Heterocyclic Building Blocks-Tetrahydropyran

Further insight into the mechanism of human PMN lysis following phagocytosis of Staphylococcus aureus was written by Rungelrath, Viktoria;Porter, Adeline R.;Malachowa, Natalia;Freedman, Brett A.;Leung, Jacqueline M.;Voyich, Jovanka M.;Otto, Michael;Kobayashi, Scott D.;DeLeo, Frank R.. And the article was included in Microbiology Spectrum in 2021.Computed Properties of C56H92O29 This article mentions the following:

Staphylococcus aureus is an important human pathogen that can cause a variety of diseases ranging from mild superficial skin infections to life-threatening conditions like necrotizing pneumonia, endocarditis, and septicemia. Polymorphonuclear leukocytes (PMNs; neutrophils in particular herein) are essential for host defense against S. aureus infections, and the microbe is phagocytosed readily. Most ingested bacteria are killed, but some S. aureus strains-such as the epidemic USA300 strain- have an enhanced ability to cause PMN lysis after phagocytosis. Although progress has been made, the mechanism for lysis after phagocytosis of S. aureus remains incompletely determined Here, we tested the hypothesis that disruption of phagosome integrity and escape of S. aureus from the PMN phagosome into the cytoplasm precedes PMN lysis. We used USA300 wild-type and isogenic deletion strains to evaluate and/or verify the role of selected S. aureus mols. in this cytolytic process. Compared to the wild-type USA300 strain, Δagr, Δhla, ΔlukGH, and Δpsm strains each caused significantly less lysis of human PMNs 3 h and/or 6 h after phagocytosis, consistent with previous studies. Most notably, confocal microscopy coupled with selective permeabilization assays demonstrated that phagosome membrane integrity is largely maintained prior to PMN lysis after S. aureus phagocytosis. We conclude that PMN lysis does not require escape of S. aureus from the phagosome to the cytoplasm and that these are independent phenomena. The findings are consistent with the ability of S. aureus (via selected mols.) to trigger lysis of human PMNs by an undetermined signaling mechanism. In the experiment, the researchers used many compounds, for example, Digitonin (cas: 11024-24-1Computed Properties of C56H92O29).

Digitonin (cas: 11024-24-1) belongs to tetrahydropyran derivatives. In organic synthesis, the 2-tetrahydropyranyl group is used as a protecting group for alcohols. 2-(Arylmethylene)cyclopropylcarbinols could be converted to the corresponding tetrahydropyrans stereoselectively in the presence of Brønsted acids under mild conditions. A plausible Prins-type reaction mechanism has been proposed.Computed Properties of C56H92O29

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Early exposure of pregnant women to non-steroidal anti-inflammatory drugs delivered outside hospitals and preterm birth risk: nationwide cohort study was written by Quantin, C.;Yamdjieu Ngadeu, C.;Cottenet, J.;Escolano, S.;Bechraoui-Quantin, S.;Rozenberg, P.;Tubert-Bitter, P.;Gouyon, J-B.. And the article was included in BJOG in 2021.Related Products of 41340-25-4 This article mentions the following:

To assess the risk of preterm birth associated with nonsteroidal anti-inflammatory drugs (NSAIDs), focusing on early exposure in the period from conception to 22 wk of gestation (WG). National population-based retrospective cohort study. The French National Health Insurance Database that includes hospital discharge data and health claims data. Singleton pregnancies (2012-2014) with a live birth occurring after 22WG from women between 15 and 45 years old and insured the year before the first day of gestation and during pregnancy were included. We excluded pregnancies for which anti-inflammatory medications were dispensed after 22WG. The association between exposure and risk of preterm birth was evaluated with GEE models, adjusting on a large number of covariables, socio-demog. variables, maternal comorbidities, prescription drugs and pregnancy complications. Main outcome measures : Prematurity, defined as a birth that occurred before 37WG. Among our 1 598 330 singleton pregnancies, early exposure to non-selective NSAIDs was associated with a significantly increased risk of preterm birth, regardless of the severity of prematurity: adjusted odds ratio (aOR) = 1.76 (95CI 1.54-2.00) for extreme prematurity (95CI 22-27WG), 1.28 (95CI 1.17-1.40) for moderate prematurity (28-31WG) and 1.08 (95CI 1.05-1.11) for late prematurity (32-36WG), with non-overlapping confidence intervals. We identified five NSAIDs for which the risk of premature birth was significantly increased: ketoprofen, flurbiprofen, nabumetone, etodolac and indomethacin: for the latter, aOR = 1.92 (95CI 1.37-2.70) with aOR = 9.33 (95CI 3.75-23.22) for extreme prematurity. Overall, non-selective NSAID use (delivered outside hospitals) during the first 22WG was found to be associated with an increased risk of prematurity. However, the association differs among NSAIDs. French study for which early exposure to non-selective NSAIDs was associated with increased risk of prematurity. In the experiment, the researchers used many compounds, for example, 2-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid (cas: 41340-25-4Related Products of 41340-25-4).

2-(1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-yl)acetic acid (cas: 41340-25-4) belongs to tetrahydropyran derivatives. Numerous natural products have tetrahydropyran skeleton as the building block for designing new natural products and their derivatives e.g. aplysiatoxins, avermectins, oscillatoxins, talaromycins, latrunculins and acutiphycins. The Prins reaction of homoallylic alcohols with aldehydes afforded an alternative method for the preparation of tetrahydropyrans.Related Products of 41340-25-4

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Diverse Effects on M₁ Signaling and Adverse Effect Liability within a Series of M₁ Ago-PAMs was written by Rook, Jerri M.;Abe, Masahito;Cho, Hyekyung P.;Nance, Kellie D.;Luscombe, Vincent B.;Adams, Jeffrey J.;Dickerson, Jonathan W.;Remke, Daniel H.;Garcia-Barrantes, Pedro M.;Engers, Darren W.;Engers, Julie L.;Chang, Sichen;Foster, Jarrett J.;Blobaum, Anna L.;Niswender, Colleen M.;Jones, Carrie K.;Conn, P. Jeffrey;Lindsley, Craig W.. And the article was included in ACS Chemical Neuroscience in 2017.Application In Synthesis of (3S,4S)-3-Aminotetrahydro-2H-pyran-4-ol This article mentions the following:

Both historical clin. and recent preclin. data suggest that the M1 muscarinic acetylcholine receptor is an exciting target for the treatment of Alzheimer’s disease and the cognitive and neg. symptom clusters in schizophrenia; however, early drug discovery efforts targeting the orthosteric binding site have failed to afford selective M1 activation. Efforts then shifted to focus on selective activation of M1 via either allosteric agonists or pos. allosteric modulators (PAMs). While M1 PAMs have robust efficacy in rodent models, some chemotypes can induce cholinergic adverse effects (AEs) that could limit their clin. utility. Here, the authors report studies aimed at understanding the subtle structural and pharmacol. nuances that differentiate efficacy from adverse effect liability within an indole-based series of M1 ago-PAMs. The authors’ data demonstrate that closely related M1 PAMs can display striking differences in their in vivo activities, and especially their propensities to induce adverse effects. The authors report the discovery of a novel PAM in this series that is devoid of observable adverse effect liability. Interestingly, the mol. pharmacol. profile of this novel PAM is similar to that of a representative M1 PAM that induces severe AEs. For instance, both compounds are potent ago-PAMs that demonstrate significant interaction with the orthosteric site (either bi-topic or neg. cooperativity). However, there are subtle differences in efficacies of the compounds at potentiating M1 responses, agonist potencies, and abilities to induce receptor internalization. While these differences may contribute to the differential in vivo profiles of these compounds, the in vitro differences are relatively subtle and highlight the complexities of allosteric modulators and the need to focus on in vivo phenotypic screening to identify safe and effective M1 PAMs. In the experiment, the researchers used many compounds, for example, (3S,4S)-3-Aminotetrahydro-2H-pyran-4-ol (cas: 1240390-32-2Application In Synthesis of (3S,4S)-3-Aminotetrahydro-2H-pyran-4-ol).

(3S,4S)-3-Aminotetrahydro-2H-pyran-4-ol (cas: 1240390-32-2) belongs to tetrahydropyran derivatives. Tetrahydropyran is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuff. The most notable anticancer agent, bryostatin, and eribulin are marine macrolides having intriguing tetrahydropyran and furan motif. Application In Synthesis of (3S,4S)-3-Aminotetrahydro-2H-pyran-4-ol

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Photoinduced Copper-Catalyzed Asymmetric Three-Component Coupling of 1,3-Dienes: An Alternative to Kharasch-Sosnovsky Reaction was written by Wang, Peng-Zi;Wu, Xue;Cheng, Ying;Jiang, Min;Xiao, Wen-Jing;Chen, Jia-Rong. And the article was included in Angewandte Chemie, International Edition in 2021.Product Details of 5337-03-1 This article mentions the following:

Herein, an alternative to the asym. Kharasch-Sosnovsky reaction that utilized a chiral copper catalyst and purple-LED irradiation to enable the three-component coupling of 1,3-dienes RCH=CHC(R¹)=CHR² (R = H, Me; R¹ = H, Me; R² = Ph, 2-phenylethyl, furan-3-yl, etc.), oxime esters I (R³ = H, Me; R⁴ = H; R³R⁴ = -CH=CH-CH=CH-; R⁵ = H; R⁴R⁵ = -CH₂N(Boc)CH₂-, -(CH₂)₂N(Boc)(CH₂)₂-), and carboxylic acids R⁶C(O)OH (R⁵ = t-Bu, Ph, 2H-1,3-benzodioxol-5-yl, etc.) is reported. This protocol features mild conditions, remarkable scope and functional group tolerance as evidenced by >80 examples and utility in the late-stage modification of pharmaceuticals and natural products. Detailed mechanistic studies provide evidences for the radical-based reaction pathway. In the experiment, the researchers used many compounds, for example, Tetrahydropyran-4-yl-carboxylic acid (cas: 5337-03-1Product Details of 5337-03-1).

Tetrahydropyran-4-yl-carboxylic acid (cas: 5337-03-1) belongs to tetrahydropyran derivatives. Dihydropyrans and tetrahydropyrans are examples of cyclic ethers widespread in nature. The most notable anticancer agent, bryostatin, and eribulin are marine macrolides having intriguing tetrahydropyran and furan motif. Product Details of 5337-03-1

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Pregnane X receptor promotes liver enlargement in mice through the spatial induction of hepatocyte hypertrophy and proliferation was written by Tian, Jianing;Wang, Ruimin;Yang, Xiao;Yang, Jie;Zhang, Yifei;Li, Xuan;Liang, Hangfei;Fan, Shicheng;Gao, Yue;Zhang, Simin;Qu, Xiangyang;Huang, Min;Bi, Huichang. And the article was included in Chemico-Biological Interactions in 2022.COA of Formula: C56H92O29 This article mentions the following:

Nuclear receptor pregnane X receptor (PXR) can induce significant liver enlargement through hepatocyte hypertrophy and proliferation. A previous report showed that during the process of PXR-induced liver enlargement, hepatocyte hypertrophy occurs around the central vein (CV) area while hepatocyte proliferation occurs around the portal vein (PV) area. However, the features of this spatial change remain unclear. Therefore, this study aims to explore the features of the spatial changes in hepatocytes in PXR-induced liver enlargement. PXR-induced spatial changes in hepatocyte hypertrophy and proliferation were confirmed in C57BL/6 mice. The liver was perfused with digitonin to destroy the hepatocytes around the CV or PV areas, and then the regional expression of proteins related to hepatocyte hypertrophy and proliferation was further measured. The results showed that the expression of PXR downstream proteins, such as cytochrome P 450 (CYP) 3A11, CYP2B10, P-glycoprotein (P-gp) and organ anion transporting polypeptide 4 (OATP4) was upregulated around the CV area, while the expression of proliferation-related proteins such as cyclin B1 (CCNB1), cyclin D1 (CCND1) and serine/threonine NIMA-related kinase 2 (NEK2) was upregulated around the PV area. At the same time, the expression of cyclin-dependent kinase inhibitors such as retinoblastoma-like protein 2 (RBL2), cyclin-dependent kinase inhibitor 1B (CDKN1B) and CDKN1A was downregulated around the PV area. This study demonstrated that the spatial change in PXR-induced hepatocyte hypertrophy and proliferation is associated with the regional expression of PXR downstream targets and proliferation-related proteins and the regional distribution of triglycerides (TGs). These findings provide new insight into the understanding of PXR-induced hepatomegaly. In the experiment, the researchers used many compounds, for example, Digitonin (cas: 11024-24-1COA of Formula: C56H92O29).

Digitonin (cas: 11024-24-1) belongs to tetrahydropyran derivatives. Tetrahydropyran is a useful synthetic intermediate. Tetrahydropyranyl (THP-) ethers derived from the reaction of alcohols and dihydropyran are common intermediates in organic synthesis. 2-(Arylmethylene)cyclopropylcarbinols could be converted to the corresponding tetrahydropyrans stereoselectively in the presence of Brønsted acids under mild conditions. A plausible Prins-type reaction mechanism has been proposed.COA of Formula: C56H92O29

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Ab Initio Examination of Anomeric Effects in Tetrahydropyrans, 1,3-Dioxanes, and Glucose was written by Salzner, Ulrike;Schleyer, Paul v. R.. And the article was included in Journal of Organic Chemistry in 1994.Application In Synthesis of 2-Methoxytetrahydro-2H-pyran This article mentions the following:

Axial and equatorial structures of 2-methyl-, 2-hydroxy-, 2-methoxy-, 2-amino-, 2-fluoro-, and 2-chlorotetrahydropyran, of the 2-tetrahydropyranylammonium cation, of 2-methyl-, 2-hydroxy, and 2-methoxy-1,3-dioxane, and of the corresponding cyclohexanes have been fully optimized at the HF/6-31G^* level. NBO anal. of the Hartree-Fock wave functions confirms that the anomeric effects of hydroxy-, methoxy-, fluoro-, and chloropyrans and of glucose and Me glucoside are indeed due to hyperconjugation. In cyclohexane, tetrahydropyran, and glucose theor. ΔE values involving the OH and OMe substituents are nearly identical. The exptl. observed differences of about 1 kcal/mol in the ΔH° and ΔG° values of the OH and OMe compounds are very likely due to solvent interactions involving the OH group. In the gas phase glucose orients its ring hydroxy groups and the CH₂OH group differently than in the crystal. The structures observed in the crystal lead to 7.9 kcal/mol higher energies. This might be rationalized by the fact that the isolated mol. tries to maximize the number of intramol. hydrogen bonds. 2-Hydroxy-1,3-dioxane prefers an equatorial conformation. NBO anal. reveals that the exo-anomeric effect favoring the equatorial form dominates over the endo-anomeric effect in dioxanes. In contrast, 2-methoxy-1,3-dioxane shows an axial preference which is not due to hyperconjugation. The reverse anomeric effect in 2-aminotetrahydropyran is due to steric repulsions because the axial conformation with the largest hyperconjugation contribution requires one of the NH₂ hydrogens to point above the ring. The equatorial preference of NH₃⁺ is a result of steric and other (probably electrostatic) contributions, since hyperconjugation strongly favors the axial conformation. For all cases for which the hyperconjugation contributions are overcompensated by the Lewis energies, steric repulsions are also indicated by significant ring distortions. Dipole moments correlate with relative energies qual. in some cases, but a quant. relationship cannot be ascertained. Single point calculations with Huzinaga basis sets reveal that at the HF/6-31G^* level axial-equatorial energy differences of all compounds considered in this investigation are biased toward axial structures by 0.5-1 kcal/mol. Thus, the 6-31G^* basis set fails to reproduce the small equatorial preference of 2-fluorohexane at the HF as well as at correlated levels. In the experiment, the researchers used many compounds, for example, 2-Methoxytetrahydro-2H-pyran (cas: 6581-66-4Application In Synthesis of 2-Methoxytetrahydro-2H-pyran).

2-Methoxytetrahydro-2H-pyran (cas: 6581-66-4) belongs to tetrahydropyran derivatives. Dihydropyrans and tetrahydropyrans are examples of cyclic ethers widespread in nature. The reaction of tertiary 1,4- and 1,5-diols with cerium ammonium nitrate at room temperature gives tetrahydrofuran and tetrahydropyran derivatives in high yield and stereoselectivity. Various fragrant compounds have been synthesized using this method.Application In Synthesis of 2-Methoxytetrahydro-2H-pyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Stereoselective gem-C,B-Glycosylation via 1,2-Boronate Migration was written by Zhao, Wei-Cheng;Li, Rui-Peng;Ma, Chao;Liao, Qi-Ying;Wang, Miao;He, Zhi-Tao. And the article was included in Journal of the American Chemical Society in 2022.HPLC of Formula: 6581-66-4 This article mentions the following:

A novel protocol is established for the long-standing challenge of stereoselective geminal bis-glycosylations of saccharides. The merger of PPh₃ as a traceless glycosidic leaving group and 1,2-boronate migration enables the simultaneous introduction of C-C and C-B bonds at the anomeric stereogenic center of furanoses and pyranoses. The power of this method is showcased by a set of site-selective modifications of glycosylation products for the construction of bioactive conjugates and skeletons. A scarce metal-free 1,1-di-functionalization process of alkenes is also concomitantly demonstrated. In the experiment, the researchers used many compounds, for example, 2-Methoxytetrahydro-2H-pyran (cas: 6581-66-4HPLC of Formula: 6581-66-4).

2-Methoxytetrahydro-2H-pyran (cas: 6581-66-4) belongs to tetrahydropyran derivatives. Tetrahydropyran is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuff. The most notable anticancer agent, bryostatin, and eribulin are marine macrolides having intriguing tetrahydropyran and furan motif. HPLC of Formula: 6581-66-4

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

Formulation, phytochemical estimation of active principles by spectroscopic methods and comparison of the poly herbal anti-diabetic tablet with the commercial tablets was written by Chauhan, Nidhi N.;Mistry, Rujuta;Vasava, Parul;Mandale, Drasti. And the article was included in International Journal of Pharmaceutical Sciences and Drug Research in 2021.Category: tetrahydropyran This article mentions the following:

Diabetes mellitus is a group of metabolic disorders characterized by increased glucose levels over a prolonged period. The poly-herbal anti-diabetic tablet was formulated in the laboratory by using herbs of Enicostemma littorale (EL) (Gentianaceae), roots of Aconitum heterophyllum (AH) (Ranunculaceae), rhizomes of Picrorhiza kurroa (PK) (Scrophulariaceae), and fruits of Piper longum (PL) (Piperaceae). Furthermore, Laboratory formulation (LF) and Marketed formulations (MFs) were tested for Phytochem. screening and Qual. chem. examination From their result, isolation of active principles, Swertiamarin (EL-1) and Piperine (PN-1), was done and subjected to phytochem. examination by Modern anal. methods like TLC, UV, FTIR. Finally, the quantification and estimation of the afore-mentioned compounds were achieved by HPTLC. SSE of all the four formulations and the chem. tests proved alkaloids, flavonoids, carbohydrates, tannins, phenols and phytosterols. Comparing the data from the m.p., TLC, UV, and IR studies of EL-1 and PN-1 with standard Biomarkers, further calculation of both markers concentrations was done with the help of the calibration equation and the peak area derived from the chromatogram. Study outcomes signify that LF was more potent than MFs for anti-diabetic activity, signifying as a promising natural and safe remedy for the prevention of diabetic complications. In the experiment, the researchers used many compounds, for example, (4aR,5R,6S)-4a-Hydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-4,4a,5,6-tetrahydropyrano[3,4-c]pyran-1(3H)-one (cas: 17388-39-5Category: tetrahydropyran).

(4aR,5R,6S)-4a-Hydroxy-6-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-5-vinyl-4,4a,5,6-tetrahydropyrano[3,4-c]pyran-1(3H)-one (cas: 17388-39-5) belongs to tetrahydropyran derivatives. Tetrahydropyran is an important raw material and intermediate used in Organic Synthesis, Pharmaceuticals, Agrochemicals and dyestuff. The bismuth chloride-assisted cross-cyclization between homoallylic alcohols and epoxides provided various benzyl tetrahydropyran derivatives. The reaction afforded good yields of desired products and occurred under mild conditions.Category: tetrahydropyran

Referemce:
Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics