Academic literature on the topic 'C-nucleoside'

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Journal articles on the topic "C-nucleoside"

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Maeba, Isamu, Masakazu Wakimura, Yasutaka Ito, and Chihiro Ito. "C-Nucleosides. 22. Synthesis of Quinoxaline Acyclo-C-nucleoside." HETEROCYCLES 36, no. 11 (1993): 2591. http://dx.doi.org/10.3987/com-93-6501.

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Rondla, Ramu, Steven J. Coats, Tamara R. McBrayer, Jason Grier, Melissa Johns, Phillip M. Tharnish, Tony Whitaker, Longhu Zhou, and Raymond F. Schinazi. "Anti-hepatitis C Virus Activity of Novel β-D-2′-C-methyl-4′-azido Pyrimidine Nucleoside Phosphoramidate Prodrugs." Antiviral Chemistry and Chemotherapy 20, no. 2 (October 2009): 99–106. http://dx.doi.org/10.3851/imp1400.

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Background: 2′- C-methyl and 4′-azido nucleosides have previously demonstrated inhibition of hepatitis C virus (HCV) replication by targeting the RNA-dependent RNA polymerase NS5B. In an effort to discover new and more potent anti-HCV agents, we envisioned synthesizing nucleoside analogues by combining the 2′- C-methylmoiety with the 4′-azido-moiety into one molecule. Methods: 2′- C-methyl-4′-azido pyrimidine nucleosides were synthesized by first converting 2′- C-methyl ribonucleosides to the corresponding 4′-exocyclic methylene nucleosides. Treatment with iodine azide, benzoylation of the 2′- and 3′-hydroxy groups, oxidative displacement of the 5′-iodo group with meta-chloroperoxybenzoic acid, and debenzoylation gave the desired 2′- C-methyl-4′-azido uridine and thymidine analogues in good yield. Standard conversion of uridine to cytidine via the 4-triazole yielded 2′- C-methyl-4′-azido cytidine. In addition, 5′-phosphoramidate derivatives of 2′-C-methyl-4′-azido uridine and cytidine were synthesized to bypass the initial phosphorylation step. Results: The prepared nucleosides and their 5′-monophosphate prodrugs were evaluated for their ability to inhibit replication of the hepatitis C virus in a subgenomic replicon cell based assay. Cytotoxicity in Huh7 cells was determined simultaneously with anti-HCV activity by extraction and amplification of both HCV RNA and ribosomal RNA. Among the newly synthesized compounds, only the 5′-monophosphate nucleoside prodrugs had modest and selective anti-HCV activity. All prepared pyrimidine nucleosides and 5′-monophosphate nucleoside prodrugs displayed no evidence of cytotoxicity at high concentrations. Conclusions: This work is the first example of both inactive uridine and cytidine analogues of a nucleoside being converted to active anti-HCV nucleosides via 5′-monophosphate prodrugs.
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Kaczmarek, Renata, Dariusz Korczyński, James R. Green, and Roman Dembinski. "Extension of the 5-alkynyluridine side chain via C–C-bond formation in modified organometallic nucleosides using the Nicholas reaction." Beilstein Journal of Organic Chemistry 16 (January 2, 2020): 1–8. http://dx.doi.org/10.3762/bjoc.16.1.

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Dicobalt hexacarbonyl nucleoside complexes of propargyl ether or esters of 5-substituted uridines react with diverse C-nucleophiles. Synthetic outcomes confirmed that the Nicholas reaction can be carried out in a nucleoside presence, leading to a divergent synthesis of novel metallo-nucleosides enriched with alkene, arene, arylketo, and heterocyclic functions, in the deoxy and ribo series.
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MAEBA, I., M. WAKIMURA, Y. ITO, and C. ITO. "ChemInform Abstract: C-Nucleosides. Part 22. Synthesis of Quinoxaline Acyclo-C-Nucleoside." ChemInform 25, no. 11 (August 19, 2010): no. http://dx.doi.org/10.1002/chin.199411183.

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Hassan, Mohamed Ezeldin. "Palladium-catalyzed cross-coupling reaction of organostannanes with nucleoside halides." Collection of Czechoslovak Chemical Communications 56, no. 9 (1991): 1944–47. http://dx.doi.org/10.1135/cccc19911944.

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A general reaction is described for the synthesis of C-5 substituted nucleosides through the coupling of organostannanes with nucleoside-palladium intermediate derived in situ from 5-iodouridine (or 5-iodo-2’-deoxyuridine) and [PdCl2(PPh3)2]. The reaction was used for the synthesis of C-5 aryl, heteroaryl, vinyl, allyl and alkyl substituted nucleosides.
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Grouiller, Annie, and Hassan Essadiq. "Behaviour of 2′-O-p-toluenesulfonyl uridine towards excess of a Grignard reagent." Canadian Journal of Chemistry 67, no. 4 (April 1, 1989): 708–9. http://dx.doi.org/10.1139/v89-108.

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Two C-methylated base nucleosides were obtained when 2′-O-tosyl-5′-O-trityluridine was reacted with 30 equivalents of methylmagnesium iodide. Keywords: nucleoside, Grignard reaction, C-methyl pyrimidinone, anhydro derivative, arabinofuranosyl.
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Iwasaki, Hiromichi, Peng Huang, Michael J. Keating, and William Plunkett. "Differential Incorporation of Ara-C, Gemcitabine, and Fludarabine Into Replicating and Repairing DNA in Proliferating Human Leukemia Cells." Blood 90, no. 1 (July 1, 1997): 270–78. http://dx.doi.org/10.1182/blood.v90.1.270.

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Abstract The major actions of nucleoside analogs such as arabinosylcytosine (ara-C) and fludarabine occurs after their incorporation into DNA, during either replication or repair synthesis. The metabolic salvage and DNA incorporation of the normal nucleoside, deoxycytidine, is functionally compartmentalized toward repair synthesis in a process regulated by ribonucleotide reductase. The aim of this study was to investigate the metabolic pathways by which nucleoside analogs that do (fludarabine, gemcitabine) or do not (ara-C) affect ribonucleotide reductase are incorporated into DNA in proliferating human leukemia cells. Using alkaline density-gradient centrifugation to separate repaired DNA from replicating DNA and unreplicated parental DNA strands, approximately 60% of ara-C nucleotide in DNA was incorporated by repair synthesis in CCRF-CEM cells; the remainder was incorporated by replication. In contrast, fludarabine and gemcitabine, nucleosides that inhibit ribonucleotide reductase and decreased deoxynucleotide pools, were incorporated mainly within replicating DNA. Hydroxyurea also depleted deoxynucleotide pools and increased the incorporation of ara-C into DNA by replicative synthesis. Stimulation of DNA repair activity by UV irradiation selectively enhanced the incorporation of all nucleosides tested through repair synthesis. These findings suggest that the pathways by which therapeutically useful nucleoside analogs are incorporated into DNA are affected by cellular dNTP pools from de novo synthesis and by the relative activities of DNA repair and replication. The antitumor activity of these drugs may be enhanced by combination with either ribonucleotide reductase inhibitors to increase their incorporation into replicating DNA or with agents that induce DNA damage and evoke the DNA repair process.
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Iwasaki, Hiromichi, Peng Huang, Michael J. Keating, and William Plunkett. "Differential Incorporation of Ara-C, Gemcitabine, and Fludarabine Into Replicating and Repairing DNA in Proliferating Human Leukemia Cells." Blood 90, no. 1 (July 1, 1997): 270–78. http://dx.doi.org/10.1182/blood.v90.1.270.270_270_278.

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The major actions of nucleoside analogs such as arabinosylcytosine (ara-C) and fludarabine occurs after their incorporation into DNA, during either replication or repair synthesis. The metabolic salvage and DNA incorporation of the normal nucleoside, deoxycytidine, is functionally compartmentalized toward repair synthesis in a process regulated by ribonucleotide reductase. The aim of this study was to investigate the metabolic pathways by which nucleoside analogs that do (fludarabine, gemcitabine) or do not (ara-C) affect ribonucleotide reductase are incorporated into DNA in proliferating human leukemia cells. Using alkaline density-gradient centrifugation to separate repaired DNA from replicating DNA and unreplicated parental DNA strands, approximately 60% of ara-C nucleotide in DNA was incorporated by repair synthesis in CCRF-CEM cells; the remainder was incorporated by replication. In contrast, fludarabine and gemcitabine, nucleosides that inhibit ribonucleotide reductase and decreased deoxynucleotide pools, were incorporated mainly within replicating DNA. Hydroxyurea also depleted deoxynucleotide pools and increased the incorporation of ara-C into DNA by replicative synthesis. Stimulation of DNA repair activity by UV irradiation selectively enhanced the incorporation of all nucleosides tested through repair synthesis. These findings suggest that the pathways by which therapeutically useful nucleoside analogs are incorporated into DNA are affected by cellular dNTP pools from de novo synthesis and by the relative activities of DNA repair and replication. The antitumor activity of these drugs may be enhanced by combination with either ribonucleotide reductase inhibitors to increase their incorporation into replicating DNA or with agents that induce DNA damage and evoke the DNA repair process.
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Ogawa, Jun, Sou Takeda, Sheng-Xue Xie, Haruyo Hatanaka, Toshihiko Ashikari, Teruo Amachi, and Sakayu Shimizu. "Purification, Characterization, and Gene Cloning of Purine Nucleosidase from Ochrobactrum anthropi." Applied and Environmental Microbiology 67, no. 4 (April 1, 2001): 1783–87. http://dx.doi.org/10.1128/aem.67.4.1783-1787.2001.

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ABSTRACT A bacterium, Ochrobactrum anthropi, produced a large amount of a nucleosidase when cultivated with purine nucleosides. The nucleosidase was purified to homogeneity. The enzyme has a molecular weight of about 170,000 and consists of four identical subunits. It specifically catalyzes the irreversibleN-riboside hydrolysis of purine nucleosides, theKm values being 11.8 to 56.3 μM. The optimal activity temperature and pH were 50°C and pH 4.5 to 6.5, respectively. Pyrimidine nucleosides, purine and pyrimidine nucleotides, NAD, NADP, and nicotinamide mononucleotide are not hydrolyzed by the enzyme. The purine nucleoside hydrolyzing activity of the enzyme was inhibited (mixed inhibition) by pyrimidine nucleosides, with Ki and Ki ′ values of 0.455 to 11.2 μM. Metal ion chelators inhibited activity, and the addition of Zn2+ or Co2+ restored activity. A 1.5-kb DNA fragment, which contains the open reading frame encoding the nucleosidase, was cloned, sequenced, and expressed inEscherichia coli. The deduced 363-amino-acid sequence including a 22-residue leader peptide is in agreement with the enzyme molecular mass and the amino acid sequences of NH2-terminal and internal peptides, and the enzyme is homologous to known nucleosidases from protozoan parasites. The amino acid residues forming the catalytic site and involved in binding with metal ions are well conserved in these nucleosidases.
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Kryczka, Tomasz, Maciej Bero, Janusz Kasperczyk, Piotr Dobrzyński, Barbara Marciniec, Maria Popielarz-Brzezińska, and Pawel Grieb. "In vitro release of cytotoxic nucleoside analogs from lactide-caprolactone and lactide-glycolide copolymers." Acta Biochimica Polonica 49, no. 1 (March 31, 2002): 205–10. http://dx.doi.org/10.18388/abp.2002_3837.

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The aims of our study were to assess the release of cytotoxic nucleoside analogs 5-fluorouracil and 2-chloro-2'-deoxyadenosine from different lactide-glycolide or lactide-caprolactone biodegradable copolymers and the effects of sterilization on this release. The polymers were sterilized either with ethylene oxide at 37 degrees C, or with gamma radiation (15 kGy, 20 kGy, or 25 kGy). The kinetics of nucleoside release from the copolymers were measured over 50 days. Four copolymers exhibited relatively constant release of nucleosides in micromolar concentrations during the entire observation period. Sterilization with either ethylene oxide or gamma radiation only slightly influenced nucleoside release. Further development of these copolymers as an intracerebral nucleoside delivery system for local treatment of brain tumors is indicated.
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Dissertations / Theses on the topic "C-nucleoside"

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Kirkman, Joseph. "Synthesis of Heterocyclic C-Nucleoside Mimics." Thesis, University of Exeter, 2006. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.531679.

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Chan, Heng Ming. "Synthesis of pyrimidine C-nucleoside analogues and triphosphate derivatives." Thesis, Boston College, 2008. http://hdl.handle.net/2345/36.

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Five pyrimidine C-nucleosides were prepared via Heck-type coupling reactions. These derivatives are designed to mimic dC and dU (or T). The minor groove O2 carbonyl in each derivative is replaced by a hydrogen, a fluorine, or a methyl group. The hydrogen-substituted dC analogue was converted into a 2’,3’-dideoxynucleoside, which was converted into a 5’-triphosphate derivative. The other two dC analogues were transformed into 5’-triphosphate derivatives immediately after Heck coupling reactions. These analogues will allow an examination of the nature and role of minor groove interactions between incoming triphosphates and various polymerases
Thesis (MS) — Boston College, 2008
Submitted to: Boston College. Graduate School of Arts and Sciences
Discipline: Chemistry
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Stefan, Carmen Mirela. "Synthesis of C-nucleoside analogues for mechanistic study of uracil DNA glycosylase." [Gainesville, Fla.] : University of Florida, 2004. http://purl.fcla.edu/fcla/etd/UFE0002412.

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Loemba, Hugues D. "Genotypic and phenotypic characteristics of HIV-1 clade C resistant variants selected in vitro against nucleoside and non-nucleoside inhibitors of reverse transcriptase." Thesis, McGill University, 2001. http://digitool.Library.McGill.CA:80/R/?func=dbin-jump-full&object_id=38225.

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This thesis project was designed to investigate the phenotypic and genotypic variability of human immunodeficiency virus type 1 (HIV-1) drug-naive clade C reverse transcriptase (RT) and its potential impact in the development of resistance against inhibitors of RT. Five treatment-naive HIV-1 Ethiopian isolates were classified as subtype C on the basis of env gene heteroduplex mobility assays (HMA) profile and phylogenetic analysis of RT sequences. In subtype C RT, a specific KVEQ motif of silent mutations (amino acid 65, 106, 138, 161) at resistance sites was present. Two Ethiopian strains were naturally resistant to non-nucleoside RT inhibitors (NNRTI), as well as to zidovudine (ZDV), based on the natural polymorphisms of G190A and K70R, respectively. The final drug concentration that selected for NNRTI primary resistance mutations in tissue culture assays was significantly higher for clade B than clade C for each of nevirapine (NW) (10 muM versus 2 or 4 muM), efavirenz (EFV) (1muM versus 0.01muM) and delaviridine (DLV) (10muM versus 1 or 4muM), respectively. In the middle of the selection period with all the NNRTIs, subtype B viruses were harboring a mixture of both wild type and mutated forms, whereas in clade C viruses, primary resistance mutations were fully generated. Thus, we have found that clade C isolates developed more rapidly resistance (8 or 9 weeks with NVP or DLV and 13 weeks with EFV) as compared with clade B controls (at least 15 weeks with NW or DLV and 30 weeks with EFV). Odd mutations were detected during selection with NNRTIs, such as S98I, and two mutations (A62V and V75E), at sites associated to multi-drug resistance against nucleoside inhibitors (NRTIs). The substitution A62V was initially observed as a drug-naive silent mutation A62A. NW and DLV mutants were broadly cross-resistants. Following in vitro selection for drug-resistance with NNRTIs (NVP, DLV and EFV) and NRTIs [lamivudine (3TC) and ZDV], RT immunodominant regions of 14 HIV-1 s
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Grand, Simon Christopher. "The synthesis of carbocyclic nucleoside analogues using rhodium carbenoid C-H insertion reactions." Thesis, University of Nottingham, 2002. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.367403.

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Marcé, Villa Patricia. "Hydroacylation and C-N Coupling Reactions. Mechanistic Studies and Application in the Nucleoside Synthesis." Doctoral thesis, Universitat Rovira i Virgili, 2008. http://hdl.handle.net/10803/9026.

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The PhD work "Hydroacylation and C-N coupling Reactions. Mechanistic Studies and Application in the Nucleoside Synthesis" tackle two different objectives, a) developing new methods of synthesis of nucleosides (introduction, and chapters 1 and 2) and b) to carry out a mechanistic study of the intermolecular hydroacylation and hydroiminoacylation reaction with and cationic rhodium complexes (chapter 3).
Concerning the synthesis nucleosides, in chapter 1 we have explored new methods of synthesis of 2',3'-dideoxynucleosides and isonucleosides using a palladium or copper catalyzed C-N coupling reaction, aiming to overcome the stereoselectivity problems of the glycosylation reaction. The synthesis of the iodo-vinyl derivatives required as starting materials has been tried by different procedures, all of them unsuccessful. Finally, the coupling reaction has been explored in 1-iodo-glucal derivatives. Palladium catalysts were unsuccessful in coupling with benzimidazol used as model of purinic bases. Copper catalysts provided very low conversions. However, the oxidative addition of 1-iodo-glucal to palladium was proved and it was also observed that the reaction with aniline proceeds. That, suggest that the problem is in the steps involving the benzimidazol.
In chapter 2, it has been developed a new method of synthesis of carbocyclic nucleosides using and enantioselective intramolecular hydroacylation reaction as a key step. This reaction leaded to the 3-hydroxymethyl-cyclopentanones in good yields and excellent enantioselectivities. When (S,S)-Me-Duphos was used the 3S-cyclopentanone was obtained, in contrast whether the (R,R)-Me-Duphos was employed the reaction proceed giving the opposite enantiomer. In both cases. The reduction of the ketone can be carried out in a stereoselective way using a hydroxyl-assited reduction with NaBH(OAc)3. Alternatively, the diastereomeric mixture obtained by a direct reduction can be resolved by using a DKR process using a combined enzyme/Ru complex catalytic system. A Mitsunobu reaction has allowed finally to link adenine to the cyclopentane moiety.
In the third chapter, the mechanism of both cationic and neutral rhodium catalyst precursors in the hydroiminoacylation of alkenes was studied. The oxidative addition step was studied using both NMR and DFT techniques. Using the neutral complex, this step is a thermodynamically favoured process, as demonstrated by the isolation of the stable complex. Furthermore, DFT calculations showed the existence of an agostic intermediate on the route to the C-H activation product. In the cationic system, the oxidative addition reaction was shown by DFT calculations to be an endothermic process, hence un-favoured. This was in agreement with the NMR experiments, in which an oxidative addition product was only detected in the presence of a chloride source.
Furthermore, the transition states involved in both systems were identified using DFT calculations, which proved that the presence of chloride not only stabilize the oxidative addition product but also lower the energy barrier of the overall process.
Using the neutral system, it was identified the coupling product still coordinated to rhodium, which is in an enamine tautomeric form. After removal of the coupling product the stable complex [Rh(μ-Cl)(PPh3)2]2 was formed. This species was reported as a precursor for the oxidative addition step, from which the catalytic cycle can start again. However in the cationic system, the system did not yield any stable rhodium species and quickly evolved towards decomposition.
Durante la última década la terapia del SIDA ha experimentado una evolución notable. El conocimiento del modo de actuación y proliferación del virus ha permitido incrementar el número de dianas biológicas para su neutralización. Así, hoy en día se conocen compuestos que inhiben la entrada del virus en la célula, la transcripción del RNA en DNA, la integración del DNA vírico en DNA celular, la producción del envolvente proteico del virus, entre otros. Todo ello, ha permitido la realización de tratamientos dirigidos a diferentes dianas, que han neutralizado la evolución del virus mejorando la calidad de vida de los pacientes.
Existen numerosas metodologías diseñadas para obtener los retrovirales mencionados anteriormente, pero en la mayoría de ellas se requieren numerosos pasos de síntesis y además en muchas de ellas se obtienen mezclas de los isómeros α/β. De este modo se pretende diseñar una alternativa sintética general para la preparación de la familia de nucleósidos arriba indicadas y al mismo tiempo que sea una alternativa práctica y eficaz a los métodos descritos hasta el momento.
En el capítulo uno la obtención de isonucleosidos y 2',3'-dideoxinucleosidos se abordó utilizando como etapa clave de reacción el acoplamiento C-N entre los derivados de 4-halo-2,3-dihidrofurano y 5-halo-2,3-dihidrofurano con bases púricas y pirimidínicas, la posterior hidrogenación enantioselectiva del doble enlace nos permitiría obtener los mencionados compuestos de una forma sencilla. En el estudio realizado bajas conversiones de los productos de acoplamiento cruzado fueron detectados aunque actualmente se están intentado mejorar los resultados.
Referente a la obtención de carbociclonucleosidos abordada en el capítulo 2, se ha llevado cabo una nueva metodología sintética en la que se ha aplicado la reacción de hidroacilación intramolecular enantioselectiva catalizada por rodio. Así pentenales substituidos en posición cuatro han sido convertidos en las ciclopentanonas correspondientes. En función de la quiralidad de la fosfina empleada se han obtenido tanto los enantiomeros R como S con excelentes conversiones y enantioselectividades.
Con el fin de incorporar la base nitrogenada en la ciclopentanona la reducción diastereoselectiva se ha llevado a cabo dos procedimientos: a) reducción racémica de la ciclopentanona y posterior resolución cinética dinámica, b) reducción diastereoselectiva utilizando como agente reductor el triacetoxiborohidruro de sodio. En ambos casos se obtuvieron diastereoselectividades excelentes pudiendo así obtener un distereoisomero u otro en función del procedimiento y el enantiomero utilizado como material de partida. La posterior reacción de Mitsunobu sobre el alcohol y la desprotección del grupo protector nos ha permitido obtener el carbociclonucleosido con buenos rendimientos y excelentes esteroselectividades.
En el capitulo tres se ha realizado un estudio sobre la reacción de hidroacilación intramolecular de alquenos cataliza por rodio, donde se ha estudiado la diferencia de comportamiento de los sistemas catiónicos y neutros de rodio en la etapa de adición oxidante. Estos estudios se han realizado utilizando técnicas espectroscópicas de resonancia magnética nuclear y cálculos teóricos mediante técnicas DFT. El estudio computacional ha mostrado que en el caso de los sistemas neutros la etapa de adición oxidante es una etapa termodinámicamente favorable hecho que se gratifica con el hecho de que el producto de adición oxidante es estable y aislable. Además se ha encontrado la existencia de un intermedio agóstico en el proceso de activación del enlace C-H. Sin embargo, en los sistemas catiónicos la etapa de adición oxidante resultó ser un proceso endotérmico. Los estados de transición encontrados no solo han demostrado que la presencia de cloruro estabiliza el producto de adición oxidante sino que también disminuye la barrera energética del proceso global. La etapa de inserción del alqueno también fue estudiada para ambos sistemas utilizando estireno como sustrato. En el sistema neutro se detectó una nueva especie de rodio la cual no había sido descrita anteriormente y fue completamente caracterizada mediante RMN multinuclear.
En el sistema catiónico se consiguió detectar el hidruro correspondiente al producto de adición oxidante el cual también fue completamente caracterizado por técnicas de RMN. Sin embargo, en el estudio de la inserción del alqueno no se observó la ningún producto que indicase que el mencionado proceso se llevará acabo indicado que la inserción de alqueno es además la etapa lenta del proceso.
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Robinson, N. G. "New amino acid syntheses : Applications to studies on penicillin biosynthesis and C-nucleoside synthesis." Thesis, University of Oxford, 1986. http://ethos.bl.uk/OrderDetails.do?uin=uk.bl.ethos.375322.

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Cheng, Kwan-wai. "Regulation of equilibrative nucleoside transporter-1 by protein kinase C and mitogen-activating protein kinase /." View the Table of Contents & Abstract, 2005. http://sunzi.lib.hku.hk/hkuto/record/B31494912.

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Liang, Yong. "Novel Approaches for the Synthesis of C-5 Modified Pyrimidine Nucleosides." FIU Digital Commons, 2014. http://digitalcommons.fiu.edu/etd/1591.

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The antiviral or anticancer activities of C-5 modified pyrimidine nucleoside analogues validate the need for the development of their syntheses. In the first half of this dissertation, I explore the Pd-catalyzed cross-coupling reaction of allylphenylgermanes with aryl halides in the presence of SbF5/TBAF to give various biaryls by transferring multiple phenyl groups, which has also been applied to the 5-halo pyrimidine nucleosides for the synthesis of 5-aryl derivatives. To avoid the use of organometallic reagents, I developed Pd-catalyzed direct arylation of 5-halo pyrimidine nucleosides. It was discovered that 5-aryl pyrimidine nucleosides could be synthesized by Pd-catalyzed direct arylation of N3-free 5-halo uracil and uracil nucleosides with simple arenes or heteroaromatics in the presence of TBAF within 1 h. Both N3-protected and N3-free uracil and uracil nucleosides could undergo base-promoted Pd-catalyzed direct arylation, but only with electron rich heteroaromatics. In the second half of this dissertation, 5-acetylenic uracil and uracil nucleosides have been employed to investigate the hydrogermylation, hydrosulfonylation as well as hydroazidation for the synthesis of various functionalized 5-vinyl pyrimidine nucleosides. Hydrogermylation of 5-alkynyl uracil analogues with trialkylgermane or tris(trimethylsilyl)germane hydride gave the corresponding vinyl trialkylgermane, or tris(trimethylsilyl)germane uracil derivatives. During the hydrogermylation with triphenylgermane, besides the vinyl triphenylgermane uracil derivatives, 5-[2-(triphenylgermyl)acetyl]uracil was also isolated and characterized and the origin of the acetyl oxygen was clarified. Tris(trimethylsilyl)germane uracil derivatives were coupled to aryl halides but with decent yield. Iron-mediated regio- and stereoselective hydrosulfonylation of the 5-ethynyl pyrimidine analogues with sulfonyl chloride or sulfonyl hydrazine to give 5-(1-halo-2-tosyl)vinyluracil nucleoside derivatives has been developed. Nucleophilic substitution of the 5-(β-halovinyl)sulfonyl nucleosides with various nucleophiles have been performed to give highly functionalized 5-vinyl pyrimidine nucleosides via the addition-elimination mechanism. The 5-(β-keto)sulfonyluracil derivative has also been synthesized via the aerobic difunctionalization of 5-ethynyluracil analogue with sulfinic acid in the presence of catalytic amount of pyridine. Silver catalyzed hydroazidation of protected 2'-deoxy-5-ethynyluridine with TMSN3 in the presence of catalytic amount of water to give 5-(α-azidovinyl)uracil nucleoside derivatives was developed. Strain promoted Click reaction of the 5-(α-azidovinyl)uracil with cyclooctyne provide the corresponding fully conjugated triazole product.
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Cong, Mei. "Design, synthesis and characterization of novel triazole nucleoside analogues." Thesis, Aix-Marseille, 2015. http://www.theses.fr/2015AIXM4018.

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Les analogues de nucléosides sont d'une importance considérable dans la recherche de nouveaux candidats médicaments antiviraux et anticancéreux. La ribavirine est en effet le premier nucléoside triazole antiviral synthétique. Elle est toujours activement utilisée en milieu hospitalier pour le traitement de l'hépatite C et celui des pandémies virales émergentes. Récemment, le besoin de nouveaux agents thérapeutiques efficaces dotés de nouveaux mécanismes d'action a donc créé un regain d'intérêt dans la création de nouvelles entités structurelles de nucléosides triazoles. Au cours de mon doctorat, j’ai été activement engagée dans l’élaboration de nouvelles structures O-arylées et S-arylées de nucléosides triazoles. Les nucléosides triazoles O-arylés ont été obtenus par substitution nucléophile aromatique initiée par micro-ondes, tandis que les nucléosides triazoles S-arylés ont été synthétisés par réaction de couplage C-S en utilisant un catalyseur palladié possédant des ligands mixtes nouvellement mis au point dans notre laboratoire. Le concept du système de catalyseur à ligands mixtes est extrêmement avantageux et enrichissant puisqu’il permet de combiner de façon rationnelle des ligands possédant des fonctionnalités complémentaires afin de promouvoir des réactions avec des substrats pour lesquels ces réactions sont très compliquées. Enfin, afin d'améliorer la solubilité dans l'eau des analogues nucléosidiques triazoles actifs que nous avons identifiés, j’ai tenté de conjuguer le nucléoside triazole à un dendrimère amphiphile dans le but d'élaborer un système de délivrance efficace des médicaments et ainsi d’améliorer leur biodisponibilité
Nucleoside mimics are of considerable importance in the search of antiviral and anticancer drug candidates. One noteworthy example is ribavirin, the first synthetic antiviral triazole nucleoside discovered 40 years ago, which is still actively in clinic use for treating hepatitis C infection and emerging viral pandemics. Recently, ribavirin has been also reported to demonstrate apoptosis-related anticancer effects and is in clinical trial for treating leukemia. Consequently, there is a renewed interest in creating new structural entities of triazole nucleosides with the aim of developing potent therapeutic agents with novel mechanisms of action. During my PhD program, I have been actively engaged in constructing structurally novel O-arylated and S-arylated triazole nucleosides. The O-arylated triazole nucleosides were obtained via microwave promoted aromatic nucleophilic substitution, whereas the S-arylated triazole nucleosides were synthesized via C-S coupling reaction using our newly developed mixed ligand Pd catalyst (Pd2(dba)3/Xantphos/CyPF-tBu). The concept of the mixed ligand catalyst system is extremely advantageous and rewarding, offering a unique opportunity to rationally combine ligands with complementary features in order to promote the reactions with challenging substrates which are otherwise difficult to proceed. Finally, in order to improve bioavailability of the active triazole nucleoside analogues identified in our group, I have attempted to conjugate the triazole nucleoside to an amphiphilic dendrimer in the view to establishing an effective drug delivery system and offering a better bioavailability
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Books on the topic "C-nucleoside"

1

Mohr, Marion. Pseudouridin, ein natürlich vorkommendes C-Nucleosid, und seine Verwendung in der Oligonucleotidsynthese. Konstanz: Hartung-Gorre, 1992.

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Book chapters on the topic "C-nucleoside"

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Carroll, Steven S., and Robert L. LaFemina. "Nucleoside Analog Inhibitors of Hepatitis C Viral Replication." In Antiviral Research, 153–66. Washington, DC, USA: ASM Press, 2014. http://dx.doi.org/10.1128/9781555815493.ch9.

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Postel, E. H. "NM23/Nucleoside Diphosphate Kinase as a Transcriptional Activator of c-myc." In Current Topics in Microbiology and Immunology, 233–52. Berlin, Heidelberg: Springer Berlin Heidelberg, 1996. http://dx.doi.org/10.1007/978-3-642-61109-4_11.

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Franchetti, P., L. Cappellacci, M. Grifantini, H. N. Jayaram, and B. M. Goldstein. "C-Nucleoside Analogs of Tiazofurin and Selenazofurin as Inosine 5'-Monophosphate Dehydrogenase Inhibitors." In ACS Symposium Series, 212–30. Washington, DC: American Chemical Society, 2003. http://dx.doi.org/10.1021/bk-2003-0839.ch011.

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Miras-Portugal, M. Teresa, Esmerilda G. Delicado, Teresa Casillas, and Raquel P. Sen. "Control of Nucleoside Transport in Neural Cells Effect of Protein Kinase C Activation." In Advances in Experimental Medicine and Biology, 435–38. Boston, MA: Springer US, 1991. http://dx.doi.org/10.1007/978-1-4899-2638-8_100.

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Liu, Yaya, Yupeng He, and Akhteruzzaman Molla. "Hepatitis C Virus Polymerase as a Target for Antiviral Drug Intervention: Non-Nucleoside Inhibitors." In Antiviral Research, 137–51. Washington, DC, USA: ASM Press, 2014. http://dx.doi.org/10.1128/9781555815493.ch8.

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Beaulieu, Pierre L. "CHAPTER 8. Design and Development of NS5B Polymerase Non‐nucleoside Inhibitors for the Treatment of Hepatitis C Virus Infection." In Drug Discovery, 248–94. Cambridge: Royal Society of Chemistry, 2013. http://dx.doi.org/10.1039/9781849737814-00248.

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Watanabe, Kyoichi A. "The Chemistry of C-Nucleosides." In Chemistry of Nucleosides and Nucleotides, 421–535. Boston, MA: Springer US, 1994. http://dx.doi.org/10.1007/978-1-4757-9667-4_5.

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Jalluri, Ravi K., Young H. Yuh, and E. Will Taylor. "O—C—N Anomeric Effect in Nucleosides." In ACS Symposium Series, 277–93. Washington, DC: American Chemical Society, 1993. http://dx.doi.org/10.1021/bk-1993-0539.ch015.

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Crisalli, Pete, and Eric T. Kool. "Fluorescent C-Nucleosides and their Oligomeric Assemblies." In Fluorescent Analogs of Biomolecular Building Blocks, 320–55. Hoboken, NJ, USA: John Wiley & Sons, Inc, 2016. http://dx.doi.org/10.1002/9781119179320.ch14.

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Vismara, E., F. Minisci, and F. Fontana. "New Procedures of Homolytic Alkylation of Heteroaromatic Bases: Synthesis of C-Nucleosides." In Organic Free Radicals, 225–26. Berlin, Heidelberg: Springer Berlin Heidelberg, 1988. http://dx.doi.org/10.1007/978-3-642-73963-7_112.

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Conference papers on the topic "C-nucleoside"

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Siqueira, Edmilson Clarindo de, Alexander Y.Nazarenko, and Bogdan Doboszewski. "Dehydration of D-mannitol: building block for C-nucleoside synthesis." In 14th Brazilian Meeting on Organic Synthesis. São Paulo: Editora Edgard Blücher, 2013. http://dx.doi.org/10.5151/chempro-14bmos-r0023-2.

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Hamann, Marie, Claire Pierra, Jean-Pierre Sommadossi, Chiara Musiu, Luana Vargiu, Michel Liuzzi, Richard Storer, and Gilles Gosselin. "Synthesis and antiviral evaluation of 7,9-dideaza-8-thiapurine C-nucleoside derivatives." In XIVth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2008. http://dx.doi.org/10.1135/css200810347.

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Smits, Helmars, Māris Turks, Dace Katkevica, and Ērika Bizdēna. "Synthesis of protected 3,5-dideoxy-3-C-azidomethyl-D-allofuranose, precursor of 3',5'-C-modified nucleoside analogs." In XIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 1999. http://dx.doi.org/10.1135/css199902039.

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Sedláček, Ondřej, Radek Pohl, and Antonín Holý. "Synthesis of 8-C-substituted 2,6-diaminopurine acyclic nucleoside phosphonates by Negishi cross-coupling." In XIVth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2008. http://dx.doi.org/10.1135/css200810449.

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Gazivoda, Tatjana, Silvana Raić-Malić, Sandra Kraljević-Pavelić, Krešimir Pavelić, Jan Balzarini, and Mladen Mintas. "The new unsaturated acyclic C-5 pyrimidine nucleoside analogues: synthesis, cytostatic and anti-HIV evaluations." In XIVth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2008. http://dx.doi.org/10.1135/css200810439.

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Liu, Xiaojun, Akira Matsuda, and William Plunkett. "Abstract 3638: DNA strand breaks induced by 2′-C-cyano-2′-deoxy-nucleoside analogs are repaired by homologous recombination." In Proceedings: AACR 101st Annual Meeting 2010‐‐ Apr 17‐21, 2010; Washington, DC. American Association for Cancer Research, 2010. http://dx.doi.org/10.1158/1538-7445.am10-3638.

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Fernández-Calotti, Paula, Albert Català, MarÇal Pastor-Anglada, Roberta Malatesta, Susana Rives, and Mireia Camos. "Abstract C46: Implication of FLT3 in human equilibrative nucleoside transporter 1 (hENT1)-mediated uptake of Ara-C in pediatric acute leukemia." In Abstracts: AACR-NCI-EORTC International Conference: Molecular Targets and Cancer Therapeutics--Oct 19-23, 2013; Boston, MA. American Association for Cancer Research, 2013. http://dx.doi.org/10.1158/1535-7163.targ-13-c46.

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Štambaský, Jan, Pavel Kočovský, and Michal Hocek. "Towards a novel approach to C-nucleosides." In XIIIth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2005. http://dx.doi.org/10.1135/css200507277.

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Čerňa, Igor, and Michal Hocek. "Direct C–H arylation of purines and purine nucleosides." In XIVth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2008. http://dx.doi.org/10.1135/css200810327.

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Kubelka, Tomáš, Martin Štefko, Jan Bárta, Nicolas Joubert, Milan Urban, Hubert Chapuis, and Michal Hocek. "Development of a general and modular approach to C-nucleosides." In XVth Symposium on Chemistry of Nucleic Acid Components. Prague: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, 2011. http://dx.doi.org/10.1135/css201112180.

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