Category: 56632-83-8

2′-Deoxy-2′-fluoro-β-D-arabinonucleosides and oligonucleotides (2’F-ANA): synthesis and physicochemical studies was written by Wilds, Christopher J.; Damha, Masad J.. And the article was included in Nucleic Acids Research on September 15,2000.Electric Literature of C9H12FN3O4 The following contents are mentioned in the article:

Recently, hybrids of RNA and D-arabinonucleic acids (ANA) as well as the 2′-deoxy-2′-fluoro-D-arabinonucleic acid analog (2’F-ANA) were shown to be substrates of RNase H. This enzyme is believed to be involved in the primary mechanism by which antisense oligonucleotides cause a reduction in target RNA levels in vivo. To gain a better understanding of the properties of arabinose based oligonucleotides, we have prepared a series of 2’F-ANA sequences of homopolymeric (A and T) and mixed base composition (A, T, G and C). UV thermal melting and circular dichroic (CD) studies were used to ascertain the thermodn. stability and helical conformation of 2’F-ANA/RNA and 2’F-ANA/DNA hybrids. It is shown that 2’F-ANA has enhanced RNA affinity relative to that of DNA and phosphorothioate DNA. The 2′-fluoroarabino modification showed favorable pairing to single-stranded DNA also. This is in sharp contrast to ANA, which forms weak ANA/DNA hybrids at best. According to the measured thermodn. parameters for duplex formation, the increased stability of hybrids formed by 2’F-ANA (e.g., 2’F-ANA/RNA) appears to originate from conformational pre-organization of the fluorinated sugars and a favorable enthalpy of hybridization. In addition, NMR spectroscopy revealed a five-bond coupling between the 2’F and the base protons (H6/H8) of 2′-deoxy-2′-fluoro-β-D-arabinonucleosides. This observation is suggesting of a through-space interaction between 2’F and H6/H8 atoms. CD experiments indicate that 2’F-ANA/RNA hybrids adopt an ‘A-like’ structure and show more resemblance to DNA/RNA hybrids than to the pure RNA/RNA duplex. This feature is believed to be an important factor in the mechanism that allows RNase H to discriminate between 2’F-ANA/RNA (or DNA/RNA) and RNA/RNA duplexes. This study involved multiple reactions and reactants, such as 4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8Electric Literature of C9H12FN3O4).

4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8) belongs to pyrimidine derivatives. The pyrimidine derivatives can easily interact with enzymes, genetic materials, and bio components within the cell. A Cu-catalyzed and 4-HO-TEMPO-mediated [3 + 3] annulation of commercially available amidines with saturated ketones enables an efficient and facile synthesis of structurally important pyrimidines via a cascade reaction of oxidative dehydrogenation/annulation/oxidative aromatization.Electric Literature of C9H12FN3O4

56632-83-8;4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;The future of 56632-83-8;New trend of C9H12FN3O4;function of 56632-83-8

Pharmacological disposition and metabolic fate of 2′-fluoro-5-iodo-1-β-D-arabinofuranosylcytosine in mice and rats was written by Chou, Ting-Chao; Feinberg, Aaron; Grant, Alan J.; Vidal, Pedro; Reichman, Uri; Watanabe, Kyoichi A.; Fox, Jack J.; Philips, Frederick S.. And the article was included in Cancer Research on September 30,1981.Name: 4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one The following contents are mentioned in the article:

2′-Fluoro-5-iodo-1-β-D-arabinofuranosylcytosine-HCl (FIAC)(I) [69123-90-6] was synthesized and labeled with 14C in the 2 position for the study of pharmacol. disposition and metabolic fate. FIAC is deaminated by cytosine nucleoside deaminase [9025-06-3] at a rate comparable to that of 1-β-D-arabinofuranosylcytosine. The deaminated product, 2′-fluoro-5-iodo-1-β-D-arabinofuranosyluracil (FIAU) [69123-98-4] is, like FIAC, an active antiviral agent. After i.v. injection of [2-14C]-FIAC in mice, most of the radioactivity in plasma appears as FIAU. In i.v.-injected rats which lack cytosine nucleoside deaminase, plasma radioactivity is largely present in unchanged FIAC. If mice are pretreated with tetrahydrouridine, an inhibitor of the nucleoside deaminase, plasma radioactivity is mostly FIAC. The radioactivity of [2-14C]-FIAC injected i.v. is excreted in urine, at 63 to 93% of the dose in mice and >90% of the dose in rats within 0 to 24 h. Most of the radioactivity in urine of rats and in mice pretreated with tetrahydrouidine is present as unchanged FIAC; in control mice, most of the radioactivity is found as FIAU. Chromatog. anal. of urine from control mice receiving labeled FIAC has revealed that radioactivity is present in the following nucleosides: FIAC (14.5); FIAU (73); 2′-fluoro-5-methyl-1-β-D-arabinofuranosyluracil (FMAU) [69256-17-3] (5.4); and 2′-fluoro-1-β-D-arabinofuranosyluracil [69123-94-0] (2.3%). These metabolites are also present in acid-soluble fractions of mouse blood, small intestine, and liver. Like FIAC and FIAU, FMAU is a potent antiherpetic agent. Only ∼4.3% of the radioactivity of injected [2-14C]-FIAC appears in mouse respiratory CO2; degradation to CO2 can be blocked by tetrahydrouridine. Less than 2% of the total radioactivity is excreted in bile in rats. Small amounts of radioactivity are also recovered in feces, mostly in deaminated products. FIAC and FIAU, with a 2′-F substituent in the arabino configuration, are less susceptible to metabolic glycosyl cleavage than is 5-iodo-2′-deoxyuridine. The radioactivity of [2-14C]-FIAC is incorporated into DNA fractions of highly proliferating organs such as intestine, spleen, and thymus, although preliminary results indicate that the substances incorporated are arabinofuranosyl nucleoside metabolites of FIAC. This study involved multiple reactions and reactants, such as 4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8Name: 4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one).

4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8) belongs to pyrimidine derivatives. The aromatic compound pyrimidine, and its derivatives, are ubiquitous in nature. They are found in nucleic acids, vitamins, amino acids, antibiotics, alkaloids, and a variety of toxins. Therapy for fungal infections is based mainly on four classes of antifungals: azoles, echinocandins, polyenes, and pyrimidine analogs.Name: 4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one

56632-83-8;4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;The future of 56632-83-8;New trend of C9H12FN3O4;function of 56632-83-8

Incorporation and metabolism of 2′-fluoro-5-substituted arabinosyl pyrimidines and their selective inhibition of viral DNA synthesis in herpes simplex virus type 1 (HSV-1)-infected and mock-infected Vero cells was written by Kong, Xiang Bin; Scheck, Adrienne C.; Price, Richard W.; Vidal, Pedro M.; Fanucchi, Michael P.; Watanabe, Kyoichi A.; Fox, Jack J.; Chou, Ting Chao. And the article was included in Antiviral Research on December 1,1988.COA of Formula: C9H12FN3O4 The following contents are mentioned in the article:

The incorporation and metabolism of 2′-fluoro-5-substituted arabinosyl pyrimidine analogs I and II (R = H, I, Me, Et, or CHF2) and their selective inhibition of viral DNA synthesis in herpes simplex virus type 1 (HSV-1)-infected and mock-infected Vero cells were studied by HPLC and CsCl isopycnic d. gradient anal. of isolated DNAs. The amounts of radiolabeled analogs incorporated as parent compound following 10 μM exposure for 4 h were 10-fold higher in HSV-1-infected vs. mock-infected cells for 2′-fluoro-5-difluoromethyl-Ara-U (F2FMAU); 4.3-fold higher for 5-Et deoxyuridine (EdU); 2.6-fold higher for 2′-fluoro-5-methyl-Ara-U (FMAU) and 1.7-fold higher for dThd. For 2′-fluoro-5-ethyl-Ara-U (FEAU), 3.0 pmole of unchanged moiety was incorporated per 106 HSV-1-infected cells but no incorporation was detected in mock-infected cells. HPLC profiles showed that the percentages of radiolabeled analogs incorporated as parent compound in the DNA extracted from HSV-1-infected cells were 31.0% for F2FMAU, 99.6% for EdU, 83.5% for FEAU and 98.3% for FMAU; from mock-infected cells, they were 63.6% for F2FMAU, 96.7% for EdU, 97.3% for FMAU and no incorporation into DNA for FEAU was detected. CsCl d. gradient analyses of isolated DNA showed that viral DNA synthesis was inhibited 98% by 10 μM FEAU, 92% by 10 μM F2FMAU, 90% by 2 μM FMAU and 80% by 50 μM EdU, whereas cellular DNA synthesis was inhibited by 53, 44, 61, 66 and 54%, resp. It was shown that: (a) FEAU incorporation into host-cell DNA was not detectable but FEAU was selectively incorporated into HSV-infected cells; (b) FMAU and FEAU were metabolically stable; however, F2FMAU was extensively metabolized; (c) FEAU and F2FMAU were among the most selective inhibitors of HSV-1 DNA synthesis while allowing cellular DNA synthesis to continue. This study involved multiple reactions and reactants, such as 4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8COA of Formula: C9H12FN3O4).

4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8) belongs to pyrimidine derivatives. The aromatic compound pyrimidine, and its derivatives, are ubiquitous in nature. They are found in nucleic acids, vitamins, amino acids, antibiotics, alkaloids, and a variety of toxins. We all know its importance to life – pyrimidine and purine bases are included in the structure of DNA and RNA.COA of Formula: C9H12FN3O4

56632-83-8;4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;The future of 56632-83-8;New trend of C9H12FN3O4;function of 56632-83-8

2′ -Fluoroarabinonucleic acid modification traps G-quadruplex and i-motif structures in human telomeric DNA [Erratum to document cited in CA171:021472] was written by Assi, Hala Abou; El-Khoury, Roberto; Gonzalez, Carlos; Damha, Masad J.. And the article was included in Nucleic Acids Research on November 16,2017.SDS of cas: 56632-83-8 The following contents are mentioned in the article:

There is no abstract available for this document. This study involved multiple reactions and reactants, such as 4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8SDS of cas: 56632-83-8).

4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8) belongs to pyrimidine derivatives. Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. Therapy for fungal infections is based mainly on four classes of antifungals: azoles, echinocandins, polyenes, and pyrimidine analogs.SDS of cas: 56632-83-8

56632-83-8;4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;The future of 56632-83-8;New trend of C9H12FN3O4;function of 56632-83-8

Detailed Computational Study of the Active Site of the Hepatitis C Viral RNA Polymerase to Aid Novel Drug Design was written by Barakat, Khaled H.; Law, John; Prunotto, Alessio; Magee, Wendy C.; Evans, David H.; Tyrrell, D. Lorne; Tuszynski, Jack; Houghton, Michael. And the article was included in Journal of Chemical Information and Modeling on November 25,2013.Computed Properties of C9H12FN3O4 The following contents are mentioned in the article:

The hepatitis C virus (HCV) RNA polymerase, NS5B, is a leading target for novel and selective HCV drug design. The enzyme has been the subject of intensive drug discovery aimed at developing direct acting antiviral (DAA) agents that inhibit its activity and hence prevent the virus from replicating its genome. In this study, we focus on one class of NS5B inhibitors, namely nucleos-(t)-ide mimetics. Forty-one distinct nucleotide structures have been modeled within the active site of NS5B for the six major HCV genotypes. Our comprehensive modeling protocol employed 287 different mol. dynamics simulations combined with the mol. mechanics/Poisson-Boltzmann surface area (MM-PBSA) methodol. to rank and analyze these structures for all genotypes. The binding interactions of the individual compounds have been investigated and reduced to the at. level. The present study significantly refines our understanding of the mode of action of NS5B-nucleotide-inhibitors, identifies the key structural elements necessary for their activity, and implements the tools for ranking the potential of addnl. much needed novel inhibitors of NS5B. This study involved multiple reactions and reactants, such as 4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8Computed Properties of C9H12FN3O4).

4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8) belongs to pyrimidine derivatives. The pyrimidine nitrogenous bases are derived from the organic compound pyrimidine through the addition of various functional groups. We all know its importance to life – pyrimidine and purine bases are included in the structure of DNA and RNA.Computed Properties of C9H12FN3O4

56632-83-8;4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;The future of 56632-83-8;New trend of C9H12FN3O4;function of 56632-83-8

2′-Fluoroarabinonucleic acid modification traps G-quadruplex and i-motif structures in human telomeric DNA was written by Abou Assi, Hala; El-Khoury, Roberto; Gonzalez, Carlos; Damha, Masad J.. And the article was included in Nucleic Acids Research on November 16,2017.Synthetic Route of C9H12FN3O4 The following contents are mentioned in the article:

Human telomeres and promoter regions of genes fulfill a significant role in cellular aging and cancer. These regions comprise of guanine and cytosine-rich repeats, which under certain conditions can fold into G-quadruplex (G4) and i-motif structures, resp. Herein, we use UV, CD and NMR spectroscopy to study several human telomeric sequences and demonstrate that G4/i-motif-duplex interconversion kinetics are slowed down dramatically by 2′-β-fluorination and the presence of G4/i-motif-duplex junctions. NMR-monitored kinetic experiments on 1:1 mixtures of native and modified Cand G-rich human telomeric sequences reveal that strand hybridization kinetics are controlled by G4 or i-motif unfolding. Furthermore, we provide NMR evidence for the formation of a hybrid complex containing G4 and i-motif structures proximal to a duplex DNA segment at neutral pH. While the presence of i-motif and G4 folds may be mutually exclusive in promoter genome sequences, our results suggest that they may co-exist transiently as intermediates in telomeric sequences. This study involved multiple reactions and reactants, such as 4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8Synthetic Route of C9H12FN3O4).

4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8) belongs to pyrimidine derivatives. The pyrimidine ring system has wide occurrence in nature as substituted and ring fused compounds and derivatives. Pyrimidine derivatives also play an important role in drug development, either in concert with other compounds or on their own.Synthetic Route of C9H12FN3O4

56632-83-8;4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;The future of 56632-83-8;New trend of C9H12FN3O4;function of 56632-83-8

Conformational analysis of 2′-fluoro-5-iodoarabinosyl-cytosine (FIAC) and 2′-fluoro-5-iodoribofuranosylcytosine (FIRC) was written by Hsu, Ling Yih; Liu, Kang Chien. And the article was included in Zhonghua Yaoxue Zazhi on December 31,1993.Application of 56632-83-8 The following contents are mentioned in the article:

Ribonucleoside I (R = H, R1 = F) is less active against HSV-1 and HSV-2 than arabinonucleoside I [R = F, R1 = H (II)]. The relationship between mol. conformation and antiviral activity of I is discussed. The rotational energy caused probably by the 2′-“”up””-fluoro substituent in the sugar moiety might lock II in an anti conformation, which might account for the potent antiviral activity. This study involved multiple reactions and reactants, such as 4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8Application of 56632-83-8).

4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8) belongs to pyrimidine derivatives. Pyrimidine is an aromatic heterocyclic organic compound similar to pyridine. A Cu-catalyzed and 4-HO-TEMPO-mediated [3 + 3] annulation of commercially available amidines with saturated ketones enables an efficient and facile synthesis of structurally important pyrimidines via a cascade reaction of oxidative dehydrogenation/annulation/oxidative aromatization.Application of 56632-83-8

56632-83-8;4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;The future of 56632-83-8;New trend of C9H12FN3O4;function of 56632-83-8

Synthesis and some properties of modified oligonucleotides. 2. Oligonucleotides containing 2′-deoxy-2′-fluoro-β-D-arabinofuranosylpyrimidine nucleotides was written by Kois, Pavol; Tocik, Zdenek; Spassova, Maria; Ren, Wu Yun; Rosenberg, Ivan; Soler, Jaume Farras; Watanabe, Kyoichi A.. And the article was included in Nucleosides & Nucleotides on December 31,1993.Electric Literature of C9H12FN3O4 The following contents are mentioned in the article:

In order to find the effects of unnatural nucleosides on the stability of duplex, several oligonucleotides containing 1-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-uracil (FAU), -cytosine (FAC) and -thymine (FMAU) were synthesized by two alternative approaches: phosphoramidite method on an ABI 392 synthesizer and H-phosphonate procedure on the authors’ GeneSyn I universal module synthesizer. It was shown from the melting profiles that the presence of FMAU has a large stabilizing effect on the duplex. Replacement of thymidine with FAU, or deoxycytidine with FAC resulted in the formation of less stable duplexes. Temperature-dependent CD spectroscopy demonstrated that the structures of the fluorine containing oligomers are very similar to those of unmodified oligomers. This study involved multiple reactions and reactants, such as 4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8Electric Literature of C9H12FN3O4).

4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one (cas: 56632-83-8) belongs to pyrimidine derivatives. The pyrimidine nitrogenous bases are derived from the organic compound pyrimidine through the addition of various functional groups. Pyrimidine derivatives have been used in a wide variety of pharmaceuticals including general anesthetics, anti-epilepsy medication, anti-malaria medication, drugs for treating high blood pressure, and HIV medication.Electric Literature of C9H12FN3O4

56632-83-8;4-Amino-1-((2R,3S,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one;The future of 56632-83-8;New trend of C9H12FN3O4;function of 56632-83-8