- Method for preparing N6-benzoyladenosine
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The invention discloses a method for preparing N6-benzoyladenosine. The method comprises the following steps: (1) weighing and adding adenosine and a protectant in a flask, adding a solvent and a catalyst, carrying out stirring refluxing for a period of t
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- Tricyclanos: Conformationally constrained nucleoside analogues with a new heterotricycle obtained from a d-ribofuranose unit
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A novel type of nucleoside analogue in which the sugar part is replaced by a new tricycle, 3,7,10-trioxa-11-azatricyclo[5.3.1.05,11]undecane has been prepared by substrate-controlled asymmetric synthesis. 1,5-Dialdehydes obtained from properly protected or unprotected uridine, ribothymidine, cytidine, inosine, adenosine and guanosine by metaperiodate oxidation reacted readily with tris(hydroxymethyl)aminomethane to provide the corresponding tricyclic derivatives with three new stereogenic centers. Through a double cyclisation cascade process the tricyclic compounds were obtained in good to high yields, with very high diastereoselectivity. Formation of one stereoisomer, out of the eight possible, was observed in all cases. The absolute configuration of the new stereotriad-containing tricyclic systems was aided by conventional NMR experiments followed by chemical shift calculations using an X-ray crystal structure as reference that was in good agreement with H-H distances obtained from a new ROESY NMR method. The synthesis was compatible with silyl, trityl and dimethoxytrityl protecting groups. A new reagent mixture containing ZnCl2, Et3SiH and hexafluoroisopropanol was developed for detritylation of the acid-sensitive tricyclano nucleosides.
- Kicsák, Máté,Mándi, Attila,Varga, Szabolcs,Herczeg, Mihály,Batta, Gyula,Bényei, Attila,Borbás, Anikó,Herczegh, Pál
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supporting information
p. 393 - 401
(2018/02/06)
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- CYCLIC DI-NUCLEOTIDE COMPOUNDS AND METHODS OF USE
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Disclosed are cyclic-di-nucleotide cGAMP analogs, methods of synthesizing the compounds, pharmaceutical compositions comprising the compounds thereof, and use of compounds and compositions in medical therapy.
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Paragraph 0288
(2017/10/11)
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- Preparation N6 -Improved method for benzoyl - D D-adenosine
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The invention relates to an improved process for preparing N6-benzoyl-D-adenosine, which is characterized in that in a generated trimethyl silicon-based protected D-adenosine reaction system, benzoyl chloride is added for a benzoylation reaction, the crud
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Page/Page column 6-8
(2018/02/04)
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- In vivo neurochemical monitoring using benzoyl chloride derivatization and liquid chromatography-mass spectrometry
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In vivo neurochemical monitoring using microdialysis sampling is important in neuroscience because it allows correlation of neurotransmission with behavior, disease state, and drug concentrations in the intact brain. A significant limitation of current practice is that different assays are utilized for measuring each class of neurotransmitter. We present a high performance liquid chromatography (HPLC)-tandem mass spectrometry method that utilizes benzoyl chloride for determination of the most common low molecular weight neurotransmitters and metabolites. In this method, 17 analytes were separated in 8 min. The limit of detection was 0.03-0.2 nM for monoamine neurotransmitters, 0.05-11 nM for monoamine metabolites, 2-250 nM for amino acids, 0.5 nM for acetylcholine, 2 nM for histamine, and 25 nM for adenosine at sample volume of 5 μL. Relative standard deviation for repeated analysis at concentrations expected in vivo averaged 7% (n = 3). Commercially available 13C benzoyl chloride was used to generate isotope-labeled internal standards for improved quantification. To demonstrate utility of the method for study of small brain regions, the GABAA receptor antagonist bicuculline (50 μM) was infused into a rat ventral tegmental area while recording neurotransmitter concentration locally and in nucleus accumbens, revealing complex GABAergic control over mesolimbic processes. To demonstrate high temporal resolution monitoring, samples were collected every 60 s while neostigmine, an acetylcholine esterase inhibitor, was infused into the medial prefrontal cortex. This experiment revealed selective positive control of acetylcholine over cortical glutamate.
- Song, Peng,Mabrouk, Omar S.,Hershey, Neil D.,Kennedy, Robert T.
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experimental part
p. 412 - 419
(2012/03/11)
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- COMPOUNDS
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Disclosed herein are 2'-spiro-nucleosides of formula I and derivatives thereof useful for treating a subject infected by hepatitis C virus or dengue virus. Formula (I), where z is a four-or five-membered ring selected from among radicals a-o represented b
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Page/Page column 143-145
(2012/06/16)
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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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- 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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- Synthesis of Leishmania cap-4 intermediates, cap-2 and cap-3
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Synthesis of Leishmania mRNA 5′-cap analogs, m7Gpppm26AmpAm (cap-2), and m7Gpppm26AmpAmpCm (cap-3) is reported. Binding affinities of those cap analogs for LeishIF4E proteins were determined using fluorescence spectroscopy. Cap-3 showed similar affinity to LeishIF4Es compared to the mature trypanosomatids cap structure (cap-4). Copyright Taylor & Francis Group, LLC.
- Lewdorowicz, Magdalena,Stepinski, Janusz,Kierzek, Ryszard,Jemielity, Jacek,Zuberek, Joanna,Yoffe, Yael,Shapira, Michal,Stolarski, Ryszard,Darzynkiewicz, Edward
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p. 1339 - 1348
(2008/09/18)
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- INHIBITORS OF E1 ACTIVATING ENZYMES
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This invention relates to compounds that inhibit El activating enzymes, pharmaceutical compositions comprising the compounds, and methods of using the compounds. The compounds are useful for treating disorders, particularly cell proliferation disorders, including cancers, inflammatory and neurodegenerative disorders; and inflammation associated with infection and cachexia.
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Page/Page column 123-124
(2008/06/13)
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- Synthesis of fluorescein-labeled oligonucleotides bearing a tag in position 2′ of modified adenosine and arabinoadenosine
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Oligonucleotide conjugates containing fluorescein residues in the sugar-phosphate back-bone were synthesized by the standard solid-phase phosphoramidite method using phosphor-amidites of 9-[2-deoxy-5-O-(4,4′- dimethoxytrityl)-2-methoxalylamino-β-D-ribofur
- Vasileva,Krasnousova,Donina,Abramova,Zhdanova,Kovalenko,Silnikov
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p. 1677 - 1683
(2008/02/09)
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- Antisense modulation of polo-like kinase expression
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Antisense compounds, compositions and methods are provided for modulating the expression of polo-like kinase. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding polo-like kinase. Methods of using these compounds for modulation of polo-like kinase expression and for treatment of diseases associated with expression of polo-like kinase are provided.
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Page/Page column 18
(2008/06/13)
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- Polymer supported carbodiimide strategy for the synthesis of N-acylated derivatives of deoxy- and ribo purinenucleosides using active esters
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A cost-effective synthetic strategy has been used for the selective protection of the exocyclic amino function of purine nucleosides. Instead of using the common protecting groups in their chloride or anhydride forms, the less expensive and nontoxic acidic form was chosen. The acids were first activated to an active ester form using DCC and further successfully used for N-acylation of purine nucleosides. The contamination of the N-acylated product with DCU was inconvenient and was avoided by use of polymer supported- carbodiimide that has the additional advantage of reusability.
- Tripathi, Snehlata,Misra, Krishna,Sanghvi, Yogesh S.
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p. 5045 - 5048
(2007/10/03)
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- Antisense modulation of resistin expression
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Antisense compounds, compositions and methods are provided for modulating the expression of resistin. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding resistin. Methods of using these compounds for modulation of resistin expression and for treatment of diseases associated with expression of resistin are provided.
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Page/Page column 18
(2010/02/05)
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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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- Efficient synthesis of protected 3′-deoxyadenosine and 3′-deoxyguanosine from adenosine and guanosine
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Highly efficient synthesis of protected 3′-deoxyadenosine and 3′-deoxyguanosine from adenosine and guanosine were described. The 2′,3′-diol of protected adenosine and guanosine were reacted with α-acetoxyisobutyryl bromide to yield 9-(2′-O-acetyl-3′-bromo
- Cui, Zhiyong,Zhang, Lei,Zhang, Biliang
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p. 561 - 563
(2007/10/03)
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- Synthesis and properties of modified oligodeoxyribonucleotides containing 9-(2-amino-2-deoxy-β-D-arabinofuranosyl)adenine
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The synthesis of modified oligodeoxyribonucleotides containing 2'- amino-2'-deoxyarabinoadenosine residues (aA(n)) was carried out by means of the standard phosphoramidite chemistry. A high reactivity of such compounds to electrophilic reagents was shown.
- Zubin, Eugene M.,Antsypovich, Sergey I.,Oretskaya, Tatiana S.,Romanova, Elena A.,Volkov, Eugene M.,Tashlitsky, Vadim N.,Dolinnaya, Nina G.,Shabarova, Zoe A.
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p. 425 - 440
(2007/10/03)
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- Alteration of DNA primary structure by DNA topoisomerase I. Isolation of the covalent topoisomerase I-DNA binary complex in enzymatically competent form
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DNA ligation by DNA topoisomerase I was investigated employing synthetic DNA substrates containing a single strand nick. Site-specific cleavage of the DNA by topoisomerase I in proximity to the nick resulted in uncoupling of the cleavage and ligation reac
- Henningfeld, Kristine A.,Arslan, Tuncer,Hecht, Sidney M.
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p. 11701 - 11714
(2007/10/03)
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- 'Active' conformation of the inositol monophosphatase substrate, adenosine 2'-phosphate: role of the ribofuranosyl O-atoms in chelating a second Mg2+ ion
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In the presence of Mg2+ ions, inositol monophosphatase from bovine brain catalyses the hydrolysis of the phosphate ester of a range of purine- and pyrimidine-containing nucleoside 2'-phosphates including adenosine 2'-phosphate (2'-AMP) but not adenosine 2'-phosphorothioate (2'-AMPS). 2'-AMPS also fails to serve as an inhibitor under these conditions.In contrast to the situation for the alcohol hydrolysis product, inositol, adenosine does not serve as a product inhibitor for the enzyme or mediate the enzyme-catalysed exchange of 18O-label from water into inorganic phosphate.However, in the presence of Mn2+ ions 2'-AMPS is a substrate for the enzyme.These findings indicate that the product adenosine does not bind to the enzyme in its ground-state conformations and that a strong phosphate group-holoenzyme interaction is required to stabilise a high-energy arrangement in the enzyme-substrate complexes of 2'-AMPS and, probably, 2'-AMP.On the basis of these results and those from previous kinetic and substrate modification studies it is proposed that a second Mg2+ ion might stabilise a conformation in which the adenine moiety of bound 2'-AMP occupies a C-1'-axial ribofuranosyl position through the direct chelation of the second Mg2+ ion to the bridging phosphate ester 2'-O-atom and the ribofuranose ring O-atom.An alternative high-energy arrangement in which the interaction of the second Mg2+ ion with the ribofuranose ring O-atom is mediated via water, such that the conformational strain in the furanose ring is relaxed, but where the entropy of the water is decreased, is also a possibility.
- Cole, Andrew G.,Gani, David
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p. 2685 - 2694
(2007/10/02)
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- 2,',5'-phosphorothioate oligoadenylates and plant antiviral uses thereof
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Optically active compounds of the formula STR1 wherein n is 1 or 2 and m is 0, 1, 2 or 3 have antiviral activity. Compounds of the formula wherein at least one of the internucleotide phosphorothioate linkages is of the Sp configuration possess increased antiviral activity and/or metabolic stability.
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- USE OF 3,4-DIMETHOXYBENZYL GROUP AS A PROTECTING GROUP FOR THE 2'-HYDROXYL GROUP IN THE SYNTHESIS OF OLIGORIBONUCLEOTIDES
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The 3,4-dimethoxybenzyl group was introduced to the 2'-hydroxyl group by the reaction of nucleosides with 3,4-dimethoxybenzyl trichloroacetimidate or 3,4-dimethoxybenzyl bromide-NaH.Further, this group can be used as a protecting group for the O6-amide group of the guanine residue.The protected nucleosides are useful starting materials for the synthesis of oligoribonucleotides.The 3,4-dimethoxybenzyl group was removed rapidly from the oligoribonucleotides by treatment with oxidizing agents without any damage to the glycosidic bonds.
- Takaku, Hiroshi,Ito, Tsunehiko,Imai, Kazuaki
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p. 1005 - 1008
(2007/10/02)
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- SYNTHESIS OF OLIGORIBONUCLEOTIDES USING 4-METHOXYBENZYL GROUP AS A NEW PROTECTING GROUP OF THE 2'-HYDROXYL GROUP OF ADENOSINE
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4-Methoxybenzyl group was introduced directlyto the 2'-hydroxyl group from the reaction of adenosine with 4-methoxybenzyl bromide in the presence of sodium hydride.The 2'-O-(4-methoxybenzyl)-adenosine can be successfully used in the synthesis of oligoribo
- Takaku, Hiroshi,Kamaike, Kazuo
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p. 189 - 192
(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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