Heterocyclic Building Blocks-Tetrahydropyran

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

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

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

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

Chen, Ji published the artcileCatalytic vinylogous cross-coupling reactions of rhenium vinylcarbenoids, Formula: C10H16O2, the publication is Chemical Science (2018), 9(9), 2489-2492, database is CAplus and MEDLINE.

The first example of the rhenium-catalyzed allylation reaction of indoles by means of cross-coupling with propargyl ethers as non-obvious allylating reagents is reported. Data from isotope-labeling and kinetic isotopic studies are consistent with a mechanism that proceeds by vinylidene formation as the rate determining step, followed by 1,5-hydride shift to generate a key rhenium vinylcarbenoid complex. Bond formation occurs at the vinylogous site and the reaction is conveniently carried out in air.

Chemical Science 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, Formula: C10H16O2.

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

Gerona, Roy R. published the artcileBisphenol-A (BPA), BPA Glucuronide, and BPA Sulfate in Midgestation Umbilical Cord Serum in a Northern and Central California Population, Product Details of C21H24O8, the publication is Environmental Science & Technology (2013), 47(21), 12477-12485, database is CAplus and MEDLINE.

Bisphenol-A (BPA) is an endocrine disrupting chem. used in numerous consumer products, resulting in universal exposure in the United States. Prenatal exposure to BPA is associated with numerous reproductive and developmental effects in animals. However, little is known about human fetal exposure or metabolism of BPA during midgestation. In the present study, the authors present a new liquid chromatog.-tandem mass spectrometry method to directly measure concentrations of BPA and two predominant metabolic conjugates-BPA glucuronide and BPA sulfate-in umbilical cord serum collected from elective second trimester pregnancy terminations. The authors detected at least one form of BPA in all umbilical cord serum samples: BPA (GM 0.16, range < LOD-52.26 ng/mL), BPA glucuronide (GM 0.14, range < LOD-5.41 ng/mL) and BPA sulfate (GM 0.32, range < LOD-12.65 ng/mL). Levels of BPA ranged from less than 1/100th to over 400 times higher than levels of BPA in conjugated form. Although levels of BPA in conjugated form exceeded BPA levels in about 3/4 of the samples, BPA levels were higher in samples with total BPA above the median. The authors’ findings suggest universal fetal exposure to BPA in the authors’ study population, with some at relatively high levels, and the authors provide the first evidence of detectable BPA sulfate in midgestation fetuses.

Environmental Science & Technology 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, Product Details of C21H24O8.

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

Coughlin, Janis L. published the artcileMeasurement of bisphenol A, bisphenol A β-D-glucuronide, genistein, and genistein 4′-β-D-glucuronide via SPE and HPLC-MS/MS, Product Details of C21H24O8, the publication is Analytical and Bioanalytical Chemistry (2011), 401(3), 995-1002, database is CAplus and MEDLINE.

Bisphenol A (BPA) is a synthetic industrial reactant used in the production of polycarbonate plastics, and genistein is a natural phytoestrogen abundant in the soybean. Current studies investigating the endocrine-disrupting effects of concomitant exposures to BPA and genistein have warranted the development of an anal. method for the simultaneous measurement of BPA and genistein, as well as their primary metabolites, bisphenol A β-D-glucuronide (BPA gluc) and genistein 4′-β-D-glucuronide (genistein gluc), resp. All four analytes were extracted from rat plasma via solid phase extraction (SPE). Three SPE cartridges and four elution schemes were tested. Plasma extraction using Bond Elut Plexa cartridges with sequential addition of Et acetate, methanol, and acetonitrile yielded optimal average recoveries of 98.1 ± 1.8% BPA, 94.9 ± 8.0% genistein, 91.4 ± 6.1% BPA gluc, and 103 ± 6.1% genistein gluc. Identification and quantification of the four analytes were performed by a validated HPLC-MS/MS method using electrospray ionization and selective reaction monitoring. This novel anal. method should be applicable to the measurement of BPA, genistein, BPA gluc, and genistein gluc in urine, cultures, and tissue following in vivo exposures. While reports of the determination of BPA and genistein independently exist, the simultaneous optimized extraction and detection of BPA, genistein, BPA gluc, and genistein gluc have not previously been reported. FigureBPA and genistein co-exposure scenario. BPA-laden polycarbonate plastic baby bottle filled with soy milk, a rich source of genistein, provides a classic exposure scenario to young children-a population that is particularly vulnerable to the effects of endocrine-disrupting compounds

Analytical and Bioanalytical Chemistry 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, Product Details of C21H24O8.

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

Michalak, Karol published the artcileTotal Synthesis of a CD-Ring: Side-Chain Building Block for Preparing 17-epi-Calcitriol Derivatives from the Hajos-Parrish Dione, Formula: C10H16O2, the publication is Journal of Organic Chemistry (2011), 76(16), 6906-6911, database is CAplus and MEDLINE.

An efficient synthesis of the key building block I for 17-epi-calcitriol from the Hajos-Parrish dione involving a sequence of diastereoselective transformation of the azulene core and the side-chain construction is presented.

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, Formula: C10H16O2.

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

Smith, Edward H. published the artcileCoupling of Alkynyllithiums to 1,3-Diynes by Reaction with Dichlorobis(triphenylphosphine)nickel(II) in the Presence of Triphenylphosphine and Guanidine or Amidine Bases, Application of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Organometallics (1994), 13(12), 5169-72, database is CAplus.

Reaction of alkynyllithiums with NiCl₂(PPh₃)₂ and 2L [L = PPh₃, tetramethylguanidine, 1,8-diazabicyclo[5.4.0]undec-7-ene, ArN:CMeNMe₂, or ArN:C(NMe₂)NMe₂ (Ar = aryl group)] at low temperatures in THF resulted in moderate to good yields of the homocoupled products, 1,3-diynes. Experiments on cross-coupling suggested that the 1,3-diynes are produced by reductive elimination from intermediate dialkynylnickel species.

Organometallics 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 C7H8O3, Application of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

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

Allan, R. D. published the artcileFlavanone quinones from Cyperus species, Related Products of tetrahydropyran, the publication is Tetrahedron Letters (1973), 7-8, database is CAplus.

The flavonone quinones remerin, breverin, and scaberin (I R = R1 = H; R or R1 = Me or H; R1 = Me, resp.) were isolated from Remeria maritima, C. brevibracteatus, an C. scaber, resp. Methylation of (±)-hesperetin (II, R = H) gave II (R = Me) which on oxidation gave I (R = R1 = H).

Tetrahedron Letters 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, Related Products of tetrahydropyran.

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