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1.
Jean M. J. Tronchet Imre Kovacs Françoise Barbalat-Rey Naz Dolatshahi 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):337-347
Abstract TSAO analogues, 2′,5′-O-bis-TBDMS uridine-3′-spiro-3′-isoxazolidin-5′-one (9) and its thymidine congener 10, as well as model spiro sugar derivatives (3 and 4) have been prepared from the corresponding nitrones through a stereospecific tandem nucleophilic attack. Compounds 9 and 10 which are bioisosters of TSAO-U and T respectively but which lack an amino group on the spiro ring, were found inactive against both HIV-1 and HIV-2. 相似文献
2.
Interaction of (2′ -5′) and (3′ -5′) Linked 2-Aminoadenylyl-3-aminoadenosines with Polyuridylic Acid
Masako Muraoka Seizo Takahashi Seiichi Uesugi 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1503-1518
Abstract 2′-5′ and 3′-5′ linked 2-aminoadenylyl-2-aminoadenosines [(2′-5′)n2Apn2A (1) and (3′-5′)n2Apn2A (2)] were synthesized by condensation of 5′-O-monomethoxytrityl-N 2 N 6-dibenzoyl-2-aminoadenosine and N 2,N 6,2′,3′-O-tetrabenzoyl-2-aminoadenosine 5′-phosphate using dicyclohexylcarbodiimide (DCC). The conformational properties of these dimers 1 and 2 were examined by UV, NMR and CD spectroscopy. The results reveal that the 2′-5′-isomer 1 takes a stacked conformation, which contains a larger base-base overlap and is more stable against thermal perturbation with respect to the 3′-5′-isomer 2. Interactions of 1 and 2 with polyuridylic acid (Poly (U)) were also examined by Tm, mixing curves, UV and CD spectra. Both the dinucleoside isomers 1 and 2 formed a complex of 1 : 2 stoichiometry with poly(U), which was much more stable than that of the corresponding ApA isomer 相似文献
3.
Yukio Aoyama Takeshi Sekine Yoshiaki Iwamoto Etsuko Kawashima Yoshiharu Ishido 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):733-738
Abstract Efficient syntheses of 2′-bromo-2′-deoxy-3′,5′-O-TPDS-uridine (5a) and 1-(2-bromo-3,5-O-TPDS-β-D-ribofuranosyl)thymine (5b) from uridine and 1-(β-D-ribofuranosyl)thymine are described, respectively. The key step is a treatment of 3′,5′-O-TPDS-O2,2′-anhydro-1-(β-D-ardbinofuranosyl)uracil (4a) and -thymine (4b) with LiBr in the presence of BF3-OEt2 in 1,4-dioxane at 60°C to give 5a and 5b in 98%, and 96% yield, respectively. 相似文献
4.
Anthony Romieu Didier Gasparutto Didier Molko Jean Cadet 《Nucleosides, nucleotides & nucleic acids》2013,32(6-7):1331-1333
Abstract Oligodeoxynucleotides containing the two 5′R and 5′S diastereoisomers of 5′,8-cyclo-2′-deoxyadenosine (CyclodAdo) and 5′,8-cyclo-2′-deoxyguanosine (CyclodGuo) have been synthesized using the phosphoramidite chemistry. The structural assignment and a few biochemical features of these modified DNA fragments are reported. 相似文献
5.
Sidney D. Selvidge III James Jang Partha S. Ray 《Nucleosides, nucleotides & nucleic acids》2013,32(10-11):2019-2024
Abstract 5-Formyl-2′,3′-O-isopropylideneuridine and 5-formyl-2′,3′,5′-tri-O-acetyluridine were prepared by a new procedure involving palladium-catalyzed coupling of 5-iodouridine with styrene, followed by reaction with acetic anhydride or acetone and ozonolysis of the resulting 5-styryluridine derivatives. 相似文献
6.
Tomoharu Iino Satoshi Shuto Akira Matsuda 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):169-181
Abstract A synthetic method for (2′S)-2′-C-alkyl-2′-deoxyuridines (9) has been described. Catalytic hydrogenation of 1-[2-C-alkynyl-2-O-methoxalyl-3,5-O-TIPDS-β-D-arabino-pentofuranosyl]uracils (5) gave 1-[2-C-(2-alkyl)-2-O-methoxalyl-3,5-O-TIPDS-β-D-arabino-pentofuranosyl]uracils (4) as a major product, which were then subjected to the radical deoxygenation, affording (2′S)-2′-alkyl-2′-deoxy-3′,5′-O-TIPDS-uridines (7) along with a small amount of their 2′R epimers. 相似文献
7.
Abstract 2′-Deoxy-5′-0-(4,4′-dimethoxytrityl)-5-methyl-N 4-(1-pyrenylmethyl)-α-cytidine (5) was prepared by reaction of 1-pyrenylmethylamine with an appropriate protected 4-(l,2,4-triazolyl)-α-thymidine derivative 3 which was synthesized from 5-O-DMT protected α-thymidine 1. Aminolysis of 3 afforded 3′-O-acetyl-2′-deoxy-5′-O-(4,4′-dimethoxytrityl)-5-methyl-α-cytidine (8). Benzoylation of 8 and removal of acetyl afforded N 4-benzoyl-2-deoxy-5–0-(4,4′-dimethoxytrityl)-5-methyl-α-cytidine (10). The amidites of compounds 5and 10 were prepared and used in α-oligonucleotide synthesis. DNA three-way junction (TWJ) is stabilized when an α-ODN is used for targeting the dangling flanks of the stem in a DNA hairpin. Further stabilization of the TWJ is observed when 5 is inserted into the α-ODN at the junction region. 相似文献
8.
Rakesh Kumar Edward E. Knaus Leonard I. Wiebe 《Nucleosides, nucleotides & nucleic acids》2013,32(9):895-904
Abstract (E)-5-(2-lodovinyl)-2′-fluoro-3′-0-(1-methyl-1,4-dihydropyridyl-3-carbonyl)-2′-deoxyuridine (11) was synthesized for future evaluation as a lipophilic, brain-selective, pyrimidine phosphorylase-resistant, antiviral agent for the treatment of Herpes simplex encephalitis (HSE). Treatment of (E)-5-(2-iodovinyl)-2′-fluoro-2′-deoxyuridine (6) with TBDMSCI in the presence of imidazole in DMF yielded the protected 5′-O-t-butyldimethylsilyl derivative (7). Subsequent reaction with nicotinoyl chloride hydrochloride in pyridine afforded (E)-5-(-2-iodovinyl)-2′-fluoro-3′-O-(3-pyridylcarbonyl)-5′-O-t-butyldimethylsily-2′-deoxyuridine (8). Deprotection of the silyl ether moiety of 8 with n-Bu4N+F? and quaternization of the resulting 3′-O-(3-pyridylcarbonyl) derivative 9 using iodomethane afforded the corresponding 1-methylpyridinium salt 10. The latter was reduced with sodium dithionite to yield (E)-5-(2-iodovinyl)-2′-fluoro-3′-O-(1-methyl-1,4-dihydropyridyl-3-carbonyl)-2′-deoxyuridine (11). 相似文献
9.
Olga Adelfinskaya Weidong Wu V. Jo Davisson Donald E. Bergstrom 《Nucleosides, nucleotides & nucleic acids》2013,32(10-12):1919-1945
Two novel C-linked oxadiazole carboxamide nucleosides 5-(2′-deoxy-3′,5′-β-D-erythro-pentofuranosyl)-1,2,4-oxadiazole-5-carboxamide (1) and 5-(2′-deoxy-3′,5′-β-D-erythro-pentofuranosyl)-1,2,4-oxadiazole-3-carboxamide (2) were successfully synthesized and characterized by X-ray crystallography. The crystallographic analysis shows that both unnatural nucleoside analogs 1 and 2 adapt the C2′-endo (“south”) conformation. The orientation of the oxadiazole carboxamide nucleobase moiety was determined as anti (conformer A) and high anti (conformer B) in the case of the nucleoside analog 1 whereas the syn conformation is adapted by the unnatural nucleoside 2. Furthermore, nucleoside analogs 1 and 2 were converted with high efficiency to corresponding nucleoside triphosphates through the combination chemo-enzymatic approach. Oxadiazole carboxamide deoxyribonucleoside analogs represent valuable tools to study DNA polymerase recognition, fidelity of nucleotide incorporation, and extension. 相似文献
10.
Naganna M. Goudgaon Yahya A. El-Kattan Xiaoyang Xia Jeff McAtee José Soria Shiow-Jyi Wey 《Nucleosides, nucleotides & nucleic acids》2013,32(12):2133-2150
Abstract Previous biochemical and pharmacological studies indicated that 5-o-carboranyl-2′-deoxyuridine is a lead candidate for boron neutron capture therapy. This prompted the development of a rapid and stereoselective N 1-glycosylation reaction of silylated 5-o-carboranyluracil with a variety of protected sugars. The key intermediate, 5-o-carboranyluracil (6), was prepared from 5-iodouracil in six steps. A novel coupling procedure of the 2,4-dimethoxy-5-ethynylpyrimidine (4) with decaborane without activator was used. Silylated 6 was coupled with a variety of carbohydrates under mild conditions to produce several carborane containing nucleosides. In each case, the stereochemistry and stereoselectivity of the glycosylation reaction was not affected by the presence of the carborane at the 5-position of the uracil and produced exclusively closo [closo-1,2-C2B10H12 cage] nucleosides. This was confirmed by X-ray structure determination of racemic 5-carboranyl-2′,3′-dideoxy-3′-thiauridine. This compound demonstrated an anti-conformation with the oxathiolane ring in a pseudo C-2′-endo conformation. The toxicity profile of the new compounds and their precursors was determined in three cell culture systems, two of human origin (PBM and CEM cells) and one of monkey origin (Vero cells). The compounds were also evaluated for their potential antiviral activity against human immunodeficiency virus and herpes simplex virus in vitro. 5-o-Carboranyl-xylofuranosyluracil (12) demonstrated low toxicity in culture and in mice. 相似文献
11.
D. Gavriliu C. Fossey G. Fontaine S. Benzaria A. Ciurea Z. Delbederi 《Nucleosides, nucleotides & nucleic acids》2013,32(5-6):1017-1031
Abstract A general strategy is reported for the preparation of C-5-methylamino- or methyldiamino-d4T analogues of “different sizes”. Reactions of the 2′,3′-didehydro-2′,3′-dideoxy-C-5 hydroxymethyl precursor (7) with either polymethylene diamines (n = 6, 8, 10 and 12) or propargylamine proceed regioselectively via subtitution reactions at the C-5 position of uracil. The compounds were evaluated for antiviral activity and cytotoxicity. No significant activity was observed for compounds 9, 11, and 13, but 10 and 12 exhibited a weak activity against HIV-1. 相似文献
12.
《Bioscience, biotechnology, and biochemistry》2013,77(4):1086-1089
Three compounds, 20-O-acetyl-[3-O-(2′E,4′Z)-decadienoyl]-ingenol (1), 20-O-acetyl-[5-O-(2′E,4′Z)-decadienoyl]-ingenol (2) and 3-O-(2′E,4′Z)-decadienoylingenol (3), were isolated from Euphorbia kansui under the bioassay-guided method. Each compound showed the same antinematodal activity against the nematode, Bursaphelenchus xylophilus, at a minimum effective dose (MED) of 5 μg/cotton ball. 相似文献
13.
《Nucleosides, nucleotides & nucleic acids》2013,32(12):2161-2170
Abstract 1-O-Acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-D-erythro-pentofuranose and 2-deoxy-1,3,5-tri-O-acetyl-4-thio-L-threo-pentofuranose were coupled with 5-azacytosine to obtain α and β anomers of nucleosides. All four nucleosides were reduced to the corresponding dihydro derivatives and deblocked to give target compounds. All eight target compounds were evaluated in a series of human cancer cell lines in culture. Only 2′-deoxy-4′-thio-5-azacytidine (3β) was found to be cytotoxic in all the cell lines and was further evaluated in vivo. Details of the synthesis and biological activity are reported. 相似文献
14.
15.
Akira Matsuda Hitomi Okajima Akira Masuda Akio Kakefuda Yuichi Yoshimura Tohru Ueda 《Nucleosides, nucleotides & nucleic acids》2013,32(2-4):197-226
Abstract New methods for the synthesis of 2′,3′-didehydro-2′,3′-dideoxy-2′ (and 3′)-methyl-5-methyluridines and 2′,3′-dideoxy-2′ (and 3′)-methylidene pyrimidine nucleosides have been developed from the corresponding 2′ (and 3′)-deoxy-2′ (and 3′)-methylidene pyrimidine nucleosides. Treatment of a 3′-deoxy-3′-methylidene-5-methyluridine derivative 8 with 1,1′-thiocarbonyldiimidazole gave the allylic rearranged 2′,3′-didehydro-2′,3′-dideoxy-3′-[(imidazol-1-yl)carbonylthiomethyl] derivative 24. On the other hand, reaction of 8 with methyloxalyl chloride afforded 2′-O-methyloxalyl ester 25. Radical deoxygenation of both 24 and 25 gave 26 exclusively. Palladium-catalyzed reduction of 2′,5′-di-O-acetyl-3′-deoxy-3′-methylidene-5-methyluridine (32) with triethylammonium formate as a hydride donor regioselectively afforded the 2′,3′-dideoxy-3′-methylidene derivative 35 and 2′,3′-didehydro-2′,3′-dideoxy-3′-methyl derivative 34 in a ratio of 95:5 in 78% yield. These reactions were used on the corresponding 2′-deoxy-2′-methylidene derivatives. An alternative synthesis of 2′,3′-dideoxy-2′-methylidene pyrimidine nucleosides (43, 52, and 54) was achieved from the corresponding 1-(3-deoxy-β-D-thero-pentofuranosyl)pyrimidines (44 and 45). The cytotoxicity against L1210 and KB cells and inhibitory activity of the pathogenicity of HIV-1 are also described 相似文献
16.
P. G. Wyatt A. S. Anslow B. A. Coomber R. P.C. Cousins D. N. Evans V. S. Gilbert 《Nucleosides, nucleotides & nucleic acids》2013,32(9-10):2039-2049
Abstract A short high yielding synthesis of the potent anti-varicella-zoster virus (VZV) carbocyclic nucleoside analogue carba-BVDU 1 starting from aminodiol 2 is described. Reaction of 2 with acyl carbamate 3 and subsequent ring closure under acidic conditions afforded 5-ethyl-2′-deoxy-4′a-carbauridine 5. In situ acetylation of 5 afforded 3′,5′-di-O-acetyl-5-ethyl-2′-deoxy-4′a-carbauridine 6 in 78% overall yield from 2. Radical bromination of 6 with either bromine or NBS and subsequent treatment with triethylamine gave an efficient conversion to 3′,5′-di-O-acetyl-5-(E)-(2-bromovinyl)-2′-deoxy-4′a-carbauridine 7. Deacetylation of 7 afforded 1 in an overall 45–53% yield from 2. 相似文献
17.
Masanobu Suzuki Takeyoshi Sugiyama Masashi Watanabe Tetsuya Murayama Kyohei Yamashita 《Bioscience, biotechnology, and biochemistry》2013,77(4):1121-1127
A total synthesis of optically active pyriculol is described. The Wittig reaction between an aldehyde 19 and a triphenylphosphonium ylide 12 gave an intermediate 20. Successive treatment of 20 with p-toluenesulfonic acid, active manganese dioxide, and potassium carbonate gave (3′R,4′S)-pyriculol (23), which was identical with natural pyriculol (1) in all respects. From this synthesis, the absolute stereochemistry of pyriculol (1) was determined to be 2-[(3′R,4′S)-3′,4′-dihydroxy- (1′E,5′E)-1′,5′-heptadienyl]-6-hydroxybenzaldehyde 相似文献
18.
Hitoshi Hotoda Makoto Koizumi Rika Koga Kenji Momota Toshinori Ohmine Hidehiko Furukawa 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):531-538
Abstract Hexadeoxyribonucleotides (6-mers) having a 5′-TGGGAG-3′ sequence bearing hydrophobic substituents at their 5′-ends via phosphodiester linkages were prepared and evaluated for anti-HIV-1 activity in vitro. Some of these modified 6-mers showed weak anti-HIV-1 activities and they were less potent than the 6-mer having a DMTr group directly attached at its 5′-terminus. 相似文献
19.
Abstract Thymidine was converted to its 5′-epoxy derivative, which was reacted with nucleophiles to give 5′-C-aminomethyl-, 5′-C-bromomethyl-, 5′-C-cyanomethyl, and 5′-C-methoxymethylthymidine derivatives with defined stereochemistry. 5′-C-ally-, 5′-C-hydroxymethyl-, 5′-C-hydroxypropyl-, and 5′-C-(imidazole-4-acetamido)methyl-thymidine derivatives were also prepared. The 5′-C-branched thymidines were converted to the corresponding phosphoramidites. 相似文献
20.
《Nucleosides, nucleotides & nucleic acids》2013,32(4-7):879-882
The thioamide derivatives 3′-deoxy-5′-O-(4,4′-dimethoxytrityl)-3′-[(2-methyl-1-thioxo-propyl)amino]thymidine 1 and 3′-deoxy-5′-O-(4,4′-dimethoxytrityl)-3′-{{6-{[(9H-(fluo-ren-9-ylmethoxy)carbonyl]-amino}-1-thioxohexyl}amino} thymidine 2 were synthesized by regioselective thionation of their corresponding amides 7 and 8 with 2,4-bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphet-ane-2,4-disulfide (Lawesson's reagent). The thioamides were converted into the corresponding 5′-triphosphates 3 and 4. Compound 3 was chosen for DNA sequencing experiments and 4 was further labelled with fluorescein. 相似文献