- Microwaves - A powerful tool for the base protection of cytidine
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Use of microwaves for the base protection of cytidine is described. The procedure gives N-acylcytidine in nearly quantitative yield in 40-60 seconds.
- Nahar, Pradip
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Read Online
- A Chemical Strategy for Intracellular Arming of an Endogenous Broad-Spectrum Antiviral Nucleotide
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The naturally occurring nucleotide 3′-deoxy-3′,4′-didehydro-cytidine-5′-triphosphate (ddhCTP) was recently found to exert potent and broad-spectrum antiviral activity. However, nucleoside 5′-triphosphates in general are not cell-permeable, which precludes
- Antczak, Nicole M.,Arnold, Jamie J.,Caldwell, Haley S.,Cameron, Craig E.,Ciota, Alexander T.,Harki, Daniel A.,Jose, Joyce,Narayanan, Anoop,Ngo, Kiet A.,Passow, Kellan T.,Sturla, Shana J.
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p. 15429 - 15439
(2021/11/12)
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- Synthesis method for azvudine
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The invention discloses a synthesis method for azvudine. The method comprises the following steps of carrying out a hydroxyl substitution reaction on a compound 4 and an iodine elementary substance toobtain a compound 5, carrying out an elimination reaction on an iodo group in the compound 5 to obtain a compound 6, reacting the compound 6 with azide under the catalysis of ICl to obtain a compound7, carrying out an iodine substitution reaction on the compound 7 and carboxylic acid to obtain a compound 8, and carrying out an amino and hydroxyl deprotection reaction on the compound 8 to obtaina compound 9, namely the alzvudine. Compared with an existing synthesis method, the synthesis method has the advantages of short synthesis route, shortened reaction time, mild reaction conditions andeasily controlled reaction process, can be used for preparing the alzvudine with the lower cost, and has a very good application prospect.
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Paragraph 0079-0081
(2020/11/22)
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- New tools in nucleoside toolbox of tick-borne encephalitis virus reproduction inhibitors
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Design and development of nucleoside analogs is an established strategy in the antiviral drug discovery field. Nevertheless, for many viruses the coverage of structure-activity relationships (SAR) in the nucleoside chemical space is not sufficient. Here we present the nucleoside SAR exploration for tick-borne encephalitis virus (TBEV), a member of Flavivirus genus. Promising antiviral activity may be achieved by introduction of large hydrophobic substituents in the position 6 of adenosine or bulky silyl groups to the position 5′. Introduction of methyls to the ribose moiety does not lead to inhibition of TBEV reproduction. Possible mechanisms of action of these nucleosides include the inhibition of viral entry or interaction with TBEV non-structural protein 5 methyltransferase or RNA-dependent RNA polymerase domains.
- Orlov, Alexey A.,Drenichev, Mikhail S.,Oslovsky, Vladimir E.,Kurochkin, Nikolay N.,Solyev, Pavel N.,Kozlovskaya, Liubov I.,Palyulin, Vladimir A.,Karganova, Galina G.,Mikhailov, Sergey N.,Osolodkin, Dmitry I.
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supporting information
p. 1267 - 1273
(2017/06/19)
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- N4 -Process for the preparation of benzoyl - D D-cytidine
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The invention relates to a preparation method of N4-benzoyl-D-cytidine, and belongs to the field of nucleoside compounds. The preparation method comprises the following steps: carrying out a benzoylation reaction in an organic solvent by taking D-cytidine
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Paragraph 0035-0036
(2017/06/20)
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- Alternative nucleic acid molecules and uses thereof
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The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.
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- ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF
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The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.
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Page/Page column 636
(2016/06/15)
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- ALTERNATIVE NUCLEIC ACID MOLECULES AND USES THEREOF
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The present disclosure provides alternative nucleosides, nucleotides, and nucleic acids, and methods of using them.
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Page/Page column 644
(2016/06/28)
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- The aqueous N-phosphorylation and N-thiophosphorylation of aminonucleosides
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We demonstrate N-phosphorylation and N-thiophosphorylation of unprotected aminonucleosides in aqueous media. N-Phosphorylations using phosphoric chloride and N-thiophosphorylations using thiophosphoryl chloride were explored as functions of pH using 5′-amino-5′-deoxyguanosine as substrate. These reagents were compared to phosphodichloridate and thiophosphodichloridate ions, and the methodology was applied to other aminonucleosides. S-Alkylations of the nucleoside N-thiophosphoramidates were investigated as functions of pH and alkylating agent. the Partner Organisations 2014.
- Conway, Louis P.,Delley, Richard J.,Neville, Jonathan,Freeman, Gemma R.,Maple, Hannah J.,Chan, Vincent,Hall, Alexander J.,Hodgson, David R. W.
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p. 38663 - 38671
(2014/11/07)
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- METHODS FOR TREATING HCV
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This invention relates to combinations of therapeutic molecules useful for treating hepatitis C virus infection. The present invention relates to methods, uses, dosing regimens, and compositions.
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Page/Page column 93
(2013/03/28)
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- METHODS FOR TREATING HCV
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This invention relates to combinations of therapeutic molecules useful for treating hepatitis C virus infection. The present invention relates to methods, uses, dosing regimens, and compositions.
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Paragraph 0355
(2013/10/22)
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- A convenient synthesis of the cytidyl 3′-terminal monomer for solid-phase synthesis of RNG oligonucleotides
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Replacing the phosphodiester backbone of RNA with positively charged guanidinium linkages has been shown to enable RNA oligomers to overcome electrostatic repulsion and bind double-stranded DNA in a triplex with high affinity. Ribonucleotide monomers with
- Awad, Ahmed M.,Collazo, Michael J.,Carpio, Kathrinna,Flores, Christina,Bruice, Thomas C.
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scheme or table
p. 3792 - 3794
(2012/09/10)
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- Synthesis of oligoribonucleotides containing 2'-o-methoxymethyl group by the phosphotriester method
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An effective procedure for the synthesis of ribonucleotide monomers containing a 2'-methoxymethyl-modifying group was developed. These monomers were used for the synthesis of RNA fragments by the solid-phase phosphotriester method under O-nucleophilic intramolecular catalysis. The properties of 2'-methoxymethyl-containing oligoribonucleotides were examined. Copyright Taylor and Francis Group, LLC.
- Efimov, Vladimir A.,Aralov, Andrey V.,Chakhmakhcheva, Oksana G.
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p. 565 - 576
(2011/12/22)
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- Selective deacylation of peracylated ribonucleosides
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A protocol for chemoselective deprotection of N,O-acylated ribonucleosides has been developed. Peracylated pyrimidine ribonucleosides subjected to guanidinium nitrate and NaOMe in MeOH/CH2Cl2 at 0 °C undergo high yielding O-deacylation, while even more pronounced chemoselectivity is observed with peracylated purine ribonucleosides as O5′-acyl groups are preserved. Nucleobase-protecting groups (ABz, CBz, GiBu, and UBz) are stable to these conditions, rendering this reagent mixture as a valuable addition to the collection of protecting group protocols in nucleoside chemistry.
- Rigoli, Jared W.,?stergaard, Michael E.,Canady, Kirsten M.,Guenther, Dale C.,Hrdlicka, Patrick J.
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scheme or table
p. 1751 - 1753
(2009/07/05)
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- Phosphoramidate dinucleosides as hepatitis C virus polymerase inhibitors
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GC dinucleosides exhibiting a phosphoramidate internucleosidic linkage with neutral, amphiphile, positively or negatively charged side chains were synthesized. Their potential inhibitory effect on the hepatitis C virus (HCV) NS5B polymerase was evaluated
- Zlatev, Ivan,Dutartre, Hélène,Barvik, Ivan,Neyts, Johan,Canard, Bruno,Vasseur, Jean-Jacques,Alvarez, Karine,Morvan, Fran?ois
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supporting information; experimental part
p. 5745 - 5757
(2009/09/29)
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- Semisynthesis of 3′(2′)-O-(aminoacyl)-tRNA derivatives as ribosomal substrate
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An efficient synthesis of (3′-terminally) 3′(2′)-O- aminoacylated pCpA derivatives is described, which could lead to the production of (aminoacyl)-tRNAs following T4 RNA ligase mediated ligation. The tetrahydrofuranyl (thf) group was used as a permanent p
- Cui, Zhiyong,Zhang, Biliang
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p. 297 - 310
(2008/02/08)
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- MODIFIED FLUORINATED NUCLEOSIDE ANALOGUES
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The disclosed invention provides compositions and methods of treating a Flaviviridae infection, including hepatitis C virus, West Nile Virus, yellow fever virus, and a rhinovirus infection in a host, including animals, and especially humans, using a (2’R)-2'-deoxy-2'-fluoro-2'-C-methyl nucleosides, or a pharmaceutically acceptable salt or prodrug thereof.
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- Design, synthesis, and antiviral activity of 2′-deoxy-2′- fluoro-2′-C-methylcytidine, a potent inhibitor of hepatitis C virus replication
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The pyrimidine nucleoside beta-D-2′-deoxy-2′-fluoro-2′-C- methylcytidine (1) was designed as a hepatitis C virus RNA-dependent RNA polymerase (HCV RdRp) inhibitor. The title compound was obtained by a DAST fluorination of N4-benzoyl-1-(2-methyl-3,5-di-O-benzoyl-β-D- arabinofuranosyl]cytosine (6) to provide N4-benzoyl-1-[2-fluoro-2- methyl-3,5-di-O-benzoyl-β-D-ribofuranosyl]cytosine (7a). The protected 2′-C-methylcytidine (7c) was obtained as a byproduct from the DAST fluorination and allowed for the preparation of two biologically active compounds from a common precursor. Compound 1 and 2′-C-methylcytidine were assayed in a subgenomic HCV replicon assay system and found to be potent and selective inhibitors of HCV replication. Compound 1 shows increased inhibitory activity in the HCV replicon assay compared to 2′-C-methylcytidine and low cellular toxicity.
- Clark, Jeremy L.,Hollecker, Laurent,Mason, J. Christian,Stuyver, Lieven J.,Tharnish, Phillip M.,Lostia, Stefania,McBrayer, Tamara R.,Schinazi, Raymond F.,Watanabe, Kyoichi A.,Otto, Michael J.,Furman, Phillip A.,Stec, Wojciech J.,Patterson, Steven E.,Pankiewicz, Krzysztof W.
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p. 5504 - 5508
(2007/10/03)
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- Antisense molecules and method of controlling expression of gene function by using the same
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An antisense molecule which acts on both directions of the inhibition and expression of a gene function and is capable of on-off switching of a gene function appropriately depending on the external factors (orientation controlling factors); and a method for reversibly controlling the expression of a gene function by using the antisense molecule. Such an antisense molecule, which has at least one sugar-base moiety consisting of sugar and a purine or pyrimidine base bonded thereto via a glucoside bond, can bind to a mRNA/gene and/or dissociate therefrom under the orientation control of the base moiety in the molecule by the orientation controlling factors.
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- Nucleoside derivatives
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Novel nucleoside derivatives represented by the following general formula (1): 1wherein X is(are) the same or different and each represents a pyrimidine or purine base or a derivative thereof, Y-and Y′ are the same or different and each represents at least one amino acid or amino acid derivative selected from the group consisting of serine, threonine, ornithine, aspartic acid, glutamic acid, lysine, arginine, cysteine, methionine, δ-hydroxylysine, N-aminoethylglycine, N-aminoethylserine, N-aminoethyllysine, N-aminoethylornithine, N-aminoethylaspartic acid, N-aminoethylglutamic acid, homoglutamic acid, β-thiocarbonylaspartic acid, γ-thiocarbonylglutamic acid, and δ-thiocarbonylhomoglutamic acid, R1 represents a hydrogen atom or a hydroxyl group, A represents a single bond or a carbonyl or thiocarbonyl group, 1 is an integer of 0 to 5, and n is an integer of 1 to 100.
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- An improved transient method for the synthesis of N-benzoylated nucleosides
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The Jones' transient method for the synthesis of N-benzoylated nucleosides is improved by reducing the amounts of chlorotrimethylsilane (TMSCl) and benzoyl chloride to nearly equivalent quantities. The easy work-up and high yields of products are the major advantages of this approach. Jones' method is further simplified by omitting the addition of ammonium hydroxide. The utility of this modification for the preparation of some useful protected nucleosides is also presented.
- Zhu, Xue-Feng,Williams Jr., Howard J.,Scott, A. Ian
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p. 1233 - 1243
(2007/10/03)
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- A new laboratory scale synthesis for the anticancer drug 3′-C-ethynylcytidine
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A new synthetic route for the preparation of larger quantities of the anticancer nucleoside analogue 3′-C-ethynylcytidine is described. Starting from cytidine which was orthogonally protected in three steps, the ketonucleoside analogue as the key intermediate was obtained through oxidation of the unprotected 3′-hydroxy group. Stereoselective addition of the trimethylsilyl-protected acetylide residue at the 3′-carbonyl group followed by a complete deprotection afforded 3′-C-ethynylcytidine in an overall yield of 24% in seven steps.
- Ludwig, Peter S.,Schwendener, Reto A.,Schott, Herbert
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p. 2387 - 2392
(2007/10/03)
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- Some observations relating to the use of 1-aryl-4-alkoxypiperidin-4-yl groups for the protection of the 2′-hydroxy functions in the chemical synthesis of oligoribonucleotides
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The comparative rates of acid-catalysed removal often 1-aryl-4-methoxypiperidin-4-yl 8 (R = Me) [including the previously reported Ctmp 5 and Fpmp 6] protecting groups for the 2′-hydroxy functions in oligoribonucleotide synthesis are discussed. These studies have led to the development of the 1-(4-chlorophenyl)-4-ethoxypiperidin-4-yl (Cpep) protecting group 8 (R = Et, R1 = R2 = H, R3 = Cl) which is both more stable than the Ctmp and Fpmp groups at pH 0.5 and more labile at pH 3.75. The influence of the ribonucleoside aglycone on the stability of the 2′-O-Fpmp and 2′-O-Ctmp protecting groups both at low and high pH is examined. The Royal Society of Chemistry 2000.
- Lloyd, Wayne,Reese, Colin B.,Song, Quanlai,Vandersteen, Anthony M.,Visintin, Cristina,Zhang, Pei-Zhou
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p. 165 - 176
(2007/10/03)
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- Synthesis and DNA cleavage of 2′-O-amino-linked metalloporphyrin-oligonucleotide conjugates
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A new general method for an easy 2′-O-modification of nucleosides is reported. We describe the preparation of modified 19-mer oligonucleotides carrying an aminoalkyl linker at the 2′-position of cytidine residues and the covalent attachment of an artifici
- Dubey, Igor,Pratviel, Genevieve,Meunier, Bernard
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p. 3088 - 3095
(2007/10/03)
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- Deuterated nucleosides
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Deuterated nucleotide and nucleoside units are used to synthesize strands of RNA and DNA wherein one unit is non-deuterated, with adjacent units deuterated. The deuteration is sufficiently high in order that resonance from the deuterated units do not overlap with resonances from non-deuterated units in NMR-experiments. Thereby a "NMR"-window is created in the DNA or RNA strands, which can be beneficially used for advanced studies of structure versus biological activity in DNA and RNA.
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- General Approach to the Synthesis of Specifically Deuterium-Labeled Nucleosides
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Starting from D-(-)-ribose, a set of synthetic routes sharing common intermediates has been developed and exemplified in -, -, -, (5'R)--, and (5'S)--N4-benzoylcytidine and, by deoxygenation, their corresponding 2'-deoxynucleosides.These syntheses provide convenient access to millimolar quantities of deuterium/tritium-labeled natural or unnatural nucleosides for direct use or automated oligonucleotide synthesis.
- Voss, James J. De,Hangeland, Jon J.,Townsend, Craig A.
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p. 2715 - 2723
(2007/10/02)
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- Synthesis of Ribooligonucleotides Using the 4-Methoxybenzyl Group as a New Protecting Group for the 2'-Hydroxyl Group
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The 4-methoxybenzyl group was introduced to protect the 2'-hydroxyl group of uridine, cytidine, and N2-benzoylguanosine by treatment of 2',3'-O-(dibutylstannylene)uridine or NaH-treated nucleosides with 4-methoxybenzyl bromide.The 2'-O-(4-methoxybenzyl)nucleosides can be used as useful starting materials for the synthesis of 3',5'-linked ribooligonucleotides.The 4-methoxybenzyl group was removed rapidly from the ribooligonucleotides by treatment with triphenylmethyl fluoroborate, and the completely deblocked ribooligonucleotides were characterized by enzymatic hydrolysis.
- Takaku, Hiroshi,Kamaike, Kazuo,Tsuchiya, Hiromichi
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- Modified phosphotriester method for chemical synthesis of ribooligonucleotides. Part I. Synthesis of riboundecaadenylate and two fragments constituting the sequence of R-17 translation control signal
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A modified phosphotriester method has been succesfully applied for the chemical synthesis of ribooligonucleotides.The starting material is a fully protected ribomononucleoside containing a 3'-phosphotriester group 5.The coupling reaction is performed usin
- Sung, Wing L.,Narang, Saran A.
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p. 111 - 120
(2007/10/02)
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- Nucleosides, XXXVII. - Synthesis and Properties of 2'-O- and 3'-O-(tert-Butyldimethylsilyl)-5'-O-(4-methoxytrityl)- and 2',3'-Bis(O-tert-butyldimethylsilyl)ribonucleosides - Starting Materials for Oligoribonucleotide Syntheses
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The synthesis of aminoacylated 5'-O-(4-methoxytrityl)ribonucleosides of adenosine (1), guanosine (9), cytidine (31), uridine (17), and 5,6-dihydrouridine (23) have been optimized and these compounds (4, 12, 33, 18 and 24) silylated by tert-butyldimethylsilyl chloride.The corresponding 2'- and 3'-mono-O- as well as 2',3'-bis-O-(tert-butyldimethylsilyl) derivatives have been isolated by combination of chromatographical methods and fractional crystallization procedures in preparative scale.The characterization of the newly synthesized compounds was achieved by UV and 13C-NMR spectra.
- Flockerzi, Dieter,Silber, Gunter,Charubala, Ramamurthy,Schlosser, Wilhelm,Varma, Rajendra Singh,et al.
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p. 1568 - 1585
(2007/10/02)
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