Heterocyclic Building Blocks-Tetrahydrofuran

Development of modified nucleosides that have supremely high anti-HIV activity and low toxicity and prevent the emergence of resistant HIV mutants was written by Ohrui, Hiroshi. And the article was included in Proceedings of the Japan Academy, Series B: Physical and Biological Sciences in 2011.Quality Control of (2R,3S,5R)-5-(6-Amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3-ol This article mentions the following:

An idea to use 4′-C-substituted-2′-deoxynucleoside derivatives was proposed based on a working hypothesis to solve the problems of existing acquired immune deficiency syndrome chemotherapy (highly active antiretroviral therapy). Subsequent studies have successfully proved the validity of the idea and resulted in the development of 2′-deoxy-4′-G-ethynyl-2-fluoroadenosine and 2′-deoxy-4′-C-ethynyl-2-chloroadenosine, nucleoside reverse transcriptase inhibitors, which have supremely high activity against all human immunodeficiency viruses including multidrug-resistant HIV and low toxicity. In the experiment, the researchers used many compounds, for example, (2R,3S,5R)-5-(6-Amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3-ol (cas: 865363-93-5Quality Control of (2R,3S,5R)-5-(6-Amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3-ol).

(2R,3S,5R)-5-(6-Amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3-ol (cas: 865363-93-5) 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. THF (Tetrahydrofuran) is also used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.Quality Control of (2R,3S,5R)-5-(6-Amino-2-fluoro-9H-purin-9-yl)-2-ethynyl-2-(hydroxymethyl)tetrahydrofuran-3-ol

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

An efficient one-pot N-acylation of deoxy- and ribo-cytidine using carboxylic acids activated in situ with 2-chloro-4,6-dimethoxy-1,3,5-triazine was written by Rode, Ambadas B.;Son, Sang Jun;Hong, In Seok. And the article was included in Bulletin of the Korean Chemical Society in 2010.Related Products of 4836-13-9 This article mentions the following:

The authors describe their success in using 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) for the in situ activation of carboxylic acid to synthesize N⁴-acetyl, benzoyl and phenoxy acetyl derivatives of cytidine and 2′-deoxycytidine. The acylation of the exocyclic amine was carried out in a one-step process. Instead of using acyl halides or anhydrides, this strategy involves the enhancement of the reactivity of the carbonyl group of the acid moiety using the 4,6-dimethoxy-1,3,5-triazine group. In standard procedures, first the CDMT reacts with N-Me morpholine (NMM) to form 4-(4,6-di- methoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride, and then the carboxylic acid is added to generate an active ester. This resulting reaction mixture was further treated with a nucleoside to afford the N-acylated nucleoside. The byproducts, such as N-methylmorpholine hydrochloride and the triazine derivative were removed by aqueous work-up, and the desired N-acylated product was purified easily by silica gel column chromatog. To optimize the reaction condition, acetylation reactions of 2′-deoxycytidine were carried out in the different molar combinations of the acylating agent and in the different reaction temperature for the synthesis of N4-acetyl-2′-deoxycytidine. In the experiment, the researchers used many compounds, for example, N-(1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (cas: 4836-13-9Related Products of 4836-13-9).

N-(1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (cas: 4836-13-9) 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 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.Related Products of 4836-13-9

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

Mechanism of inhibition of DNA methyltransferases by cytidine analogs in cancer therapy was written by Gowher, Humaira;Jeltsch, Albert. And the article was included in Cancer Biology & Therapy in 2004.Safety of 4-Amino-5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one This article mentions the following:

Hypermethylation of tumor suppressor genes caused by aberrant activity of DNA methyltransferases is an important mechanism that contributes to cancer. The reaction mechanism of DNA methyltransferases, which includes formation of a covalent intermediate between the enzyme and the target base, is the basis of the success of several anticancer drugs that are targeted against DNA methylation. These include 5-fluoro-2′-deoxycytidine, 5-aza-2′-deoxycytidine (Decitabine) and 2-H pyrimidinone-1-βD(2′-deoxyriboside) (Zebularine). This review provides an insight to how the chem. of DNA methylation is involved in the performance of these drugs targeted against it. In the experiment, the researchers used many compounds, for example, 4-Amino-5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 10356-76-0Safety of 4-Amino-5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one).

4-Amino-5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 10356-76-0) belongs to tetrahydrofuran derivatives.Tetrahydrofuran has many industry uses as a solvent including in natural and synthetic resins, high polymers, fat oils, rubber, polymer. 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.Safety of 4-Amino-5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

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

Alteration of cross-linking selectivity with the 2′-OMe analogue of 2-amino-6-vinylpurine and evaluation of antisense effects was written by Imoto, Shuhei;Hori, Tsuneaki;Hagihara, Shinya;Taniguchi, Yosuke;Sasaki, Shigeki;Nagatsugi, Fumi. And the article was included in Bioorganic & Medicinal Chemistry Letters in 2010.Application of 2140-71-8 This article mentions the following:

We previously reported that oligodeoxynucleotides containing 2-amino-6-vinylpurine (2-AVP) exhibit efficient selective crosslinking to cytosine. In this study, the 2′-OMe nucleoside analog (2) of 2-AVP was designed in order to increase its affinity to RNA and enhance metabolic stability. It has been demonstrated that 2′-OMe oligonucleotides bearing 2 achieve highly selective crosslinking to the thymine base in DNA and show higher antisense effect on luciferase production in cell lysate. 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 of 2140-71-8).

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. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. THF (Tetrahydrofuran) is also used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.Application of 2140-71-8

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

Evaluation of nucleotide C-Br···O-P contacts from ONIOM calculations: Theoretical insight into halogen bonding in nucleic acids was written by Xu, Lin;Sang, Peng;Zou, Jian-Wei;Xu, Ming-Biao;Li, Xue-Ming;Yu, Qing-Sen. And the article was included in Chemical Physics Letters in 2011.Recommanded Product: 5-Bromo-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione This article mentions the following:

Halogen bonding can direct the local stereochem. properties of nucleic acids by unique geometric preferences but has been inaccessible to most theor. studies. Using a two-layer ONIOM method, halogen bonds buried in nucleic acid environments were studied by modeling the nucleotide C-Br···O-P contacts in 1P54 and 1RLG (PDB code). Several unconventional methods, associated with the electron d. distributions of the interacting atoms, showed the formation of halogen bonds through visualization of such non-covalent interactions in real space. The contributions of halogen bonds to the local conformation of the backbones were also demonstrated through comparison with parallel binding of non-brominated nucleotides. In the experiment, the researchers used many compounds, for example, 5-Bromo-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (cas: 957-75-5Recommanded Product: 5-Bromo-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione).

5-Bromo-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione (cas: 957-75-5) 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. Oxidations have also proved to be valuable and efficient approaches to chiral tetrahydrofuran derivatives.Recommanded Product: 5-Bromo-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

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

Chemoenzymatic Syntheses and Anti-HIV-1 Activity of Glucose-Nucleoside Conjugates as Prodrugs was written by Rodriguez-Perez, Tatiana;Fernandez, Susana;Sanghvi, Yogesh S.;Detorio, Mervi;Schinazi, Raymond F.;Gotor, Vicente;Ferrero, Miguel. And the article was included in Bioconjugate Chemistry in 2010.Application of 4097-22-7 This article mentions the following:

Phosphodiester linked conjugates of various nucleosides such as d4U, d4T, IdUrd, ddI, ddA, virazole, ara-A, and ara-C containing a glucosyl moiety have been described. These compounds were designed to act as prodrugs, where the corresponding 5′-monophosphates may be generated intracellularly. The synthesis of the glycoconjugates was achieved in good yields by condensation of a glucosyl phosphoramidite with nucleosides in the presence of an activating agent. It was demonstrated that the glucose conjugates improve the water solubility of the nucleoside analogs, for example, up to 31-fold for the ara-A conjugate compared to that of ara-A alone. The new conjugates were tested for their anti-HIV-1 activity in human lymphocytes. These derivatives offer a convenient design for potential prodrug candidates with the possibility of improving the physicochem. properties and therapeutic activity of nucleoside analogs. In the experiment, the researchers used many compounds, for example, ((2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methanol (cas: 4097-22-7Application of 4097-22-7).

((2S,5R)-5-(6-Amino-9H-purin-9-yl)tetrahydrofuran-2-yl)methanol (cas: 4097-22-7) 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. 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.Application of 4097-22-7

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

Pyrimidine-Purine and Pyrimidine Hetero-dinucleosides Synthesis Containing a Triazole Linkage was written by Lucas, R.;Elchinger, P. H.;Faugeras, P. A.;Zerrouki, R.. And the article was included in Nucleosides, Nucleotides & Nucleic Acids in 2010.Quality Control of N-(1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide This article mentions the following:

This article describes a synthetic route to generate two purine-pyrimidine and pyrimidine hetero-dinucleosides, e.g. I. Both microwave activated regioselective alkylation using hydride and copper-catalyzed-azide-alkyne-cycloaddition (CuAAC) were used in order to perform the synthesis. In the experiment, the researchers used many compounds, for example, N-(1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (cas: 4836-13-9Quality Control of N-(1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide).

N-(1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide (cas: 4836-13-9) belongs to tetrahydrofuran derivatives. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. Tetrahydrofuran reaction with hydrogen sulfide: In the presence of a solid acid catalyst, tetrahydrofuran reacts with hydrogen sulfide to give tetrahydrothiophene.Quality Control of N-(1-((2R,4S,5R)-4-Hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-2-oxo-1,2-dihydropyrimidin-4-yl)benzamide

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

Hormonal interplay in the regulation of fruit ripening and cold acclimation in avocados was written by Vincent, Celia;Mesa, Tania;Munne-Bosch, Sergi. And the article was included in Journal of Plant Physiology in 2020.Computed Properties of C15H21N5O4 This article mentions the following:

Avocados (Persea americana Mill.) are climacteric fruits, the ripening of which during postharvest at room temperature is strongly ethylene dependent. Here, we hypothesized that the ripening of avocados at room temperature may be governed not only by ethylene, but also by other phytohormones. With this aim, we analyzed the hormonal profiling of avocados subjected to either 4°C and 25°C during 10 days of postharvest. A biphasic response was observed during postharvest ripening of avocados at room temperature While ethylene alone appeared to govern fruit ripening during the first transfer from cold to room temperature, a complex hormonal interplay occurred during ripening of avocados leading to a progressive fruit softening at room temperatures Aside from ethylene, auxin, gibberellins, jasmonates and ABA appeared to be involved in avocado fruit ripening during postharvest at room temperature Cold storage for a period of 10 days inhibited this hormonal response related to ripening. Furthermore, avocados stored at cold temperatures underwent a quick response in order to tolerate cold stress leading to changes in endogenous ABA and jasmonates. We conclude that a complex hormonal interplay, rather than ethylene alone, modulates postharvest ripening of avocados and that cold storage can effectively be employed as a technique to prevent avocados from a rapid ripening thanks to the cold stress tolerance mechanisms deployed by fruits through multiple hormonal regulation. In the experiment, the researchers used many compounds, for example, N6-(3-Methyl-2-butenyl)adenosine (cas: 7724-76-7Computed Properties of C15H21N5O4).

N6-(3-Methyl-2-butenyl)adenosine (cas: 7724-76-7) 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. THF (Tetrahydrofuran) is also used as a starting material for the synthesis of poly(tetramethylene ether) glycol (PTMG), etc.Computed Properties of C15H21N5O4

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

Surpassing limits of static RNA modification analysis with dynamic NAIL-MS was written by Reichle, Valentin F.;Kaiser, Steffen;Heiss, Matthias;Hagelskamp, Felix;Borland, Kayla;Kellner, Stefanie. And the article was included in Methods (Amsterdam, Netherlands) in 2019.Recommanded Product: 2140-69-4 This article mentions the following:

Ribonucleic acids (RNA) are extensively modified. These modifications are quantified by mass spectrometry (LC-MS/MS) to determine the abundance of a modification under certain conditions or in various genetic backgrounds. With LC-MS/MS the steady state of modifications is determined, and thus we only have a static view of the dynamics of RNA modifications. With nucleic acid isotope labeling coupled mass spectrometry (NAIL-MS) we overcome this limitation and get access to the dynamics of RNA modifications. We describe labeling techniques for E. coli, S. cerevisiae and human cell culture and the current instrumental limitations. We present the power of NAIL-MS but we also outline validation experiments, which are necessary for correct data interpretation. As an example, we apply NAIL-MS to study the demethylation of adenine and cytidine, which are methylated by the damaging agent methyl-methanesulfonate in E. coli. With NAIL-MS we exclude the concurrent processes for removal of RNA methylation, namely RNA degradation, turnover and dilution We use our tool to study the speed and efficiency of 1-methyladenosine and 3-methylcytidine demethylation. We further outline current limitations of NAIL-MS but also potential future uses for e.g. relative quantification of tRNA isoacceptor abundances. 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: 2140-69-4Recommanded Product: 2140-69-4).

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. Tetrahydrofurans and furans are important oxygen-containing heterocycles that often exhibit interesting properties for biological applications or applications in the cosmetic industry. 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.Recommanded Product: 2140-69-4

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

Biological properties of Roakin strain of NDV and TK900 strain of ADV after serial passages in CECC in the presence of methisoprinol and KLP-602. was written by Małaczewska, J;Rotkiewicz, Z. And the article was included in Polish journal of veterinary sciences in 2005.Recommanded Product: 36703-88-5 This article mentions the following:

Twenty serial passages of the TK900 strain of Aujeszky’s disease virus (ADV) and the Roakin strain of Newcastle disease virus (NDV) were made in a chicken embryo cell culture (CECC), in the presence of two antiviral agents: Methisoprinol and KLP-602. The physicochemical properties of passaged viruses were determined. The results obtained suggest that Methisoprinol causes changes in the structure of viral proteins, whereas KLP-602 affects the envelope-dependent properties of the virus. It was also found that the alternations observed in passaged viruses were temporary phenotypic changes only, and not a consequence of permanent transformations of their genotypes. In the experiment, the researchers used many compounds, for example, 4-Acetamidobenzoic acid,9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3H-purin-6(9H)-one,1-(Dimethylamino)propan-2-ol (3:1:3) (cas: 36703-88-5Recommanded Product: 36703-88-5).

4-Acetamidobenzoic acid,9-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3H-purin-6(9H)-one,1-(Dimethylamino)propan-2-ol (3:1:3) (cas: 36703-88-5) 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.Recommanded Product: 36703-88-5

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