The following contents are mentioned in the article:

To explore the effects of wedelolactone (WEL) on sepsis-induced renal injury in the human renal proximal tubular epithelial cell line HK-2. HK-2 cells were stimulated by 1μg/mL lipopolysaccharide (LPS) to trigger renal injury in vitro. HK-2 cells were pretreated with or without WEL (0.1, 1 and 10μM) before LPS stimulation. Protein and mRNA analyses were performed using enzyme-linked immunosorbent assays, Western blot anal. and quant. reverse transcription-polymerase chain reaction. The MTT assay and flow cytometry were used to measure cell viability and the rate of cell apoptosis. Protein tyrosine phosphatase non-receptor type 2 (PTPN2) knockdown was induced by the transection of HK-2 cells with short hairpin RNA. Cell viability was significantly increased in a dose-dependent manner by WEL in LPS-induced HK-2 cells. WEL also decreased the levels of four inflammatory cytokines and cell apoptosis in LPS-induced HK-2 cells. The level of PTPN2 was increased after WEL treatment. PTPN2 knockdown partly abolished the inhibitory effects of WEL on cell apoptosis, the levels of inflammatory cytokines and on p38 mitogen-activated protein kinase/nuclear factor-kappaB signalling in LPS-induced HK-2 cells. WEL improved renal injury by suppressing inflammation and cell apoptosis through upregulating PTPN2 in HK-2 cells. PTPN2 might be used as a potential therapeutic target for LPS-induced sepsis. This study involved multiple reactions and reactants, such as 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9Synthetic Route of C16H10O7).

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Ding, Shumin et al. published their research in Frontiers in Pharmacology in 2018 | 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. In nature, benzofurans have occupied an important role among the plant phenols & several pharmacologically active compounds.Electric Literature of C16H10O7

Autophagy flux contributes to regulation of components of Eclipta prostrata L. on cigarette smoking-induced injury of bronchial epithelial cells was written by Ding, Shumin;Hou, Xuefeng;Wang, Gang;Qiu, Huihui;Liu, Ying;Zhou, Yuanli;Du, Mei;Tan, Xiaobin;Song, Jie;Wei, Yingjie;Shu, Luan;Li, Zhiyong;Feng, Liang;Jia, Xiaobin. And the article was included in Frontiers in Pharmacology in 2018.Electric Literature of C16H10O7 The following contents are mentioned in the article:

Excessive autophagy plays a crucial role in cigarette smoking extract (CSE)-induced inflammation response and oxidative damage of respiratory epithelial cells. The components from Eclipta prostrata L. (CCE) have been shown to be beneficial for CSE-induced epithelial cells injury. However, whether its protection on CSE-stress injury is related to its regulation on autophagy remains still unclear. In this study, CCE, containing mainly wedelolactone of 45.88% and demethylwedelolactone of 23.74%, could improve significantly 10% CSE-induced cell viability of normal human bronchial epithelial (NHBE) cells using CCK-8 kit. We revealed that CCE could remarkably increase autophagic factors Beclin-1, Atg5, ATF4 proteins expression levels and the transformation of LC3-I to LC3-II. Addnl., CCE up-regulated significantly p-p16 and p-p21 phosphorylation levels whereas down-regulated p-p53 in NHBE cells. The changes of typical autolysosom and representative autophagosome in the presence of CCE or/and autophagy inhibitor chloroquine (CQ) were also observed by transmission electron microscopy. These data demonstrated that CCE reduced CSE-induced autophagy flux activation in NHBE cells. The blockade of CCE on autophagy flux contributes to its protection against CSE-induced NHBE cells damage, and CCE is promising to be combination therapeutic mols. to excessive autophagic damage in respiratory diseases. This study involved multiple reactions and reactants, such as 1,8,9-Trihydroxy-3-methoxy-6H-benzofuro[3,2-c]chromen-6-one (cas: 524-12-9Electric Literature of C16H10O7).

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem