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1.
Claire Pierra Sureyya Olgen Sócrates C. H. Cavalcanti Yung-Chi Cheng Raymond F. Schinazi Chung K. Chu 《Nucleosides, nucleotides & nucleic acids》2013,32(1-2):253-268
Abstract Cyclopropyl carbocyclic nucleosides have been synthesized from the key intermediate 2 which was converted to the mesylated cyclopropyl methyl alcohol 3. Condensation of compound 3 with various purine and pyrimidine bases gave the desired nucleosides. All synthesized nucleosides were evaluated for antiviral activity and cellular toxicity. Among them adenine 22 and guanine 23 derivatives showed moderate antiviral activity against HIV-1 and HBV. None of the other compounds showed any significant antiviral activities against HIV-1, HBV, HSV-1 and HSV-2 in vitro up to 100μM. 相似文献
2.
Y. F. Zhao M. G. Lee T.-F. Yang B. K. Chun J. F. Du R. F. Schinazi 《Nucleosides, nucleotides & nucleic acids》2013,32(3-5):303-305
Abstract A number of nucleosides have been synthesized as potential antiviral and antitumor agents.1 More recently, various dideoxynucleosides have been synthesized and found to be potent anti-HIV agents.2 As a part of our drug discovery program for the treatment of HIV and HBV, we have initiated to synthesize cyclopropyl carbocyclic nucleosides as potential antiviral agents. Several papers regarding the synthesis of cyclopropyl carbocyclic nucleosides have appeared in the literature.3–5 However, they are all reported as racemic mixtures. In this abstract, we wish to report the asymmetric synthesis of cylopropyl carbocyclic nucleosides from optically active common intermediates, 6 and 11. 相似文献
3.
Michael E. Jung Christopher J. Nichols Oliver Kretschik Yue Xu 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):541-546
Abstract New efficient routes for the high-yielding synthesis of several classes of modified nucleosides have been developed. We have prepared both the D- and L-enantiomers of the methylene-expanded oxetanocin isonucleosides 1a-c and the L-2′,3′-dideoxy isonucleosides 2abc (both the oxa and thia analgoues) as well as new routes for the preparation of L-ribose and 2-deoxy L-ribose 3ab and their modified nucleosides 4. 相似文献
4.
Janis Jansons Yuris Maurinsh Margeris Lidaks 《Nucleosides, nucleotides & nucleic acids》2013,32(8):1709-1724
Abstract 9-(β-D-Xylofuranosyl) adenine and 9-(α-L-arabinofuranosyl)-adenine have been modified to give a series of 8-amino-substituted nucleosides. Convenient methods of halogenation of these nucleosides and reactions of 8-halogenated nucleosides with various amines are described. No significant cytotoxic or antiviral activity was found. 相似文献
5.
Abstract The properties of the degenerate nucleosides dP and dK, in templates and primers were determined. dP was copied as either pyrimidine, dK as either purine. In primers, an equimolar mixture of the two nucleosides functioned as a universal base equivalent in both sequencing and the polymerase chain reactions. Cloning of DNA containing dP or dK produced transition mutations in vivo. 相似文献
6.
Ibrahim A. I. Ali 《Nucleosides, nucleotides & nucleic acids》2013,32(3):129-140
A series of quinoxaline azido reverse nucleosides 3a-c and their O-regioisomers 4a-c was prepared by reaction of quinoxaline 1a-c with 3-azido-3-deoxy-1,2-O-isopropylidene-5-p-toluenesulfonyl-D-ribofuranose (2) in the presence of sodium hydride. Structure modification of these interesting structures includes reduction and the subsequent acetylation reactions to give quinoxaline amino and acetyl amino reverse nucleosides and their O-regioisomers. 相似文献
7.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):1623-1625
Abstract The introduction of sulfonamido group on the C-2 position of pyrimidine nucleosides was achieved by ring opening of 2,2′- and 2,3′-anhydronucleosides. N-sulfonyl derivatives of nucleobases and sulfonamido derivatives of nucleosides were assayed for in vitro antitumor activity. 相似文献
8.
Nobuya Katagiri Yumiko Ito Takuya Shiraishi Tokumi Maruyama Yoshiko Sato Chikara Kaneko 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):631-647
Abstract The deamination of eight kinds of racemic carbocyclic adenine nucleosides by adenosine deaminase under high-pressure (400 MPa) was examined and the result was compared with that obtained from the reaction under atmospheric pressure. The deamination of all carbocyclic nucleosides irrespective to their ring size of carbocycles was facilitated remarkably high-pressure. The reaction of three and five membered carbocyclic nucleosides resulted in the very high enantioselectivity both under high- and atmospheric Plessure whereas the enantioselectivity of six membered carbocyclic nucleosides was suppressed under high-pressure. However, the enantioselectivity of four membered nucleosides was low under both conditions. 相似文献
9.
Carmen Ochoa Rafael Provencio Maria Luisa Jimeno Jan Balzarini Erik De Clercq 《Nucleosides, nucleotides & nucleic acids》2013,32(5):901-910
Abstract Synthesis of 1,2,4,6-thiatriazine 1,1-dioxide nucleosides is now reported for the first time. In order to know the conformation of the nucleosides, a NMR study has been carried out. Anti-HIV-1 and HIV-2 properties of the nucleosides have been tested. These compounds have not shown activity at subtoxic concentrations. 相似文献
10.
Noriaki Minakawa Akira Matsuda Tohru Ueda Takuma Sasaki 《Nucleosides, nucleotides & nucleic acids》2013,32(8):1067-1078
Abstract 5-Ethynyl-1-(2-deoxy-β-D-ribofuranosyl)imidazole-4-carbonitrile (4) and -carboxamide (5) and 5-ethynyl-1-(5-deoxy-β-D-ribofuranosyl)imidazole-4-carbonitrile (11) and -carboxamide (12) have been synthesized from the corresponding 5-iodo derivatives 2 and 7 by a palladium-catalyzed cross-coupling reaction with (tri-methylsilyl)acetylene. The aglycons, 5-ethynylimidazole derivatives 14 and 15 were synthesized by the hydrolytic cleavage of the corresponding nucleosides. The antileukemic activity of these nucleosides and base analogues are also described. 相似文献
11.
V. C. Solan G. L. Szekeres E. K. Ryu H. Kung Y. K. Ho T. J. Bardos 《Nucleosides, nucleotides & nucleic acids》2013,32(5):419-434
Abstract The synthesis of a series of new nucleosides and nucleotides, including ribo-, 2-deoxyribo- and arabinofuranosides of 5-sulfur-substituted cytosines, is described. The synthetic methods employed involve 5-thiolation of the appropriate cytosine or 5-bromocytosine nucleosides and nucleotides, or alternatively, 4-thiation followed by amination of the corresponding protected 5-(S-benzyl)mercaptouracil nucleosides and subsequent deblocking with sodium and liquid ammonia. 相似文献
12.
Adel M. E. M. Attia Elsayed I. Ibrahim Fouad E. A. Hay Mohammed M. A. Abbasi Hanaa A. E. Mansour 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1581-1590
Abstract A novel synthesis of 1-(β-D-pentopyranosyl)pyridinethione nucleosides utilizing pyridine-2(1H)-thiones and α-bromoxylose or β-bromoarabinose triacetate as starting components is described. The free nucleosides were tested for their potential activity against HIV and different types of tumor virus. 相似文献
13.
Takashi Ogawa Hiroshi Takaku Naoki Yamamoto 《Nucleosides, nucleotides & nucleic acids》2013,32(4):499-504
Abstract The azidation of unprotected acyclic nucleosides (4) was carried out in a one-pot reaction by means of the reagent triphenylphosphine-carbon tetraiodide-sodium azide to give the corresponding mono-azido-acyclic nucleosides (6) in good yields without by-products such as the di-azido-acyclic nucleosides. 相似文献
14.
B. Fera B. Singrün G. Kupferschmitt J. Schmidt F. Buck H. Ruterjans 《Nucleosides, nucleotides & nucleic acids》2013,32(1-2):477-481
Abstract Microbiological and chemical methods for the preparation of 15N labeled nucleosides are described. Oligonucleotides are synthesized from the labeled nucleosides on a large scale by the phosphoramidite procedure using a self-developed DNA - Synthesizer. Preliminary 15N-NMR studies are reported. 相似文献
15.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-7):1043-1046
A study of C-nucleophilic substitution at the C4-position on pyrimidine and C6-position on 2′-deoxyguanosine to produce novel nucleosides is presented with the spectroscopic properties of their respective substitution products. C4-(1,2,4-triazol-1-yl) pyrimidine nucleosides 1 were treated with nitroalkanes, malononitrile, acetylacetone, ethyl nitroacetate, acetoacetate and cyanoacetate at 100°C in dioxane in the presence of DBU resulting in the production of novel nucleosides 2–11. To explore the application of this methodology to purine chemistry, this approach was used to produce novel analogs from 2′-deoxyguanosine. We found that the triazolo derivative 12 undergoes C-nucleophilic substitution with nitromethane, malononitrile, acetylacetone, ethyl nitroacetate and cyanoacetate in the presence of potassium carbonate (K2CO3) in DMF at 100°C to give novel nucleosides 13–7. 相似文献
16.
Aihong Kim Joon Hee Hong Chang Hyun Oh 《Nucleosides, nucleotides & nucleic acids》2013,32(12):1399-1406
A simple synthetic route for novel acyclic phosphonate nucleosides is described. The characteristic cyclopropyl moiety 8 was constructed employing the Simmons-Smith reaction as key step starting from simple acyclic 2-butene-1,4-diol. The condensation of the mesylate 11 with natural nucleosidic bases (A,C,T,U) under nucleophilic substitution conditions (K2CO3, 18-Crown-6, DMF) and hydrolysis afforded the target nucleosides 16, 17, 18, and 19. In addition, the antiviral evaluations against various viruses were performed. 相似文献
17.
Sungjoong Kim Wooyeon Won Yonghan Kang 《Nucleosides, nucleotides & nucleic acids》2013,32(10-11):2025-2033
Abstract Synthesis of pyrazolo[3,4-c]maleimide nucleosides was attempted, but ring opening reaction of the maleimide part was observed during ammonolysis of sugar-protected pyrazolo[3,4-c]maleimide nucleosides. The isolated pyrazole nucleosides were characterized by NMR spectra and X-ray analysis. 相似文献
18.
M. Belmans I. Vrijens E. L. Esmans J. A. Lepoivre F. C. Alderweireldt L. L. Wotring 《Nucleosides, nucleotides & nucleic acids》2013,32(1-2):245-248
Abstract Condensation of 2-fluoro-3-lithio pyridine and 3-chloro-4-lithio pyridine with 2,4:3,5-di-O-benzylidene-alde-hydo-D-ribose gives the corresponding D-allo- and D-altro-addition products. These were converted into the corresponding mesylates and cyclized to the ribofuranosyl nucleosides with an overall yield of 60–70 %. Both nucleosides did not show any inhibitory effect on L-1210-cells. 相似文献
19.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):987-989
Abstract Extracts of urinary nucleosides have been sequentially purified and examined by mass spectrometric analysis. Seventeen modified nucleosides have been unequivocally identified and a further five provisionally identified. While several nucleosides were found only in a small number of extracts, the occurrence and levels of others were found to correlate with the tumour type and stage. 相似文献
20.
Hiroyuki Hayakawa Hiromichi Tanaka Kazuhiro Haraguchi Masami Mayumi Masako Nakajima Takashi Sakamaki 《Nucleosides, nucleotides & nucleic acids》2013,32(1):121-128
Abstract Chlorination of purine nucleosides protected with tert-butyldimethylsilyl (TBDMS) group was examined by the reaction of the C-8 lithiated species, generated by LDA, with p-toluenesulfonyl chloride as an electrophile. This provides a new method for the preparation of 8-chloropurine nucleosides. 相似文献