Heterocyclic Building Block-benzofuran

Hydrophobicity parameters determined by reversed-phase liquid chromatography. VIII. Hydrogen-bond effects of ester and amide groups in heteroaromatic compounds on the relationship between the capacity factor and the octanol-water partition coefficient was written by Yamagami, Chisako;Yokota, Miho;Takao, Narao. And the article was included in Journal of Chromatography A in 1994.Category: benzofurans This article mentions the following:

The logarithms of the capacity factors, log k’, for several heteroaromatic systems (furan, pyrrole, benzofuran, indole, benzene and their alkyl, ester and amide derivatives) were determined on a Capcell Pak C₁₈ column using methanol-buffer (pH 7.4) mobile phases of different compositions These results and the log k_w values, derived by a linear extrapolation of the plot of log k’ against the volume fraction of methanol to 0% methanol, were correlated with exptl. log P values by taking into account the hydrogen-acceptor and hydrogen-donor effects. Whereas the hydrogen-donor effect is minimized by using the log k_w parameter, the hydrogen-acceptor effect was found to become insignificant in an eluent containing 50% methanol. Isocratic data determined at this eluent composition gave the simplest and best correlation. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1Category: benzofurans).

Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives. Many natural or synthetic compounds containing benzofuran skeletons have been found to possess remarkable activity as agrochemicals and pharmaceuticals. 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

Biologically Active Heterocyclic Hybrids Based on Quinazolinone, Benzofuran and Imidazolium Moieties: Synthesis, Characterization, Cytotoxic and Antibacterial Evaluation was written by Asadi, Parvin;Khodarahmi, Ghadamali;Jahanian-Najafabadi, Ali;Saghaie, Lotfollah;Hassanzadeh, Farshid. And the article was included in Chemistry & Biodiversity in 2017.SDS of cas: 38220-75-6 This article mentions the following:

Cytotoxic and antimicrobial agents structurally based on quinazolinone, benzofuran and imidazole pharmacophores, have been designed and synthesized. Spectral (IR, ¹H-NMR) and elemental anal. data established the structures of these novel 3-[1-(1-benzofuran-2-yl)-2-(4-oxoquinazolin-3(4H)-yl)ethyl]-1-methyl-1H-imidazol-3-ium chloride hybrid derivatives All the synthesized compounds were evaluated for in vitro cytotoxicity and antimicrobial activities. Cytotoxic evaluation using MTT assay revealed that compounds 12c, 12g and 12i exhibited significant cytotoxicity with IC₅₀ values 1, 1, and 0.57 μM on this cell line, resp. Biol. activity of the synthesized compounds as antibacterial agent were also evaluated against three Gram-neg. (Escherichia coli, Pseudomonas aeruginosa and Salmonella typhi), three Gram-pos. (Staphylococcus aureus, Bacillus subtilis and Listeria monocitogenes) and one yeast-like fungi (Candida albicans) strains. All compounds 12a – 12i showed slightly higher activity against Gram-pos. bacteria than the Gram-neg. one. Among the nine new compounds screened, 3-[1-(5-bromo-1-benzofuran-2-yl)-2-(6-chloro-4-oxoquinazolin-3(4H)-yl)ethyl]-1-methyl-1H-imidazol-3-ium chloride (12e) has pronounced higher antimicrobial activity against all tested strains. These results demonstrated potential importance of mol. hybridization in the development of new lead mols. with major cytotoxicity and antimicrobial activity. In the experiment, the researchers used many compounds, for example, 1-(5-Bromobenzofuran-2-yl)ethanone (cas: 38220-75-6SDS of cas: 38220-75-6).

1-(5-Bromobenzofuran-2-yl)ethanone (cas: 38220-75-6) belongs to benzofurans derivatives. Benzofuran derivatives are one of the most important oxygen-containing heterocycles. Substituted benzofurans find applications such as fluorescent sensors, oxidants, in drug discovery, and in another field of chemistry and agriculture.SDS of cas: 38220-75-6

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

2-Mercapto-4,6-disubstituted nicotinonitriles: versatile precursors for novel mono- and bis[thienopyridines] was written by Salem, Mostafa E.;Darweesh, Ahmed F.;Elwahy, Ahmed H. M.. And the article was included in Journal of Sulfur Chemistry in 2018.Formula: C10H7BrO2 This article mentions the following:

A series of novel thieno[2,3-b]pyridines were prepared from the reaction of the appropriate bromoacetylbenzofurans or bromoacetylbenzothiazole with the corresponding pyridinethione derivatives in ethanolic sodium ethoxide at reflux. New bis(thieno[2,3-b]pyridine) derivatives were synthesized by the reaction of the appropriate bis-bromoacetyl derivatives with the corresponding pyridinethiones in the presence of sodium ethoxide. Attempts to synthesize the target bis(thieno[2,3-b]pyridine) derivatives by bis-alkylation of the corresponding (thieno[2,3-b]pyridin-2-yl)(hydroxyphenyl)methanone with the appropriate dihaloalkanes using a mild base were unsuccessful. 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. 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.Formula: C10H7BrO2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Microwave assisted synthesis and pharmacological evaluation of some potent naphthofuryl- and benzofurylthiazole, -oxazole, -thiadiazine and -oxadiazine derivatives was written by Kumar, D. B. Aruna;Prakash, G. K.;Nandeshwarappa, B. P.;Kiran, B. M.;Sherigara, B. S.;Mahadevan, K. M.. And the article was included in Indian Journal of Pharmaceutical Sciences in 2006.Synthetic Route of C10H7BrO2 This article mentions the following:

Bromination of substituted 2-acetylbenzofurans gave substituted 2-(2-bromoacetyl)benzofurans. 2-(2-Bromoacetyl)benzofurans reacted with thiourea, urea, thiosemicarbazide and semicarbazide in presence of sodium acetate under microwave irradiation to give heterocyclyl benzo- and naphthofuran derivs, e.g., I and II. The structures of synthesized compounds have been established by elemental anal., spectral data. All the synthesized compounds were screened for antimicrobial, anthelmintic, antiinflammatory and analgesic activities. 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. 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.Synthetic Route of C10H7BrO2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Protective effects of kefir against zearalenone toxicity mediated by oxidative stress in cultured HCT-116 cells was written by El Golli-Bennour, Emna;Timoumi, Rim;Koroit, Meriam;Bacha, Hassen;Abid-Essefi, Salwa. And the article was included in Toxicon in 2019.COA of Formula: C20H10Cl2O5 This article mentions the following:

Kefir is a fermented milk with numerous health favors counting restorative properties of bacterial flora, reduction of the symptoms of lactose intolerance, immune system stimulation, cholesterol reduction, as well as anti-mutagenic and anti-tumor properties. Zearalenone (ZEN) is a mycotoxin produced by some Fusarium species. ZEN often occurs as a contaminant in cereal grains and animal feeds. Human exposure occurs by ingestion of mycotoxin-contaminated products and can cause serious health problems. This study aimed to assess the preventive effect of kefir against ZEN toxicity in cultured HCT-116 colorectal carcinoma cells; by the evaluation of cell viability, oxidative stress status and the initiation of apoptotic cell death pathway. Our results demonstrated that ZEN inhibits cell proliferation which was accompanied by an increase in the generation of free radicals as measured by fluorescent 2,7-dichlorofluorescein (DCF) and Malondialdehyde (MDA). As an adaptive response to this redox status, we showed an induction of heat shock protein expression (Hsp 70) and an activation of antioxidant enzymes; catalase and Superoxide Dismutase (SOD). Moreover, a loss of mitochondrial membrane potential (Δψm) was observed The co-treatment as well as the pre-treatment by kefir showed a reduction of ZEN induced damages for all tested markers. However, the pre-treatment seems to be the most efficient, it prevented almost all ZEN hazards. Consequently, oxidative damage appears to be a key determinant of ZEN induced toxicity in cultured HCT-116 cells. In conclusion, we showed that kefir may better exert its virtue on preventive mode rather than on curative one. By this way, kefir as a beverage with highly antioxidant properties could be relevant particularly with the emergent demand for natural products which may counteract the detrimental effects of oxidative stress and therefore prevent multiple human diseases. 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: 76-54-0COA of Formula: C20H10Cl2O5).

2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one (cas: 76-54-0) belongs to benzofurans derivatives. Benzofurans are only weakly aromatic in nature and they are cleaved by many oxidative and reductive conditions. 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: C20H10Cl2O5

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Hydrophobicity parameters determined by reversed-phase liquid chromatography. V. Relationship between the capacity factor and the octanol-water partition coefficient for simple heteroaromatic compounds and their ester derivatives was written by Yamagami, Chisako;Takao, Narao. And the article was included in Chemical & Pharmaceutical Bulletin in 1992.COA of Formula: C10H8O3 This article mentions the following:

The log k‘ (k‘: capacity factor) values of various heteroaromatic compounds were measured by reversed-phase high-performance liquid chromatog. (RPLC) using a Capcell pack C₁₈ column and methanol-water eluents, and the relation with log P values (P: 1-octanol-water partition coefficient) was examined as a function of the mobile phase composition Furans having nonhydrogen-bonding or weakly hydrogen-accepting substituents exhibited a good linear relation at 50% MeOH concentration Amphiprotic substituents, CONHR, showed an acceleration effect (less retained than nonhydrogen-bonders and hydrogen-acceptors under the condition of equivalent log P), as is often observed in heterocyclic systems. The relation was more complicated at other methanol contents, due to different retention behavior demonstrated by the ester-type substituents, CO₂R and CONR₂ (ester effect). To gain more insight into this ester effect, the retention behavior of ester derivatives of various heteroaromatics such as furan, benzofuran, N-methylpyrrole and indole was also studied. The factors affecting the log P-log k‘ relation were discussed, and the optimum RPLC condition for predicting the log P value was described. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1COA of Formula: C10H8O3).

Methyl benzofuran-2-carboxylate (cas: 1646-27-1) 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. 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.COA of Formula: C10H8O3

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Study on synthesis and photochemical behavior of carbamate photobase generators for fluorescence imaging was written by Liu, Lanlan;Guo, Jinbao;Wei, Jie. And the article was included in Journal of Applied Polymer Science in 2014.Electric Literature of C17H10O4 This article mentions the following:

A fluorescence imaging system is designed based on the photodecomposition of photobase generators embedded in polyvinyl butyral (PVB) matrix. These photobase generators were synthesized with Pr and phenethyl units served as leaving groups, and phthalimido, succinimido, di-2-thienyl ketoximino, and benzophenoneoximino units acted as photosensitive species, resp. The influences of the two leaving groups and four photosensitive species on the photochem. behavior were investigated in detail. The results demonstrate that the photochem. properties of these photobase generators depend on the photosensitive species other than the leaving groups. And further study shows that succinimido propylcarbamate (SPrC) exhibits the best thermal stability and relatively quick rate of photodecomposition among all the photobase generators. Therefore, a PVB film embedded with SPrC is used as a fluorescence imaging material. The patterned fluorescence image obtained from the fluorescamine-treated irradiated PVB film showed bright green fluorescence, which provides potential application for optical storage or color electronic displays. © 2014 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2014, 131, 41058. In the experiment, the researchers used many compounds, for example, 4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9Electric Literature of C17H10O4).

4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antiviral, antimicrobial, antitumor, anti-inflammatory.Electric Literature of C17H10O4

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Exposure to TiO2 nanoparticles increases Listeria monocytogenes infection of intestinal epithelial cells was written by Ammendolia, Maria Grazia;De Berardis, Barbara;Maurizi, Linda;Longhi, Catia. And the article was included in Nanomaterials in 2020.Name: 2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one This article mentions the following:

Titanium dioxide nanoparticles (TiO2 NPs) are widely used in a variety of consumer products. Cellular exposure to TiO2 NPs results in complex effects on cell physiol. that could impact biol. systems. We investigated the behavior of Listeria monocytogenes in intestinal epithelial cells pre-treated with either a low or high (1 and 20μg/cm2) dose of TiO2 NPs. Our results indicate that the pre-treated cells with a low dose became more permissive to listeria infection; indeed, both adhesion and invasion were significantly increased compared to control. Increased invasion seems to be correlated to cytoskeletal alterations induced by nanoparticles, and higher bacterial survival might be due to the high levels of listeriolysin O that protects L. monocytogenes from reactive oxygen species (ROS). The potential risk of increased susceptibility to L. monocytogenes infection related to long-term intake of nanosized TiO2 at low doses should be considered. 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 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.Name: 2′,7′-Dichloro-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Multispectroscopic and synergistic antioxidant study on the combined binding of caffeic acid and (-)-epicatechin gallate to lysozyme was written by Liu, He;Wang, Danfeng;Ren, Yongfang;Wang, Lu;Weng, Tianxin;Liu, Jie;Wu, Yushu;Ding, Zhuang;Liu, Min. And the article was included in Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy in 2022.Product Details of 76-54-0 This article mentions the following:

The binding of caffeic acid (CA) and/or (-)-epicatechin gallate (ECG) to lysozyme was investigated by multispectroscopic methods and mol. docking. The effects of the single and combined binding on the structure, activity and stability of lysozyme and the synergistic antioxidant activity of CA and ECG were also studied. Fluorescence quenching spectra, time-resolved fluorescence spectra, and UV-vis absorption difference spectra all ascertained the static quenching mechanism of lysozyme by CA/ECG. Thermodn. parameters indicated that CA and ECG competitively bound to lysozyme, and CA had a stronger binding affinity, which was consistent with the results of mol. docking. Hydrogen bonding, van der Waals’ force and electrostatic interaction were the main driving forces for the binding process. Synchronous fluorescence spectra displayed that the interaction of CA/ECG exposed the tryptophan residues of lysozyme to a more hydrophilic environment. CD spectroscopy, Fourier transform IR spectroscopy and dynamic light scattering indicated that the binding of CA and/or ECG to lysozyme resulted in the change of the secondary structure and increased the particle size of lysozyme. The binding of CA and/or ECG to lysozyme inhibited the enzyme activity and enhanced the thermal stability of lysozyme. The combined application of CA and ECG showed antioxidant synergy which was influenced by the encapsulation of lysozyme and cellular uptake. In summary, this work provides theor. guidance for lysozyme as a carrier for the combined application of CA and ECG. 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: 76-54-0Product Details of 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. 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 antioxidant, antitubercular, antiplasmodial, insecticidal.Product Details of 76-54-0

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Determination of histamine by a rapid fluorescamine-UPLC method was written by Murakami, Yuuki;Nakai, Natsuki;Ando, Naoko;Okayama, Akiko. And the article was included in Shokuhin Eiseigaku Zasshi in 2018.Application of 38183-12-9 This article mentions the following:

The author has developed a rapid anal. method for determination of histamine using ultra-performance liquid chromatog. and fluorescamine derivatization. Histamine was extracted from foods with trichloroacetic acid after homogenization. The supernatant obtained by centrifugation was filtered and derivatized without solid-phase extraction The mobile phase was 10 mM phosphate-acetonitrile (75 : 25) without ion-pairing. Recovery tests of histamine from fishes, seasoning and fish products gave acceptable recovery (95.8-117.7%). This method should be useful for rapid evaluation of food poisoning outbreaks. In the experiment, the researchers used many compounds, for example, 4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9Application of 38183-12-9).

4-Phenyl-3H,3’H-spiro[furan-2,1′-isobenzofuran]-3,3′-dione (cas: 38183-12-9) 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. 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 of 38183-12-9

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem