- Lipid-conjugated oligonucleotides via click chemistry efficiently inhibit hepatitis C virus translation
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Conjugation of a lipid moiety via click chemistry potentiates the cellular uptake of oligonucleotides and allows their intracellular delivery. These nontoxic lipid conjugates efficiently inhibit hepatitis C virus internal ribosome entry site (IRES)-mediated translation in human hepatic Huh7 cells. The biological activity of the lipid-conjugated oligonucleotides is not affected by the presence of serum.
- Godeau, Guilhem,Staedel, Cathy,Barthélémy, Phílippe
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Read Online
- Glycosyl-nucleoside fluorinated amphiphiles as components of nanostructured hydrogels
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The synthesis of two novel glycosyl-nucleoside fluorinated amphiphiles (GNFs) derived from the 2H,2H,3H,3H-perfluoro-undecanoyl hydrophobic chain is described. The GNF amphiphiles, which feature either β-d-glucopyranosyl or β-d-lactopyranosyl moieties linked to a thymine base via a 1,2,3 triazole linker, were prepared using a 'double click' chemistry route. Surface tension measurements, gelation properties, and TEM studies show that GNFs spontaneously assemble into supramolecular structures. Similarly to their hydrocarbon analogues (GNLs), the GNFs have unique gelation properties in water. A minimum hydrogelation concentration of 0.1% (w/w), was determined in the case of the β-d-glucopyranosyl derivative. Cell viability studies indicate that fluorocarbon GNF 5 was not toxic for human cells (Huh7), whereas hydrocarbon analogue GNL is toxic above 100 μm.
- Godeau, Guilhem,Brun, Christophe,Arnion, Hélène,Staedel, Cathy,Barthélémy, Philippe
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Read Online
- Microwave-assisted synthesis of a triazole-linked 3′-5′ dithymidine using click chemistry
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Synthesis of a triazole-linked 3′-5′ thymidine dimer making use of 1,3-dipolar cycloaddition is described. The azido-precursor was obtained by regioselective chlorination of thymidine, followed by azidation. The second precursor, a propargyl derivative, was obtained by selective 3′-O-alkylation of thymidine. Two 'click systems' were compared to obtain the desired dimer. These reactions were performed by microwave irradiation.
- Lucas, Romain,Neto, Virginie,Hadj Bouazza, Amel,Zerrouki, Rachida,Granet, Robert,Krausz, Pierre,Champavier, Yves
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- Synthesis of bioconjugated sym -pentasubstituted corannulenes: Experimental and theoretical investigations of supramolecular architectures
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Applications of supramolecular architectures span a broad range of fields from medicinal chemistry to materials science and gas storage, making the design and synthesis of such structures a goal of high interest. The unique structural and symmetric proper
- Mattarella, Martin,Berstis, Laura,Baldridge, Kim K.,Siegel, Jay S.
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- Synthesis and characterization of ferrocene-labeled oligodeoxynucleotides
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Using a facile on-column derivatization procedure, oligodeoxynucleotides (ODNs) are labeled with a ferrocene derivative at specific sites. A Sonagashira cross-coupling reaction, using Pd(PPh3)4 and CuI, links ferrocene propargylamide
- Beilstein, Amy E.,Grinstaff, Mark W.
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- Photodimerisation of glycothymidines in solution and in micelles
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Glycothymidines were designed and synthesized as a new class of functional glycomimetics in which a photochemical [2+2] cycloaddition of the thymine moiety induces structural changes of carbohydrate presentation. To test if photodimerisation of these glycothymidines is feasible within an array of molecules, the photochemical reaction was investigated using NMR and NMR diffusion experiments in solution as well as in the supramolecular context of detergent micelles that mimic cellular membranes.
- Schwekendiek, Kirsten,Kobarg, Hauke,Daumlechner, Lena,Soennichsen, Frank D.,Lindhorst, Thisbe K.
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Read Online
- Tightly linked morpholino-nucleoside chimeras: new, compact cationic oligonucleotide analogues
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The polyanionic phosphodiester backbone of nucleic acids contributes to high nuclease sensitivity and low cellular uptake and is therefore a major obstacle to the biological application of native oligonucleotides. Backbone modifications, particularly charge alterations is a proven strategy to provide artificial oligonucleotides with improved properties. Here, we describe the synthesis of a new type of oligonucleotide analogues consisting of a morpholino and a ribo- or deoxyribonucleoside in which the 5′-amino group of the nucleoside unit provides the nitrogen of the morpholine ring. The synthetic protocol is compatible with trityl and dimethoxytrityl protecting groups and azido functionality, and was extended to the synthesis of higher oligomers. The chimeras are positively charged in aqueous medium, due to theN-alkylated tertiary amine structure of the morpholino unit.
- Batta, Gyula,Bege, Miklós,Bereczki, Ilona,Borbás, Anikó,Debreczeni, Nóra,Herczeg, Mihály,Herczegh, Pál
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p. 8711 - 8721
(2021/10/22)
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- Design, Synthesis and Biological Evaluation of Novel Anthraniloyl-AMP Mimics as PQS Biosynthesis Inhibitors against Pseudomonas aeruginosa Resistance
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The Pseudomonas quinolone system (PQS) is one of the three major interconnected quorum sensing signaling systems in Pseudomonas aeruginosa. The virulence factors PQS and HHQ activate the transcription regulator PqsR (MvfR), which controls several activiti
- Black, David StC,Das, Theerthankar,Kumar, Naresh,Rice, Scott A.,Sabir, Shekh,Subramoni, Sujatha
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- Deoxynucleic Guanidines (DNG)- Modified Oligonucleotides and Methods of Synthesizing Deoxynucleic Guanidine Strands
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Disclosed herein are spherical nucleic acids (SNAs) comprising oligonucleotides comprising one or more modified oligonucleotides, and methods of use thereof. Also disclosed are methods of synthesizing modified oligonucleotides for use in therapeutics, inc
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- A hydroxamic-acid-containing nucleoside inhibits DNA repair nuclease SNM1A
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Nine modified nucleosides, incorporating zinc-binding pharmacophores, have been synthesised and evaluated as inhibitors of the DNA repair nuclease SNM1A. The series included oxyamides, hydroxamic acids, hydroxamates, a hydrazide, a squarate ester and a squaramide. A hydroxamic acid-derived nucleoside inhibited the enzyme, offering a novel approach for potential therapeutic development through the use of rationally designed nucleoside derived inhibitors.
- Doherty, William,Dürr, Eva-Maria,Baddock, Hannah T.,Lee, Sook Y.,McHugh, Peter J.,Brown, Tom,Senge, Mathias O.,Scanlan, Eoin M.,McGouran, Joanna F.
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supporting information
p. 8094 - 8105
(2019/09/19)
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- Synthesis and biological assay of new 2’-deoxyuridine dimers containing a 1,2,3-triazole linker. Part I
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We describe a simple method for the synthesis of modified dinucleosides containing pyrimidine nucleoside analogues (2’-deoxyuridine, thymidine and 5-fluoro-2’-deoxyuridine). Six different dimers with a 1,2,3-triazole linkage were obtained by azide–alkyne
- Michalska, Lucyna,Wawrzyniak, Dariusz,Szymańska-Michalak, Agnieszka,Barciszewski, Jan,Boryski, Jerzy,Baraniak, Dagmara
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p. 218 - 235
(2019/01/04)
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- Synthesis and in vitro anticancer activity of new gemcitabine-nucleoside analogue dimers containing methyltriazole or ester-methyltriazole linker
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Two series of novel gemcitabine-nucleoside analogue dimers were synthesized using the ‘click’ chemistry approach. In the first series of dimers (21–30), the nucleoside units were connected with a stable methyltriazole 4N-3′(or 5′)C linker whereas in the second series (31–40) with a cleavable ester-methyltriazole 4N-3′(or 5′)C linker. Dimers 21–40 were evaluated for their cytotoxic activity in five human cancer cell lines such as cervical (HeLa), nasopharyngeal (KB), lung (A549), brain (U87), liver (HepG2) and normal dermal fibroblast cell line (HDF) using the sulforhodamine B (SRB) assay. Compound 29 comprising two gemcitabine (dFdC) units exhibited the highest activity among dimers 21–30. The activity of compound 29 was higher than that of dFdC in all the studied cancer cell lines. A similar order of activity was observed for compounds 25, 28, and 30. The best activity among all the dimers synthesized was displayed by compound 39, comprising two gemcitabine units with a cleavable linker. The activity of compound 39 was 5 to 9 times higher than that of dFdC, depending on the cell line. In addition, marked cytotoxic activity was shown by compounds 31, 36, 38, and 40.
- Trznadel, Roksana,Singh, Aleksandra,Kleczewska, Natalia,Liberska, Joanna,Ruszkowski, Piotr,Celewicz, Lech
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p. 2587 - 2594
(2019/08/12)
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- Mercury-Free Automated Synthesis of Guanidinium Backbone Oligonucleotides
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A new method for synthesizing deoxynucleic guanidine (DNG) oligonucleotides that uses iodine as a mild and inexpensive coupling reagent is reported. This method eliminates the need for the toxic mercury salts and pungent thiophenol historically used in me
- Skakuj, Kacper,Bujold, Katherine E.,Mirkin, Chad A.
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p. 20171 - 20176
(2020/01/02)
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- Synthesis of sulfamide analogues of deoxthymidine monophosphate as potential inhibitors of mycobacterial cell wall biosynthesis
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The recently discovered enzyme Mycobacterium tuberculosis thymidine monophosphate kinase (TMPKmt), which catalyses the phosphorylation of deoxythymidine monophosphate (dTMP) to give deoxythymidine diphosphate (dTDP), is indispensable for the growth and survival of M. tuberculosis as it plays an essential role in DNA synthesis. Inhibition of TMPKmt is an attractive avenue for the development of novel anti-tuberculosis agents. Based on the premise that sulfamide may be a suitable isostere of phosphate, deoxythymidine analogues comprising various substituted sulfamides at C5′ were modelled in silico into the active site of TMPKmt (PDB accession code: 1N5K) using induced-fit docking methods. A selection of modelled compounds was synthesized, and their activity as inhibitors of TMPKmt was evaluated. Three compounds showed competitive inhibition of TMPKmt in the micromolar range (10–50 μM). Compounds were tested in vitro for anti-mycobacterial activity against M. smegmatis: three compounds showed weak anti-mycobacterial activity (MIC 250 μg/mL).
- Suthagar, Kajitha,Jiao, Wanting,Munier-Lehmann, Hélène,Fairbanks, Antony J.
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- A new way to do an old reaction: highly efficient reduction of organic azides by sodium iodide in the presence of acidic ion exchange resin
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Organic azides are readily reduced to the corresponding amines by treatment with sodium iodide in the presence of acidic ion exchange resin. The process, optimal when performed at 40 °C and 200 mbar pressure on a rotatory evaporator, is extremely efficient, clean, and tolerant of a variety of functional groups.
- Suthagar, Kajitha,Fairbanks, Antony J.
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supporting information
p. 713 - 715
(2017/01/13)
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- Synthesis of triazole-linked morpholino oligonucleotides via CuI catalysed cycloaddition
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Triazole-linked morpholino (TLMO) oligonucleic acids were synthesised using the CuI catalysed (3 + 2) azide-alkyne cycloaddition (CuAAC) reaction. The modified DNA analogues were incorporated into 13-mer sequences via solid phase syn
- Palframan, Matthew J.,Alharthy, Rima D.,Powalowska, Paulina K.,Hayes, Christopher J.
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p. 3112 - 3119
(2016/03/19)
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- Self-assembled nanofiber hydrogels for mechanoresponsive therapeutic anti-TNFα antibody delivery
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Low molecular weight hydrogels, prepared from glycosyl-nucleoside-lipid amphiphiles, exhibit shear-thinning behaviour and reversible thermally- and mechanically-triggered sol-gel transitions. Using mechanical shear stimulation, the release of entrapped anti-TNFα increases and the released anti-TNFα demonstrates efficacy in in vitro neutralization bioassays. Delivery of anti-TNFα is of general interest and broad medicinal utility for treating autoimmune diseases such as rheumatoid arthritis.
- Kaplan,Barthélémy,Grinstaff
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supporting information
p. 5860 - 5863
(2016/05/19)
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- New [(η5-C5H5)Ru(N-N)(PPh3)][PF6] compounds: Colon anticancer activity and GLUT-mediated cellular uptake of carbohydrate-appended complexes
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Eight ruthenium(ii) compounds of the general formula [(η5-C5H5)Ru(N-N)(PPh3)][PF6] were rationally designed, exhibiting high cytotoxicity against HCT116 human colon cancer cells, with IC50
- Florindo, Pedro R.,Pereira, Diane M.,Borralho, Pedro M.,Costa, Paulo J.,Piedade,Rodrigues, Cecília M. P.,Fernandes, Ana C.
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p. 11926 - 11930
(2016/08/05)
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- Supramolecular assemblies of novel aminonucleoside phospholipids and their bonding to nucleic acids
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A novel class of aminonucleoside phospholipids has been developed. These molecules could spontaneously assemble into supramolecular structures including multilamellar organization, hydrogels, superhelical strands, and vesicles. Their ability to bind to DNA by hydrogen bonding and π-π stacking interactions was investigated by many means. This journal is
- Pan, Delin,Sun, Jing,Jin, Hongwei,Li, Yating,Li, Liyu,Wu, Yun,Zhang, Lihe,Yang, Zhenjun
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p. 469 - 472
(2015/02/19)
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- DERIVATIVES OF PHENYL (THIO) UREA DEOXYTHYMIDINE AND USE THEREOF AS ANTIMALARIALS
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Deoxythymidine derivatives according to formula (I) are disclosed. wherein: X may be O or S; and R1, R2, R3, R4 and R5 may each be independently selected from H, halo, C1-C6 alkyl, C1-C6 haloalkyl, nitro, phenyl, heteroaryl, substituted heteroaryl wherein the substituents may be C1-C6 alkyl or C1-C6 haloalkyl, benzyl, -CH2OAr, -OR6 and six-membered ring heterocyclic groups containing 1 or more O and/or N heteroatoms wherein any N heteroatom may be C1-C6 alkyl-substituted; and R6 may be selected from C1-C6 alkyl, phenyl, six-membered ring heterocyclic groups containing at least one O heteroatom, benzyl and substituted benzyl wherein the substituents may be halo, C1-C6 alkyl or C1-C6 alkoxy; R7 may be H or C1-C6 alkyl; and the stereochemistry of the bond depicted as ? is either α or β. Such derivatives have shown good inhibitory activity against malaria-causing parasites, e.g. Plasmodium falciparum, but have shown low levels of toxicity to human cells.
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Page/Page column 15; 20
(2013/03/26)
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- Synthesis and evaluation of α-thymidine analogues as novel antimalarials
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Plasmodium falciparum thymidylate kinase (PfTMPK) is a key enzyme in pyrimidine nucleotide biosynthesis. 3-Trifluoromethyl-4-chloro-phenyl-urea- α-thymidine has been reported as an inhibitor of Mycobacterium tuberculosis TMPK (MtTMPK). Starting from this
- Cui, Huaqing,Carrero-Lérida, Juana,Silva, Ana P. G.,Whittingham, Jean L.,Brannigan, James A.,Ruiz-Pérez, Luis M.,Read, Kevin D.,Wilson, Keith S.,González-Pacanowska, Dolores,Gilbert, Ian H.
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supporting information
p. 10948 - 10957
(2013/03/13)
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- Two-step synthesis of a 5-azidothymidine building block for the assembly of oligonucleotides for triazole-forming ligations
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A two-step synthesis converting thymidine into a phosphotriester building block of 5-azido-5-deoxythymidine in 60% overall yield is presented. The building block was used to assemble an oligonucleotide with an azido group at its 5-terminus, which underwen
- Said, Hassan,Guttroff, Claudia,El-Sagheer, Afaf H.,Richert, Clemens
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p. 2923 - 2926
(2013/02/23)
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- Design and synthesis of dephosphono dna analogues containing 1,2,3-triazole linker and their uv-melting studies with DNA/RNA
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This article describes the synthesis of 3/5 linked 1,2,3-triazolyl dithymidine derivatives, their incorporation into oligonucleotides, and evaluation of their thermal stabilities toward complementary DNA/RNA. Copyright Taylor and Francis Group, LLC.
- Madhuri, Vangala,Kumar, Vaijayanti A.
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scheme or table
p. 97 - 111
(2012/07/13)
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- Method for Preparing Nanoparticles Based on Functional Amphiphilic Molecules or Macromolecules, and the Use Thereof
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The invention relates to a method for preparing nanoparticles based on functional amphiphilic molecules or macromolecules, optionally in the presence of at least one colipide, enabling the encapsulation of therapeutic agents, especially anti-tumoral agent
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- Glycosyl-nucleoside-lipid based supramolecular assembly as a nanostructured material with nucleic acid delivery capabilities
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A glycosyl-nucleoside-lipid self-assembles to give highly organized structures such as fibers and nanotubes, which can stabilize hydrogels; carbohydrate moieties provide a suitable environment to deliver nucleic acids into human cells. The Royal Society o
- Godeau, Guilhem,Bernard, Julie,Staedel, Cathy,Barthelemy, Philippe
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supporting information; experimental part
p. 5127 - 5129
(2009/12/08)
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- Novel Dideoxynucleoside Derivatives
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The present invention discloses a 5′-amino-2′-fluoro-2′,5′-dideoxynucleoside derivative represented by the following formula [1]: (wherein R1 represents a nucleic acid base which may have a protecting group; R2 represents a hydrogen atom or a protecting group of an amino group; R3 represents a hydrogen atom or a protecting group of a hydroxyl group); a dideoxynucleoside-insoluble carrier bound substance prepared by binding said dideoxynucleoside derivative to an insoluble carrier, and an oligonucleotide analogue into which said dideoxynucleoside derivative is introduced. The oligonucleotide analogue being introduced with a dideoxynucleoside derivative of the present invention has excellent thermal stability and also high binding affinity when duplex is formed. Also, it is anticipated that it has high resistance to nucleases. Further, the dideoxynucleoside derivative of the present invention can be used as an amidite reagent to be used for nucleic acid synthesis, and also as a starting material for solid phase synthesis of nucleic acid by binding the amidite reagent to a solid phase.
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Page/Page column 10-11
(2008/06/13)
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- A rapid efficient microwave-assisted synthesis of a 3′,5′-pentathymidine by copper(I)-catalyzed [3+2] cycloaddition
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Starting from 5′-O-tosylthymidine, sequential azidation and Cu-catalyzed [3+2] azide-alkyne 1,3-dipolar cycloaddition led to the formation of a 3′,5′-pentathymidine in high yield. The whole process needed only work-up/precipitation steps and was completed
- Lucas, Romain,Zerrouki, Rachida,Granet, Robert,Krausz, Pierre,Champavier, Yves
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p. 5467 - 5471
(2008/09/21)
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- Solid-phase synthesis and evaluation of TAR RNA targeted β-carboline-nucleoside conjugates
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Four types of β-carboline-nucleoside conjugates were synthesized. The binding affinities of these β-carboline-nucleoside conjugates 4-11, 13 and 15 to TAR RNA were evaluated by affinity capillary electrophoresis. The data of binding affinities to TAR RNA show that conjugates 9 and 13 are stronger binders than the parent compound MC3. Computer modeling indicates that the β-carboline-nucleoside conjugate 13 can fit to the UCU three-nucleotide bulge region of TAR RNA. The Royal Society of Chemistry 2008.
- Zhao, Peng,Jin, Hong-Wei,Yang, Zhen-Jun,Zhang, Liang-Ren,Zhang, Li-He
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scheme or table
p. 3741 - 3750
(2009/02/05)
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- Deoxynucleic guanidine: Synthesis and incorporation of purine nucleosides into positively charged DNG oligonucleotides
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The synthesis of purine nucleosides capable of making the guanidinium linkage is described for the first time starting from the corresponding 2′-deoxynucleosides. The positively charged mixed base DNG oligomer containing guanine was synthesized on solid-p
- Challa, Hemavathi,Bruice, Thomas C.
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p. 1475 - 1481
(2007/10/03)
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- 5′-modified nucleotides and the application thereof in molecular biology and medicine
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The invention relates to 5′-modified nucleotides and to nucleic acids which contain these nucleotides. Processes for incorporating the 5′-modified nucleotides into nucleic acids, and the subsequent site-specific cleavage of the nucleic acids at the 5′-modified monomer building blocks, are also disclosed. These processes can be employed for nucleic acid sequencing, for generating nucleic acid libraries, for detecting mutations, for preparing support-bound nucleic acids and for pharmaceutical purposes.
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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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- Solid-phase synthesis of positively charged deoxynucleic guanidine (DNG) oligonucleotide mixed sequences
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Positively charged DNG oligonucleotide mixed sequences containing A/T bases were prepared by solid-phase synthesis. Synthesis proceeds in 3′→5′ direction and involves coupling of 3′-Fmoc protected thiourea in the presence of HgCl2/TEA with the corresponding 5′-amine of the growing oligo chain. DNG binding characteristics with complementary DNA and with itself have been evaluated.
- Reddy, Putta Mallikarjuna,Bruice, Thomas C.
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p. 1281 - 1285
(2007/10/03)
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- Nucleomimetic strategy for the inhibition of HIV-1 nucleocapsid protein NCp7 activities
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We report the synthesis and biological properties of three modified dinucleotides T*G G*T and T*T in which the natural phosphodiester linkage has been replaced by a methylene carboxamide unit. They have been designed to act as nucleomimetics of a sequence
- Druillennec, Sabine,Meudal, Herve,Roques, Bernard P.,Fournie-Zaluski, Marie-Claude
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p. 627 - 632
(2007/10/03)
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- Novel diastereomeric thymidine cyclic 3',5'-threo-phosphoramidates
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Novel diastereomeric thymidine cyclic 3',5'-threo-phosphoramidates were prepared by the treatment of 5'-azido derivative of threo-thymidine with triphenyl phosphite as well as by the treatment of the corresponding amino derivative with phenyl phosphodichloridate. Phosphoramidation of the regioisomeric 3'- and 5'-azido derivatives of erythro-thymidine by means of triphenyl phosphite afforded the open-chain 3'- and 5'-phosphoramidates. The reaction which afforded the cyclic products was assumed to proceed via the cyclic tetraoxazaphosphorane intermediates.
- Katalenic, Darinka,Zinic, Mladen
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p. 1231 - 1236
(2007/10/03)
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- Synthesis of sulfamide linked dinucleotide analogues
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Novel sulfamide [-NHSO2NH-] linked dinucleotide analogues d(TnsnT) and d(TnsnA) have been synthesised from 3'- and 5'-amino nucleosides. Treatment of these amino nucleosides with catechol sulfate results in the formation of 2-hydroxyphenyl sulf
- Micklefield, Jason,Fettes, Kevin J.
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p. 5387 - 5390
(2007/10/03)
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- Oligonucleotide analogs with sulfamate linkages
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Oligonucleotides possessing at least one sulfamate or sulfamide internucleotides linkages. These compounds can be used as specific hybridization probes to detect complementary nucleic acid sequences.
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- 5'-Azido and 5'-fluoro alpha-nucleosides as analogues of AZT and FLT.
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5-Azido-2,5-dideoxy-beta-D-erythro-pentofuranosyl nucleosides 10 and their corresponding alpha-anomers 11 have been synthesized by condensation of methyl 3-O-acetyl-5-azido-2,5-dideoxy-beta-D-erythro-pentofuranoside (7) with silylated nucleobases followed by deprotection with methanolic ammonia. Reaction of silylated thymine (19) with methyl 2,3-di-O-benzoyl-5-deoxy-5-fluoro-D-arabino-pentofuranoside (15) and methyl 5-azido-2,3-di-O-benzoyl-5-deoxy-alpha-D-arabino-pentofuranoside (17 alpha) afforded a mixture of the alpha-nucleosides 20 and the acyclo nucleosides 5-fluoro- and 5-azido-2,3-O-dibenzoyl-5-deoxy-1-O-methyl-1-(thymin-1-yl)-D -arabinitol (22). Compounds 20 and 22 were deprotected with methanolic ammonia to give the acyclic nucleosides 21 and 23, respectively. The new nucleosides were inactive against HSV-1 and HIV-1.
- Schmidt,Pedersen,Nielsen
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p. 215 - 221
(2007/10/02)
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- Synthesis and antiretrovirus properties of 5'-isocyano-5'-deoxythymidine, 5'-isocyano-2',5'-dideoxyuridine, 3'-azido-5'-isocyano-3',5'-dideoxythymidine, and 3'-azido-5'-isocyano-2',3',5'-trideoxyuridine
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The 5'-azidonucleosides 3 and 4 were obtained by treating thymidine and 2'-deoxyuridine with TPP/DEAD/HN3.The 3'-O-silylated 5'-azido-5'-deoxythymidine 5 and the corresponding 2'-deoxyuridine derivative 6 were transformed to the formamides (7 and 8, respectively) and dehydrated to the protected 5'-isocyano derivatives 9 and 10; deblocking gave 5'-isocyano-5'-deoxythymidine (11) and 5'-isocyano-2',5'-dideoxyuridine (12). 2,3'-anhydro-5'-formamido derivatives of thymidine and 2'-deoxyuridine (19 and 20, respectively) were prepared by three different ways.In the most direct synthesis 3 and 4 were transformed to the 2,3'-anhydro-5'-azidonucleosides 17 and 18 by using TPP/DEAD; following the reaction with TPP/HCO2COCH3 gave 19 and 20.Nucleophilic opening reaction with LiN3 yielded the 3'-azido-5'-formylamino derivatives 21 and 22.Dehydration to 3'-azido-5'-isocyano-3',5'-dideoxythymidine (23) and 3'-azido-5'-isocyano-2',3',5'-trideoxyuridine (24) was achieved with tosyl chloride/pyridine.In contrast with 3'-azido-3'-deoxythymidine, compounds 11, 12, 23 and 24 were devoid of any marked inhibitory effect against DNA and RNA viruses including human immunodeficiency virus type I (HIV).
- Hiebl, Johann,Zbiral, Erich,Balzarini, Jan,Clercq, Erik De
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p. 1426 - 1430
(2007/10/02)
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- SYNTHESIS OF -OXYACETAMIDO LINKED NUCLEOSIDES
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A convenient procedure has been developed for the preparation of non-ionic, achiral -oxyacetamido analogues using the 4-methoxytrityl (MMTr) group for the protection of exocyclic amino function of 2'-deoxyadenosine, 2'-deoxycytidine and 2'-de
- Nyilas, A.,Glemarec, C.,Chattopadhyaya, J.
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p. 2149 - 2164
(2007/10/02)
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- Solid-Phase Synthesis of Oligodeoxynucleotides Containing Phosphoramidate Internucleotide Linkages and their Specific Chemical Cleavage
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Oligonucleotides bearing phosphoramidate internucleotide linkages can be prepared chemically by standard solid-phase DNA synthesis.Thus, phosphoramidate internucleotide bonds can be placed at will into specific positions within a given DNA fragment.The ba
- Bannwarth, Willi
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p. 1517 - 1527
(2007/10/02)
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- One-Step Synthesis of 5'-Azido-nucleosides
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Regioselective azidation of unprotected or appropriately protected nucleosides was conducted by means of the reagent triphenylphosphine-carbon tetrabromide-lithium azide.By use of this reagent, 5'-azido-5'-deoxynucleosides were prepared conveniently in one step from nucleosides in high yields.Secondary hydroxy-groups of appropriately 5'-protected nucleosides were also converted by the reagent to azido-functions with complete inversion.
- Yamamoto, Isamu,Sekine, Mitsuo,Hata, Tsujiaki
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p. 306 - 310
(2007/10/02)
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