Category: tetrahydropyran

Cho, Seung Hee published the artcileUrinary bisphenol A versus serum bisphenol A concentration and ovarian reproductive outcomes among IVF patients: Which is a better biomarker of BPA exposure?, Synthetic Route of 267244-08-6, the publication is Molecular & Cellular Toxicology (2017), 13(4), 351-359, database is CAplus.

A review. Bisphenol A (BPA) is an endocrine-disrupting compound (EDC) that is used widely in com. products in the production of polycarbonate plastics for baby and water bottles, epoxy resins for lacquer lining of food and beverage cans and water pipes, dental sealants, dental composites and thermal receipts paper. There is inhibitory effect of BPA on nuclear estrogen (E2) production in granulosa cells of developing follicles that disrupt normal development to the antral follicles via suppression of E2 in granulosa cells of developing follicles during the menstrual cycle followed by reduction in the number of oocytes retrieved in in-vitro fertilization (IVF) patients. Several studies corroborate an inverse association between serum and/or urinary BPA concentration and the IVF outcome: Peak E2 levels and the number of oocytes retrieved. Upon oral ingestion, 99.5% of unconjugated parent BPA (free BPA) is metabolized to either BPA glucuronide (BPA-G) or BPA sulfate (BPA-S). The unconjugated BPA can bind to the estrogen receptors (ER) while conjugated BPA (biol. inactive BPA) do not bind the estrogen receptor (ER). The challenge is to assess the relationship between BPA exposure among infertile patients with respect to follicular response and health during IVF. The establishment of temporal sequence between BPA exposure and infertility would be the research question to answer: Which route is a better biomarker. The advantages of urine BPA collection would provide pragmatic advantages for clinicians in order to practice cost-effective medicine. However, unconjugated BPA measurement (compared to total BPA) introduces challenges in measurement accuracy since unconjugated BPA requires higher magnitude of limit of detection (LOD) with higher risk of contamination from the medical equipment. The difference in route of BPA assessment could introduce bias in the interpretation of results in terms of the association between BPA levels and the number of oocytes. Fujimoto et al. and Bloom et al. analyzed the relationship between serum BPA and IVF outcome in infertile women. It may sound hypothetically justified due to utilizing serum unconjugated BPA, this strategy is not successful in choosing a practical biomarker of BPA exposure due to toxicokinetic properties of BPA metabolism and excretion in humans.

Molecular & Cellular Toxicology 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

Zhen, Jing published the artcileSynthesis of novel flavonoid alkaloids as α-glucosidase inhibitors, Synthetic Route of 69097-99-0, the publication is Bioorganic & Medicinal Chemistry (2017), 25(20), 5355-5364, database is CAplus and MEDLINE.

A series of novel flavonoid alkaloids were synthesized with different flavonoids and attached nitrogen-containing moieties. These new compounds were screened for inhibitory activity of α-glucosidase, among which compound I was found to show the lowest IC₅₀ of 4.13 μM. Kinetic anal. indicates that the synthesized compounds II and I inhibit the enzyme in a non-competitive model with Ki value of 37.8 ± 0.8 μM and 13.2 ± 0.6 μM. Further docking studies suggest that the preferred binding pocket is close to the catalytic center, correlating to the exptl. results. Structure activity relationship studies (SAR) indicate that 4′-hyroxyl group and the 4-position carbonyl group in the flavonoid structure are important for this biol. activity. Addition of extra hydrogen bonding and hydrophobic groups on ring A would increase the inhibitory activity.

Bioorganic & Medicinal Chemistry 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 C7H11N3O, Synthetic Route of 69097-99-0.

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

Scott, Lawrence T. published the artcileCyclynes. Synthesis and characterization of octamethylcyclododeca-1,3,7,9-tetrayne, Name: 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Tetrahedron Letters (1976), 2663-6, database is CAplus.

Deprotonation of Me2C(OR)CCH (R = Ac, tetrahydropyranyl) with BuLi and decomposition of resulting anion with CuCl gave low yields of the tetrayne I. The uv, ir, Raman, photoelectron, and NMR spectra for I are reported. I was formed by Cu+-catalyzed formation of the cumulene Me2C:C:C:C:C:CMe2 (II) which dimerized. II was isolated if the reaction was stopped before completion.

Tetrahedron Letters 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 C12H17NS2, Name: 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

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

Scott, Lawrence T. published the artcileTetramethyl-1,2,3,4,5-hexapentaene, Category: tetrahydropyran, the publication is Journal of Organic Chemistry (1980), 45(20), 4055-6, database is CAplus.

Me₂C:C:C:C:C:C:CMe₂ (I) was prepared in 5-10% yields by treating HCCCMe₂OR (R = tetrahydropyranyl) successively with EtMgCl and CuCl. I polymerized readily in absence of solvent or O. Hydrogenation over Rh-alumina gave 2,7-dimethyloctane.

Journal of Organic Chemistry 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 C12H17NS2, Category: tetrahydropyran.

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

Lepri, L. published the artcileReversed-phase planar chromatography of racemic flavanones, Synthetic Route of 69097-99-0, the publication is Journal of Liquid Chromatography & Related Technologies (1999), 22(1), 105-118, database is CAplus.

The direct resolution of nineteen structurally related racemic flavanones was evaluated by reversed-phase planar chromatog. using both home-made microcrystalline cellulose triacetate (MCTA) layers and mobile phase modifiers, such as β-cyclodextrin and bovine serum albumin, on com. available Sil C₁₈-50/UV₂₅₄ plates. Except for the two glycosides, 5-methoxy-, 7-hydroxy- and 5-hydroxy-7-methoxyflavanone, the enantiomers of other flavanones were all resolved by at least one of the three chiral phases tested. Densitograms of racemic flavanones were measured on MCTA layers developed with alc.-water mixtures and on Sil C₁₈-50/UV₂₅₄ plates after elution with chiral mobile phases.

Journal of Liquid Chromatography & Related Technologies 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, Synthetic Route of 69097-99-0.

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

Lepri, Luciano published the artcileReversed-phase planar chromatography of enantiomeric compounds on microcrystalline cellulose triacetate (MCTA), Formula: C16H14O6, the publication is Journal of Planar Chromatography–Modern TLC (1997), 10(2), 108-113, database is CAplus.

Several racemates were resolved on home-made microcrystalline cellulose triacetate (MCTA) plates eluted with aqueous – organic mixtures containing MeOH, EtOH, or iso-PrOH. The roles of the chem. structures of the solutes and concentration of organic solvent on the resolving capability of this polysaccharide were evaluated. Detection of enantiomeric mixtures in the ratios 50:1, 100:1, and 200:1 was performed by scanning densitometry of the MCTA chromatograms.

Journal of Planar Chromatography–Modern TLC 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, Formula: C16H14O6.

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

Ye, Xian-wen published the artcileStudy on the mechanism of treating COVID-19 with Shenqi Wan based on network pharmacology, Application of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is Drug Development and Industrial Pharmacy (2021), 47(8), 1279-1289, database is CAplus and MEDLINE.

Through the method of network pharmacol., the active components and targets of Shenqi Wan (SQW) were excavated, the relationship with novel Coronavirus pneumonia (COVID-19) was discussed, and the possible mechanism of SQW in the treatment of COVID-19 was revealed from the aspects of multicomponents, multitargets, and multipathways. Firstly, the active components of SQW were screened from traditional Chinese medicine systems pharmacol. database and anal. platform and the 2020 edition of Chinese Pharmacopeia, and the related targets of the components were obtained. Then the disease targets related to COVID-19 were screened from GeneCards and Online Mendelian Inheritance in Man. Venny was used to map the relationship between component-target and disease-target, and String was used to analyze the interaction of common targets. The network was constructed and analyzed by Cytoscape, the function of Gene ontol. (GO) and Kyoto Encyclopedia of Genes and Genomes (KEGG) genes was enriched by Metascape, and the mol. docking was verified by CB-Dock. Finally, 45 active components of SQW were obtained, and 72 potential targets were related to COVID-19, angiotensin-converting enzyme 2 (ACE2), interleukin (IL)-6, nitric oxide synthase (NOS3) and, C-reactive protein (CRP),may be the key targets. GO enrichment of 1715 projects, such as lipopolysaccharide stress response, active oxygen metabolism, pos. regulation of cell migration, and other GO enrichment. About 136 KEGG pathways, tumor necrosis factor signaling pathway, IL-17 signaling pathway, hypoxia-inducible factor 1-α signaling pathway were obtained. Mol. docking showed that kaempferol, quercetin, luteolin, astragaloside, calyx isoflavone glucoside, matrine, and other COVID-19-related targets such as ACE2, chymotrypsin-like protease (3CLpro), papain-like protease (PLpro), prostaglandin-endoperoxide synthase 2 (PTGS2) have good binding ability. According to the above results, it is suggested that SQW may play a role in the treatment of COVID-19 by directly or indirectly combining kaempferol, quercetin, and luteolin with ACE2, 3CLpro, PLpro, and PTGS2 to regulate multiple biol. functions and signaling pathways.

Drug Development and Industrial Pharmacy 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 C14H14N2O2, 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

Naapuri, Janne M. published the artcileArylative Allenol Cyclization via Sequential One-pot Enzyme & Palladium Catalysis, Application In Synthesis of 27943-46-0, the publication is ChemCatChem (2021), 13(2), 763-769, database is CAplus.

The one-pot combination of halogenation biocatalysis and Suzuki-type cross coupling enables the direct arylative cyclization of allenic alcs. with boronic acids. This modular approach to unsaturated five-membered O-heterocycles proceeds in an aqueous emulsion with air as terminal oxidant. Here, the enzymic oxidative activation of simple halide salts acts as traceless ring-closure-inducing event to trigger the subsequent C-C coupling. With the original protocol merging soluble proteins and a homogeneous SPhos-based palladium catalyst as a template, a novel heterogeneous nanobiohybrid was developed. Consisting of an oxidase matrix hosting small spherical palladium nanoparticles, this enzyme-metal hybrid exhibits catalytic competence for both the biocyclization as well as the C-C bond-forming cross coupling, underlining the potential of this new techniques for streamlining chemoenzymic approaches.

ChemCatChem 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 C10H16O2, Application In Synthesis of 27943-46-0.

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

Kavuru, Padmini published the artcileHierarchy of Supramolecular Synthons: Persistent Hydrogen Bonds Between Carboxylates and Weakly Acidic Hydroxyl Moieties in Cocrystals of Zwitterions, Safety of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is Crystal Growth & Design (2010), 10(8), 3568-3584, database is CAplus.

Whereas carboxylic acids are well explored in the context of cocrystals, the same cannot be said about carboxylate moieties. This Cambridge Structural Database (CSD) and exptl. study demonstrates that carboxylate moieties persistently form charge-assisted H-bonds with weakly acidic hydroxyl moieties such as phenols. CSD statistics reveal that 58 of 103 relevant structures exhibit carboxylate-hydroxyl (phenolic) supramol. heterosynthons even in the presence of competing functional groups. The following neutral cocrystal formers sustain 15 new cocrystals of zwitterions and their crystal structures reveal that all exhibit carboxylate-hydroxyl supramol. heterosynthons: citric acid (CIT), L-ascorbic acid (ASC), hesperetin (HES), quercetin (QUE), resveratrol (RES), catechol (CAT), protocatechuic acid (PCA), ferulic acid (FER), ellagic acid (ELA), and gallic acid (GAL). Zwitterions used were betaine (BTN), sarcosine (SAR), di-Me glycine (DMG), baclofen (BAC), nicotinic acid (NAC), and isonicotinic acid (INA). Carboxylate-hydroxyl supramol. heterosynthons were observed as follows: 2-point carboxylate-vicinal diol R²₂ (9) in ASCSAR, ASCNAC, and BTNASC; R⁴₄ (18) between two carboxylate and two catechol moieties in BTNGAL, ELASAR, and ELADMG; CITINA·2H₂O, GALINA·H₂O, and HESNAC (+ and ± forms) exhibit 1-point H-bonds.

Crystal Growth & Design 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, Safety of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one.

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

Dormeyer, Matthias published the artcileRational design of anticytoadherence inhibitors for Plasmodium falciparum based on the crystal structure of human intercellular adhesion molecule 1, Application of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is Antimicrobial Agents and Chemotherapy (2006), 50(2), 724-730, database is CAplus and MEDLINE.

Adhesion of Plasmodium falciparum-infected erythrocytes (IE) to host endothelium has been associated with pathol. in malaria. Although the interaction with endothelial cells can be complex due to the relatively large number of host receptors available for binding, specific proteins have been identified that are more commonly used than others. For example, binding to intercellular adhesion mol. 1 (ICAM 1) is found frequently in parasites from pediatric cases of malaria. The binding site for P. falciparum-infected erythrocytes on ICAM 1 has been mapped in some detail and is distinct from the site for lymphocyte function-associated antigen 1 (LFA-1). Part of the ICAM 1 binding site for P. falciparum-infected erythrocytes (the DE loop) was used to screen a library of compounds based on its structure (derived from the crystal structure of human ICAM 1). This resulted in the identification of 36 structural mimeotopes as potential competitive inhibitors of binding. One of these compounds, (+)-epigalloyl-catechin-gallate [(+)-EGCG], was found to inhibit IE adhesion to ICAM 1 in a dose-dependent manner with two variant ICAM 1-binding parasite lines, providing the first example of a potential mimeotope-based anticytoadherence inhibitor for Plasmodium falciparum.

Antimicrobial Agents and Chemotherapy 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