Category: tetrahydropyran

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

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

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

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

Ramurthy, Savithri published the artcileDesign and Discovery of N-(3-(2-(2-Hydroxyethoxy)-6-morpholinopyridin-4-yl)-4-methylphenyl)-2-(trifluoromethyl)isonicotinamide, a Selective, Efficacious, and Well-Tolerated RAF Inhibitor Targeting RAS Mutant Cancers: The Path to the Clinic, SDS of cas: 624734-19-6, the publication is Journal of Medicinal Chemistry (2020), 63(5), 2013-2027, database is CAplus and MEDLINE.

Direct pharmacol. inhibition of RAS has remained elusive, and efforts to target CRAF have been challenging due to the complex nature of RAF signaling, downstream of activated RAS, and the poor overall kinase selectivity of putative RAF inhibitors. Herein, we describe 15, a selective B/C RAF inhibitor, which was developed by focusing on drug-like properties and selectivity. Our previous tool compound, 3, was potent, selective, efficacious, and well tolerated in preclin. models, but the high human intrinsic clearance precluded further development and prompted further investigation of close analogs. A structure-based approach led to a pyridine series with an alc. side chain that could interact with the DFG loop and significantly improved cell potency. Further mitigation of human intrinsic clearance and time-dependent inhibition led to the discovery of 15. Due to its excellent properties, it was progressed through toxicol. studies and is being tested in phase 1 clin. trials.

Journal of Medicinal Chemistry 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, SDS of cas: 624734-19-6.

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

Wang, Xiao-jun published the artcileRegioselective Synthesis of Unsymmetrical 3,5-Dialkyl-1-arylpyrazoles, Recommanded Product: 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Organic Letters (2000), 2(20), 3107-3109, database is CAplus and MEDLINE.

3-Alkoxylmethyl-5-alkylpyrazoles undergo regioselective N-arylation with 4-fluoronitrobenzene in the presence of base to yield the corresponding 1-(4-nitro-phenyl)pyrazoles. Further elaboration of these intermediates furnishes a practical synthesis of unsym. 3,5-dialkyl-1-arylpyrazoles. A tentative explanation of the observed regioselectivities is provided.

Organic 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 C7H6Cl2, Recommanded Product: 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

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

Kimura, Masanari published the artcileSilver(I)-catalyzed aminocyclization of 2,3-butadienyl and 3,4-pentadienyl carbamates: an efficient and stereoselective synthesis of 4-vinyl-2-oxazolidinones and 4-vinyltetrahydro-2H-1,3-oxazin-2-ones, Quality Control of 27943-46-0, the publication is Bulletin of the Chemical Society of Japan (1995), 68(6), 1689-705, database is CAplus.

Silver(I) salts in combination with an appropriate base (mostly triethylamine) catalyzed the aminocyclization of N-substituted 2,3-butadienyl carbamates I (benzene, 50°) to provide 4-vinyl-2-oxazolidinones II in good yields. The stereoselectivity (trans-II/cis-II) ranged from 1.4 for C₅-Me to >30 for C₅-Ph, isopropenyl, and t-Bu derivatives 3,4-Pentadienyl tosylcarbamates III, the one-carbon higher homologues of I, underwent a similar cyclization to give 4-vinyltetrahydro-2H-1,3-oxazin-2-one IV in synthetically useful yields and in higher trans selectivities than I.

Bulletin of the Chemical Society of Japan 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, Quality Control of 27943-46-0.

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

Nakagawa, Yoshio published the artcileMetabolism and cytotoxicity of bisphenol A and other bisphenols in isolated rat hepatocytes, Category: tetrahydropyran, the publication is Archives of Toxicology (2000), 74(2), 99-105, database is CAplus and MEDLINE.

The relation between the metabolism and the cytotoxic effects of bisphenol A (BPA, 2,2-bis(4-hydroxyphenyl)propane) has been studied in freshly isolated rat hepatocytes and isolated hepatic mitochondria. The incubation of hepatocytes with BPA (0.25-1.0 mM) elicited a concentration- and time-dependent cell death, accompanied by losses of intracellular ATP and total adenine nucleotide pools. BPA at a low-toxic level (0.25 mM) in the hepatocyte suspensions was rapidly converted to its major conjugate, BPA-glucuronide, and other minor products without marked loss of cell viability, although at a toxic level (0.5 mM), more than 65% of the compound presented in an unaltered form 2 h after the incubation. Addition of salicylamide (2 mM), non-toxic to hepatocytes during the incubation period, enhanced BPA-induced cytotoxicity and reduced the loss of BPA and the formation of BPA-glucuronide. The addition of BPA to isolated hepatic mitochondria caused a concentration (0-0.5 mM)-dependent increase in the rate of state 4 oxygen consumption in the presence of an FAD-linked substrate (succinate), indicating an uncoupling effect, whereas the rate of state 3 oxygen consumption was inhibited by BPA. Further, the addition of BPA (0.25 mM) reduced state 3 respiration with NAD⁺-linked substrates (pyruvate plus malate) and/or with the FAD-linked substrate, whereas state 3 respiration with ascorbate plus tetramethyl-p-phenylenediamine (cytochrome oxidase-linked respiration) was not significantly affected by BPA. A comparative study of the toxic effects of BPA and some bisphenols on cell viability (at 1.0 mM) and mitochondrial respiration (at 0.25 mM) revealed that 4,4′-(1,2-diethyl-1,2-ethenediyl)bisphenol (diethylstilbestrol) was more toxic than BPA, followed by 4,4′-methylenediphenol and 4,4′-biphenol. These results indicate that the onset of cytotoxicity caused by BPA may depend on the intracellular energy status and that mitochondria are important targets of the compound The toxicity caused by the inhibition of ATP synthesis may be related to the concentration of unmetabolized free BPA remaining in the cell suspensions. In addition, the toxic potency of bisphenols to hepatocytes and mitochondria depends on the relative elongation and/or mol. size of the hydrocarbon bridge between the phenolic groups.

Archives of 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, Category: tetrahydropyran.

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

Jacobson, Roy published the artcileNaturally occurring spirocyclic ketals from lactones. III, Related Products of tetrahydropyran, the publication is Journal of Organic Chemistry (1982), 47(16), 3140-2, database is CAplus.

Treatment of (S)-propylene oxide with Li acetylide-ethylenediamine complex in NH₃(l) gave (S)-4-pentyn-2-ol which was converted to the tetrahydropyranyl ether; the lithium anion was generated followed by condensation with butyrolactone to give (7S)-I with optical purity of 80% identical to the ketals isolated from Andrena and Vespula species. Addnl. obtained was II identical to that isolated from Japanese hop oil. A simplified synthesis of chalcogran (III) from γ-caprolactone and the Li reagent prepared from Br(CH₂)₃OCH(OEt)Me was described.

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, Related Products of tetrahydropyran.

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

Huang, Juntao published the artcileThe possible mechanism of Hippophae fructus oil applied in tympanic membrane repair identified based on network pharmacology and molecular docking, Category: tetrahydropyran, the publication is Journal of Clinical Laboratory Analysis (2022), 36(1), e24157, database is CAplus and MEDLINE.

This study aimed to explore the mechanisms of Hippophae fructus oil (HFO) in the treatment of tympanic membrane (TM) perforation through network pharmacol.-based identification. The compounds and related targets of HFO were extracted from the TCMSP database, and disease information was obtained from the OMIM, GeneCards, PharmGkb, TTD, and DrugBank databases. A Venn diagram was generated to show the common targets of HFO and TM, and GO and KEGG analyses were performed to explore the potential biol. processes and signaling pathways. The PPI network and core gene subnetwork were constructed using the STRING database and Cytoscape software. A mol. docking anal. was also conducted to simulate the combination of compounds and gene proteins. A total of 33 compounds and their related targets were obtained from the TCMSP database. After screening the 393 TM-related targets, 21 compounds and 22 gene proteins were selected to establish the network diagram. GO and KEGG enrichment analyses revealed that HFO may promote TM healing by influencing cellular oxidative stress and related signaling pathways. A critical subnetwork was obtained by analyzing the PPI network with nine core genes: CASP3, MMP2, IL1B, TP53, EGFR, CXCL8, ESR1, PTGS2, and IL6. In addition, a mol. docking anal. revealed that quercetin strongly binds the core proteins. According to the anal., HFO can be utilized to repair perforations by influencing cellular oxidative stress. Quercetin is one of the active compounds that potentially plays an important role in TM regeneration by influencing 17 gene proteins.

Journal of Clinical Laboratory Analysis 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, Category: tetrahydropyran.

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