Category: tetrahydropyran

Domoradzki, J. Y. published the artcileMetabolism and Pharmacokinetics of Bisphenol A (BPA) and the Embryo-Fetal Distribution of BPA and BPA-Monoglucuronide in CD Sprague-Dawley Rats at Three Gestational Stages, HPLC of Formula: 267244-08-6, the publication is Toxicological Sciences (2003), 76(1), 21-34, database is CAplus and MEDLINE.

The pharmacokinetics of bisphenol A (BPA), including the quantification of the major BPA metabolite BPA-monoglucuronide conjugate (BPA-glucuronide) was studied in Sprague-Dawley rats at different stages of gestation. ¹⁴C-BPA was administered orally at 10 mg BPA/kg body weight (0.2 mCi/rat) to nongravid rats and to other groups on gestation days (GD) 6, 14, and 17. GD 0 was when the vaginal smear was sperm pos. or a copulatory plug was observed Radioactivity derived from ¹⁴C-BPA was quantified in the maternal blood, selected tissues, and the embryo or fetus. BPA and BPA-glucuronide were quantified in maternal plasma and excreta. Addnl. rats were dosed orally at 10 mg ¹⁴C-BPA/kg (0.2 mCi/rat or 0.5 mCi/rat) on GD 11, 13, and 16 to further study the distribution of BPA and BPA-glucuronide to the embryo/fetal tissue. The tissue distribution, metabolism, or the rates or routes of excretion of BPA, or the plasma concentration-time profiles of BPA-glucuronide did not appear to be altered at any stage of gestation as compared to nonpregnant rats. In the GD 11 group, neither BPA nor BPA-glucuronide was detected in the yolk sacs or embryos, except for trace concentrations of BPA-glucuronide in the yolk sacs at 15 min postdosing. In the GD 13 group, both BPA and BPA-glucuronide were detected in the yolk sacs of the conceptus but not in the embryos/fetuses, except for BPA at 15 min. For the animals dosed with 0.2 mCi/rat on GD 16, both analytes were detected in the placentae at 15 min and 12 h, but not at 96 h. Traces of both analytes were detected in fetal tissue in two of five specimens at 15 min only. In rats dosed on GD 16 with 0.5 mCi/rat, the BPA-glucuronide and BPA concentrations in maternal plasma at 15 min were 1.7 and 0.06 μg equivalent (eq)/g plasma, resp. At the same time postdosing in these animals, the placental BPA-glucuronide concentrations were lower (0.34 μg eq BPA [as glucuronide]/g), and the BPA concentrations were about equivalent (0.095 μg/g). Fetal BPA-glucuronide and BPA concentrations were markedly lower, 0.013 and 0.018 μg eq/g, resp. Therefore, no selective affinity of either yolk sac/placenta or embryo/fetus for BPA or BPA metabolites relative to maternal plasma or tissues was observed in this study.

Toxicological 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, HPLC of Formula: 267244-08-6.

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

Seka, R. published the artcileNew synthesis of chrysin and other hydroxyflavones, COA of Formula: C16H14O6, the publication is Monatshefte fuer Chemie (1936), 284-91, database is CAplus.

The complex prepared from 2.4 g. 1,3,5-C₆H₃(OH)₃ and 7.5 g. AlCl₃ in 40 cc. PhNO₂ and 3.12 g. PhCCCOCl, allowed to stand 14 days at room temperature, gives chrysin (5,7-dihydroflavone), purified by distillation of the Al compound with HCl, steam distillation of the PhNO₂, sublimation of the resinous residue and extraction with boiling C₆H₆. In the same manner m-C₆H₄(OH)₂ yields 7-hydroxyflavone and 1,2,3-C₆H₃(OH)₃ gives 7,8-dihydroxyflavone. Natural and synthetic hesperetin (4′-methoxy-3′,5,7-trihydroxyflavanone), m. 233°, are purified by sublimation at 0.003-0.004 mg. Hg at a temperature not exceeding 205°; homoeriodictyol. similarly purified, m. 324° (cf. Shinoda and Kawagoye, C. A. 23, 2957; S. and Sato, C. A. 23, 4210).

Monatshefte fuer Chemie 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 C5H6N2O2, COA of Formula: C16H14O6.

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

Kong, Wangqing published the artcileExclusive 1,2-Aryl Shift in Platinum(II) Chloride-Catalyzed Cyclization of 1-(Indol-2-yl)-2,3-allenols, Category: tetrahydropyran, the publication is Advanced Synthesis & Catalysis (2012), 354(11-12), 2339-2347, S2339/1-S2339/79, database is CAplus.

An efficient cyclization of 1-(indole-2-yl)-2,3-allenols in the presence of platinum(II) chloride leading to polysubstituted carbazoles via 1,2-Me or an exclusive 1,2-aryl migration of the metal-carbene intermediate was observed The reaction proceeds via the intermediacy of a metal carbene intermediate, which induces the carbon-carbon bond cleavage via 1,2-migration to afford the products.

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 C10H16O2, Category: tetrahydropyran.

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

Edwards, J. Michael published the artcileAntitumor plants. Part VII. Antineoplastic activity and cytotoxicity of flavones, isoflavones, and flavanones, Application of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is Journal of Natural Products (1979), 42(1), 85-91, database is CAplus and MEDLINE.

Two hundred and seventeen natural and synthetic flavonoid derivatives I, II, and III, which were tested in the screening program of the National Cancer Institute, were examd for antineoplastic activity and cytotoxicity. No structure-activity relations were observed Apparently, in spite of occasional activity these compounds do not warrant further investigation as antitumor agents.

Journal of Natural Products 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

Khan, Muhammad Kamran published the artcileChemical Synthesis of Citrus Flavanone Glucuronides, Application In Synthesis of 69097-99-0, the publication is Journal of Agricultural and Food Chemistry (2010), 58(14), 8437-8443, database is CAplus and MEDLINE.

Flavanone glucuronides are the major phenolic metabolites detected in human plasma after consumption of citrus fruits. As such, they might display significant cardioprotective effects. In this work, glucuronides of naringenin (4′- and 7-O-β-D-glucuronides) and hesperetin (3′- and 7-O-β-D-glucuronides), the major flavanone aglycons in grapefruit and orange, resp., have been chem. synthesized. On the one hand, the most reactive hydroxyl group, C7-OH, was protected by selective benzoylation to allow subsequent glucuronidation of C4′-OH (naringenin) or C3′-OH (hesperetin) (B-ring). On the other hand, the selective debenzoylation at C₇-OH of the per-benzoylated flavanone aglycons allowed glucuronidation at the same position (A-ring). After careful deprotection, the target compounds were purified and characterized by NMR and mass spectrometry.

Journal of Agricultural and Food 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 C16H14O6, Application In Synthesis of 69097-99-0.

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

Kumari, G. N. Krishna published the artcileCarbon-13 NMR data of flavonol methyl ethers of Solanum pubescens, HPLC of Formula: 69097-99-0, the publication is Proceedings – Indian Academy of Sciences, Chemical Sciences (1986), 97(2), 171-6, database is CAplus.

The ¹³C NMR data of flavonol 3-Me ethers indicated that the methylation of one of the OH groups in the o-dihydroxy system causes an upfield shift in the unsubstituted o-carbon as usual, but with the other hydroxylated o-carbon the shift is always downfield. The spectra of the acetates indicated that 5-acetoxy resonated downfield compared to that of other acetoxy groups. The ¹³C NMR data of these compounds is reported for the 1st time.

Proceedings – Indian Academy of Sciences, Chemical Sciences 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, HPLC of Formula: 69097-99-0.

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

Grigg, Ronald published the artcilePalladium catalyzed triscyclization-anion capture queuing cascades, Synthetic Route of 27943-46-0, the publication is Tetrahedron Letters (1997), 38(10), 1825-1828, database is CAplus.

Palladium catalyzed regio- and, where appropriate, stereospecific triscyclization-anion capture processes are described involving vinyl- and allenyl-starter species, alkene/alkyne relay and terminating species and anion capture by allene/nucleophile (PhSO₂Na or s-amine) or (2-thienyl)tributylstannane. Thus, enetriyne HCCCH₂CH₂CCCH₂C(CO₂Et)₂CH₂CH:CICH₂CH₂CCH reacted with allene and nucleophiles (piperidine, NaO₂SPh) to give tricyclic compounds I (R = piperidino, O₂SPh).

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 C10H16O2, Synthetic Route of 27943-46-0.

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

Ezzat, Mohammed oday published the artcileMolecular modelling design and opioid binding affinity evaluation of new 4-chromanone derivatives, Computed Properties of 69097-99-0, the publication is Journal of Microbiology, Biotechnology and Food Sciences (2021), 10(4), 531-535, database is CAplus.

The pharmacotherapy treatment of pain is an active and motivated area of investigation for treatment with free side effects. This paper presents the docking ability of twenty-five analogs of 4-Chromanone derivatives inside the crystal structure of μ opioid receptor to estimate the binding affinity of each derivative Mol. modeling design approach applied to identify the effective substation position with generation of 989 novel 4-Chromanone derivatives The final result of the most active twenty novel 4-Chromanone derivatives with docking affinity range (-9.89 to -9.34) kcal/mol were selected as promising hit ligand drugs comparing with morphine docking affinity at (-6.02) kcal/mol.

Journal of Microbiology, Biotechnology and Food Sciences 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, Computed Properties of 69097-99-0.

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

Yanez, Jaime A. published the artcilePharmacokinetics of selected chiral flavonoids: hesperetin, naringenin and eriodictyol in rats and their content in fruit juices, Application of 5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)chroman-4-one, the publication is Biopharmaceutics & Drug Disposition (2008), 29(2), 63-82, database is CAplus and MEDLINE.

The majority of pharmacokinetic studies of individual flavonoids or after ingestion of foodstuffs have overlooked the chirality of some of these xenobiotics. In order to characterize for the first time the stereoselective pharmacokinetics of three flavonoids, hesperetin, naringenin and eriodictyol were i.v. administered (20 mg/kg) to male Sprague-Dawley rats, and their stereospecific content was assessed in various fruit juices. Concentrations in serum, urine and fruit juices were characterized via HPLC and verified by LC/MS. Short half-lives (3-7 h) in serum were observed, while a better estimation of half-life (12-48 h) and the other pharmacokinetic parameters was observed using urinary data. The three flavonoids are predominantly excreted via non-renal routes (f_e values of 3-7%), and undergo rapid and extensive phase II metabolism The (2S)-epimers of the flavonoid glycosides and the S(-)-enantiomers of the aglycons were predominant and in some instances the organic fruit juices had higher concentrations than the conventional fruit juices. This study reports for the first time the stereospecific pharmacokinetics of three chiral flavonoids and their stereospecific content in fruit juices. It also reports for the first time the stereospecific pharmacokinetics of flavonoids employing urine as a more reliable biol. matrix.

Biopharmaceutics & Drug Disposition 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 C12H15NO, 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

Trdan Lusin, Tina published the artcileEvaluation of bisphenol A glucuronidation according to UGT1A1*28 polymorphism by a new LC-MS/MS assay, 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 Toxicology (2012), 292(1), 33-41, database is CAplus and MEDLINE.

The endocrine disruptor bisphenol A (BPA) is a frequently used chem. in the manufacture of consumer products. In humans, BPA is extensively metabolized to BPA glucuronide (BPAG) by different UDP-glucuronosyltransferase (UGT) isoforms. The study has been performed with the intention to improve the accuracy of published physiol. based pharmacokinetic models and to improve regulatory risk assessments of BPA. In order to gain insight into intestine, kidney, liver, and lung glucuronidation of BPA, human microsomes of all tested organs were used. BPAG formation followed Michaelis-Menten kinetics in the intestine and kidney, but followed substrate inhibition kinetics in the liver. Human lung microsomes did not show glucuronidation activity towards BPA. While the liver intrinsic clearance was very high (857 mL min^-1 kg body weight^-1), the tissue intrinsic clearances for the kidney and intestine were less than 1% of liver intrinsic clearance. Since BPA is a UGT1A1 substrate, we postulated that the common UGT1A1*28 polymorphism influences BPA glucuronidation, and consequently, BPA detoxification. Hepatic tissue intrinsic clearances for UGT1A1*1/*1, UGT1A1*1/*28, and UGT1A1*28/*28 microsomes were 1113, 1075, and 284 mL min^-1 kg body weight^-1, resp. Prior to microsomal experiments, the bioprodn. of BPAG and stable isotope-labeled BPAG (BPAG_d16) was performed for the purpose of the reliable and accurate quantification of BPAG. In addition, a sensitive LC-MS/MS anal. method for the simultaneous determination of BPA and BPAG based on 2 stable isotope-labeled internal standards was developed and validated. In conclusion, our in vitro results show that the liver is the main site of BPA glucuronidation (K _m 8.9 μM, V _max 8.5 nmol min^-1 mg^-1) and BPA metabolism may be significantly influenced by a person’s genotype (K _m 10.0-13.1 μM, V _max 3.4-16.2 nmol min^-1 mg^-1). This discovery may be an important fact for the currently on-going worldwide BPA risk assessments and for the improvement of physiol. based pharmacokinetic models.

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 C12H17NO2, 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