- Synthesis and antitumor activity of novel 2-(thymin-1′-ylmethoxy) ethyl alkyl sulfides and their oxidation products
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A series of novel 2-(thymin-1′-ylmethoxy)ethyl alkyl sulfides have been synthesized in three steps from thymine. They have been oxidized into sulfoxide and sulfone derivatives by means of NaIO4 and H 2O2 30%/diethyl azodicarboxylate (DEAD), respectively, in high yields. All products were characterized by 1H NMR and IR spectra and elemental analyses. The preliminary bioassay indicates that the compound 6g exhibited potential antitumor activity. Copyright Taylor & Francis Inc.
- Liu, Xue-Jun,Chen, Ru-Yu,Bai, Dong-Lu
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- Molecular Assemblies of Metal Complexes via Base-Pairing of Nucleic Acids in the Crystalline State
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The nature of the molecular assemblies formed in the crystalline state by cobalt(II) terpyridine (terpy) complexes incorporating appended adenine (A) or thymine (T) bases was found to be controlled by which bases are present. Single-crystals of the cobalt(II) complexes [Co(A-C6-terpy)2](BF4)2 (1) and [Co(T-C6-terpy)2](BF4)2 (2) have needle and block habits, respectively. Subsequent mixing of 1 and 2 in MeOH resulted in isolation of [Co(A-C6-terpy)1.5(T-C6-terpy)0.5](BF4)2 (3) as plate-like crystals. A 3D network structure is present in 1 that incorporates 1D chains, whereas 2 adopts a 2D stacked structure constructed from ladder-type assemblies. For 3, “dimer-rings” consisting of [Co(A-C6-terpy)2]2+ and [Co(A-C6-terpy)(T-C6-terpy)]2+ units are generated by means of base-pairing between A and T. Notably, 3 displays the first crystal structure of a heteroleptic cobalt(II) complex of [Co(A-C6-terpy)(T-C6-terpy)](BF4)2. These assembly differences involving the terpyridine cobalt(II) complex units in 1–3 affect the cooperativities influencing their spin crossover (SCO) behavior. The influence of the terminal nucleobases on the resulting assembly has been probed by investigating the co-crystallization of [Co(terpy)2](BF4)2 (4) with [Co(C6-terpy)2](BF4)2 (5) and 1 with 5.
- Nakaya, Manabu,Ohtani, Ryo,Sugimoto, Kunihisa,Nakamura, Masaaki,Lindoy, Leonard F.,Hayami, Shinya
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- Efficient formation of H-addition radical and secondary alkyl radical in pentylthymines γ-irradiated at 77 K
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EPR detection of three pentylthymines γ-irradiated at 77 K showed the production of a 5,6-dihydro-5-thymyl radical (5-thymyl radical) as an H-addition radical and a secondary alkyl radical formed by C-H bond fission at the second carbon from the end of the pentyl group. The introduction of the pentyl group into thymine increased total radical yields at 77 K up to about twice that of thymine and considerably enhanced 5-thymyl radical yields. Several discussions on the radical formation suggest that the efficient production of 5-thymyl radical is related to the concomitant formation of the secondary radical.
- Ohta, Nobuaki,Tanaka, Noriyuki,Ito, Sotaro
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- Synthesis of 1′-[14C]-stavudine (d4T)
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1-(1′-[ 14C]-2′,3′-Dideoxy-β-D-glyceropent-2′- enofuranosyl)thymine (1′-[14C]-d4T), was synthesized from 1-[14C]-ribose, 1, in 7 steps in an overall yield of 29.3%. 1-[14C]-Ribose was converted in one step to 1-
- Discordia, Robert P.
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- Thiosugars, 17. Preparation and structure of a novel deoxythionucleoside
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1-(3′,5′-Anhydro-2′-deoxy-3′-thio-D-lyxo-furanosyl)thymine is prepared from the corresponding methyl pentofuranoside by using the silyl Hilbert-Johnson reaction. The α- and β-anomers are separated by column chromatography and their configuration is elucidated by NMR spectroscopy and, in case of the α-anomer, by an X-ray structure determination.
- Voss, Jürgen,Otzen, Dirk,Adiwidjaja, Gunadi
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- Synthesis of the four 1-(1-deoxy-d-pentitol-1-yl)thymines and conformational properties of the acyclic sugar chain
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Acetylated d-pentose diethyl dithioacetals were coupled by way of 1-bromo-1-ethylthio derivatives with 2,4-bis(trimethylsilyl)thymine to afford diastereomeric pairs of acyclic-sugar nucleoside analogues bearing a thymin-1-yl and an ethylthio group at C-1. Free-radical desulfurization by the action of tributylstannane removed the ethylthio group to afford the corresponding acetylated 1-(1-deoxy-d-pentitol-1-yl)thymines and subsequently the free title compounds in the arabino, lyxo, ribo, and xylo series. Conformations of the intermediates and products were studied in detail and the final products were evaluated for their potential as agents active against plant viruses and rice blast fungus.
- Vejcik, Scott M.,Horton, Derek
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- Efficient pyrimidine N-1-alkylation via activation of electron rich olefins with oxoammonium salts: Synthesis of Methoxy TEMPO substituted pyrimidine nucleoside analogs
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Our work outlines the use of oxoammonium salts in a formal 1,2 addition process to olefins giving nucleoside analogs as products. Specifically, oxoammonium salts can be added to a solution of olefin and silylated heterocycle to give Methoxy TEMPO substituted nucleoside analogs after hydrolytic workup and chromatographic purification.
- Church, Kevin M.,Holloway, Liesel M.,Matley, Ryan C.,Brower III, Robert J.
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- Synthesis of bicyclo-DNA nucleosides with additional functionalization in the carbocyclic ring
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Two novel bicyclo nucleoside isomers carrying the base thymine in the furanose ring and an ester substituent in the carbocyclic ring were synthesized from a common bicyclic sugar precursor via a cyclopropanation/ fragmentation pathway in nine steps. The relative configuration of the ester substituent in both isomers as well as the anomeric configuration in one nucleoside was determined by 1H-NMR difference NOE spectroscopy. Schweizerische Chemische Gesellschaft.
- Luisier, Samuel,Leumann, Christian J.
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- Synthesis of 1-[cis-2-hydroxy-cis-3-(hydroxymethyl)-cyclobutyl]thymine, a novel method for the synthesis of cyclobutyl nucleosides and related compounds
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Syntheses of 1-[cis-2-hydroxy-cis-3-(hydroxymethyl)cyclobutyl]thymine (1) and related compounds by a novel method are reported. Coupling of 3- benzyloxymethyl-1-cyclobutene (2) with silylated thymine in the presence of NIS, followed by treatment with DBU, basic hydrolysis and catalytic hydrogenation produced the target compound (1) and its isomer (12).
- Lin,Luo,Liu
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- Sodium cation complexation in a macrocycle containing thymines as sidearm donor groups
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Previous studies of macrocycles having alkyl sidearms terminated in adenine or thymine have been focused on intermolecular association. Electrospray mass spectrometric analyses suggested that sodium complexation could be a major alternative process in the presence of the appropriate cation. Sodium cation complexation by N,N′-bis(3-(1-thyminyl)propyl)-4,13-diaza-18-crown-6 has been confirmed by X-ray crystallographic analysis. A sodium cation is bound in the center of the macroring. The four ether oxygens and two thyminyl carbonyl donors have the shortest contacts with the two, macroring nitrogen atoms being somewhat more remote. Neither the iodide counterion nor an acetone of solvation appears to interact with the sodium cation. Crystal Data: Triclinic, P1, a = 11.9371(12), b = 12.1588(13), c = 13.7885(14) A, α = 78.083(2)°, β = 83.213(2)°, γ = 78.997(2)°, and Dcalc = 1.392 g cm-3, Ζ= 2.
- De Wall, Stephen L.,Barbour, Leonard J.,Schall, Otto F.,Gokel, George W.
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- Synthesis, biophysical properties, and RNase H activity of 6’-difluoro[4.3.0]bicyclo-DNA
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Here we present the synthesis, the biophysical properties, and the RNase H profile of 6’-difluorinated [4.3.0]bicyclo-DNA (6’-diF-bc4,3-DNA). The difluorinated thymidine phosphoramidite building block was synthesized starting from an already kn
- Frei, Sibylle,Katolik, Adam K.,Leumann, Christian J.
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- Chemical synthesis and properties of long-chain alkoxymethyl-nucleobase derivatives
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New nucleobase derivatives were synthesized, containing both octyloxymethyl (LCAS) and octadecyloxymethyl (LCA18) substituents at N1 position of pyrimidine and N9 of purine. These substances were studied with respect to the formation of supramolecular structures, i.a. molecular associates as the result of noncovalent interactions. Special attention has been paid to complex formation. The properties of these molecules were investigated by DSC and polarizing microscopy.
- Kovalenko,Madre,Lindau,Bohley,Panchenko,Meister,Zhuk,Hoffmann
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- Synthesis and anti-human immunodeficiency virus activity of 4′-branched (±)-4′-thiostavudines
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Motivated by our recent finding that 4′-ethynylstavudine (4) is a promising anti-human immunodeficiency virus type 1 (HIV-1) agent, we synthesized its 4′-thio analogue, as well as other 4′-thiostavudines having a carbon substituent at the 4′-position, as
- Kumamoto, Hiroki,Nakai, Takahito,Haraguchi, Kazuhiro,Nakamura, Kazuo T.,Tanaka, Hiromichi,Baba, Masanori,Cheng, Yung-Chi
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- Lignin Nanoparticles Deliver Novel Thymine Biomimetic Photo-Adducts with Antimelanoma Activity
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We report here the synthesis of novel thymine biomimetic photo-adducts bearing an alkane spacer between nucleobases and characterized by antimelanoma activity against two mutated cancer cell lines overexpressing human Topoisomerase 1 (TOP1), namely SKMEL28 and RPMI7951. Among them, Dewar Valence photo-adducts showed a selectivity index higher than the corresponding pyrimidine-(6-4)-pyrimidone and cyclobutane counterpart and were characterized by the highest affinity towards TOP1/DNA complex as evaluated by molecular docking analysis. The antimelanoma activity of novel photo-adducts was retained after loading into UV photo-protective lignin nanoparticles as stabilizing agent and efficient drug delivery system. Overall, these results support a combined antimelanoma and UV sunscreen strategy involving the use of photo-protective lignin nanoparticles for the controlled release of thymine dimers on the skin followed by their sacrificial transformation into photo-adducts and successive inhibition of melanoma and alert of cellular UV machinery repair pathways.
- Gabellone, Sofia,Piccinino, Davide,Filippi, Silvia,Castrignanò, Tiziana,Zippilli, Claudio,Del Buono, Davide,Saladino, Raffaele
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- Synthesis of 1,2,3-triazolyl nucleoside analogues and their antiviral activity
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Abstract: Based on the fact that a search for influenza antivirals among nucleoside analogues has drawn very little attention of chemists, the present study reports the synthesis of a series of 1,2,3-triazolyl nucleoside analogues in which a pyrimidine fragment is attached to the ribofuranosyl-1,2,3-triazol-4-yl moiety by a polymethylene linker of variable length. Target compounds were prepared by the Cu alkyne-azide cycloaddition (CuAAC) reaction. Derivatives of uracil, 6-methyluracil, 3,6-dimethyluracil, thymine and quinazolin-2,4-dione with ω-alkyne substituent at the N1 (or N5) atom and azido 2,3,5-tri-O-acetyl-D-β-ribofuranoside were used as components of the CuAAC reaction. All compounds synthesized were evaluated for antiviral activity against influenza virus A/PR/8/34/(H1N1) and coxsackievirus B3. The best values of IC50 (inhibiting concentration) and SI (selectivity index) were demonstrated by the lead compound 4i in which the 1,2,3-triazolylribofuranosyl fragment is attached to the N1 atom of the quinazoline-2,4-dione moiety via a butylene linker (IC50 = 30?μM, SI = 24) and compound 8n in which the 1,2,3-triazolylribofuranosyl fragment is attached directly to the N5 atom of the 6-methyluracil moiety (IC50 = 15?μM, SI = 5). According to theoretical calculations, the antiviral activity of the 1,2,3-triazolyl nucleoside analogues 4i and 8n against H1N1 (A/PR/8/34) influenza virus can be explained by their influence on the functioning of the polymerase acidic protein (PA) of RNA-dependent RNA polymerase (RdRP). Graphic abstract: [Figure not available: see fulltext.]
- Andreeva, Olga V.,Garifullin, Bulat F.,Zarubaev, Vladimir V.,Slita, Alexander V.,Yesaulkova, Iana L.,Saifina, Liliya F.,Shulaeva, Marina M.,Belenok, Maya G.,Semenov, Vyacheslav E.,Kataev, Vladimir E.
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p. 473 - 490
(2020/09/22)
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- S-ANTIGEN TRANSPORT INHIBITING OLIGONUCLEOTIDE POLYMERS AND METHODS
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Various embodiments provide STOPS? polymers that are S-antigen transport inhibiting oligonucleotide polymers, processes for making them and methods of using them to treat diseases and conditions. In some embodiments the STOPS? modified oligonucleotides include an at least partially phosphorothioated sequence of alternating A and C units having modifications as described herein. The sequence independent antiviral activity against hepatitis B of embodiments of STOPS? modified oligonucleotides, as determined by HBsAg Secretion Assay, is an EC50 that is less than 100 nM.
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Paragraph 0056; 0332
(2021/06/22)
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- Chitosan–silica sulfate nanohybrid: a highly efficient and green heterogeneous nanocatalyst for the regioselective synthesis of N-alkyl purine, pyrimidine and related N-heterocycles via presilylated method
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Abstract: The presilylation of purine and pyrimidine nucleobases as well as other related N-heterocycles with HMDS utilizing chitosan–silica sulfate nanohybrid (CSSNH) is described. CSSNH is proved to be a useful, highly efficient and eco-friendly heterogeneous nanohybrid catalyst for silylation of nucleobases. The presilylated nucleobases then underwent the reaction with different sources of carbon electrophiles to afford the desired N-alkyl-substituted derivatives in good-to-excellent yields. CSSNH exhibits several advantageous involving ease of handling and preparation, low cost, reusability and environmental benignity. These unique properties render the CSSNH to be an ideal candidate for use in green industrial processes. Graphic abstract: [Figure not available: see fulltext.].
- Behrouz, Somayeh,Soltani Rad, Mohammad Navid,Piltan, Mohammad Amin
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p. 113 - 124
(2019/07/30)
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- Practical and reliable synthesis of 2′,3′,5′,5″-tetradeuterated uridine derivatives
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Deuterated drugs are valuable in the fields of drug discovery and medicinal chemistry. 2′,3′,5′,5″-tetradeuterated uridine derivatives were synthesised from 2,3,5,5′-selectively tetradeuterated ribose using Sajiki’s H–D exchanged Ru/C–H2–D2O–NaOH system and silyl–Hilbert–Johnson methods. The total deuterium content of the tetradeuterated uridines was over 92% using either basic or acidic reaction conditions. These derivatives would be expected as building blocks for the synthesis of deuterium-substituted nucleic acid probes for tracking the pharmacokinetics of nucleic acid drugs.
- Miyamoto, Noriko,Ohno, Hiroki,Kitamura, Yoshiaki,Park, Kwihwan,Sawama, Yoshinari,Sajiki, Hironao,Kitade, Yukio
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p. 236 - 244
(2019/11/13)
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- Ruthenium(II)–arene and triruthenium-carbonyl cluster complexes with new water-soluble phopsphites based on glucose: Synthesis, characterization and antiproliferative activity
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New water-soluble 3,5,6-bicyclophosphite ligands based on glucose modified with uracil, 5-fluorouracil or thymine are reported. The phosphite ligands were subsequently reacted with bis[dichlorido(η6-p-cymene)ruthenium(II)] and trirutheniumdodecacarbonyl to afford monoruthenium analogues of RAPTA-C and triruthenium clusters with 1–3 phosphite ligands, respectively. The influence of ligands on the stability of the compounds and the antiproliferative activity of the compounds was investigated.
- Burdina, Tatiana A.,Dyson, Paul J.,Gonchar, Maria R.,Matnurov, Egor M.,Milaeva, Elena R.,Nazarov, Alexey A.,Ridel, Tina,Zava, Oliver
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- Efficient and selective catalytic N-Alkylation of pyrimidine by ammonium Sulfate?Hydro-thermal carbone under eco-friendly conditions
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Abstract: An efficient and inexpensive method for the N-alkylation of pyrimidines using ammonium sulfate coated Hydro-Thermal-Carbone (HTC) (AS?HTC) as reused heterogeneous catalyst was developed. The catalyst was characterized by several analytical techniques such as SEM, XRD, and FTIR. The effect of various parameters was studied including catalyst loading, mole ratio, to achieve excellent selectivity and yields in 80–90%. Significantly, the present protocol offers the use of an inexpensive and environmentally friendly catalyst and simple workup. The simplicity of the procedure, excellent yield of the products, and the recyclability of the catalyst are the main advantages of this method. Graphic Abstract: Ammonium sulfate coated Hydro-Thermal-Carbone (HTC) (AS?HTC); an efficient and reused heterogeneous catalyst of the N-alkylation of pyrimidines was developed. Excellent selectivity and yields (80–90%) toward N1-alkylpyrimidines were achieved. Significantly, the present protocol offers the use of an inexpensive and environmentally friendly catalyst and simple workup.[Figure not available: see fulltext.]
- Ait Ali, Mustapha,Belkharchach, Soumia,Ighachane, Hana,Lachgar, Abdessadek,Lazrek, Hassan B
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- HMDS/KI a simple, a cheap and efficient catalyst for the one-pot synthesis of N-functionalized pyrimidines
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The syntheses of N-Alkylpyrimidine derivatives by reacting pyrimidin-2,4-diones with appropriate alkyl halide under microwave irradiation at 400 W were compared to the conventional synthesis route. These methodologies are regioselective and compatible with numerous substrates and furnish the corresponding N-alkylpyrimidines in good yields using a cheap catalyst HMDS/KI in MeCN. A comparison study between these two different modes of heating was investigated.
- Mansouri, Az-Eddine El,Zahouily, Mohamed,Lazrek, Hassan B.
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supporting information
p. 1802 - 1812
(2019/05/15)
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- Synthesis of self-Assembled nucleobases and their anhydrous proton conductivity
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We synthesized self-Assembled nucleobases (SANs), such as 1-dodecylthymine (DOT) or 9-dodecyladenine (DOA), in which the nucleobase is immobilized on a long alkyl chain. The thermal stability of the SAN was increased by mixing with the acidic surfactant mono-dodecyl phosphate (MDP). Additionally, the SAN-MDP composite material showed proton conductivity of 4.62 × 10-4 S cm-1 at 160 °C under anhydrous conditions. Additionally, the activation energy of the proton conduction was approximately 0.2 eV and this value was one order of magnitude higher than that of a typical humidified perfluorinated membrane, in which the proton can be moved by vehicle molecules, such as water molecules. In contrast, when the nucleobase without the immobilization of a long alkyl chain was mixed with MDP, the proton conductivity of these composite materials was two orders of magnitude less than that of the SAN-MDP composite. Therefore, we measured the XRD spectra of the SAN-MDP composite material. As a result, the SAN-MDP composite material showed a self-Assembled structure with a two-dimensional proton conducting pathway, such as a lamellar structure, and that the anhydrous proton conduction was related to the interaction between the nucleobase of the SAN and the phosphate group of MDP. Consequently, the self-Assembled nucleobase derivatives have the potential for use as novel anhydrous proton conductors with a two-dimensional proton conducting pathway.
- Yamada, Masanori,Tanoue, Kento
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p. 36416 - 36423
(2019/11/20)
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- Triplet Energy Transfer versus Excited State Cyclization as the Controlling Step in Photosensitized Bipyrimidine Dimerization
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Polymethylene-linked bipyrimidine models have been designed with different C5 substitutions and bridge lengths. Selective irradiation of 2′-methoxyacetophenone (2M) with the bipyrimidine models affords cyclobutane pyrimidine dimers, even in the presence of bulky substituents. Substitution at C5 affects both the relative triplet energies (ET(rel)) of the pyrimidines (Pyr) and the steric hindrance toward intermolecular energy transfer and intramolecular triplet Pyr? quenching. Photophysical studies showed that alkyl substitution resulted in a significant decrease in the ET(rel) value. Quenching of the triplet excited state of 2M by the Pyr derivatives was proven and established their quenching rate constants (kq). As a general trend, the thymine-containing compounds showed kq values higher than 109 M-1 s-1, while in the uracil and tert-butyluracil analogues, kq was markedly lower. These data are explained considering three different scenarios: (a) triplet energy transfer is the rate controlling step, (b) excited state cyclization is the rate controlling step, and (c) the rate controlling step switches along the reaction. Thus, by introducing variations in the substitution at C5, the length of the linking bridge, or the substrate concentration, it is possible to switch from a process governed by the intrinsic dimerization step to an energy transfer-controlled process.
- Alzueta, Ofelia R.,Cuquerella, M. Consuelo,Miranda, Miguel A.
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p. 13329 - 13335
(2019/10/16)
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- Highly convergent synthesis and antiviral activity of (E)-but-2-enyl nucleoside phosphonoamidates
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Several hitherto unknown (E)-but-2-enyl nucleoside phosphonoamidate analogs (ANPs) were prepared directed with nitrogen reagents by cross-metathesis in water-under ultrasound irradiation. Two diastereoisomers were formally identified by X-ray diffraction. These compounds were evaluated against a large spectrum of DNA and RNA viruses. Among them, the phosphonoamidate thymine analogue 19 emerged as the best prodrug against varicella-zoster virus (VZV) with EC50 values of 0.33 and 0.39 μM for wild-type and thymidine kinase deficient strains, respectively, and a selectivity index ≥200 μM. This breakthrough approach paves the way for new purine and pyrimidine (E)-but-2-enyl phosphonoamidate analogs.
- Bessières, Maxime,Hervin, Vincent,Roy, Vincent,Chartier, Agnès,Snoeck, Robert,Andrei, Graciela,Lohier, Jean-Fran?ois,Agrofoglio, Luigi A.
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p. 678 - 686
(2018/02/09)
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- Β-selective D-psicofuranosylation of pyrimidine bases and thiols
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N-Glycosidation of D-psicofuranosyl donor 1 with pyrimidine bases took place β-selectively in a β/α-ratio of 8:1 ~ 7:1. For S-glycosidation, 3,4-O-(3-pentylidene)-protected D-psicofuranosyl donor 15 was effective to increase β-selectivity up to 7:1.
- Ueda, Atsushi,Nishimura, Yuri,Makura, Yui,Tanaka, Masakazu,Uenishi, Junichi
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p. 729 - 743
(2019/04/26)
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- Pyrimidine derivatives of n-acetylguanidine: Novel inhibitors of sodium-hydrogen exchanger 1
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Sodium-hydrogen exchanger (Na+/H+) type 1 (NHE-1) inhibitors have been shown to protect the heart during ischaemia and early reperfusion. As such, NHE-1 inhibitors are of special interest for clinical development for the attenuation of both acute and chronic post-myocardial infarction responses. New pyrimidine derivatives of N-acetylguanidine containing fragments of uracil, thymine, and their 3-benzyl derivatives were synthesised. These compounds showed in vitro inhibitory effects on NHE-1 that were significantly higher than those of zoniporide in platelet swelling assays.
- Ozerov, Alexander,Novikov, Mikhail,Spasov, Alexander,Iezhitsa, Igor,Gurova, Natalia,Gurova, Valeria
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p. 1101 - 1107
(2018/08/28)
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- 2-D and 3-D porous structures from tetrakis(4-thyminylmethylphenyl)methane
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Using tetraphenylmethane as a scaffold, a potent hub for generation of organic porous networks has been synthesized by introduction of thymine functionalities in all para-positions. Depending on the choice of solvent, crystal structures are produced with 35-46% solvent volume organized in two- or three-dimensional channel systems. The intermolecular interactions are dominated by two features: formation of dimers connected by six C-H?O hydrogen bonds, and links between these dimers as R22(8) ring motifs formed by pairs of thymines. These are the first structures of their kind and suggest further use of DNA-inspired building units in supermolecular engineering of biocompatible functional materials.
- Qi,Gundersen,G?rbitz
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p. 1179 - 1184
(2018/03/06)
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- A solid-supported acidic oxazolium perchlorate as an easy-handling catalyst for the synthesis of modified pyrimidine nucleosides via Vorbrüggen-type N-glycosylation
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A solid-supported acidic oxazolium perchlorate was investigated as a heterogeneous catalyst in N-glycosylation reactions using silylated modified pyrimidines and an acylated ribose or glucose to afford the corresponding pyrimidine nucleosides. This salt is a nonhygroscopic and stable powder whose activity is comparable to that of 2-methyl-5-phenylbenzoxazolium perchlorate. A reaction with this polymer catalyst can be conducted on a gram scale. Reusability of the solid-supported catalyst was also investigated.
- Basu, Nabamita,Oyama, Kin-ichi,Tsukamoto, Masaki
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supporting information
p. 1921 - 1924
(2017/04/27)
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- Effective synthesis of nucleosides utilizing O-acetyl-glycosyl chlorides as glycosyl donors in the absence of catalyst: Mechanism revision and application to silyl-hilbert-johnson reaction
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An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently accepted mechanism advanced by Vorbrueggen has been proposed and verified by experiments. In practice, this catalyst-free method provides easy access to Capecitabine in high yield.
- Liang, Chengyuan,Ju, Weihui,Ding, Shunjun,Sun, Han,Mao, Gennian
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supporting information
(2017/01/24)
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- METHOD FOR PRODUCING 2'-FLUORO-5-METHYL-4'-THIOARABINOURIDINE AND METHOD COMPRISING SOME STEPS THEREOF
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PROBLEM TO BE SOLVED: To provide a method for producing a glycosylated product capable of producing a β-glycosylated product with high selectivity in a glycosylation step including a reaction between thioarabinose and thymine having a protecting group; a method for producing 2'-fluoro-5-methyl-4'-thioarabinouridine comprising the method for producing the glycosylated product; and a method for separating and purifying β-glycosylated substance from a mixture of α-glycosylated substance and β-glycosylated substance by recrystallization. SOLUTION: According to the present invention, there is provided a method for producing a compound, the method comprising: reacting thioarabinose with thymine having a protecting group in a solvent containing chloroform to obtain a compound represented by the following formula (3): In the formula, R1 and R2 each independently represent a hydroxyl protecting group. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPO&INPIT
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Paragraph 0064; 0068
(2017/12/27)
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- A 3 ', 5' - b - oxygen - (4 - methyl benzoyl) - beta - L - thymine preparation method
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The invention discloses a preparation method of 3',5'-di-oxy-(4-p-methylbenzoyl)-beta-L-thymine. The preparation method comprises the following steps: mixing 3,5-di-oxy-p-methylbenzoyl-2-deoxy-alpha,beta-L-furan glucoside with an organic solvent, producing chlorinated sugar reaction in the presence of an acidic catalyst, adding hydroxy-protected thymine for glycosylation reaction, post-treating, and refining to obtain a product. The preparation method is characterized in that when the content of raw materials is lower than 20% by mass in the chlorinated sugar reaction process, hydroxy-protected thymine is added and the chlorinated sugar reaction and the glycosylation reaction are simultaneously produced, so that 3',5'-di-oxy-(4-p-methylbenzoyl)-beta-L-thymine is prepared in one step. The preparation method is simple, low in production cost, high in yield and suitable for large-scale production.
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Paragraph 0031; 0032; 0033; 0038; 0043; 0049
(2017/08/25)
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- Synthetic method for 5-methyluridine
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The invention discloses a synthetic method for 5-methyluridine. The synthetic method is optimized based on a 5-methyluridine chemical synthesis method; the key points are that a byproduct trimethylsilyl acetate in a condensation reaction is separated, and reacts with ammonia to generate hexamethyldisilazane which can be repeatedly utilized; meanwhile, tail gas generated by the reaction is absorbed by absolute methanol to obtain aminomethanol, which can be used in an alcoholysis reaction during the synthesis of 5-methyluridine. The synthetic method for 5-methyluridine provided by the invention combines the advantages of the 5-methyluridine chemical synthesis method and optimizes the defects in production, so that on one hand, a utilization rate of a trisilicane protective group is increased, on the other hand, emission of waste liquor and waste gas is reduced, thereby overcoming the defect that the chemical synthesis method is not environment-friendly while being free of affecting the total yield.
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Paragraph 0044-0045
(2017/01/17)
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- A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor
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Based on a preactivation strategy using the (p-Tol)2SO/Tf2O system, a series of nucleosides were synthesized by coupling various thioglycosides with pyrimidines and purines under mild conditions. High yields and excellent β-stereoselectivities were obtained with either armed or disarmed N-glycosylation donors by tuning the amount of (p-Tol)2SO additive.
- Liu, Guang-Jian,Zhang, Xiao-Tai,Xing, Guo-Wen
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supporting information
p. 12803 - 12806
(2015/08/06)
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- Scaffold hopping: Exploration of acetanilide-containing uracil analogues as potential NNRTIs
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In order to identify novel nonnucleoside inhibitors of HIV-1 reverse transcriptase two series of amide-containing uracil derivatives were designed as hybrids of two scaffolds of previously reported inhibitors. Subsequent biological evaluation confirmed acetamide uracil derivatives 15a-k as selective micromolar NNRTIs with a first generation-like resistance profile. Molecular modeling of the most active compounds 15c and 15i was employed to provide insight on their inhibitory properties and direct future design efforts.
- Babkov, Denis A.,Valuev-Elliston, Vladimir T.,Paramonova, Maria P.,Ozerov, Alexander A.,Ivanov, Alexander V.,Chizhov, Alexander O.,Khandazhinskaya, Anastasia L.,Kochetkov, Sergey N.,Balzarini, Jan,Daelemans, Dirk,Pannecouque, Christophe,Seley-Radtke, Katherine L.,Novikov, Mikhail S.
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p. 1069 - 1081
(2015/03/04)
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- SUNLESS TANNING COMPOUNDS AND COMPOSITIONS
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The invention provides sunless tanning compositions comprising a compounds of formula (I): or a salt thereof as described herein as well as methods for tanning mammalian skin by contacting the skin with the compounds of formula (I) or compositions comprising compounds of formula (I).
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Page/Page column 34
(2015/01/16)
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- Synthesis and anti-HCMV activity of 1-[ω-(phenoxy)alkyl]uracil derivatives and analogues thereof
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HCMV infection represents a life-threatening condition for immunocompromised patients and newborn infants and novel anti-HCMV agents are clearly needed. In this regard, a series of 1-[ω-(phenoxy)alkyl]uracil derivatives were synthesized and examined for antiviral properties. Compounds 17, 20, 24 and 28 were found to exhibit highly specific and promising inhibitory activity against HCMV replication in HEL cell cultures with EC50 values within 5.5-12 μM range. Further studies should be undertaken to elucidate the mechanism of action of these compounds and the structure-activity relationship for the linker region.
- Novikov, Mikhail S.,Babkov, Denis A.,Paramonova, Maria P.,Khandazhinskaya, Anastasia L.,Ozerov, Alexander A.,Chizhov, Alexander O.,Andrei, Graciela,Snoeck, Robert,Balzarini, Jan,Seley-Radtke, Katherine L.
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p. 4151 - 4157
(2013/07/27)
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- Antifreeze protein-induced selective crystallization of a new thermodynamically and kinetically less preferred molecular crystal
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The formation of a new, dihydrate crystalline form of 5-methyluridine (m5U) was selectively induced by a protein additive, antifreeze protein (AFP) in a highly efficient manner (in 10-6molar scale, whereas known kinetic additives nee
- Wang, Sen,Wen, Xin,Golen, James A.,Arifin, Josh F.,Rheingold, Arnold L.
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p. 16104 - 16112
(2014/04/03)
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- Photoprotection of DNA (in vitro) by acyclothymidine dinucleosides
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Excessive exposure to sunlight is primarily implicated in ultraviolet (UV) induced skin cancers worldwide. Direct absorption of UV radiation by DNA leads to the formation of cyclobutane pyrimidine dimers (CPDs) resulting in DNA damage. The molecular mechanisms involved in the mutagenicity of CPDs are well established. Photoprotection of the skin from the detrimental effects of UV is essential in preventing skin damage. A variety of formulations, which essentially contain UV filters have been used as photoprotective agents of the skin. These comprise aromatic and inorganic molecules, whose mechanism of action involves either absorption, reflection, or scattering of UV radiation. However, the downstream photoproducts of some of these molecules have undesirable characteristics which compromise their utility. A biomimetic approach involving structural analogs of nucleic acids can help overcome these limitations. Herein, we show the photoprotective action of acyclothymidine dinucleosides on both plasmid and cellular DNA.
- Raza, Abbas,Dreis, Christine D.,Vince, Robert
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supporting information
p. 620 - 623
(2013/02/23)
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- AGENTS THAT PREVENT OR REPAIR SKIN DAMAGE
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The invention provides compounds of formula I: or a salt thereof as described herein. The invention also provides dermatological compositions comprising a compound of formula I or mixtures of one or more compounds of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods for protecting skin or DNA from photodamage or repairing photodamaged skin or DNA.
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Page/Page column 31
(2013/07/25)
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- Experimental and theoretical study of thymine and cytosine derivatives: The crucial role of weak noncovalent interactions
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In this paper we report the synthesis of N1-hexylthymine (1), N1-hexylcytosine (2), N1-hexylcytosine hydrobromide (3) and [(N1-hexylcytosinium)·(N1-hexylcytosine)] 2·[Cl2Hg(μ-Cl)
- Barcelo-Oliver, Miquel,Baquero, Beatriz A.,Bauza, Antonio,Garcia-Raso, Angel,Terron, Angel,Mata, Ignasi,Molins, Elies,Frontera, Antonio
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p. 5777 - 5784
(2012/11/06)
-
- Glassy dynamics of hydrogen-bonded heteroditopic molecules
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A self-complementary heteroditopic molecule composed of thymine and diamidopyridine end groups and a flexible aliphatic interconnecting chain has been synthesized. The glassy dynamics of this hydrogen-bonded supramolecule have been investigated by using dielectric and rheological measurements, in combination with infra-red spectroscopy and solid-state 13C NMR experiments. Decoupling of main dielectric relaxation from viscosity has been found in the vicinity of the glass transition and the temperature dependence of viscosity appears to be stronger than that of dielectric relaxation. The unusual dynamic decoupling phenomenon is ascribed to the chemical/dynamic heterogeneity and formation of hydrogen bonds in the supramolecules.
- Lou, Nan,Wang, Yangyang,Li, Haixia,Sokolov, Alexei P.,Xiong, Huiming
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p. 4455 - 4460
(2012/11/13)
-
- HIV-1 X4 activities of polycationic Viologen based dendrimers by interaction with the chemokine receptor CXCR4: Study of structure-activity relationship
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A series of viologen based dendrimers with polycationic scaffold carrying 10, 18, 26, 42, and 90 charges per molecule were used to determine the structure-activity relationship (SAR) with regard to HIV-1 inhibitory activity. The studies involved five comp
- Asaftei, Simona,Huskens, Dana,Schols, Dominique
-
supporting information
p. 10405 - 10413
(2013/02/23)
-
- Synthesis of 3′-S-phosphonomethyl-modified nucleoside phosphonates with a 3′-deoxy-3′-thio-α- L -threosyl sugar moiety
-
The synthesis and antiviral evaluation of 3′-deoxy-3′-S- phosphonomethyl-3′-thio-α-L-threosyl nucleosides as well as the 2′-deoxy analogues related to PMDTT are described. The key transformations involved the synthesis of the 3′-deoxy-3′-thio-L-threosyl a
- Huang, Qiuya,Herdewijn, Piet
-
experimental part
p. 3450 - 3457
(2011/09/15)
-
- Design, synthesis and biological evaluation of 2′-deoxy-2′, 2′-difluoro-5-halouridine phosphoramidate ProTides
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We report the synthesis of a series of novel 2′-deoxy-2′, 2′-difluoro-5-halouridines and their corresponding phosphoramidate ProTides. All compounds were evaluated for antiviral activity and for cellular toxicity. Interestingly, 2′-deoxy-2′,2′-difluoro-5-iodo- and -5-bromo-uridines showed selective activity against feline herpes virus replication in cell culture due to a specific recognition (activation) by the virus-encoded thymidine kinase.
- Quintiliani, Maurizio,Persoons, Leentje,Solaroli, Nicola,Karlsson, Anna,Andrei, Graciela,Snoeck, Robert,Balzarini, Jan,McGuigan, Christopher
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experimental part
p. 4338 - 4345
(2011/09/12)
-
- 1-[2-(2-Benzoyl- and 2-benzylphenoxy)ethyluracils as potent anti-HIV-1 agents
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Non-nucleoside reverse transcriptase inhibitors (NNRTI) are key components in highly active antiretroviral therapy for treating HIV-1. Herein we present the synthesis for a series of N1-alkylated uracil derivatives bearing ω-(2-benzyl- and 2-benzoylphenoxy)alkyl substituents as novel NNRTIs. These compounds displayed anti-HIV activity similar to that of nevirapine and several of them exhibited activity against the K103N/Y181C RT mutant HIV-1 strain. Further evaluation revealed that the inhibitors were active against most nevirapine-resistant mono- and di-substituted RTs with the exception of the V106A RT. Thus, the candidate compounds can be regarded as potential lead compounds against the wild-type virus and drug-resistant forms.
- Novikov, Mikhail S.,Ivanova, Olga N.,Ivanov, Alexander V.,Ozerov, Alexander A.,Valuev-Elliston, Vladimir T.,Temburnikar, Kartik,Gurskaya, Galina V.,Kochetkov, Sergey N.,Pannecouque, Christophe,Balzarini, Jan,Seley-Radtke, Katherine L.
-
body text
p. 5794 - 5802
(2011/11/04)
-
- Computationally-guided optimization of a docking hit to yield catechol diethers as potent anti-HIV agents
-
A 5-μM docking hit has been optimized to an extraordinarily potent (55 pM) non-nucleoside inhibitor of HIV reverse transcriptase. Use of free energy perturbation (FEP) calculations to predict relative free energies of binding aided the optimizations by identifying optimal substitution patterns for phenyl rings and a linker. The most potent resultant catechol diethers feature terminal uracil and cyanovinylphenyl groups. A halogen bond with Pro95 likely contributes to the extreme potency of compound 42. In addition, several examples are provided illustrating failures of attempted grafting of a substructure from a very active compound onto a seemingly related scaffold to improve its activity. (Figure presented)
- Bollini, Mariela,Domaoal, Robert A.,Thakur, Vinay V.,Gallardo-Macias, Ricardo,Spasov, Krasimir A.,Anderson, Karen S.,Jorgensen, William L.
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supporting information; experimental part
p. 8582 - 8591
(2012/02/02)
-
- Synthesis and antiviral evaluation of α-l-2′- deoxythreofuranosyl nucleosides
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The synthesis of a series of α-l-2′-deoxythreofuranosyl nucleosides featuring the nucleobases A, T, C and U is described in seven steps from 1,2-O-isopropyledene-α-l-threose, involving a Vorbru?ggen coupling and a Barton-McCombie deoxygenation protocol as the key steps. All analogues, including a phosphoramidate nucleoside phosphate prodrug of the T analogue, were evaluated against a broad panel of different viruses but found inactive, while also lacking notable cellular toxicity. The thymidine analogue showed inhibition to mitochondrial thymidine kinase-2 (TK-2), herpes simplex virus type 1 (HSV-1) TK, varicella-zoster virus (VZV) TK and Mycobacterium tuberculosis thymidylate kinase.
- Toti, Kiran S.,Derudas, Marco,McGuigan, Christopher,Balzarini, Jan,Van Calenbergh, Serge
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experimental part
p. 3704 - 3713
(2011/11/07)
-
- One-flow, multistep synthesis of nucleosides by Bronsted acid-catalyzed glycosylation
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Nucleosides in flow: A general, scalable method of Bronsted acid-catalyzed nucleoside formation is described. Because of the high reaction temperatures readily available to the flow reaction format, mild Bronsted acids, particularly pyridinium triflates, can be used. A one-flow multistep synthesis of unprotected nucleosides is also reported (see scheme).
- Sniady, Adam,Bedore, Matthew W.,Jamison, Timothy F.
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supporting information; body text
p. 2155 - 2158
(2011/04/23)
-
- Novel compounds with a viologen skeleton and N-heterocycles on the peripheries: Electrochemical and spectroscopic properties
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The present article deals with novel compounds comprising a redox-active group as core and a nucleobase in the peripheries, linked covalently via a spacer. The new derivatives 1,1′,1″-(benzene-1,3,5- triyltrimethanediyl)tris{1′-[3-(3,4-dihydro-5-methyl-2,
- Asaftei, Simona,Lepadatu, Ana Maria,Ciobanu, Marius
-
experimental part
p. 1091 - 1101
(2011/08/05)
-
- Poly(ε-caprolactone)-poly(isobutylene): A crystallizing, hydrogen-bonded pseudo-block copolymer
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The crystallization of block copolymers (BCPs) under homogeneous and heterogeneous nucleation is currently well understood revealing the strong interplay of crystallization in competition to microphase separation. This article reports investigations on sy
- Ostas, Elena,Schroeter, Klaus,Beiner, Mario,Yan, Tingzi,Thurn-Albrecht, Thomas,Binder, Wolfgang H.
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experimental part
p. 3404 - 3416
(2012/05/19)
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- Electrophilic glycosidation employing 3,5-O-(di-tert-butylsilylene)-erythro-furanoid glycal leads to exclusive formation of the β-anomer: synthesis of 2′-deoxynucleosides and its 1′-branched analogues
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Stereoselectivity in N-iodosuccimide (NIS)-mediated electrophilic glycosidation was examined by employing 2,4-bis-O-(trimethylsilyl)thymine and three different silyl-protected erythro-furanoid glycals 12, 16, and 18. As a result, it was found that 3,5-O-(di-t-butylsilylene)-protected 18 gave only the β-anomer (21). The remarkable stereoselectivity observed by employing 18 is discussed on the basis of its X-ray crystallographic analysis. 1-Substituted glycals gave the corresponding β-anomer, again exclusively, to provide access to 1′-branched 2′-deoxynucleosides.
- Haraguchi, Kazuhiro,Konno, Kiju,Yamada, Kaori,Kitagawa, Yasuyuki,Nakamura, Kazuo T.,Tanaka, Hiromichi
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body text
p. 4587 - 4600
(2010/07/05)
-
- One-pot synthesis of azanucleosides from proline derivatives stereoselectivity in sequential processes
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Common amino acid derivatives can be transformed in onestep fashion into N-azanucleosides. The method is a sequential process initiated, by a domino radical decarboxylation/ oxidation reaction; an acyliminium ion is formed as an intermediate and can be trapped by nitrogen bases (purines, pyrimidines, and benzotriazole). The mildness of the reaction conditions and the good, yields obtained make this procedure an interesting alternative to the conventional processes. Good stereoselectivities were obtained with 4-(silyloxy)proline derivatives as substrates.
- Boto, Alicia,Hernandez, Dacil,Hernandez, Rosendo
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experimental part
p. 3847 - 3857
(2010/09/05)
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- A procedure for facile synthesis of nucleosides using N, O-Bistrimethyl- silylacetamide in the presence of natural phosphate coated with potassium iodide
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Several α-D/L-arabino and β-D/L- xylonucleosides were synthesized in good yields under mild conditions by N-glycosylation of 1-O-acetyl D/L- arabino, and xylofuranose, with silylated nucleobases (uracil, thymine and 6- azauracil) in acetonitrile using natural phosphate (NP) coated with potassium iodide in BSA as catalyst.
- Baddi, Laila,Smietana, Michael,Sebti, Said,Vasseur, Jean-Jacques,Lazrek, Hassan B.
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experimental part
p. 196 - 199
(2011/07/08)
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- Highly stereoselective synthesis of 2′-deoxy-β-ribonucleosides via a 3′-(N-acetyl)-glycyl-directing group
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A facile synthesis of 2′-deoxy-β-ribonucleosides from 3′-O-(N-acetyl)-glycyl-protected 2′-deoxyribofuranose has been developed. The coupling reactions between the protected 2′-deoxyribose and silylated bases exhibited β-selectivity up to 98% presumably vi
- Liu, Zhaogui,Li, Deyao,Yin, Biaolin,Zhang, Jiancun
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experimental part
p. 240 - 243
(2010/03/24)
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- Synthesis and anti-HIV activity of 2′-deoxy-2′-fluoro-4′-C-ethynyl nucleoside analogs
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Based on the favorable antiviral profiles of 4′-substituted nucleosides, novel 1-(2′-deoxy-2′-fluoro-4′-C-ethynyl-β-d-arabinofuranosyl)-uracil (1a), -thymine (1b), and -cytosine (2) analogs were synthesized. Compounds 1b and 2 exhibited potent anti-HIV-1 activity with IC50 values of 86 and 1.34 nM, respectively, without significant cytotoxicity. Compound 2 was 35-fold more potent than AZT against wild-type virus, and also retained nanomolar antiviral activity against resistant strains, NL4-3 (K101E) and RTMDR. Thus, 2 merits further development as a novel NRTI drug.
- Wang, Qiang,Li, Yanfeng,Song, Chuanjun,Qian, Keduo,Chen, Chin-Ho,Lee, Kuo-Hsiung,Chang, Junbiao
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supporting information; experimental part
p. 4053 - 4056
(2010/08/19)
-
- Synthesis and antitumor activity of novel 2′,3′-diethanethio- 2′,3′,5′-trideoxy-5′-triazolonucleoside analogues
-
A series of novel 2′,3′-diethanethio-2′,3′, 5′-trideoxy-5′-triazoloribonucleosides was synthesized in excellent yields and their antitumor activity was evaluated. These nucleoside analogues with aromatic substituted triazole rings showed significantly improved activity towards a broad range of tumor cell lines and those without arene substitutes were inactive.
- Yu, Jin-Lan,Wu, Qin-Pei,Zhang, Qing-Shan,Xi, Xiao-Dong,Liu, Ning-Ning,Li, Yun-Zheng,Liu, Yan-Hong,Yin, Hong-Quan
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supporting information; experimental part
p. 3219 - 3222
(2010/08/20)
-
- Synthesis and antitumor activity of 5′-deoxy-4′-thio-l- nucleosides
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A series of novel 5′-deoxy-4′-thio-l-nucleosides was designed and synthesized. The absolute configuration of the target compound 23α was confirmed by X-ray crystallography. The antitumor activities of the target compounds were tested against the growth of human carcinoma of colon (LOVO), human leukemia cell line (CEM) and human breast cancer cell line (MDA-MB-435) cells in vitro. 6-cyclopentylamino and 6-cyclohexylamino purine compounds 26 and 27, both in α-configuration and in β-form, exhibited strong inhibition to CEM.
- Cong, Liqing,Zhou, Weicheng,Jin, Dongzhe,Wang, Juan,Chen, Xiuhua
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experimental part
p. 619 - 627
(2011/04/22)
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- Screening the structural space of bicyclo-DNA: Synthesis and thermal melting properties of bc4,3-DNA
-
In attempts to screen the structural and functional properties of bicyclo-DNA, in which the ribose C(3′) and C(5′) centers are integrated into an additional five-membered carbocyclic ring ([3.3.0]-series) we have now synthesized and investigated a ring en
- Stauffiger, Andrea,Leumann, Christian J.
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experimental part
p. 1153 - 1162
(2009/07/11)
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- Additive pummerer reaction of 3,5-O-(Di-tert-butyl)silylene-4-thiofuranoid glycal: A high-yield and β-selective entry to 4-thioribonucleosides
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Upon reacting 3,5-O-(di-tert-butyl)silylene-4-thiofuranoid glycal S-oxide (6) with Ac2O/TMSOAc/BF3·OEt2 in CH 2Cl2, the additive Pummerer reaction proceeded to furnish the corresponding 1,2-di-O-acetyl-4-thioribofuranose 7. Compound 7 serves as a highly β-selective glycosyl donor in the Vorbrueggen condensation carried out in the presence of TMSOTf. Thus, the 4-thio-β-D-ribofuranosyl derivatives of uracil, thymine, N4-acetylcytosine, 6-chloropurine, and 2-amino-6-chloropurine were synthesized. The use of 7 can be extended to the β-selectivesynthesis of 4-thio-C-ribonucleosides.
- Haraguchi, Kazuhiro,Matsui, Hiromitsu,Takami, Shin,Tanaka, Hiromichi
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supporting information; experimental part
p. 2616 - 2619
(2009/07/25)
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- Synthesis of spiroacetal-nucleosides as privileged natural product-like scaffolds
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The elaboration of a 6,6-spiroacetal scaffold to incorporate a nucleoside unit at the anomeric position is described. The novel spiroacetal-nucleoside hybrids 11 were generated via nucleosidation of acetoxy-spiroacetal 10 with a series of silylated nucleobases under Vorbrueggen conditions.
- Choi, Ka Wai,Brimble, Margaret A.
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experimental part
p. 1424 - 1436
(2009/12/04)
-