Heterocyclic Building Blocks-Tetrahydrofuran

Evidence for a long-term influence on morphine tolerance after previous morphine exposure: role of neuronal glucocorticoid receptors was written by Lim, Grewo;Wang, Shuxing;Zeng, Qing;Sung, Backil;Mao, Jianren. And the article was included in Pain in 2005.Application of 6698-26-6 This article mentions the following:

Opioid analgesic tolerance is a pharmacol. phenomenon that overtime diminishes the opioid analgesic effect. However, it remains unknown as to whether a previous opioid exposure would have a long-term influence on opioid tolerance upon subsequent opioid administration. Here, we show that the onset and degree of antinociceptive tolerance to a subsequent cycle of morphine exposure were substantially exacerbated in rats made tolerant to and then recovered from previous morphine administration, indicating a long-term influence from a previous morphine exposure on the development of morphine tolerance. Mechanistically, morphine exposure induced a cAMP and protein kinase A-dependent upregulation of neuronal glucocorticoid receptors (GR) within the spinal cord dorsal horn, which was maintained after discontinuation of morphine administration and significantly enhanced upon a second cycle of morphine exposure. Prevention of the GR upregulation with GR antisense oligonucleotides as well as inhibition of GR activation with the GR antagonist RU38486 effectively prevented the exacerbated morphine tolerance after subsequent cycles of morphine exposure. The results indicate that a previous morphine exposure could induce lasting cellular changes mediated through neuronal GR and influence morphine analgesia upon a subsequent exposure. These findings may have significant implications in clin. opioid therapy and substance abuse. In the experiment, the researchers used many compounds, for example, (2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-methyltetrahydrofuran-3-ol (cas: 6698-26-6Application of 6698-26-6).

(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-methyltetrahydrofuran-3-ol (cas: 6698-26-6) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. Tetrahydrofuran can also be produced, or synthesised, via catalytic hydrogenation of furan. This process involves converting certain sugars into THF by digesting to furfural. An alternative to this method is the catalytic hydrogenation of furan with a nickel catalyst.Application of 6698-26-6

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Fluorescent Probes for Ecto-5′-nucleotidase (CD73) was written by Schmies, Constanze C.;Rolshoven, Georg;Idris, Riham M.;Losenkova, Karolina;Renn, Christian;Schaekel, Laura;Al-Hroub, Haneen;Wang, Yulu;Garofano, Francesca;Schmidt-Wolf, Ingo G. H.;Zimmermann, Herbert;Yegutkin, Gennady G.;Mueller, Christa E.. And the article was included in ACS Medicinal Chemistry Letters in 2020.Reference of 3056-18-6 This article mentions the following:

Ecto-5′-nucleotidase (CD73) catalyzes the hydrolysis of AMP to anti-inflammatory, immunosuppressive adenosine. It is expressed on vascular endothelial, epithelial, and also numerous cancer cells where it strongly contributes to an immunosuppressive microenvironment. In the present study we designed and synthesized fluorescent-labeled CD73 inhibitors with low nanomolar affinity and high selectivity based on N⁶-benzyl-α,β-methylene-ADP (PSB-12379) as a lead structure. Fluorescein was attached to the benzyl residue via different linkers resulting in PSB-19416 (14b, K_i 12.6 nM) and PSB-18332 (14a, K_i 2.98 nM) as fluorescent high-affinity probes for CD73. These compounds are anticipated to become useful tools for biol. studies, drug screening, and diagnostic applications. In the experiment, the researchers used many compounds, for example, (2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6Reference of 3056-18-6).

(2R,3R,4R,5R)-2-(Acetoxymethyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl diacetate (cas: 3056-18-6) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is water-miscible and has a low viscosity making it a highly versatile solvent used in a variety of industries. Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.Reference of 3056-18-6

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

One-pot synthesis of deoxyadenosine 3′-thiophosphates was written by Szczepanik, Maciej B.;Desaubry, Laurent;Johnson, Roger A.. And the article was included in Tetrahedron Letters in 1998.Electric Literature of C10H13N5O2 This article mentions the following:

A mild and efficient one-step method of thiophosphorylation was devised for acid-sensitive nucleosides. The procedure is based on thiophosphorylation of nucleoside magnesium alkoxide by 2-chloro-2-thio-1,3,2-dioxaphospholane. The utility and efficiency of this method combined with deprotection of the resulting cyclic triester was demonstrated by its application to the synthesis of both adenosine 3′- and 5′-thiophosphates. The procedure does not require protection of the exocyclic amino group and can be successfully used for the thiophosphorylation of nucleosides that are unusually sensitive to depurination. In the experiment, the researchers used many compounds, for example, (2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-methyltetrahydrofuran-3-ol (cas: 6698-26-6Electric Literature of C10H13N5O2).

(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-methyltetrahydrofuran-3-ol (cas: 6698-26-6) belongs to tetrahydrofuran derivatives. THF (Tetrahydrofuran) is a stable compound with relatively low boiling point and excellent solvency. Oxidations have also proved to be valuable and efficient approaches to chiral tetrahydrofuran derivatives.Electric Literature of C10H13N5O2

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Signal transduction by HLA class II molecules in human T cells: induction of LFA-1-dependent and independent adhesion was written by Odum, Niels;Yoshizumi, Hideyuki;Okamoto, Yasuhiro;Kamikawaji, Nobuhiro;Kimura, Akinori;Nishimura, Yasuharu;Sasazuki, Takehiko. And the article was included in Human Immunology in 1992.Name: (2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-methyltetrahydrofuran-3-ol This article mentions the following:

Crosslinking HLA-DR mols. by monoclonal antibodies (moAbs) induces protein tyrosine phosphorylation and results in a secondary elevation of free cytoplasmic calcium concentrations in activated human T cells. Binding of bacterial superantigens or moAbs to DR mols. on activated T cells was recently reported to induce homotypic aggregation through activation of protein kinase C (PKC) and mediated by CD11a/CD54 (LFA-1/CAM-1) adhesion mols. Here, the authors report that moAbs directed against framework DR, but neither DR1, 2- and DRw52- nor DQ- and DP-specific moABs induced homotypic aggregation of antigen- and alloantigen-activated T cells, antigen-specific CD4⁺ T-cell lines, a CD8⁺ T-cytotoxic cell line, and T-leukemia cells (HUT78). Protein tyrosine kinase (PTK) inhibitor herbimycin A partly blocked class-II-induced aggregation responses. In contrast, phorbol ester (PMA)-induced aggregation was essentially unaffected. A potent inhibitor of PKC, staurosporine, inhibited both moAb- and PMA-induced aggregation responses. The aggregation responses were completely inhibited by low temperatures, cytochalasins B and E, and partly inhibited by EDTA and CD18 moAbs, but unaffected by aphidicolin, mitomycin C, an adenylate cyclase inhibitor (2’5′-dideoxyadenosine), and moAbs against other adhesion mols. (CD2/CD58, CD28/B7, CD4, and CD44). In conclusion, HLA class-II-induced aggregation responses in activated T cells appear to involve PTK and PKC activation and to be mediated through CD11a-dependent and independent adhesion pathways. In the experiment, the researchers used many compounds, for example, (2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-methyltetrahydrofuran-3-ol (cas: 6698-26-6Name: (2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-methyltetrahydrofuran-3-ol).

(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-methyltetrahydrofuran-3-ol (cas: 6698-26-6) belongs to tetrahydrofuran derivatives. Tetrahydrofuran (THF), or oxolane, is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. Commercial tetrahydrofuran contains substantial water that must be removed for sensitive operations, e.g. those involving organometallic compounds. Although tetrahydrofuran is traditionally dried by distillation from an aggressive desiccant, molecular sieves are superior.Name: (2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-methyltetrahydrofuran-3-ol

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Differential acidimetric determination of the components of nucleic acids, their derivatives, and mixtures in a methyl cellosolve medium was written by Veveris, A.;Spince, B.;Smolova, N. T.. And the article was included in Zhurnal Analiticheskoi Khimii in 1981.Safety of Sodium ((2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate This article mentions the following:

The proton-acceptor properties of many purine and pyrimidine amino derivatives were examined in methyl cellosolve (MC). Dissociation constant values indicate that in spite of many H⁺-acceptor groups in these derivatives (NH₂, heterocyclic N), these compounds are protonated in MC and H₂O as monobasic compounds (except 6-histaminopurine). H⁺ may be attached to different groups depending on the structure of these derivatives In cytidine, the protonation is at the heterocyclic N at position 3, and adenosine and guanosine with different heterocycles are protonated at 1 (in pyrimidine) and 7 (in imidazole, resp.). The differences in the dissociation constants were large for cytosine and guanosine derivatives Procedures were developed for differential titrimetric procedures for these compounds in binary and ternary mixtures with HClO₄ in MC. In the experiment, the researchers used many compounds, for example, Sodium ((2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate (cas: 6757-06-8Safety of Sodium ((2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate).

Sodium ((2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate (cas: 6757-06-8) belongs to tetrahydrofuran derivatives. Tetrahydrofuran and dihydrofuran form the basic structural unit of many naturally occurring scaffolds like gambieric acid A and ciguatoxin, goniocin, and some biologically active molecules. Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.Safety of Sodium ((2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl phosphate

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Carbohydrate-based approach to four enantiomerically pure 2-naphthylmethyl 3-hydroxy-2-methylbutanoates was written by Doboszewski, Bogdan;Herdewijn, Piet. And the article was included in Tetrahedron Letters in 2008.Application of 114861-22-2 This article mentions the following:

Chiral pool approach using D-glucose, L-xylose, and D– and L-arabinoses was used to obtain four stereoisomeric 3-hydroxy-2-methylbutanoic acids with well defined configurations. The acids were isolated as fluorescent 2-naphthylmethyl esters after reaction with 2-naphthyldiazomethane. In the experiment, the researchers used many compounds, for example, (3aS,5S,6R,6aS)-5-(Hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 114861-22-2Application of 114861-22-2).

(3aS,5S,6R,6aS)-5-(Hydroxymethyl)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol (cas: 114861-22-2) belongs to tetrahydrofuran derivatives. Solid acid catalysis, and the advantages often associated with their use, have been proved equally efficient for the synthesis of tetrahydrofurans or furans. Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.Application of 114861-22-2

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Cordycepin, a metabolite of Cordyceps militaris, reduces immune-related gene expression in insects was written by Woolley, Victoria C.;Teakle, Graham R.;Prince, Gillian;de Moor, Cornelia H.;Chandler, David. And the article was included in Journal of Invertebrate Pathology in 2020.Electric Literature of C10H13N5O3 This article mentions the following:

Hypocrealean entomopathogenic fungi (EPF) (Sordariomycetes, Ascomycota) are natural regulators of insect populations in terrestrial environments. Their obligately-killing life-cycle means that there is likely to be strong selection pressure for traits that allow them to evade the effects of the host immune system. In this study, we quantified the effects of cordycepin (3′-deoxyadenosine), a secondary metabolite produced by Cordyceps militaris (Hypocreales, Cordycipitaceae), on insect susceptibility to EPF infection and on insect immune gene expression. Application of the immune stimulant curdlan (20μg ml^-1, linear beta-1,3-glucan, a constituent of fungal cell walls) to Drosophila melanogaster S2r+ cells resulted in a significant increase in the expression of the immune effector gene metchnikowin compared to a DMSO-only control, but there was no significant increase when curdlan was co-applied with 25μg ml^-1 cordycepin dissolved in DMSO. Injection of cordycepin into larvae of Galleria mellonella (Lepidoptera: Pyralidae) resulted in dose-dependent mortality (LC₅₀ of cordycepin = 2.1 mg per insect 6 days after treatment). Incubating conidia of C. militaris and Beauveria bassiana (Hypocreales, Cordycipitaceae; an EPF that does not synthesize cordycepin) with 3.0 mg ml^-1 cordycepin had no effect on the numbers of conidia germinating in vitro. Co-injection of G. mellonella with a low concentration of cordycepin (3.0 mg ml^-1) plus 10 or 100 conidia per insect of C. militaris or B. bassiana caused a significant decrease in insect median survival time compared to injection with the EPF on their own. Anal. of predicted vs. observed mortalities indicated a synergistic interaction between cordycepin and the EPF. The injection of C. militaris and B. bassiana into G. mellonella resulted in increased expression of the insect immune effector genes lysozyme, IMPI and gallerimycin at 72 h post injection, but this did not occur when the EPF were co-injected with 3.0 mg ml^-1 cordycepin. In addition, we observed increased expression of IMPI and lysozyme at 48 h after injection with C. militaris, B. bassiana and sham injection (indicating a wounding response), but this was also prevented by application of cordycepin. These results suggest that cordycepin has potential to act as a suppressor of the immune response during fungal infection of insect hosts. In the experiment, the researchers used many compounds, for example, (2R,3R,5S)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol (cas: 73-03-0Electric Literature of C10H13N5O3).

(2R,3R,5S)-2-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3-ol (cas: 73-03-0) belongs to tetrahydrofuran derivatives. Tetrahydrofuran and dihydrofuran form the basic structural unit of many naturally occurring scaffolds like gambieric acid A and ciguatoxin, goniocin, and some biologically active molecules. Oxidations have also proved to be valuable and efficient approaches to chiral tetrahydrofuran derivatives.Electric Literature of C10H13N5O3

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

C(sp³)-H oxygenation via alkoxypalladium(II) species: an update for the mechanism was written by Zhang, Shuaizhong;Zhang, Jinquan;Zou, Hongbin. And the article was included in Chemical Science in 2022.Electric Literature of C5H8O3 This article mentions the following:

In the present study of γ-C(sp³)-H acyloxylation of amine derivatives, a different mechanism was shown when tert-Bu hydroperoxide (TBHP) was used as an oxidant-namely, a bimetallic oxidative addition-oxo-insertion process. This catalytic model results in an alkoxypalladium(II) intermediate from which acyloxylation and alkoxylation products was formed. Exptl. and computational studies, including isolation of the putative post-oxo-insertion alkoxypalladium(II) intermediates, support this mechanistic model. D. functional theory revealed that the classical alkylpalladium(IV) oxidative addition pathway was higher in energy than the bimetallic oxo-insertion pathway. Further kinetic studies revealed second-order dependence on [Pd] and first-order on [TBHP], which was consistent with DFT anal. This procedure was compatible with a wide range of acids and alcs. for γ-C(sp³)-H oxygenation. Preliminary functional group transformations of the products underscore the great potential of this protocol for structural manipulation. In the experiment, the researchers used many compounds, for example, Tetrahydrofuran-2-carboxylic acid (cas: 16874-33-2Electric Literature of C5H8O3).

Tetrahydrofuran-2-carboxylic acid (cas: 16874-33-2) belongs to tetrahydrofuran derivatives. Tetrahydrofuran (THF) is a Lewis base that bonds to a variety of Lewis acids such as I2, phenols, triethylaluminum and bis(hexafluoroacetylacetonato)copper(II). THF (Tetrahydrofuran) is also used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.Electric Literature of C5H8O3

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

A quantitative systems approach reveals dynamic control of tRNA modifications during cellular stress was written by Chan, Clement T. Y.;Dyavaiah, Madhu;DeMott, Michael S.;Taghizadeh, Koli;Dedon, Peter C.;Begley, Thomas J.. And the article was included in PLoS Genetics in 2010.Application In Synthesis of 2-Amino-9-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-1H-purin-6(9H)-one This article mentions the following:

Decades of study have revealed more than 100 ribonucleoside structures incorporated as post-transcriptional modifications mainly in tRNA and rRNA, yet the larger functional dynamics of this conserved system are unclear. To this end, we developed a highly precise mass spectrometric method to quantify tRNA modifications in Saccharomyces cerevisiae. Our approach revealed several novel biosynthetic pathways for RNA modifications and led to the discovery of signature changes in the spectrum of tRNA modifications in the damage response to mechanistically different toxicants. This is illustrated with the RNA modifications Cm, m⁵C, and m² ₂G, which increase following hydrogen peroxide exposure but decrease or are unaffected by exposure to methylmethane sulfonate, arsenite, and hypochlorite. Cytotoxic hypersensitivity to hydrogen peroxide is conferred by loss of enzymes catalyzing the formation of Cm, m⁵C, and m² ₂G, which demonstrates that tRNA modifications are critical features of the cellular stress response. The results of our study support a general model of dynamic control of tRNA modifications in cellular response pathways and add to the growing repertoire of mechanisms controlling translational responses in cells. In the experiment, the researchers used many compounds, for example, 2-Amino-9-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-1H-purin-6(9H)-one (cas: 2140-71-8Application In Synthesis of 2-Amino-9-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-1H-purin-6(9H)-one).

2-Amino-9-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-1H-purin-6(9H)-one (cas: 2140-71-8) belongs to tetrahydrofuran derivatives. Solid acid catalysis, and the advantages often associated with their use, have been proved equally efficient for the synthesis of tetrahydrofurans or furans. THF can also be synthesized by catalytic hydrogenation of furan. This allows certain sugars to be converted to THF via acid-catalyzed digestion to furfural and decarbonylation to furan, although this method is not widely practiced. THF is thus derivable from renewable resources.Application In Synthesis of 2-Amino-9-((2R,3R,4R,5R)-4-hydroxy-5-(hydroxymethyl)-3-methoxytetrahydrofuran-2-yl)-1H-purin-6(9H)-one

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Normal and modified nucleosides in urine as potential tumor markers determined by MEKC and HPLC was written by Xu, Guowang;Liebich, Hartmut. And the article was included in American Clinical Laboratory in 2001.COA of Formula: C10H14N2O6 This article mentions the following:

A study was conducted which give further credence to previous observations that patterns of urinary excretion of modified nucleosides may serve as a useful diagnostic tool for malignant disease, especially when the pattern recognition method is used together with micellar electrokinetic capillary chromatog. or high-performance liquid chromatog. (HPLC). A major advantage for using the nucleosides as possible biomarkers lies in the MEKC or HPLC method. All of them can be accurately and quickly measured per individual urine and/or serum sample in one MEKC or HPLC run. Although further studies are needed, the use of modified nucleosides in combination with other biomarkers may have potential application as an adjunct to the clin. assessment of cancer patients. In the experiment, the researchers used many compounds, for example, 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3-methylpyrimidine-2,4(1H,3H)-dione (cas: 2140-69-4COA of Formula: C10H14N2O6).

1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3-methylpyrimidine-2,4(1H,3H)-dione (cas: 2140-69-4) belongs to tetrahydrofuran derivatives. Tetrahydrofuran and dihydrofuran form the basic structural unit of many naturally occurring scaffolds like gambieric acid A and ciguatoxin, goniocin, and some biologically active molecules. It is more basic than diethyl ether and forms stronger complexes with Li+, Mg2+, and boranes. It is a popular solvent for hydroboration reactions and for organometallic compounds such as organolithium and Grignard reagents.COA of Formula: C10H14N2O6

Referemce:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem