Category: tetrahydropyran

Hauck, Zane Z. published the artcileDetermination of bisphenol A-glucuronide in human urine using ultrahigh-pressure liquid chromatography/tandem mass spectrometry, Recommanded Product: (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 Rapid Communications in Mass Spectrometry (2016), 30(3), 400-406, database is CAplus and MEDLINE.

Rationale : Used widely as a plasticizer and as a monomer for plastics, bisphenol A (BPA) is under investigation as a possible endocrine disrupter. As an indication of systemic exposure, a fast and accurate assay was developed for the major BPA metabolite in human urine, BPA-monoglucuronide (BPA-G), using ultraHPLC/tandem mass spectrometry (UHPLC/MS/MS). Methods : Urine samples were prepared using solid-phase mixed-mode reversed-phase/anion-exchange extraction BPA-G was measured using UHPLC/MS/MS with an amide UHPLC column interfaced to a triple-quadrupole mass spectrometer equipped with neg. ion electrospray, collision-induced dissociation and selected reaction monitoring. [¹³C₁₂]-BPA-G was used as a surrogate standard Results : By measuring the glucuronide metabolite of BPA, potential interference due to BPA contamination from containers, solvents, pipet, etc., was avoided. The standard curve had a linear regression coefficient of 0.999, and the intra- and inter-assay variations were less than 10%. The assay was validated according to FDA guidelines. Conclusions : A fast, accurate, and highly selective method for the determination of BPA-G in human urine was developed and validated using UHPLC/MS/MS. This method is suitable for assessing human exposure to BPA. Copyright © 2016 John Wiley & Sons, Ltd.

Rapid Communications in Mass Spectrometry 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, Recommanded Product: (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

Trujillo, John I. published the artcileDesign and synthesis of novel CCR2 antagonists: investigation of non-aryl/heteroaryl binding motifs, Recommanded Product: 3-Fluorodihydro-2H-pyran-4(3H)-one, the publication is Bioorganic & Medicinal Chemistry Letters (2011), 21(6), 1827-1831, database is CAplus and MEDLINE.

This report describes the design and synthesis of a series of CCR2 antagonists incorporating novel non-aryl/heteroaryl RHS (right hand side) motifs e. g., I. Previous SAR in the area has suggested an aryl/heteroaryl substituent as a necessary structural feature for binding to the CCR2 receptor. Herein we describe the SAR with regards to potency (binding to hCCR2), dofetilide activity and metabolic stability (in vitro HLM) for this series. The resulting outcome was the identification of compounds with excellent properties for the investigation of the role of CCR2 in disease.

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 C12H14O2, Recommanded Product: 3-Fluorodihydro-2H-pyran-4(3H)-one.

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

Wegener, Michael published the artcileSilver-Free Activation of Ligated Gold(I) Chlorides: The Use of [Me₃NB₁₂Cl₁₁]^– as a Weakly Coordinating Anion in Homogeneous Gold Catalysis, SDS of cas: 27943-46-0, the publication is Chemistry – A European Journal (2015), 21(3), 1328-1336, database is CAplus and MEDLINE.

Phosphane and N-heterocyclic carbene ligated gold(I) chlorides can be effectively activated by Na[Me₃NB₁₂Cl₁₁] under silver-free conditions. This activation method with a weakly coordinating closo-dodecaborate anion was shown to be suitable for a large variety of reactions known to be catalyzed by homogeneous gold species, ranging from carbocyclization to heterocyclization. Addnl., the capability of Na[Me₃NB₁₂Cl₁₁] in a previously unknown conversion of 5-silyloxy-1,6-allenynes was demonstrated. The synthesis of the target compounds was achieved using sodium undecachloro(methanamine)dodecaborate as anion source and (triphenylphosphine)gold chloride, [[(1,1′-biphenyl]-2-yl)bis(1,1-dimethylethyl)phosphine](chloro)gold [Au(JohnPhos)cl], [μ-Bis(diphenylphosphino)methane]dichlorodigold, [1,3-Bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene](chloro)gold as catalysts.

Chemistry – A European Journal 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 C5H6N2O2, SDS of cas: 27943-46-0.

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

Arthur, H. R. published the artcileExamination of the Rutaceae of Hong Kong. I. Flavonold glycosides from Zanthoxylum species and the occurrence of optically active hesperetin, Synthetic Route of 69097-99-0, the publication is Journal of the Chemical Society (1956), 632-5, database is CAplus.

The barks of Zanthoxylum species of Hong Kong contained hesperidin (I) and diosmin (II). Hydrolysis of I yielded a mixture of (±)- (III) and (-)-hesperetin (IV) from which pure III and IV were isolated. III and IV were characterized, and IV was racemized. III was converted into diosmetin (V) with N-bromosuccinimide. It was coneluded that I was a β-7-rutinoside of IV. Dried bark (400) g.) of Z. avicennae extracted with refluxing MeOH; and the extract concentrated gave 2.4 g. solids; the filtrate on further concentration yielded 1.5 g. brown crystals. The first crop extracted with light petroleum and then with MeOH and the residue crystallized gave II hydrate, m. 280° (decomposition) (from 50% aqueous C₅H₅N). The 2nd crop similarly treated yielded I hydrate, m. 260° (decomposition), [α]_D²⁷ -88.2° (c 1.24, C₅H₅N), and some more II hydrate. II (5 g.) left 4 days at room temperature with Ac₂O-C₅H₅N, and the product crystallized from alc. and refluxed 2 hrs. with 5 ml. H₂SO₄ and 95 ml. alc. gave V, m. 253.0-4.5° (from alc.); triacetate, m. 189-91°; both compounds gave a red test with Mg-HCl-MeOH. V was also prepared from the hydrolysis of II in (CH₂OH)₂ by the method used for the hydrolysis of I. I (10 g.) refluxed 2 hrs. with 6% NaOH yielded isoferulic acid, m. 228-9°, pos. test with FeCl₃; acetate, m. 204-5°. I (5 g.) treated at room temperature with Ac₂O-C₅H₅N gave the acetate, C₄₄H₅₀O₂₃, m. 176-9° (from alc.). I (5 g.) and 100 ml. (CH₂OH)₂ containing 5 ml. concentrated H₂SO₄ treated 40 min. in the H₂O bath gave 1.8 g. of a mixture of III and IV, m. 224-6°, [α]_D²⁶ -16.9° (c 1.42, EtOH). I (4 g.), hydrolyzed by refluxing in dilute H₂SO₄ 20 hrs., gave a mixture of III and IV, and from the filtrate glucose and rhamnose were isolated and identiffed as their osazones. The mixture (20 g.) of III and IV fractionally crystallized from EtOH by the triangular scheme gave 2.2 g. III as hexagonal prisms, m. 226-8°, [α]_D²⁷ 0.0° (c 1.56, EtOH), and 2.5 g. IV as the more-soluble fraction, triangular plates, m. 216-18°, [α]_D²⁷ -37.6° (c 1.80, EtOH). The following III derivatives were prepared: 4′,7-di-Me ether, m. 132-3°; oxime, m. 227-8° (decomposition); triacetate, m. 139-41°. IV derivatives 4′,7-di-Me ether, m. 149-51° [α]_D²⁸ -35.6° (c 1.04, CHCl₃); oxime, m. 219-20° (decomposition), [α]_D²⁷ -16.1° (c 0.40, EtOH); triacetate, m. 130-2°, [α]_D²⁶ 21.1° (c 1.28, CHCl₃). III and IV and their derivatives gave a red solution with Mg-HCl-MeOH. IV (0.4 g.) in 5 ml. (CH₂OH)₂ heated 2 hrs. at 250-60° in a sealed tube gave 0.1 g. III. Solutions of IV left 3 days in EtOH-NaOH or Et-OH-HCl did not racemize. III triacetate (0.9 g.), 0.45 g. N-bromosuccinimide, and 0.05 g. Bz₂O₂ heated 1 hr., 0.3 g. more N-bromosuccinimide added, the succinimide recovered the next morning, the filtrate concentrated, and the residue washed with hot H₂O and crystallized gave 0.08 g. V, m. and mixed m.p. 250-3°. The dried bark of Z. cuspidatum gave I hydrate. II was isolated from the root bark of Z. nitidum. I and II were not isolated from the bark of the last species.

Journal of the Chemical Society 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, Synthetic Route of 69097-99-0.

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

Sun, Dianqing published the artcileEvaluation of Flavonoid and Resveratrol Chemical Libraries Reveals Abyssinone II as a Promising Antibacterial Lead, Quality Control of 69097-99-0, the publication is ChemMedChem (2012), 7(9), 1541-1545, database is CAplus and MEDLINE.

As part of our ongoing effort to discover novel antitubercular and antibacterial agents and to exploit natural products as scaffolds for chem. diversity, we have been interested in following up emerging and underexplored naturally occurring compounds showing good antimicrobial activities. In this regard, natural phytochems. are actively being pursued for their antibacterial properties. We subsequently screened the collated flavonoid and resveratrol library against M. tuberculosis and a panel of Gram-pos. and Gram-neg. bacterial pathogens, including Enterococcus faecalis, S. aureus, S. pneumoniae, Klebsiella pneumoniae, Acine-tobacter baumannii, Escherichia co/i, and P. aeruginosa. In conclusion, the systematic screening of a focused flavonoid and resveratrol library led to the identification of abyssinone II as an anti-Gram-pos. agent that could potentially have a multitargeted mode of action, resulting from its ability to target the bacterial membrane. Such agents are increasingly becoming attractive therapeutic options owing to their potent actions, likely multitarget effects and limited potential for resistance development. The characterization of abyssinone II as a membrane-targeting mol. therefore makes it a promising natural product lead, ideal for further medicinal chem. optimization to identify advanced exptl. candidates with antimicrobial therapeutic potential.

ChemMedChem 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 C65H82N2O18S2, Quality Control of 69097-99-0.

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

Nanayakkara, N. P. Dhammika published the artcilePotential sweetening agents of plant origin. 13. An intensely sweet dihydroflavonol derivative based on a natural product lead compound, Product Details of C16H14O6, the publication is Journal of Medicinal Chemistry (1988), 31(6), 1250-3, database is CAplus and MEDLINE.

Dihydroquercetin 3-acetate [(2R,3R)-I; R = Ac, R¹ = H] (II) was isolated as a sweet constituent of the young shoots of Tessaria dodoneifolia (Hook. & Arn.) Cabrera (Compositae). II and I (R = Ac, R¹ = Me), a novel synthetic analog of II, were rated by a taste panel as being 80 and 400 times sweeter resp. than a 2% sucrose solution Synthetic I (R = H, R¹ = Me) showed a reduced sweetness intensity compared to I (R = Ac, R¹ = Me) and (+)-dihydroquercetin was devoid of sweetness. I represent a new class of potentially noncaloric and noncariogenic intense sweeteners. I (R = Ac, R¹ = Me) was prepared from acetophenone and benzaldehyde components in 5 steps. I (R = H, R¹ = Me) was obtained from hesperetin by ring cleavage with PhCH₂Cl, epoxidation and ring closure.

Journal of Medicinal 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, Product Details of C16H14O6.

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

Baggiolini, Enrico G. published the artcileStereocontrolled total synthesis of 1α,25-dihydroxycholecalciferol and 1α,25-dihydroxyergocalciferol, Category: tetrahydropyran, the publication is Journal of Organic Chemistry (1986), 51(16), 3098-108, database is CAplus.

1α,25-Dihydroxycholecalciferol and 1α,25-dihydroxyergocalciferol, the hormonally active forms of vitamin D₃ and vitamin D₂, were prepd by Horner-Wittig reaction of the phosphine oxide I [R = CH₂P(O)Ph₂] (II) with ketones III and IV, resp. The synthon III was obtained via stereospecific opening of epoxide V with NaOAc in AcOH followed by oxidative degradation of the isopropenyl side chain and dehydration of the intermediate VI. Photoisomerization of the resulting (E)-I (R = CO₂Et) gave I (R = CO₂Et), which was converted to II. III was obtained from the known intermediate VII. The introduction of the 25-hydroxy side chain was achieved by reaction of the lithium derivative of HCCCMe₂OR¹ (R¹ = tetrahydropyranyl) with the tosylate of VII; subsequent hydrogenation, deblocking, and oxidation reactions gaave III. IV was prepared by a stereocontrolled route that involves as the key step the [3 + 2] dipolar cycloaddition of nitrone VII with Me₂C:CHCO₂Me to give a 1:1 mixture of isoxazolidines IX. Stereochem. control was achieved by taking advantage of the thermal reversibility of the cycloaddition, which allows the reequilibration of undersired IX. (23S, 24S)-IX was readily transformed to amine X by reduction, followed by elimination of the nitrogen function, and finally oxidation to IV.

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

Kahyo, Tomoaki published the artcileA novel chalcone polyphenol inhibits the deacetylase activity of SIRT1 and cell growth in HEK293T cells, Synthetic Route of 69097-99-0, the publication is Journal of Pharmacological Sciences (Tokyo, Japan) (2008), 108(3), 364-371, database is CAplus and MEDLINE.

SIRT1 is one of seven mammalian orthologs of yeast silent information regulator 2 (Sir2), and it functions as a NAD (NAD)-dependent deacetylase. Recently, resveratrol and its analogs, which are polyphenols, have been reported to activate the deacetylase activity of SIRT1 in an in vitro assay and to expand the life-span of several species through Sir2 and the orthologs. To find activators or inhibitors to SIRT1, we examined thirty-six polyphenols, including stilbenes, chalcones, flavanones, and flavonols, with the SIRT1 deacetylase activity assay using the acetylated peptide of p53 as a substrate. The results showed that 3,2′,3′,4′-tetrahydroxychalcone, a newly synthesized compound, inhibited the SIRT1-mediated deacetylation of a p53 acetylated peptide and recombinant protein in vitro. In addition, this agent induced the hyperacetylation of endogenous p53, increased the endogenous p21^CIP1/WAF1 in intact cells, and suppressed the cell growth. These results indicated that 3,2′,3′,4′-tetrahydroxychalcone had a stronger inhibitory effect on the SIRT1-pathway than sirtinol, a known SIRT1-inhibitor. Our results mean that 3,2′,3′,4′-tetrahydroxychalcone is a novel inhibitor of SIRT1 and produces physiol. effects on organisms probably through inhibiting the deacetylation by SIRT1.

Journal of Pharmacological Sciences (Tokyo, Japan) 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, Synthetic Route of 69097-99-0.

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

Hirano, Yutaka published the artcileSteroid studies. 77. Synthesis of (22R- and (22S)-22,25-dihydroxyvitamin D₃ and determination of their biological activity, Name: 2-((2-Methylbut-3-yn-2-yl)oxy)tetrahydro-2H-pyran, the publication is Chemical & Pharmaceutical Bulletin (1981), 29(8), 2254-60, database is CAplus and MEDLINE.

Bisnorcholenal 3-tetrahydropyranyl ether was coupled with the lithium acetylide derived from 2-methyl-3-butyn-2-ol tetrahydropyranyl ether to give a 74% yield of a 1:1 mixture of the cholest-5-ene-3β,22,25-trihydroxy-23-yne 3,25-bis(tetrahydropyranyl)ethers. After resolution of the C-22 epimers and determination of their configurations, both isomers were converted into 22,25-dihydroxycholesterol 3,22-diacetates and into 25-hydroxy-22-methoxycholesterol 3-acetates. These compounds were converted to (22R)- and (22S)-22,25-dihydroxyvitamin D₃ and to 25-hydroxy-22-methoxyvitamin D₃. Biol. activity of these vitamin D₃ derivatives were determined

Chemical & Pharmaceutical Bulletin 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

Narukawa, Junichi published the artcileGlucuronidation of 1-naphthol and excretion into the vein in perfused rat kidney, Related Products of tetrahydropyran, the publication is Drug Metabolism and Disposition (2004), 32(7), 758-761, database is CAplus and MEDLINE.

UDP-glucuronosyltransferase is expressed in the proximal convoluted tubular cells of rat kidney. Kidney perfusion with a Krebs-Henseleit buffer containing 1-naphthol was performed to estimate the dynamics and disposition of the glucuronide conjugate formed in the epithelial cells of the renal tubules. When 1-naphthol was injected into the renal artery, and the perfusate from the renal vein was returned to a reservoir and recirculated through the kidney preparation (recirculating perfusion), most of the 1-naphthol was immediately excreted into the vein as a glucuronide conjugate and its concentration increased rapidly. In contrast, the 1-naphthol glucuronide appeared more slowly in the urine. 1-Naphthol was also injected during the initial 5 min of perfusion under single-pass perfusion conditions (single-pass perfusion) in situ, and the metabolite and parent compound in the venous perfusate and in urine were assayed. Under this condition, most of the 1-naphthol glucuronide was excreted into the renal vein, and not urine. Phenol UDP-glucuronosyltransferase was highly induced in the rat kidney by β-naphthoflavone treatment. Moreover, the amount of 1-naphthol glucuronide excreted in the renal vein was increased 2.7-fold in the perfused kidney of β-naphthoflavone-treated rats, but the amount in the urine was not significantly increased under single-pass perfusion conditions. These results indicate that the kidney can glucuronidate phenolic xenobiotics in epithelial cells of the tubules and excrete the resultant glucuronide into the renal vein.

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, Related Products of tetrahydropyran.

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