Month: November 2022

Johnson, C. David published the artcileProdrugs based on masked lactones. Cyclization of γ-hydroxy amides, Name: 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Journal of Organic Chemistry (1988), 53(21), 5130-9, database is CAplus.

A versatile approach to prodrug design based on the lactonization of γ-hydroxy carbonyl compounds is investigated. A range of γ-hydroxy amides, e.g., RR¹C(OH)CH:CHCONHR²R³ [R = R¹ = H, Me; RR¹ = (CH₂)₅; R² = H, R³ = 4-C₆H₄Br; R² = Me, R³ = Ph], I and II (R⁴ = H, 4-Br, 4-OMe, 4-Me, 3-Cl) were prepared as models for amide-linked prodrugs. The rates of lactonization of these compounds were measured, and the effects of pH, leaving group pK_a, buffer species, and ionic strength were investigated. The kinetic data are consistent with changes in the rate-determining step with the nature of the buffer and with pH over the range 6-10. Some compounds show only small changes in rate over the pH range 7-9. The best model prodrugs studied have rates of amine expulsion that would probably be adequate for therapeutic use, but precise rates of drug liberation in vivo cannot be predicted from these data due to the problems of estimating the magnitude of biol. buffer catalysis and effects due to tissue binding. However, drug liberation half-lives in vivo in the region of 1 h for aromatic amides, less for aliphatic amides, may be achieved by using prodrugs that yield 4,4-dialkyl (or spiroalkyl)-(Z)-but-2-enoic acid lactones during drug release.

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

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

Eshon, Josephine published the artcileRegioselective Rh-Catalyzed Hydroformylation of 1,1,3-Trisubstituted Allenes Using BisDiazaPhos Ligand, Product Details of C10H16O2, the publication is Journal of Organic Chemistry (2017), 82(18), 9270-9278, database is CAplus and MEDLINE.

The efficient hydroformylation of 1,1,3-trisubstituted allenes is accomplished with low loadings of a Rh catalyst supported by a BisDiazaPhos (BDP) ligand. The ligand identity is key to achieving high regioselectivity, while the mild reaction conditions minimize competing isomerization and hydrogenation to produce β,γ-unsaturated aldehydes and their derivatives in excellent yields.

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, Product Details of C10H16O2.

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

Fuerst, Andor published the artcileNew syntheses of 1α,25-dihydroxycholesterol, Computed Properties of 27943-46-0, the publication is Helvetica Chimica Acta (1982), 65(5), 1499-521, database is CAplus.

1α,25-Dihydroxycholesterol was prepared via 5 convergent syntheses by combining C₂₁– or C₂₂-steroids with C₄– or C₅-side-chain building blocks. Thus, pregnene I (R = tetrahydro-2-pyranyl, R¹ = CH₂O₃SC₆H₄Me-H) was combined with the dioxolane II, PhSO₂CH₂CH₂CMe₂OR² (R² = tetrahydro-2-pyranyl) and HCCCMe₂OR² and I (R = Ac, R¹ = CHO) was combined with Ph₃P:CHCH₂CMe₂OH. Also, pregnenone III was condensed with phosphorane IV.

Helvetica Chimica Acta 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, Computed Properties of 27943-46-0.

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

Jeon, Yukyoung published the artcileCarboxymethylated cyclosophoraose as a novel chiral additive for the stereoisomeric separation of some flavonoids by capillary electrophoresis, HPLC of Formula: 69097-99-0, the publication is Carbohydrate Research (2010), 345(16), 2408-2412, database is CAplus and MEDLINE.

A carboxymethylated cyclosophoraose (CM-Cys) was synthesized by the chem. modification of neutral Cys, which was isolated from Rhizobium trifolii TA-1. CM-Cys was successfully applied as a novel chiral selector for the separation of some flavonoids including catechin, 3,5,7,3′,4′-pentahydroxyflavanone, hesperidin, hesperetin, isosakuranetin, naringenin, naringin, and eriodictyol. The effects of pH, chiral additive concentration, and temperature on resolution and migration time were also studied.

Carbohydrate Research 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

Kihira, Kenji published the artcileComparative biological studies of bile alcohols. IV. New bile alcohols. Synthesis of (22R)- and (22S)-5β-cholestane-3α,7α,12α,22,25-pentols, Application of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Steroids (1976), 27(3), 383-93, database is CAplus and MEDLINE.

Bisnorcholanal I, prepared from triacetylcholic acid by successive oxidative-decarboxylation, alk. hydrolysis, treatment with H2O2, alk. hydrolysis, and oxidation with Pb(OAc)4, was treated with 3-methyl-3-(tetrahydropyran-2-yloxy)butynylmagnesium bromide. Hydrogenation over PtO2 of the epimeric acetylenes followed by acid hydrolysis gave (22R)- and (22S)-cholestanepentols II. (22R)-II was identical with the metabolite of 5β-cholestane-3α,7α,25-triol formed in the rabbit.

Steroids 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 of 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran.

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

Pritchett, J. J. published the artcileMetabolism of bisphenol A in primary cultured hepatocytes from mice, rats, and humans, Application 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 Drug Metabolism and Disposition (2002), 30(11), 1180-1185, database is CAplus and MEDLINE.

Studies have shown that in the rat, bisphenol A (BPA) is metabolized and eliminated primarily as a monoglucuronide, a metabolite without estrogenic activity. The purpose of this study was to determine the extent of monoglucuronide formation in monolayers of hepatocytes from rats, mice, and humans. Noncytotoxic concentrations of BPA (10, 20, and 35 μM; 1.0 μCi), as assessed by lactate dehydrogenase leakage, were incubated with isolated hepatocytes for 0-6 h. Media were collected and analyzed for metabolites by radiochem. high performance liquid chromatog. and liquid chromatog.-tandem mass spectrometry. The metabolites identified include a monoglucuronide (major metabolite), a sulfate conjugate, and a glucuronide/sulfate diconjugate (minor metabolites). In hepatocytes of male Fischer-344 rats, the predominate metabolite was the diconjugate (glucuronide/sulfate). Under these conditions, the extent of metabolism by 3 h was similar in all species tested because all BPA was converted to conjugates by 3 h. Initial rates of metabolism in hepatocytes followed the order of mice > rats > humans. However, when extrapolated to the whole liver (i.e., cells per liver), the hepatic capacity for BPA glucuronidation is predicted to be humans > rats > mice.

Drug Metabolism and Disposition 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, Application 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

Hoffmann, H. M. R. published the artcileThe intramolecular enyne Diels-Alder reaction. Stereoselective construction of tricyclic dioxa dienones and mechanistic outline, HPLC of Formula: 27943-46-0, the publication is Tetrahedron (1993), 49(40), 8999-9018, database is CAplus.

4-Methylpent-4-en-2-yn-1-ols and 6-hydroxy-2,3-dihydro-6H-pyran-3-ones are condensed in different ways to give a series of tricyclic dioxa dienones I [R = H, Me; R¹ = R² = H, Me, Et; R¹R² = (CH₂)₄, (CH₂)₅; R¹ = H, R² = Me, Ph, 2-thienyl, 3-thienyl] which contain the basic framework of the cadlinolides. A mechanism for the intramol. enyne-ene cycloisomerization and the origin of the resulting dienes is proposed.

Tetrahedron 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, HPLC of Formula: 27943-46-0.

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

Kim, Yong-Hak published the artcileGender differences in the levels of bisphenol A metabolites in urine, Formula: C21H24O8, the publication is Biochemical and Biophysical Research Communications (2003), 312(2), 441-448, database is CAplus and MEDLINE.

The metabolism of bisphenol A (BPA), a suspected endocrine disruptor, should be considered for monitoring human exposure to BPA, because the conjugation with β-D-glucuronide and sulfate reduces the estrogenic activity. In this study, BPA levels in 30 healthy Koreans (men, N=15, 42.6±2.4 yr; women, N=15, 43.0±2.7 yr) were analyzed from urine treated with/without β-glucuronidase and/or sulfatase by an RP-HPLC with fluorescence detection. The total BPA concentrations including free BPA and the urinary conjugates were similar in men and women (2.82±0.73 and 2.76±0.54 ng ml^-1, resp.), but gender differences were found in the levels of urinary BPA conjugates. Men had significantly higher levels of BPA-glucuronide (2.34±0.85 ng ml^-1) than women (1.00±0.34 ng ml^-1), whereas women had higher levels of BPA-sulfate (1.20±0.32 ng ml^-1) than men (0.49±0.27 ng ml^-1).

Biochemical and Biophysical Research Communications 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, Formula: C21H24O8.

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

Tsunekawa, Ryuji published the artcileSynthesis of 5-Hydroxy-3′,4′,7-trimethoxyflavone and Related Compounds and Elucidation of Their Reversal Effects on BCRP/ABCG2-Mediated Anticancer Drug Resistance, Formula: C16H14O6, the publication is ChemBioChem (2019), 20(2), 210-220, database is CAplus and MEDLINE.

3′,4′,7-Trimethoxyflavone (TMF) has been reported to show a potent reversal effect on drug resistance mediated by breast cancer resistance protein (BCRP)/ATP-binding cassette subfamily G member 2 (ABCG2). In this study, we designed and synthesized five derivatives with either a hydroxy group or a fluorine atom at C-5 and several kinds of capping moiety at the C-7 hydroxy group, on the same 3′,4′-dimethoxy-substituted flavone skeleton. We subsequently evaluated the efficacies of these compounds against BCRP-expressing human leukemia K562/BCRP cells. Reversal of drug resistance was expressed as the concentration of compound causing a twofold reduction in drug sensitivity (RI50). Of the synthesized compounds, the reversal effect of 5-hydroxy-3′,4′,7-trimethoxyflavone (HTMF, RI50 7.2 nM) towards 7-ethyl-10-hydroxycamptothecin (SN-38) was stronger than that of TMF (RI50 18 nM). Fluoro-substituted 5-fluoro-3′,4′,7-trimethoxyflavone (FTMF, RI50 25 nM) and monoglycosylated 7-(β-glucosyloxy)-5-hydroxy-3′,4′-dimethoxyflavone (GOHDMF, 91 nM) also exhibited reversal effects, whereas the di- and triglycoside derivatives did not. TMF, HTMF and FTMF at 0.01-10 μM upregulated the K562/BCRP cellular accumulation of Hoechst 33342 nuclear staining dye. HTMF showed the strongest inhibition of BCRP-mediated efflux and suppression of BCRP expression of the three effective synthesized flavones.

ChemBioChem 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 C6H13NO2, Formula: C16H14O6.

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

Veiga-Lopez, Almudena published the artcileGender-specific effects on gestational length and birth weight by early pregnancy BPA exposure, Synthetic Route of 267244-08-6, the publication is Journal of Clinical Endocrinology and Metabolism (2015), 100(11), E1394-E1403, database is CAplus and MEDLINE.

Context and Objective: Effects of prenatal exposure to bisphenol A (BPA) on gestational and birth outcomes are controversial. The aim of the study was to evaluate the relationship between prenatal exposure to BPA and birth and gestational outcomes. Design, Setting, Participants, and Outcome: Levels of unconjugated (uBPA) and BPA glucuronide in 80 matching samples of pregnant women during the first trimester of pregnancy and at delivery and matching term cord blood obtained from a prospective study conducted at the University of Michigan Hospitals were determined using a methodol. validated in the National Institutes of Environmental Health Sciences funded Round Robin study and related to pregnancy outcomes. Results: Highest levels of uBPA were found in maternal term samples followed by first trimester maternal (M1) samples and cord blood. A 2-fold increase in M1 uBPA was associated with 55-g less birth weight when male and female pregnancies were combined and 183-g less birth weight with only female pregnancies. A 2-fold increase in maternal term uBPA was associated with an increased gestational length of 0.7 days for all pregnancies and 1.1 days for only female pregnancies. Conclusion: Higher uBPA exposure levels during first trimester and term are associated with sex-specific reduction in birth weight and increase in gestational length, resp. Race, parity, and employment have an effect on BPA exposure. Because low birth weight is associated with adverse health outcomes, effect of early pregnancy BPA levels on reducing birth weight highlights the risk posed by developmental exposure to BPA.

Journal of Clinical Endocrinology and Metabolism 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 C10H9IO4, Synthetic Route of 267244-08-6.

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