Heterocyclic Building Block-benzofuran

UPLC-MS identification and anticomplement activity of the metabolites of Sophora tonkinensis flavonoids treated with human intestinal bacteria was written by Jin, Xin;Lu, Yan;Chen, Shaoxin;Chen, Daofeng. And the article was included in Journal of Pharmaceutical and Biomedical Analysis in 2020.Category: benzofurans This article mentions the following:

Anticomplement activity played an important role in anti-inflammatory effects of traditional Chinese herbs. The total flavonoids of Sophora tonkinensis (TFST) were inactive on the complement system but showed obvious anticomplement activity after incubated with human intestinal bacteria in vitro. In order to discover the metabolic activation of TFST by intestinal flora, the constituents of TFST and its metabolites were identified by UPLC-ESI-LTQ/MS. Their anticomplement activities were evaluated through the classical and alternative pathway. As a result, eighteen flavonoids were identified, including seven flavonoid glycosides, five aglycons and six isoprenylated flavonoids. All the glycosides (daidzein-4′-glucoside-rhamnoside, sophorabioside, rutin, isoquercitrin, quercitrin, ononin, trifolirhizin) were metabolized into their corresponding aglycons in different extent by human intestinal bacteria, resulting in the contents of the five aglycons were highly increased in 24 h. However, no changes have occurred on the six isoprenylated flavonoids. Interestingly, three aglycons (quercetin, formononetin and maackiain) had significantly more potent anticomplement activities than their prototype glycosides. The results indicated that the enhancement of TFST anticomplement activity was attributed to the active aglycons, especially formononetin and quercetin, produced by human intestinal bacteria. These aglycons are likely to be among the potential active components of S. tonkinensis for its inhibiting inflammation effects. In the experiment, the researchers used many compounds, for example, (2S,3R,4S,5S,6R)-2-(((6aR,12aR)-6a,12a-Dihydro-6H-[1,3]dioxolo[4′,5′:5,6]benzofuro[3,2-c]chromen-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 6807-83-6Category: benzofurans).

(2S,3R,4S,5S,6R)-2-(((6aR,12aR)-6a,12a-Dihydro-6H-[1,3]dioxolo[4′,5′:5,6]benzofuro[3,2-c]chromen-3-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (cas: 6807-83-6) belongs to benzofurans derivatives. Many natural or synthetic compounds containing benzofuran skeletons have been found to possess remarkable activity as agrochemicals and pharmaceuticals. 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.Category: benzofurans

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Electron transfer in triarylmethane lactones: from the sub-100 fs regime to solvent control was written by Schmidhammer, U.;Karpiuk, J.;Lochbrunner, S.;Riedle, E.. And the article was included in Springer Series in Chemical Physics in 2007.Computed Properties of C26H29N3O2 This article mentions the following:

The electron transfer in triarylmethane lactones can be as fast as 50 fs exceeding the inertial solvation. Changing the character of the excited state switches to complete solvent control. In the experiment, the researchers used many compounds, for example, Crystal violet lactone (cas: 1552-42-7Computed Properties of C26H29N3O2).

Crystal violet lactone (cas: 1552-42-7) 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.Computed Properties of C26H29N3O2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Chain diffusion and exchange during build-up of hydrogen-bonded polymer complex film was written by Rehan, Kiran;Su, Chao;Nie, Jing;Xu, Jian;Yang, Shuguang. And the article was included in Colloids and Surfaces, A: Physicochemical and Engineering Aspects in 2018.Formula: C20H13NO5 This article mentions the following:

Poly(vinylpyrrolidone) (PVPON) and poly(acrylic acid) (PAA) were layer-by-layer (LbL) assembled to prepare thin film based on hydrogen bonding. A series of simple experiments were designed to investigate polymer chain diffusion and exchange behaviors of hydrogen-bonded PVPON/PAA film. PAA was labeled with fluorescence dye, fluorescein amine (FAM). The prepared (PVPON/PAA)₂₀ films were immersed into PAA solution, PVPON solution and PAA-FAM solution sep., for a period that was much longer than the assembly time, and the thickness, the composition and the characteristic absorbance of the film were monitored. The experiment results indicated that polymers not only diffused into the thin film from the assembly solution but also diffused out from the thin film into the assembly solution, i.e. there existed a polymer chain exchange. The growth of hydrogen-bonded PVPON/PAA film was related with polymer chain diffusion and exchange at a certain time scale. In the experiment, the researchers used many compounds, for example, 5-Amino-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 3326-34-9Formula: C20H13NO5).

5-Amino-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 3326-34-9) 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. 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: C20H13NO5

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Thermoresponsive Dynamic Covalent Polymers with Tunable Properties was written by Li, Jingyi;Yang, Shixia;Wang, Lin;Wang, Xiaobei;Liu, Li. And the article was included in Macromolecules (Washington, DC, United States) in 2013.HPLC of Formula: 3326-34-9 This article mentions the following:

A bisaldehyde-containing trithiocarbonate chain transfer agent was prepared and mediated the synthesis of polymers with bisaldehyde-functionalized α-termini by reversible addition-fragmentation chain transfer (RAFT) radical polymerization The α-termini of RAFT-derived thermoresponsive poly-(N-isopropylacrylamide) was conjugated with hydrazides via reversible acylhydrazone bonds. Introduction of hydrophilic end-groups generated a dynamic covalent polymer with “isothermal” lower critical solution temperature (LCST) response to medium pH and dynamic chain exchange character. A biofunctional dynamic covalent polymer was prepared by conjugation with biotin hydrazide. Under appropriate reaction conditions, a dynamic covalent block copolymer with an aldehyde group at the junction point was constructed through a reversible arylhydrazone linkage by coupling with acylhydrazide-terminated poly-(ethylene glycol). The dynamic covalent block copolymer exhibited pH-dependent LCST. The remaining aldehyde group was used to react with amino-containing mols. Bioconjugated dynamic covalent block copolymers containing reversible imine and arylhydrazone linkages were constructed by conjugation of the block copolymer to glucosamine and protein. In the experiment, the researchers used many compounds, for example, 5-Amino-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 3326-34-9HPLC of Formula: 3326-34-9).

5-Amino-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 3326-34-9) 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.HPLC of Formula: 3326-34-9

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Allophenylnorstatine-containing HIV-1 protease inhibitors: design, synthesis and structure-activity relationships for selected P₂ ligands was written by Abdel-Rahman, Hamdy M.;El-Koussi, Nawal A.;Alkaramany, Gamal S.;Youssef, Adel F.;Kiso, Yoshiaki. And the article was included in Bulletin of Pharmaceutical Sciences, Assiut University in 2005.Electric Literature of C10H8O4 This article mentions the following:

The design and development of potent HIV protease inhibitors remain an attractive target for antiviral therapy. A novel class of HIV protease inhibitors containing allophenylnorstatine [Apns; (2S,3S)-3-amino-2-hydroxy-4 phenylbutyric acid] as a transition state mimic have been reported. In this work we fixed P₂‘ (as tert-butylamino or 2-methylbenzylamino) and changed P₂ moiety to provide two series of dipeptide analogs. Preliminary evaluation of the activity of the synthesized derivatives were determined as percentage of enzyme inhibition at 5 μM level. The results showed that the introduction of 2-methylbenzylamino moiety as P₂‘ ligands considerably improved HIV inhibitory activity in comparison with the tert-Bu amino analogs. It was found that compounds in both series retained activity still less than the lead compounds KNI-577 and KNI-727. In the experiment, the researchers used many compounds, for example, 7-Methoxybenzofuran-2-carboxylic acid (cas: 4790-79-8Electric Literature of C10H8O4).

7-Methoxybenzofuran-2-carboxylic acid (cas: 4790-79-8) 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.Electric Literature of C10H8O4

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

MP470, a novel receptor tyrosine kinase inhibitor, in combination with Erlotinib inhibits the HER family/PI3K/Akt pathway and tumor growth in prostate cancer was written by Qi, Wenqing;Cooke, Larry S.;Stejskal, Amy;Riley, Christopher;Della Croce, Kimiko;Saldanha, Jose W.;Bearss, David;Mahadevan, Daruka. And the article was included in BMC Cancer in 2009.COA of Formula: C23H21N5O3S This article mentions the following:

Background: Prostate cancer is a common disease in men and at present there is no effective therapy available due to its recurrence despite androgen deprivation therapy. The epidermal growth factor receptor family (EGFR/HER1, HER2/neu and HER3)/PI3K/Akt signaling axis has been implicated in prostate cancer development and progression. However, Erlotinib, an EGFR tyrosine kinase inhibitor, has less effect on proliferation and apoptosis in prostate cancer cell lines. In this study, we evaluate whether MP470, a novel receptor tyrosine kinase inhibitor alone or in combination with Erlotinib has inhibitory effect on prostate cancer in vitro and in vivo. Methods: The efficacy of MP470 or MP470 plus Erlotinib was evaluated in vitro using three prostate cancer cell lines by MTS and apoptosis assays. The mol. mechanism study was carried out by phosphorylation antibody array, immunoblotting and immunohistochem. A LNCaP mouse xenograft model was also used to determine the tumor growth inhibition by MP470, Erlotinib or the combination treatments. Results: MP470 exhibits low μM IC₅₀ in prostate cancer cell lines. Additive effects on both cytotoxicity and induction of apoptosis were observed when LNCaP were treated with MP470 in combination with Erlotinib. This combination treatment completely inhibited phosphorylation of the HER family members (HER1, 2, 3), binding of PI3K regulatory unit p85 to HER3 and downstream Akt activity even after androgen depletion. Furthermore, in a LNCaP mouse xenograft model, the MP470-Erlotinib combination produced 30-65% dose-dependent tumor growth inhibition (TGI). Conclusion: We propose that MP470-Erlotinib targets the HER family/PI3K/Akt pathway and may represent a novel therapeutic strategy for prostate cancer. In the experiment, the researchers used many compounds, for example, N-(Benzo[d][1,3]dioxol-5-ylmethyl)-4-(benzofuro[3,2-d]pyrimidin-4-yl)piperazine-1-carbothioamide (cas: 850879-09-3COA of Formula: C23H21N5O3S).

N-(Benzo[d][1,3]dioxol-5-ylmethyl)-4-(benzofuro[3,2-d]pyrimidin-4-yl)piperazine-1-carbothioamide (cas: 850879-09-3) belongs to benzofurans derivatives. Benzofurans are only weakly aromatic in nature and they are cleaved by many oxidative and reductive conditions. 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.COA of Formula: C23H21N5O3S

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Fabrication of visual textile temperature indicators based on reversible thermochromic fibers was written by Zhang, Yangkai;Hu, Zexu;Xiang, Hengxue;Zhai, Gongxun;Zhu, Meifang. And the article was included in Dyes and Pigments in 2019.Application In Synthesis of Crystal violet lactone This article mentions the following:

Human body signals detection functions in fibers such as visual temperature indicator, are important aspects in future development of satisfying the warmth and comfortableness of conventional textile fibers. A series of reversible thermochromic fibers (VTFs), where thermochromic microcapsules and polypropylene (PP) was used as color indicator and polymer fiber matrix, resp., were prepared via melt spinning in this paper. The temperature-color response behaviors of VTFs were investigated in detail. The SEM images of cross section of VTFs showed that PP was an excellent matrix for the dispersion of thermochromic microcapsules and no aggregation occurred. The results of color measuring and matching indicated that VTFs exhibited various colors of red, purple and blue depending on the mass ratio of the red function and blue function microcapsules. Moreover, when the ambient temperature changed between 5 °C and 35 °C, the color of VTFs could fade and recover in a short time, and this kind of VTFs displayed excellent performance stability after 60 temperature cycles. In the experiment, the researchers used many compounds, for example, Crystal violet lactone (cas: 1552-42-7Application In Synthesis of Crystal violet lactone).

Crystal violet lactone (cas: 1552-42-7) belongs to benzofurans derivatives. Many natural or synthetic compounds containing benzofuran skeletons have been found to possess remarkable activity as agrochemicals and pharmaceuticals. 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.Application In Synthesis of Crystal violet lactone

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Phase 1B study of amuvatinib in combination with five standard cancer therapies in adults with advanced solid tumors was written by Mita, Monica;Gordon, Michael;Rosen, Lee;Kapoor, Nirmal;Choy, Gavin;Redkar, Sanjeev;Taverna, Pietro;Oganesian, Aram;Sahai, Amarpal;Azab, Mohammad;Bristow, Robert;Tolcher, Anthony W.. And the article was included in Cancer Chemotherapy and Pharmacology in 2014.Formula: C23H21N5O3S This article mentions the following:

Purpose: Amuvatinib is an oral multi-kinase inhibitor that suppresses RAD51, inhibits mutant c-KIT and platelet-derived growth factor receptor alpha, and has synergistic activity with DNA-damaging agents and topoisomerase inhibitors such as etoposide, doxorubicin, and topotecan. We conducted a phase 1B study to estimate the maximum tolerated dose (MTD) levels of amuvatinib with standard chemotherapy regimens and to define the safety profiles of specific amuvatinib + standard regimens. Methods: Five therapies each co-administered with amuvatinib 100-800 mg/day every 21 days were evaluated in treatment-naive or moderately pre-treated subjects: paclitaxel IV followed by carboplatin IV; carboplatin IV followed by etoposide; topotecan IV; docetaxel IV; and erlotinib by mouth. Results: Among 97 treated subjects, no treatment arm reached the MTD. Dose-limiting toxicities included febrile neutropenia and diarrhea. No pharmacokinetic interactions of amuvatinib with any cancer regimens occurred. Of 12/97 (12 %) partial responses overall, 11 were seen in the amuvatinib and paclitaxel/carboplatin or carboplatin/etoposide arms and most commonly in the neuroendocrine (NE), non-small cell lung cancer (NSCLC), and small cell lung cancer (SCLC) tumors. Forty-four subjects (45 %) had stable disease. Adverse events reflected combination treatment and were primarily non-hematol. (fatigue, alopecia, diarrhea, nausea, anorexia) and hematol. (neutropenia, anemia, thrombocytopenia, leukopenia). Pharmacodynamic effects as measured by decreased levels of RAD51 and increased residual DNA damage (53BP1 foci) were seen in skin punch biopsies. Conclusion: Amuvatinib was well tolerated, modulated RAD51, and showed antitumor activity when combined with paclitaxel/carboplatin and carboplatin/etoposide in NE, NSCLC, and SCLC tumors. In the experiment, the researchers used many compounds, for example, N-(Benzo[d][1,3]dioxol-5-ylmethyl)-4-(benzofuro[3,2-d]pyrimidin-4-yl)piperazine-1-carbothioamide (cas: 850879-09-3Formula: C23H21N5O3S).

N-(Benzo[d][1,3]dioxol-5-ylmethyl)-4-(benzofuro[3,2-d]pyrimidin-4-yl)piperazine-1-carbothioamide (cas: 850879-09-3) 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. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antiviral, antimicrobial, antitumor, anti-inflammatory.Formula: C23H21N5O3S

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Resonance Rayleigh scattering technique-using erythrosine B, as novel spectrofluorimetric method for determination of anticancer agent nilotinib: Application for capsules and human plasma was written by Salem, Hesham;Abo Elsoud, Fatma A.;Heshmat, Dina;Magdy, Ahmed. And the article was included in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy in 2021.Name: Sodium 2′,4′,5′,7′-tetraiodo-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-3′,6′-bis(olate) This article mentions the following:

A exceedingly touchy resonance Rayleigh scattering (RRS) strategy for the assurance of nilotinib (NILO) was introduced. In the pH 3.4 acetate buffer solution, NILO reacted with erythrosine B to produce an ion-association complex, which increased the RRS intensity of the studied system. The enhanced RRS intensity (ΔI) was linearly proportional to the concentration of NILO, the linear range of the method was 0.1-1.0μg/mL and the detection limit (DL) was 0.025μg/mL. In like manner, this test was connected to distinguish the concentration of NILO in capsules and human plasma with palatable comes about. In the experiment, the researchers used many compounds, for example, Sodium 2′,4′,5′,7′-tetraiodo-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-3′,6′-bis(olate) (cas: 16423-68-0Name: Sodium 2′,4′,5′,7′-tetraiodo-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-3′,6′-bis(olate)).

Sodium 2′,4′,5′,7′-tetraiodo-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-3′,6′-bis(olate) (cas: 16423-68-0) 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.Name: Sodium 2′,4′,5′,7′-tetraiodo-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-3′,6′-bis(olate)

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Predictive Endocrine Testing in the 21st Century Using in Vitro Assays of Estrogen Receptor Signaling Responses was written by Rotroff, Daniel M.;Martin, Matt T.;Dix, David J.;Filer, Dayne L.;Houck, Keith A.;Knudsen, Thomas B.;Sipes, Nisha S.;Reif, David M.;Xia, Menghang;Huang, Ruili;Judson, Richard S.. And the article was included in Environmental Science & Technology in 2014.Quality Control of 2,2-Dimethyl-2,3-dihydrobenzofuran-7-ol This article mentions the following:

Thousands of environmental chems. are subject to regulatory review for their potential to be endocrine disruptors (ED). In vitro high-throughput screening (HTS) assays have emerged as a potential tool for prioritizing chems. for ED-related whole-animal tests. In this study, 1814 chems. including pesticide active and inert ingredients, industrial chems., food additives, and pharmaceuticals were evaluated in a panel of 13 in vitro HTS assays. The panel of in vitro assays interrogated multiple end points related to estrogen receptor (ER) signaling, namely binding, agonist, antagonist, and cell growth responses. The results from the in vitro assays were used to create an ER Interaction Score. For 36 reference chems., an ER Interaction Score >0 showed 100% sensitivity and 87.5% specificity for classifying potential ER activity. The magnitude of the ER Interaction Score was significantly related to the potency classification of the reference chems. ERα/ERβ selectivity was also evaluated, but relatively few chems. showed significant selectivity for a specific isoform. When applied to a broader set of chems. with in vivo uterotrophic data, the ER Interaction Scores showed 91% sensitivity and 65% specificity. Overall, this study provides a novel method for combining in vitro concentration response data from multiple assays and, when applied to a large set of ER data, accurately predicted estrogenic responses and demonstrated its utility for chem. prioritization. In the experiment, the researchers used many compounds, for example, 2,2-Dimethyl-2,3-dihydrobenzofuran-7-ol (cas: 1563-38-8Quality Control of 2,2-Dimethyl-2,3-dihydrobenzofuran-7-ol).

2,2-Dimethyl-2,3-dihydrobenzofuran-7-ol (cas: 1563-38-8) 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.Quality Control of 2,2-Dimethyl-2,3-dihydrobenzofuran-7-ol

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem