Heterocyclic Building Block-benzofuran

PLGA based particles as “drug reservoir” for antitumor drug delivery: characterization and cytotoxicity studies was written by Chronopoulou, Laura;Domenici, Fabio;Giantulli, Sabrina;Brasili, Francesco;D’Errico, Chiara;Tsaouli, Georgia;Tortorella, Elisabetta;Bordi, Federico;Morrone, Stefania;Palocci, Cleofe;Silvestri, Ida. And the article was included in Colloids and Surfaces, B: Biointerfaces in 2019.Name: 5-Amino-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one This article mentions the following:

Doxorubicin (DOX) is commonly used to treat several tumor types, but its severe side effects, primarily cardiotoxicity, represent a major limitation for its use in clin. settings. In this study we developed and characterized biodegradable and stable poly(D,L-lactic-co-glycolic) acid (PLGA) submicrocarriers employing an osmosis-based patented methodol., which allowed to optimize the drug loading efficiency up to 99%. Proceeding from this, we evaluated on MCF-7, a human breast cancer cell line, the ability of PLGA to promote the internalization of DOX and to improve its cytotoxicity in vitro. We found that the in vitro uptake efficiency is dramatically increased when DOX is loaded within PLGA colloidal carriers, which adhere to the cell membrane behaving as an efficient drug reservoir. In fact, the particles provide a diffusion-driven, sustained release of DOX across the cell membrane, resulting in high drug concentration Accordingly, the cytotoxic anal. clearly showed that DOX-loaded PLGA exhibit a lower 50% inhibitory concentration than free DOX. The decay time of cell viability was successfully compared with DOX diffusion time constant from PLGA. The overall in vitro results highlight the potential of DOX-loaded PLGA particles to be employed as vectors with improved antitumor efficacy. 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. 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.Name: 5-Amino-3′,6′-dihydroxy-3H-spiro[isobenzofuran-1,9′-xanthen]-3-one

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Discovery of Desmuramylpeptide NOD2 Agonists with Single-Digit Nanomolar Potency was written by Guzelj, Samo;Bizjak, Spela;Jakopin, Ziga. And the article was included in ACS Medicinal Chemistry Letters in 2022.HPLC of Formula: 10242-11-2 This article mentions the following:

The innate immune receptor nucleotide-binding oligomerization-domain-containing protein 2 (NOD2) represents an important target for the development of structurally defined small mol. immunomodulatory compounds that have great potential to be used either as vaccine adjuvants or as general immunostimulatory agents. We report here the investigation of the structure-activity relationship of a series of novel desmuramylpeptide NOD2 agonists. Extensive exploration of chem. space culminated in the discovery of a lipophilic adamantane-moiety-featuring compound 40, the first single-digit nanomolar and the most potent NOD2 agonist in its structural class to date. Moreover, 40 acted synergistically with lipopolysaccharide and interferon-γ to induce the production of cytokines in human peripheral blood mononuclear cells and enhance their nonspecific cytotoxic activity against K562 cancer cells. These findings provide initial insight into its immunostimulatory potential, especially when used in combination with other immunopotentiators. In the experiment, the researchers used many compounds, for example, 5-Bromobenzofuran-2-carboxylic acid (cas: 10242-11-2HPLC of Formula: 10242-11-2).

5-Bromobenzofuran-2-carboxylic acid (cas: 10242-11-2) 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.HPLC of Formula: 10242-11-2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

The inhibitory effect in Fraxinellone on oxidative stress-induced senescence correlates with AMP-activated protein kinase-dependent autophagy restoration was written by Han, Xiaojuan;Chen, Honghan;Zhou, Jiao;Tai, Haoran;Gong, Hui;Wang, Xiaobo;Huang, Ning;Qin, Jianqiong;Fang, Tingting;Wang, Fei;Xiao, Hengyi. And the article was included in Journal of Cellular Physiology in 2018.Application of 28808-62-0 This article mentions the following:

As a natural metabolite of limonoids from Dictamnus dasycarpus, fraxinellone has been reported to be neuroprotective and anti-inflammatory. However, its influence on cellular metabolism remains largely unknown. In the present study, we investigated the effect of fraxinellone on cellular senescence-induced by oxidative stress and the potential mechanism. We found that fraxinellone administration caused growth arrest and certainly repressed the activity of senescence associated β-galactosidase as well as the expression of senescence-associated-genes. Interestingly, this effect of fraxinellone is closely correlated with the restoration of impaired autophagy and the activation of AMPK. Notably, fraxinellone reacts in an AMPK-dependent but mTORC1-independent manner. Together, our study demonstrates for the first time that fraxinellone has the effect on senescence inhibition and AMPK activation, and supports the notion that autophagic mechanism is important for aging prevention. These findings expanded the list of natural compounds and will be potentially utilized for aging decay and/or AMPK activation. In the experiment, the researchers used many compounds, for example, (3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0Application of 28808-62-0).

(3R,3aR)-3-(Furan-3-yl)-3a,7-dimethyl-3a,4,5,6-tetrahydroisobenzofuran-1(3H)-one (cas: 28808-62-0) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. They are also prone to polymerisation in the presence of concentrated mineral acids and Lewis acids.Application of 28808-62-0

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Integrated bioinformatics analysis to decipher molecular mechanism of compound Kushen injection for esophageal cancer by combining WGCNA with network pharmacology was written by Zhou, Wei;Wu, Jiarui;Zhang, Jingyuan;Liu, Xinkui;Guo, Siyu;Jia, ShanShan;Zhang, Xiaomeng;Zhu, Yingli;Wang, Miaomiao. And the article was included in Scientific Reports in 2020.Quality Control of (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 This article mentions the following:

Compound Kushen injection (CKI), a medicine in widespread clin. use in China, has proven therapeutic effects on cancer. However, few mol. mechanism analyses have been carried out. To address this problem, bioinformatics approaches combining weighted gene co-expression network anal. with network pharmacol. methods were undertaken to elucidate the underlying mol. mechanisms of CKI in the treatment of esophageal cancer (ESCA). First, the key gene modules related to the clin. traits of ESCA were analyzed by WCGNA. Based on the results, the hub genes related to CKI treatment for ESCA were explored through network pharmacol. Mol. docking simulation was performed to recognize the binding activity of hub genes with CKI compounds The results showed that the potential hub targets, including EGFR, ErbB2, CCND1 and IGF1R, are therapeutic targets of CKI for the treatment of ESCA. Moreover, these targets were significantly enriched in many pathways related to cancer and signalling pathways, such as the PI3K-Akt signalling pathway and ErbB signalling pathway. In conclusion, this research partially highlighted the mol. mechanism of CKI in the treatment of ESCA, offering great potential in the identification of the effective compounds in CKI and biomarkers for ESCA treatment. 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: 6807-83-6Quality Control of (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).

(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. 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. 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.Quality Control of (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

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Preclinical Development of Pentamidine Analogs Identifies a Potent and Nontoxic Antibiotic Adjuvant was written by MacNair, Craig R.;Farha, Maya A.;Serrano-Wu, Michael H.;Lee, Katie K.;Hubbard, Brian;Cote, Jean-Philippe;Carfrae, Lindsey A.;Tu, Megan M.;Gaulin, Jeffrey L.;Hunt, Diana K.;Hung, Deborah T.;Brown, Eric D.. And the article was included in ACS Infectious Diseases in 2022.Safety of (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-25-(Acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)benzofuro[4,5-e]pyrido[1,2-a]benzimidazole-1,15(2H)-dione This article mentions the following:

The difficulty in treating Gram-neg. bacteria can largely be attributed to their highly impermeable outer membrane (OM), which serves as a barrier to many otherwise active antibiotics. This can be overcome with the use of perturbant mols., which disrupt OM integrity and sensitize Gram-neg. bacteria to many clin. available Gram-pos.-active antibiotics. Although many new perturbants have been identified in recent years, most of these mols. are impeded by toxicity due to the similarities between pathogen and host cell membranes. For example, our group recently reported the cryptic OM-perturbing activity of the antiprotozoal drug pentamidine. Its development as an antibiotic adjuvant is limited, however, by toxicity concerns. Herein, we took a medicinal chem. approach to develop novel analogs of pentamidine, aiming to improve its OM activity while reducing its off-target toxicity. We identified the compound P35 (I), which induces OM disruption and potentiates Gram-pos.-active antibiotics in Acinetobacter baumannii and Klebsiella pneumoniae. Relative to pentamidine, P35 has reduced mammalian cell cytotoxicity and hERG trafficking inhibition. Addnl., P35 outperforms pentamidine in a murine model of A. baumannii bacteremia. Together, this preclin. anal. supports P35 as a promising lead for further development as an OM perturbant. In the experiment, the researchers used many compounds, for example, (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-25-(Acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)benzofuro[4,5-e]pyrido[1,2-a]benzimidazole-1,15(2H)-dione (cas: 80621-81-4Safety of (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-25-(Acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)benzofuro[4,5-e]pyrido[1,2-a]benzimidazole-1,15(2H)-dione).

(2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-25-(Acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)benzofuro[4,5-e]pyrido[1,2-a]benzimidazole-1,15(2H)-dione (cas: 80621-81-4) 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.Safety of (2S,16Z,18E,20S,21S,22R,23R,24R,25S,26R,27S,28E)-25-(Acetyloxy)-5,6,21,23-tetrahydroxy-27-methoxy-2,4,11,16,20,22,24,26-octamethyl-2,7-(epoxypentadeca[1,11,13]trienimino)benzofuro[4,5-e]pyrido[1,2-a]benzimidazole-1,15(2H)-dione

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Combination of the quick, easy, cheap, effective, rugged, and safe (QuEChERS) method and dispersive liquid-liquid microextraction in the identification and determination of pesticides from various classes in food products by gas-liquid chromatography was written by Amelin, V. G.;Lavrukhin, D. K.;Tret’yakov, A. V.. And the article was included in Journal of Analytical Chemistry in 2013.Synthetic Route of C10H12O2 This article mentions the following:

A procedure for the identification (104 substances) and quant. determination (40 substances) of the active components of combined pesticides from different classes found in water, vegetables, fruits, and meats by GC with mass spectrometric and electron capture detection was developed. The pesticides were extracted from the vegetable, fruit, and meat samples with acetonitrile using the QuEChERS method. The extracts were preconcd. 50-60-fold and addnl. purified by dispersive liquid-liquid microextraction The pesticides were extracted from water by dispersive liquid-liquid microextraction with hexane (degree of concentration >100-fold). The limits of detection by the time-of-flight MS detector were 0.01-0.02 mg/kg in solid samples and 1-2 μg/L in aqueous solutions The limits of quantitation for pesticides were 1-2 mg/kg in solid samples and 0.05-0.1 μg/L in solutions The anal. time was 1-2 h, and the RSD of the results did not exceed 18%. In the experiment, the researchers used many compounds, for example, 2,2-Dimethyl-2,3-dihydrobenzofuran-7-ol (cas: 1563-38-8Synthetic Route of C10H12O2).

2,2-Dimethyl-2,3-dihydrobenzofuran-7-ol (cas: 1563-38-8) 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.Synthetic Route of C10H12O2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Multi-residue analysis of organic pollutants in hair and urine for matrices comparison was written by Hardy, Emilie M.;Duca, Radu C.;Salquebre, Guillaume;Appenzeller, Brice M. R.. And the article was included in Forensic Science International in 2015.Formula: C10H12O2 This article mentions the following:

Urine being currently the most classically used matrix for the assessment of human exposure to pesticides, a growing interest is yet observed in hair anal. for the detection of organic pollutants. The aim of the present work was to develop and to validate multi-residue anal. methods, as similar as possible, in order to determine pesticides and their metabolites in these two biol. matrixes despite their different nature. The list of parent compounds and their metabolites investigated here consisted of 56 compounds, including organochlorines, organophosphates, pyrethroids, carbamates, other pesticides and polychlorinated biphenyls (PCBs). Two different approaches were necessary for the anal. of non-polar compounds (mainly parents) on one hand and polar analytes (mainly metabolites) on the other hand. In the final procedure, extraction from hair was carried out with acetonitrile/water after sample decontamination and pulverization. Extract was split into two fractions, which were analyzed directly with solid phase microextraction (SPME) injection for non-polar compounds and after derivatization with liquid injection for polar compounds In urine, non-polar compounds were analyzed directly using SPME. Polar compounds were analyzed after acidic hydrolysis, liquid-liquid extraction with acetonitrile-cyclohexane-Et acetate, derivatization and liquid injection. Anal. was performed with gas chromatog. tandem mass spectrometry operating in neg. chem. ionization (GC-MS/MS-NCI) for all the compounds (non-polar and polar) in the two matrixes.In hair, limits of quantification (LOQ) ranged from 0.02 pg/mg for trifluralin to 5.5 pg/mg for diethylphosphate. In urine, LOQ ranged from 0.4 pg/mL for α-endosulfan to 4 ng/mL for dimethyldithiophosphate. The anal. of samples supplemented with standards and samples collected from an animal previously submitted to chronic exposure to pesticides confirmed that all the compounds were analyzable in both hair and urine. In addition, the levels of sensitivity reached with these methods were quite satisfactory with regard to previously published studies, and also considering the number of compounds investigated. In the experiment, the researchers used many compounds, for example, 2,2-Dimethyl-2,3-dihydrobenzofuran-7-ol (cas: 1563-38-8Formula: C10H12O2).

2,2-Dimethyl-2,3-dihydrobenzofuran-7-ol (cas: 1563-38-8) belongs to benzofurans derivatives. Benzofuran derivatives are one of the most important oxygen-containing heterocycles. 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: C10H12O2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Thermochromic polymer materials was written by Seeboth, Arno;Ruhmann, Ralf;Loetzsch, Detlef. And the article was included in PMSE Preprints in 2006.Formula: C26H29N3O2 This article mentions the following:

Polymers with chromogenic behavior changing their visible optical properties in response to an external stimulus have met growing interest in the last decade. According to the external stimulus which affects the optical properties, these materials are separated into different types. This work focuses on the development and characterization of thermochromic polymer materials. Thermochromic materials variegate their color, color intensity or transparency in response to temperature changes. The thermochromic behavior of (i) hydrogels endowed with indicator dyes and (ii) polyolefins with embedded leuco dye systems are presented. The change of transparency and color in prepared hydrogels result on phase transitions and a specific interaction between dye and the microenvironment of the polymer network resp. The investigation of thermochromic polyolefins include the concentration and temperature dependence of the UV-vis spectra as well as the determination of the surface tension g by contact angle measurements. In the experiment, the researchers used many compounds, for example, Crystal violet lactone (cas: 1552-42-7Formula: C26H29N3O2).

Crystal violet lactone (cas: 1552-42-7) belongs to benzofurans derivatives. Benzofuran is a core structural unit found in many naturally occurring compounds with multidirectional biological activities. 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.Formula: C26H29N3O2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem