Heterocyclic Building Block-benzofuran

Photostimulated reactions of o-dihalobenzenes with nucleophiles derived from the 2-naphthyl system. Competition between electron transfer, fragmentation, and ring closure reactions was written by Baumgartner, Maria T.;Pierini, Adriana B.;Rossi, Roberto A.. And the article was included in Journal of Organic Chemistry in 1993.Synthetic Route of C16H10O This article mentions the following:

The photostimulated reaction of o-XC₆H₄Y (I; X = I, Br, Cl, Y = I; X = Cl, Y = Br) with 2-naphthoxide (II, Z = O) gave 1-(o-halophenyl)-2-naphthol (III; halo = I, Br, Cl) and ring-closure product IV (Z = O), III being an intermediate in the formation of IV (Z = O). The products obtained in the photostimulated reaction of II (Z = S) with I depended on the halogens. When both nucleofugal groups were iodine, only IV (Z = S) was obtained. With o-bromoiodobenzene, the photostimulated reaction gave IV (Z = S) and the substitution product on sulfur with retention of bromine, while with o-chloroiodobenzene the only observed product was the substitution product on sulfur with retention of chlorine. The photostimulated reaction of I with II (Z = Se) gave the same amount of cyclized product IV (Z = Se) and the substitution product on selenium without retention of halogen, although in an overall low yield. All these reactions may occur by the S_RN1 mechanism. Theor. studies supported the different behavior found with the nucleophiles derived from the 2-naphthyl system. In the experiment, the researchers used many compounds, for example, Naphtho[2,1-b]benzofuran (cas: 205-39-0Synthetic Route of C16H10O).

Naphtho[2,1-b]benzofuran (cas: 205-39-0) 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. 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.Synthetic Route of C16H10O

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Clickable 4-Oxo-β-lactam-Based Selective Probing for Human Neutrophil Elastase Related Proteomes was written by Ruivo, Eduardo F. P.;Goncalves, Lidia M.;Carvalho, Luis A. R.;Guedes, Rita C.;Hofbauer, Stefan;Brito, Jose A.;Archer, Margarida;Moreira, Rui;Lucas, Susana D.. And the article was included in ChemMedChem in 2016.Application of 3326-34-9 This article mentions the following:

Human neutrophil elastase (HNE) is a serine protease associated with several inflammatory processes such as chronic obstructive pulmonary disease (COPD). The precise involvement of HNE in COPD and other inflammatory disease mechanisms has yet to be clarified. Herein the authors report a copper-catalyzed alkyne-azide 1,3-dipolar cycloaddition (CuAAC, or ‘click’ chem.) approach based on the 4-oxo-β-lactam warhead that yielded potent HNE inhibitors containing a triazole moiety. The resulting structure-activity relationships set the basis to develop fluorescent and biotinylated activity-based probes as tools for mol. functional anal. Attaching the tags to the 4-oxo-β-lactam scaffold did not affect HNE inhibitory activity, as revealed by the IC₅₀ values in the nanomolar range (56-118 nM) displayed by the probes. The nitrobenzoxadiazole (NBD)-based probe presented the best binding properties (ligand efficiency (LE)=0.31) combined with an excellent lipophilic ligand efficiency (LLE=4.7). Moreover, the probes showed adequate fluorescence properties, internalization in human neutrophils, and suitable detection of HNE in the presence of a large excess of cell lysate proteins. This allows the development of activity-based probes with promising applications in target validation and identification, as well as diagnostic tools. In the experiment, the researchers used many compounds, for example, 5-Amino-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 3326-34-9Application of 3326-34-9).

5-Amino-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 3326-34-9) belongs to benzofurans derivatives. Benzofuran derivatives are one of the most important oxygen-containing heterocycles. They are also prone to polymerisation in the presence of concentrated mineral acids and Lewis acids.Application of 3326-34-9

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Development of ultrathin polyamide nanofilm with enhanced inner-pore interconnectivity via graphene quantum dots-assembly intercalation for high-performance organic solvent nanofiltration was written by Shen, Qin;Lin, Yuqing;Zhang, Pengfei;Segawa, Jumpei;Jia, Yuandong;Istirokhatun, Titik;Cao, Xingzhong;Guan, Kecheng;Matsuyama, Hideto. And the article was included in Journal of Membrane Science in 2021.Formula: C20H6I4Na2O5 This article mentions the following:

In this study, a high-performance organic solvent nanofiltration (OSN) membrane is engineered via nanoscale aminated graphene quantum dots (GQDN_H2)-mediated interfacial polymerization The GQDN_H2, featuring favorable amine monomers, can atomically regulate the diffusion rate at the interface, yielding nanofilms with controllable thickness (decreasing from 200 to 100 nm). Furthermore, the zero-dimensional GQDs_cN_H2 can serve as nanospacers to increase the inner-pore interconnectivity with loose internal architecture, while preserving the narrow free volume distribution via covalent interactions with the rubbery polymeric matrix. An improvement in solvent separation property is achieved, where the best-performing GQD_scTH₂@PA thin-film nanocomposite (TFN) membrane reaches a magnitude of 2.6-fold higher than that of the pristine polyamide (PA) membrane without significantly compromising its rejection toward organic solvation macro/micromols. solutes, exhibiting high solvent permeances for mild solvents (such as 11.1 L m^-2 h^-1·bar^-1 for methanol) and aggressive solvents (such as 5.9 L m^-2 h^-1·bar^-1 for dimethylformamide), performing a competitive perm-selectivity among the state-of-the-art OSN membranes. The long-term operations (140 h) demonstrated the excellent stability of the nanocomposite membranes. We herein report the development of TFN membrane with thin and loose architecture for highly efficient organic solvent-based separation process. 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: 16423-68-0Formula: C20H6I4Na2O5).

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 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.Formula: C20H6I4Na2O5

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Nano-Pd/Al(OH)₃-Catalyzed Suzuki-Miyaura Coupling Reaction of Potassium Aryl- and Heteroaryltrifluoroborates with Electrophiles in Alcohols was written by Zhu, Tingting;Li, Xing;Chang, Honghong;Gao, Wenchao;Wei, Wenlong. And the article was included in Synlett in 2016.Computed Properties of C8H5BF3KO This article mentions the following:

Highly active aluminum hydroxide supported nanopalladium-catalyzed Suzuki-Miyaura coupling reactions of potassium aryl- and heteroaryltrifluoroborates with aryldiazonium tetrafluoroborates or aryl halides was described. An array of functionalized aryl substrates was successfully cross-coupled to obtain biaryl products in good to excellent yields. In the experiment, the researchers used many compounds, for example, Potassium benzofuran-2-yltrifluoroborate (cas: 929626-27-7Computed Properties of C8H5BF3KO).

Potassium benzofuran-2-yltrifluoroborate (cas: 929626-27-7) 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 antiviral, antimicrobial, antitumor, anti-inflammatory.Computed Properties of C8H5BF3KO

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Compound screening identified gossypetin and isoquercitrin as novel inhibitors for amyloid fibril formations of Vλ6 proteins associated with AL amyloidosis was written by Takahashi, Daisuke;Matsunaga, Eri;Yamashita, Tomohiro;Caaveiro, Jose M. M.;Abe, Yoshito;Ueda, Tadashi. And the article was included in Biochemical and Biophysical Research Communications in 2022.Safety of Sodium 2′,4′,5′,7′-tetraiodo-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-3′,6′-bis(olate) This article mentions the following:

AL amyloidosis is a life-threatening disease characterized by the deposition of amyloidogenic Ig light chain secreted from clonal plasma cells. Here we established an in-vitro screening system of amyloid inhibition of a variable domain in λ6 light chain mutant (Vλ6), Wil, and screened a food-additive compound library to identify compounds inhibiting the fibril formation. We found gossypetin and isoquercitrin as novel inhibitors. NMR anal. showed that both compounds directly interacted with natively-folded Wil, and proteolysis experiments demonstrated that these compounds conferred proteolytic resistance, suggesting that the compounds enhance the kinetic stability of Wil. Since gossypetin and isoquercitrin specifically interacted with the protein at micromolar concentrations, these compounds could be used as lead to further develop inhibitors against AL amyloidosis. 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: 16423-68-0Safety of 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 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 have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antioxidant, antitubercular, antiplasmodial, insecticidal.Safety of Sodium 2′,4′,5′,7′-tetraiodo-3-oxo-3H-spiro[isobenzofuran-1,9′-xanthene]-3′,6′-bis(olate)

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Enhancing the Thermal Stability of Solution-Processed Small-Molecule Semiconductor Thin Films Using a Flexible Linker Approach was written by Gasperini, Andrea;Jeanbourquin, Xavier A.;Rahmanudin, Aiman;Yu, Xiaoyun;Sivula, Kevin. And the article was included in Advanced Materials (Weinheim, Germany) in 2015.Recommanded Product: 128851-73-0 This article mentions the following:

The authors demonstrate a flexible-linker strategy for mol. organic semiconductors using a common small-mol. donor, 3,6-bis(5-(benzofuran-2-yl)thiophen-2-yl)-2,5-bis(2ethylhexyl)pyrrolo[3,4-c]pyrrole-1,4(2H,5H)-dione, coded as DPP(TBFu)₂. When the flexibly linked material is employed as an additive in thin films, a unique level of control is observed over the morphol. and the thermal stability of pure donor films in transistor devices and in blends with PC₆₁BM for BHJ photovoltaics. The synthesis of the flexibly linked DPP(TBFu)₂ derivative [coded FL-DPP(TBFu)₂] is shown schematically. The Stille-coupling polycondensation between the brominated diketopyrrolopyrrole core and the stannylated benzofuran dimer followed by standard purification and finally preparatory size exclusion chromatog. afforded the pure polymer with a number average mol. weight, M_n of 10 kDa and a PDI of 1.4 ( n = 11 – 15) in the hundred-milligram scale. In the experiment, the researchers used many compounds, for example, 6-Bromobenzofuran (cas: 128851-73-0Recommanded Product: 128851-73-0).

6-Bromobenzofuran (cas: 128851-73-0) 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.Recommanded Product: 128851-73-0

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

A computational study on active constituents of Habb-ul-aas and Tabasheer as inhibitors of SARS-CoV-2 main protease was written by Shamsi, Shariq;Anjum, Hina;Shahbaaz, Mohd;Khan, Mohd Shahnawaz;Ataya, Farid S.;Alamri, Alya;Alhumaydhi, Fahad A.;Husain, Fohad Mabood;Rehman, Tabish Md.;Mohammad, Taj;Islam, Asimul;Anjum, Farah;Shamsi, Anas. And the article was included in Journal of Biomolecular Structure and Dynamics in 2022.Computed Properties of C8H8O This article mentions the following:

A respiratory pandemic known as coronavirus disease-19 (COVID-19) has created havoc since it emerged from Wuhan, China. COVID-19 is caused by a newly emerged SARS coronavirus (SARS-CoV) with increased pathogenicity named severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2). Due to the lack of understanding of the mechanism of pathogenesis, an effective therapeutic option is unavailable. Epidemics described in Unani ancient literature include nazla-e-wabai and humma-e-wabai, and most of the symptoms of COVID-19 resemble nazla-e-wabai. Hence, in light of Unani literature, the treatment of COVID-19 can be managed with the composites prescribed in Unani medicine for nazla-e-wabai. In this study, a structure-based drug design approach was carried out to check the effectiveness of the pharmacol. active constituents of the Unani composites prescribed to treat nazla-e-wabai against SARS-CoV-2. We performed mol. docking of the active constituents of these composites against the main protease (M^pro), a potential drug target in SARS-CoV-2. Using detailed mol. docking anal., Habb-ul-aas and Tabasheer were identified as potential inhibitors of SARS-CoV-2 M^pro. The active constituents of both these composites bind to the substrate-binding pocket of SARS-CoV-2 M^pro, forming interactions with key residues of the binding pocket. Mol. dynamics (MD) simulation suggested the binding of active constituents of Habb-ul-aas with SARS-CoV-2 M^pro with a strong affinity as compared to the constituents of Tabasheer. Thus, this study sheds light on the use of these Unani composites in COVID-19 therapeutics. In the experiment, the researchers used many compounds, for example, 2,3-Dihydrobenzo[b]furan (cas: 496-16-2Computed Properties of C8H8O).

2,3-Dihydrobenzo[b]furan (cas: 496-16-2) 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. 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.Computed Properties of C8H8O

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Modifications of biological activity following the addition of a second nitrofuran ring to nitroarenofuran homocycles was written by Bilger, Christine;Demerseman, Pierre;Buisson, Jean Pierre;Royer, Rene;Gayral, Philippe;Fourniat, Jacky. And the article was included in European Journal of Medicinal Chemistry in 1987.Name: 2-Nitrobenzofuran This article mentions the following:

2,7-Dinitrobenzo[1,2-b:4,3-b‘]difuran (I) was prepared by the direct nitration of II and the derivatives nitrated in the α-positions of the heterocycles, naphtho[2,1-b:7,6-b‘]difuran, naphtho[2,1-b:6,5-b‘]difuran, naphtho[1,2-b:5,6-b‘]difuran and anthra[2,1-b:6,5-b‘]difuran were obtained by the condensation of bromonitromethane with the appropriate bis[ortho-hydroxy(formyl)]naphthalenes or -anthracene. The antibacterial and antiprotozoal activity of these compounds was compared with that of condensed systems containing a single furan ring (e.g., 2-nitrobenzofuran, 2-nitronaphtho[2,1-b]furan, etc.). Trichomonas vaginalis, Entamoeba histolytica, Staphylococcus aureus, And Escherichia coli were used as the test organisms. The dinitroarenodifurans were more active against the microorganisms than the nitroarenofurans. In the experiment, the researchers used many compounds, for example, 2-Nitrobenzofuran (cas: 33094-66-5Name: 2-Nitrobenzofuran).

2-Nitrobenzofuran (cas: 33094-66-5) 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.Name: 2-Nitrobenzofuran

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

High-throughput extracellular pH monitoring and antibiotics screening by polymeric fluorescent sensor with LCST property was written by Pan, Tingting;Yang, Cheng;Li, Jiaze;Jiang, Jiapei;Wen, Jiaxing;Wang, Zijin;Zhong, Ke;Tian, Yanqing;Chen, Meiwan. And the article was included in Methods (Amsterdam, Netherlands) in 2019.Name: 5-Amino-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one This article mentions the following:

Herein, we synthesized two polymers for pHe monitoring which are soluble in water at room temperature with easy operations and high reproducibility among various micro-plate wells for high-throughput anal. P1 (P(OEGMA-co-MEO₂MA-co-pHS)) and P2 (P(OEGMA-co-pHS)) were synthesized via the Reversible Addition Fragmentation Chain Transfer (RAFT) copolymerization of OEGMA, MEO₂MA and the pH sensitive fluorescence moiety N-fluoresceinyl methacrylamide (pHS). P1 is soluble in water at room temperature (25°C) while insoluble at the temperature above 33°C, indicating its feature of lower critical solution temperature (LCST) at 33°C. Further P1 showed higher pH sensitivity and photostability than P2 (without LCST property) when used at physiol. temperature (37°C). Thus, P1 was chosen to in-situ monitor the micro-environmental acidification of E. coli, Hela and Ramos cells during their growth, and the metabolism inhibiting activity of a representative antibiotic, ampicillin. Cell concentration-dependent cellular acidification and drug concentration-dependent inhibition of cellular acidification were observed, demonstrating that the LCST polymer (P1) is suitable for real-time cellular acidification monitoring as well as for high-throughput drug screening. This study firstly demonstrated the use of a LCST polymeric sensor for high-throughput screening of antibiotics and investigation of cell metabolism In the experiment, the researchers used many compounds, for example, 5-Amino-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 3326-34-9Name: 5-Amino-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one).

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

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

The magnitude and management of functional constipation at pediatric gastroenterology clinics: A survey study of various countries was written by Osatakul, Seksit;Benninga, Marc A.;Thapar, Nikhil;Treepongkaruna, Suporn;Puetpaiboon, Areeruk. And the article was included in Journal of Gastroenterology and Hepatology in 2022.COA of Formula: C18H26ClN3O3 This article mentions the following:

There have been no large-scale epidemiol. study of functional constipation of pediatric gastroenterol. services. This survey was undertaken to investigate the prevalence of functional constipation and magnitude of related problems in hospital settings of various countries as well as the practice of pediatric gastroenterologists in management of these conditions. The survey was conducted by sending questionnaires to members of Societies for Pediatric Gastroenterol. Hepatol. and Nutrition of various continents. A total of 274 pediatric gastroenterologists from 41 countries participated in this study. Functional constipation accounted for overall 30% of patients attending pediatric gastroenterol. outpatient clinics. In comparison with non-western countries, respondents from western countries reported significantly higher median annual numbers of new patients with intractable functional constipation (10 [4,25] vs 5 [2,10], P < 0.001), dyssynergic defecation (3 [0,15] vs 1 [0,4], P < 0.001), and colonic inertia (2 [0,5] vs 0 [0,1], P < 0.001). The use of high dose polyethylene glycol for fecal disimpaction was significantly more commonly among respondents from western countries, whereas rectal enema was significantly more favored in non-western countries. Respondents from different continents reported significant discrepancies in choices of investigations and management of patients with dyssynergic defecation and colonic inertia. Functional constipation is a major problem for pediatric gastroenterol. outpatient services worldwide. There were significant variations in the investigations of choice and therapeutic management of functional constipation, intractable functional constipation, and related problems among pediatric gastroenterologists of different geog. regions. 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. Many natural or synthetic compounds containing benzofuran skeletons have been found to possess remarkable activity as agrochemicals and pharmaceuticals. 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.COA of Formula: C18H26ClN3O3

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem