Category: tetrahydropyran

Song, Yulong published the artcilePalladium-Catalyzed Triple Cyclization of 2,7-Alkadiynylic Carbonates with 2-Butyne-1,4-diol or 2-Butyne-1,4-disulfonamides, COA of Formula: C10H16O2, the publication is Advanced Synthesis & Catalysis (2019), 361(13), 3228-3233, database is CAplus.

A palladium-catalyzed highly E-selective triple cyclization of 2,7-alkadiynylic carbonates with 2-butyne-1,4-diol or 2-butyne-1,4-disulfonamides to construct different tricycles such as 6,8-dihydrobenzo[1,2-c:3,4-c’]difuran-1(3H)-one and 1,3,6,7-tetrahydro-8H-furo[3,4-e]isoindol-8-one derivatives were reported. The alkene group produced and the nucleophilic unit kept in the product provided further opportunity to construct more complicated polycycles. The control experiments showed that the reaction mainly go through an intermol. insertion of the alkynes before the lactonization or lactamization.

Advanced Synthesis & Catalysis published new progress about 27943-46-0. 27943-46-0 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Alkynyl,Ether, name is 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, and the molecular formula is Al2H32O28S3, COA of Formula: C10H16O2.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Yu, Zhenyuan published the artcileSystematic analysis of the mechanism of aged citrus peel (Chenpi) in oral squamous cell carcinoma treatment via network pharmacology, molecular docking and experimental validation, COA of Formula: C16H14O6, the publication is Journal of Functional Foods (2022), 105012, database is CAplus.

Oral squamous cell carcinoma (OSCC) is a malignant cancer and lacks ideal drugs. Aged citrus peel (Chenpi, CP) is an easily available traditional Chinese medicine (TCM) with potential anticancer effects. Network pharmacol. were used to investigate the potential mechanisms of CP in OSCC. Tangeretin was the most crucial active ingredient in CP, as shown by the establishment of the component-target-disease network (C-T-D). Protein-protein interaction (PPI) anal. and survival anal. showed that PIK3R1, ESR1, and CDK1 are core genes. Pathway enrichment anal. showed that PI3K-AKT is the top essential pathways. Mol. docking was used to predict the binding of targets and compounds In vitro experiments showed that tangeretin inhibits cell proliferation, blocks the cell cycle in S phase, induces apoptosis, regulates core gene expression in SCC25 cells, and has lower toxicity to HOK cells. In conclusion, our study lays the foundation for the use of CP in the treatment of OSCC.

Journal of Functional Foods published new progress about 69097-99-0. 69097-99-0 belongs to tetrahydropyran, auxiliary class Other Aliphatic Heterocyclic,Benzene,Phenol,Ether,Inhibitor, name is 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, and the molecular formula is C9H5ClO4S, COA of Formula: C16H14O6.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Lindholst, C. published the artcileMetabolism of bisphenol A in zebrafish (Danio rerio) and rainbow trout (Oncorhynchus mykiss) in relation to estrogenic response, Related Products of tetrahydropyran, the publication is Comparative Biochemistry and Physiology, Part C: Toxicology & Pharmacology (2003), 135C(2), 169-177, database is CAplus and MEDLINE.

The kinetics of bisphenol A (BPA) were investigated in zebrafish (Danio rerio) exposed to 100 μg BPA/l. BPA uptake was measured during a 7-day period followed by an elimination phase of similar duration. After 2, 6, 12, 24, 48, 72, 120 and 168 h of uptake/elimination, fish were analyzed for their content of BPA, bisphenol A glucuronic acid (BPAGA) and bisphenol A sulfate (BPAS). Within the first 24 h steady state levels of BPA, BPAGA and BPAS were reached and the total body concentrations were calculated to be 569, 12,600 and 39.9 ng/g fish, resp. Elimination rates of the three compounds in zebrafish were estimated by fitting the data to a compartment model. An initial rapid elimination phase was observed for BPA and BPAS with total body half lives (T_1/2) of <1.1 h and 30 min, followed by a slower second elimination phase with T_1/2 values of 139 and 71 h, resp. Excretion of BPAGA occurred from a single compartment with a T_1/2 of 35 h. The steady state concentration of BPA and its metabolites were investigated in rainbow trout (Oncorhynchus mykiss) exposed to 100 μg BPA/l. The toxicokinetic parameters from zebrafish and rainbow trout were compared; including previously published data on the rainbow trout. The data indicate that the smaller estrogenic sensitivity observed for the zebrafish may be caused by a more rapid metabolism of BPA in the zebrafish liver.

Comparative Biochemistry and Physiology, Part C: Toxicology & Pharmacology published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Related Products of tetrahydropyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Chen, Minjian published the artcileBisphenol A alters n-6 fatty acid composition and decreases antioxidant enzyme levels in rat testes: A LC-QTOF-based metabolomics study, Synthetic Route of 267244-08-6, the publication is PLoS One (2012), 7(9), e44754, database is CAplus and MEDLINE.

Background: Male reproductive toxicity induced by exposure to bisphenol A (BPA) has been widely reported. The testes have proven to be a major target organ of BPA toxicity, so studying testicular metabolite variation holds promise for the discovery of mechanisms linked to the toxic effects of BPA on reproduction Methodol./Principal Findings: Male Sprague-Dawley rats were orally administered doses of BPA at the levels of 0, 50 mg/kg/d for 8 wk. We used an unbiased liquid chromatog.-quadrupole time-of-flight (LC-QTOF)-based metabolomics approach to discover, identify and analyze the variation of testicular metabolites. Two n-6 fatty acids, linoleic acid (LA) and arachidonic acid (AA) were identified as potential testicular biomarkers. Decreased levels of LA and increased levels of AA as well as AA/LA ratio were observed in the testes of the exposed group. According to these suggestions, testicular antioxidant enzyme levels were detected. Testicular superoxide dismutase (SOD) declined significantly in the exposed group compared with that in the non-exposed group and the glutathione peroxidase (GSH-Px) as well as catalase (CAT) also showed a decreasing trend in BPA treated group. Conclusions/Significance: BPA caused testicular n-6 fatty acid composition variation and decreased antioxidant enzyme levels. This study emphasizes that metabolomics brings the promise of biomarkers identification for the discovery of mechanisms underlying reproductive toxicity.

PLoS One published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Synthetic Route of 267244-08-6.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Li, Huan-Qiu published the artcileMetronidazole-flavonoid derivatives as anti-Helicobacter pylori agents with potent inhibitory activity against HPE-induced interleukin-8 production by AGS cells, Application of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is ChemMedChem (2007), 2(9), 1361-1369, database is CAplus and MEDLINE.

Three series of metronidazole-flavonoid derivatives were generated and evaluated for antimicrobial activity against H. pylori. Among these compounds, high anti-H. pylori activities were observed in isoflavones derivatives 4-7, 19, and 20 but exhibited no inhibitory activity against other sorts of bacteria and fungi, for example, Streptococcus pneumoniae, Bacillus subtilis, Escherichia coli, Pseudomonas fluorescence, and Aspergillus niger. Genistein derivative 6 with the potent activity (MIC = 0.39 μg mL^-1) was > 50-fold more than metronidazole, and comparable to the pos. control amoxicillin. Addnl., compound 6 can significantly attenuate the increase in interleukin-8 (IL-8) levels in the AGS cells stimulated by H. pylori water extract (HPE) at concentrations of 15, 30, and 60 μmolL^-1, which did not show any effects on the cell viability.

ChemMedChem published new progress about 69097-99-0. 69097-99-0 belongs to tetrahydropyran, auxiliary class Other Aliphatic Heterocyclic,Benzene,Phenol,Ether,Inhibitor, name is 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, and the molecular formula is C16H14O6, Application of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Xue, Yan published the artcileExploring mechanism of therapeutic effect of Qingfei Huatan Decoction on chronic obstructive pulmonary disease based on network pharmacology, Recommanded Product: 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is Shijie Zhongyiyao (2021), 16(4), 558-565, database is CAplus.

Objective: To explore the potential active components and underlying mol. mechanisms of Qingfei Huatan Decoction to improve the hypersecretion of airway mucus in acute exacerbation of chronic obstructive pulmonary disease (AECOPD) through the network pharmacol. and mol. docking technol. Methods: First, the active components and potential targets of Qingfei Huatan Decoction were collected through the traditional Chinese medicine system pharmacol. anal. platform (TCMSP), and the targets related to airway mucus hypersecretion in AECOPD were screened by GeneCards database. Then, the disease target and the drug prediction target were intersected. The intersection target network and protein interaction network were constructed with the help of Cytoscape 3.7.2 software. The GO and KEGG enrichment anal. were performed by DAVID. Finally, the active ingredient of the drug was molecularly docked with the disease target. Results: A total of 54 effective active ingredients of Qingfei Huatan Decoction were obtained, which could act on AECOPD airway mucus hypersecretion through 67 potential targets, involving TNF signaling pathway, IL-17, epidermal growth factor receptor tyrosine kinase inhibitors resistance, PI3K-Akt, HIF-1, MAPK and other related signaling pathways. Mol. docking results showed that quercetin, luteolin, beta-sitosterol and other pharmaceutical active ingredients could bind to AKT1, IL6, EGF and other target proteins stably. Conclusion: The mol. docking technique reveals that Qingfei Huatan Decoction can directly improve the airway mucus hypersecretion of AECOPD and achieve therapeutic effects. Through the network pharmacol., the potential mechanism of its multi-target and multi-pathway is initially revealed, which provides ideas for further research.

Shijie Zhongyiyao published new progress about 69097-99-0. 69097-99-0 belongs to tetrahydropyran, auxiliary class Other Aliphatic Heterocyclic,Benzene,Phenol,Ether,Inhibitor, name is 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, and the molecular formula is C7H8O3, Recommanded Product: 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Shakil, N. A. published the artcileMicrowave accelerated solvent-free synthesis and antifungal evaluations of flavanones, COA of Formula: C16H14O6, the publication is Archives of Phytopathology and Plant Protection (2011), 44(20), 1958-1965, database is CAplus.

Microwave irradiation of 2-hydroxy chalcones under solvent-free conditions resulted in a “green-chem.” procedure for the preparation of flavanones in good yields, using an unmodified household microwave oven and silica as solid support. By irradiation of 2-hydroxy chalcones with trifluoroacetic acid over silica gel, 11 known flavanones were prepared in high yields. The synthesized compounds were characterized using spectroscopic techniques, namely, ¹H NMR, ¹³C NMR and IR, and screened for their antifungal activity in vitro against Sclerotium rolfsii and Rhizoctonia solani by poisoned food technique. The compounds tested were found to be more active against R. solani, whereas against S. rolfsii, moderate activity was observed, as evident from LC₅₀ values. The most potent compound 2-(4-fluorophenyl)-2,3-dihydrochromen-4-one (4a) had LC₅₀ value of 12.0 mg L^-1 followed by 11, 11a, 3a, 9a, 8a, 10a and 10 having LC₅₀ values 18.21, 18.3, 32.9, 50.7, 88.8, 118.8 and 119.7 mg L^-1, resp.

Archives of Phytopathology and Plant Protection published new progress about 69097-99-0. 69097-99-0 belongs to tetrahydropyran, auxiliary class Other Aliphatic Heterocyclic,Benzene,Phenol,Ether,Inhibitor, name is 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, and the molecular formula is C10H10O3, COA of Formula: C16H14O6.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Sturm, Sabina published the artcileDetermination of free and total bisphenol A in the urine and feces of orally and subcutaneously dosed sheep by high-performance liquid chromatography with fluorescence detection, Safety of (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, the publication is Journal of Environmental Science and Health, Part B: Pesticides, Food Contaminants, and Agricultural Wastes (2020), 55(7), 655-668, database is CAplus and MEDLINE.

An anal. procedure has been introduced to enable a study of the excretion of free bisphenol A (BPA), total BPA and its main metabolite bisphenol A glucuronide (BPA-GLUC). In the experiment, in which 100μg/kg b. w. BPA was administered daily to one Istrian Pramenka sheep for 5 days with consecutive urine and feces samples being taken, BPA and total BPA were determined in samples using high-performance liquid chromatog. (HPLC) with fluorescence detection. Because of their good recovery, precision, and sensitivity, the methods have also proved applicable to further ecotoxicol. studies of free BPA, BPA-GLUC and total BPA. The results were subsequently compared with reported field studies of BPA in livestock excreta.

Journal of Environmental Science and Health, Part B: Pesticides, Food Contaminants, and Agricultural Wastes published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C48H47FeP, Safety of (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Jasinska, Anna published the artcileBisphenol A Removal by the Fungus Myrothecium roridum IM 6482-Analysis of the Cellular and Subcellular Level, Name: (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, the publication is International Journal of Molecular Sciences (2021), 22(19), 10676, database is CAplus and MEDLINE.

Bisphenol (BPA) is a key ingredient in the production of epoxy resins and some types of plastics, which can be released into the environment and alter the endocrine systems of wildlife and humans. In this study, the ability of the fungus M. roridum IM 6482 to BPA elimination was investigated. LC-MS/MS anal. showed almost complete removal of BPA from the growth medium within 72 h of culturing. Products of BPA biotransformation were identified, and their estrogenic activity was found to be lower than that of the parent compound Extracellular laccase activity was identified as the main mechanism of BPA elimination. It was observed that BPA induced oxidative stress in fungal cells manifested as the enhancement in ROS production, membranes permeability and lipids peroxidation These oxidative stress markers were reduced after BPA biodegradation (72 h of culturing). Intracellular proteome analyses performed using 2-D electrophoresis and MALDI-TOF/TOF technique allowed identifying 69 proteins in a sample obtained from the BPA containing culture. There were mainly structural and regulator proteins but also oxidoreductive and antioxidative agents, such as superoxide dismutase and catalase. The obtained results broaden the knowledge on BPA elimination by microscopic fungi and may contribute to the development of BPA biodegradation methods.

International Journal of Molecular Sciences published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C21H24O8, Name: (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics

Zalko, Daniel published the artcileBiotransformations of bisphenol A in a mammalian model: answers and new questions raised by low-dose metabolic fate studies in pregnant CD1 mice, Category: tetrahydropyran, the publication is Environmental Health Perspectives (2003), 111(3), 309-319, database is CAplus and MEDLINE.

The authors investigated the metabolic fate of a low dose (25 μg/kg) of bisphenol A [2,2-bis(4-hydroxyphenyl)propane] (BPA) injected s.c. in CD1 pregnant mice using a tritium-labeled mol. Analytic methods were developed to allow a radio-chromatog. profiling of BPA residues in excreta and tissues, as well as in mothers’ reproductive tracts and fetuses, that contained more than 4% of the administered radioactivity. BPA was extensively metabolized by CD1 mice. Identified metabolite structures included the glucuronic acid conjugate of BPA, several double conjugates, and conjugated methoxylated compounds, demonstrating the formation of potentially reactive intermediates. Fetal radioactivity was associated with unchanged BPA, BPA glucuronide, and a disaccharide conjugate. The latter structure, as well as that of a dehydrated glucuronide conjugate of BPA (a major metabolite isolated from the digestive tract), showed that BPA metabolic routes were far more complex than previously thought. The estrogenicity of the metabolites that were identified but not tested for hormonal activity cannot be ruled out; however, in general, conjugated BPA metabolites have significantly lower potency than that of the parent compound Thus, these data suggest the parental compound is responsible for the estrogenic effects observed in fetuses exposed to BPA during gestation in this mammalian model.

Environmental Health Perspectives published new progress about 267244-08-6. 267244-08-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Chiral,Carboxylic acid,Benzene,Phenol,Alcohol,Ether,, name is (2S,3S,4S,5R,6S)-3,4,5-Trihydroxy-6-(4-(2-(4-hydroxyphenyl)propan-2-yl)phenoxy)tetrahydro-2H-pyran-2-carboxylic acid, and the molecular formula is C12H13NO3, Category: tetrahydropyran.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydropyran,
Tetrahydropyran – an overview | ScienceDirect Topics