Heterocyclic Building Blocks-Tetrahydropyran

Miyakoda, Hidekazu published the artcileComparison of conjugative activity, conversion of bisphenol A to bisphenol A glucuronide, in fetal and mature male rat, 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 Health Science (2000), 46(4), 269-274, database is CAplus.

We showed previously that orally administered bisphenol A (BPA) easily crosses the placental barrier and enters the fetus. However, BPA glucuronide transport and metabolism in the fetus was not studied. We examined the transport of orally administered BPA and BPA glucuronide into mature rat testis and fetus of pregnant rats. After administration of an oral dose of 10 mg BPA per kg body weight to pregnant female rats, BPA glucuronide in the fetus was not detected. BPA glucuronide does not easily pass through the placental barrier. One hour after oral administration of 10 mg BPA per kg body weight to mature male rats, approx. 905 of the BPA was present as BPA glucuronide in both blood plasma and testis. Although the concentration of free BPA in blood plasma decreased gradually, free BPA in the testis had increased slightly 8 h after administration. Eight hours after oral administration of BPA, BPA glucuronide gradually decreased in rat testis. In contrast, following oral BPA administration, blood plasma BPA glucuronide decreased to 55% of the maximum observed concentration after 3 h, but then increased to 100% of the maximum observed concentration after 8 h. These results suggest that BPA easily passes through the testicular barrier, is converted by UDP-glucuronosyltransferase to BPA glucuronide, and gradually breaks down to BPA by β-glucuronidase.

Journal of Health Science 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, 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

Crowley, Brendan M. published the artcileNovel oxazolidinone calcitonin gene-related peptide (CGRP) receptor antagonists for the acute treatment of migraine, Related Products of tetrahydropyran, the publication is Bioorganic & Medicinal Chemistry Letters (2015), 25(21), 4777-4781, database is CAplus and MEDLINE.

In the authors’ efforts to develop CGRP receptor antagonists as backups to MK-3207, the authors employed a scaffold hopping approach to identify a series of novel oxazolidinone-based compounds The development of a structurally diverse, potent ((I), cAMP + HS IC₅₀ = 0.67 nM), and selective compound (hERG IC₅₀ = 19 μM) with favorable rodent pharmacokinetics (F = 100%, t_1/2 = 7 h) is described. Key to this development was identification of a 3-substituted spirotetrahydropyran ring that afforded a substantial gain in potency (10 to 35-fold).

Bioorganic & Medicinal Chemistry Letters published new progress about 624734-19-6. 624734-19-6 belongs to tetrahydropyran, auxiliary class Tetrahydropyran,Fluoride,Ketone, name is 3-Fluorodihydro-2H-pyran-4(3H)-one, and the molecular formula is C5H7FO2, Related Products of tetrahydropyran.

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

Schneiders, Gail E. published the artcileSynthesis of benzofurans by the action of copper on terminal alkynes and o-halophenols, Application In Synthesis of 27943-46-0, the publication is Synthetic Communications (1980), 10(9), 699-705, database is CAplus.

Dehydrotremetone (I) was prepared by cyclization of 3,4-I(HO)C₆H₃Ac with HCCCMe:CH₂ in refluxing DMF containing K₂CO₃ and activated Cu powder. (Hydroxyisopropyl)benzofuran II, isolated previously from Podachaenium eminens, was similarly prepared from the tetrahydropyranyl ether III.

Synthetic Communications 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

Duffley, Richard P. published the artcileSynthesis of oroselol, COA of Formula: C10H16O2, the publication is Synthetic Communications (1978), 8(3), 175-80, database is CAplus.

Coupling of the cuprous salt R¹CCCMe₂OR (R = 2-tetrahydropyranyl) (I; R¹ = Cu), prepared by treating I (R¹ = H) with H₂NOH.HCl and CuSO₄ in NH₄OH, with 7-hydroxy-8-iodocoumarin (prepared by direct iodination of umbelliferone) in pyridine gave a 50% oroselol (II).

Synthetic Communications 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, COA of Formula: C10H16O2.

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

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

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

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

Robertson, Dale N. published the artcileAdducts of tert-alcohols containing an ethynyl group with dihydropyran. Potentially useful intermediates, Category: tetrahydropyran, the publication is Journal of Organic Chemistry (1960), 931-2, database is CAplus.

Acetylenic alcs. of the type RR’COHCCH (I) were found to add smoothly and in high yield to dihydropyran (II) to form tetrahydropyranyl (R²) compounds of the general structure RR’C(CCH)OR² (III). The R² grouping was stable to alkali but easily removed by aqueous acid or exchangeable with lower alcs. by acid catalysis. Organometallic intermediates were easily formed by reaction at the acetylenic H and compounds such as γ-hydroxy-α,β-acetylenic acids; esters and ketones thus were readily available. General procedure; the appropriate alc. (1 mole) and 1.2-2 moles II was swirled with a few crystals of p-MeC₆H₄SO₃H (the exothermic reaction began almost at once and was usually complete within 0.5-1.0 hr.); with higher mol. weight alcs. the mixture was heated on the steam bath 0.5-1.0 hr. to ensure completion. Anhydrous K₂CO₃ (1-2 g.) was added to the cooled mixture and the whole stirred 0.5 hr. or left overnight, the salts removed, excess II distilled at atm. pressure, and the product distilled in vacuo. Even Me₃COH added readily to II, although the product was not isolated. Since an equimolar mixture of the 2 reactants would contain the same C and H values as the products, the infrared spectrum of each product was determined The following III were obtained from I and II (R, R’, and b.p./mm. given): Me, Me, 64.5-5.5°/8; Et, Me, 62.5-4.5°/3.3; Me₂CHCH₂, Me, 47-50°/0.6-0.2; Me(CH₂)₅, Me, 76-7°/0.12; Ph, Me, 99-100.5°/0.02; (R,R’ = cyclohexyl), 101.5-2.5°/3.6-3.7.

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 C10H16O2, Category: tetrahydropyran.

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

Martineau, Louis C. published the artcileLarge enhancement of skeletal muscle cell glucose uptake and suppression of hepatocyte glucose-6-phosphatase activity by weak uncouplers of oxidative phosphorylation, Formula: C16H14O6, the publication is Biochimica et Biophysica Acta, General Subjects (2012), 1820(2), 133-150, database is CAplus and MEDLINE.

Background: Perturbation of energy homeostasis in skeletal muscle and liver resulting from a transient inhibition of mitochondrial energy transduction can produce effects of relevance for the control of hyperglycemia through activation of the AMP-activated protein kinase, as exemplified by the antidiabetic drug metformin. The present study focuses on uncoupling of oxidative phosphorylation rather than its inhibition as a trigger for such effects. Methods: The reference weak uncoupler 2,4-dinitrophenol, fourteen naturally-occurring phenolic compounds identified as uncouplers in isolated rat liver mitochondria, and fourteen related compounds with little or no uncoupling activity were tested for enhancement of glucose uptake in differentiated C2C12 skeletal muscle cells following 18 h of treatment at 25-100 μM. A subset of compounds were tested for suppression of glucose-6-phosphatase (G6Pase) activity in H4IIE hepatocytes following 16 h at 12.5-25 μM. Metformin (400 μM) was used as a standard in both assays. Results: Dinitrophenol and nine of eleven compounds that induced 50% or more uncoupling at 100 μM in isolated mitochondria enhanced basal glucose uptake by 53 to 269%; the effect of the 4′-hydroxychalcone butein was more than 6-fold that of metformin; neg. control compounds increased uptake by no more than 25%. Dinitrophenol and four 4′-hydroxychalconoids also suppressed hepatocyte G6Pase as well as, or more effectively than metformin, whereas the unsubstituted parent compound chalcone, devoid of uncoupling activity, had no effect. Conclusions: Activities key to glycemic control can be induced by a wide range of weak uncouplers, including compounds free of difficult-to-metabolize groups typically associated with uncouplers. General significance: Uncoupling represents a valid and possibly more efficient alternative to inhibition for triggering cytoprotective effects of therapeutic relevance to insulin resistance in both muscle and liver. Identification of actives of natural origin and the insights into their structure-activity relationship reported herein may lead to alternatives to metformin.

Biochimica et Biophysica Acta, General Subjects 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