共查询到20条相似文献,搜索用时 15 毫秒
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《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):887-889
Abstract Purine 2′-deoxynucleosides bearing an ethynyl or a cyano group at C-4′ of the sugar moiety were synthesized from the corresponding 2′-deoxynucleosides. These compounds exhibited very potent anti-HIV activity, and remained active against drug resistant HIV strains. 相似文献
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Victor E. Marquez Lak S. Jeong Marc C. Nicklaus Cliff George 《Nucleosides, nucleotides & nucleic acids》2013,32(3-5):555-558
Abstract The efficient DAST fluorination of deoxy-4′-thiopyrimidine nucleosides is reported. The cytidine analogue 3b was marginally effective against HIV. 相似文献
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Jacob Ravn Christoph Rosenbohm Signe M. Christensen Troels Koch 《Nucleosides, nucleotides & nucleic acids》2013,32(8):843-847
The first reported synthesis of 2′-amino-LNA purine nucleosides via a transnucleosidation is accomplished enabling the preparation of oligonucleotides incorporating 2′-amino-LNA with all four natural bases. 相似文献
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Nicolai E. Poopeiko Natalia B. Khripach Zygmunt Kazimierczuk Jan Balzarini Erik De Clercq Igor A. Mikhailopulo 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):1083-1086
Abstract Synthesis of 9-(2,3-dideoxy-3-fluoro-β-D-ribofuranosyl)-2-chloroadenine (7b) and -2-chloro-6-methoxypurine (9b), as well as the α-D-anomer 7a of the former and its N isomer 10a is reported. Among the compounds synthesized, only the β-D-anomer 7b displays moderate cytotoxic activity. 相似文献
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Toshiaki Waga Hiroshi Ohrui Hiroshi Meguro 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):287-304
Abstract A series of 2′-deoxy, 2′,3′-unsaturdted and 2′,3′-dideoxynucleoside analogues, which have an additional methyl group at the 4′-position, have been synthesized. When evaluated for their inhibitory activity against HIV in MT-4 cell, 2′-deoxy-4′-C-methyl nucleosides exhibited potent activity. 相似文献
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Mikhail Abramov Marleen Renders Piet Herdewijn 《Nucleosides, nucleotides & nucleic acids》2013,32(11-12):1042-1050
The 2′-N-formamide derivatives of adenosine, cytidine, and 9-β-d-arabinofuranosyladenine were synthesized and tested (as triphosphate) for their substrate capacities for the HCV NS5B polymerase. 相似文献
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Naina A. Van Draanen George W. Koszalka 《Nucleosides, nucleotides & nucleic acids》2013,32(8):1679-1693
Abstract A series of α-L-2′,3′-dideoxy nucleosides was prepared as potential antiviral agents. The pyrimidine nucleosides were prepared by standard Vorbrüggen coupling reactions. The purine analogues were prepared by enzymatic transfer of the dideoxy sugar from a pyrimidine to a purine base. These compounds were inactive against HIV-1, HBV, HSV-1 and -2, VZV, and HCMV. 相似文献
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Kamal N. Tiwari John A. Secrist III John A. Montgomery 《Nucleosides, nucleotides & nucleic acids》2013,32(8):1819-1828
Abstract 1,2,3,5-Tetra-O-acetyl-4-thio-D-riboruranose, prepared from 2,3,5-tri-O-benzyl-D-ribofuranose in four steps, was converted to the corresponding 2-chloroadenine nucleoside (8), which was deoxygenated to obtain 2-chloro-2′-deoxy-4′-thioadenosine (12). This is the first report of a 2′-deoxy-4′-thioribonucleoside of a purine rather than a pyrimidine. These novel nucleosides (8 and 12) were cytotoric to several human tumor cell lines in culture. 相似文献
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John A. Secrist III William B. Parker Kamal N. Tiwari Lea Messini Sue C. Shaddix Lucy M. Rose 《Nucleosides, nucleotides & nucleic acids》2013,32(3-5):675-686
Abstract Results are presented on the synthesis and biological activity of several types of 4′-thionucleosides as potential anticancer agents. Detailed studies on the mechanism of action of 4′-thiothymidine are also presented. 相似文献
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Yuichi Yoshimura Fumitaka Kano Shuichi Miyazaki Noriyuki Ashida Shinji Sakata Kazuhiro Haraguchi 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):305-324
Abstract 2′-Deoxy-, 2′-bromo-, and arabino-1′-C-cyano-pyrimidine nucleosides were synthesized from O2 ,2′-cyclouridine. Incorporation of cyano group at the anomeric position was achieved by treatment of 1′,2′-unsaturated uridine with NBS in the presence of pivalic acid followed by TMS-cyanide and stannic chloride. Antineoplastic and antiviral activities of those compounds are also discussed. 相似文献
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Tokumi Maruyama Kunihiko Utzumi Yoshiko Sato Douglas D. Richman 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):527-537
Abstract 3′,5′-Di-O-protected 6-chloropurine arabinoside 4b was treated with diethylaminosulfur trifluoride (DAST) and subsequently deprotected with pyridinium p-toluenesulfonate to give 6-chloropurine 2′-deoxy-2′-fluororiboside 6a. The displacement with nucleophile afforded the 6-substituted congener 6b-e. Treatment of 5′-O-protected 6-chloropurine arabinoside 3c with DAST gave lyxoepoxide 7. 相似文献
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Reza Fathi Kenneth J. Nawoschik Melissa Zavoda Alan F. Cook 《Nucleosides, nucleotides & nucleic acids》2013,32(10-11):1907-1920
Abstract A wide range of 2′,5′-dideoxy-nucleosides, including 6- substituted purine, pyrazolo[3,4-d]pyrimidine and 1-deazapurine derivatives, has been enzymatically prepared using purine nucleoside phosphorylase. Specificity towards cleavage by bacterial versus mammalian purine nucleoside phosphorylase was evaluated. 相似文献
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《Nucleosides, nucleotides & nucleic acids》2013,32(5):813-822
A series of 2′ and 4′‐doubly branched carbocyclic nucleosides 15, 16, 17 and 18 were synthesized starting from simple acyclic ketone derivatives. The required 4′‐quaternary carbon was constructed using Claisen rearrangement. In addition, the installation of a methyl group in the 2′‐position was accomplished using a Grignard carbonyl addition of isopropenylmagnesium bromide. Bis‐vinyl was successfully cyclized using a Grubbs’ catalyst II. Natural bases (adenine, cytosine) were efficiently coupled by using Pd(0) catalyst. 相似文献
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Yuichi Yoshimura Kenji Kitano Mikari Watanabe Hiroshi Satoh Shinji Sakata Shinji Miura 《Nucleosides, nucleotides & nucleic acids》2013,32(7-9):1103-1106
Abstract We have synthesized 4′-thioDMDC, 4′-thiogemcitabine, and 4′-thioarabinonucleosides, as potential antitumor and antiviral agents, originated from D-glucose. Biological activities of these compounds are also described. 相似文献
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Sung K. Kim Richard W. Fuller Victor E. Marquez 《Nucleosides, nucleotides & nucleic acids》2013,32(5):663-677
Abstract The cytosine analogue of Neplanocin A, cyclopentenyl cytosine (CPE-C, 4), has significant antitumor and antiviral activity. Two closely related analogues modified at the 2′-position, ara-CPE-C (6) and 2′-deoxy-CPE-C (5), have been synthesized from the corresponding uracil derivative CPE-U. Both compounds were devoid of cytotoxicity against L1210 leukemia in vitro. Ara-CPE-C displayed antiviral activity against influenza type A2 but was not very potent. 相似文献
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Kamal N. Tiwari John A. Montgomery John A. Secrist III 《Nucleosides, nucleotides & nucleic acids》2013,32(8):841-846
Abstract The procedure of Huang and Hui (Nucleosides & Nucleotide 1993, 12, 139-147) was found to give benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-L-threo-pentofuranoside (6) rather than the claimed D-erythro isomer. This sugar was converted to an anomeric mixture of the thymine nucleosides. The mixture was separated and the α-anomer (α-10) was found to be cytotoxic, whereas theβ-anomer (β-10) was inactive. 相似文献
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P. Herdewijn R. Charubala R. Pauwels E. De Clercq W. Pfleiderer 《Nucleosides, nucleotides & nucleic acids》2013,32(1-2):443-444
Abstract One of the most important mediators in the mode of action of interferon is the (2′-5′)(A)n synthetase-RNase L pathway. The 2′-5′oligoadenylates (2–5A), synthesized from ATP, activate a pre-existing endonuclease that cleaves single-stranded RNA. The biological activity of 2–5A is rapidly lost due to cleavage of the 2′-5′ internucleotide bond by a specific 2′-5′-phosphodiesterase starting at the 3′end. This rapid cleavage and the poor uptake of 2–5A in intact cells limit the use of 2–5A as an antiviral or antineoplastic agent. Although several modified 2–5A analogues have been synthesized in order to improve the enzymatic stability, only few have proven to be resistant to degradation and still able to activate the 2–5A dependent endonuclease. 1-4 On the other hand, relative drastic methodology such as calcium coprecipitation, microinjection and liposome encapsulation5 has been used to introduce 2–5A into intact cells. Here, we present the synthesis and biological activity of oligoadenylates in which one or more adenosine residues were replaced by 9-(3-azido-3-deoxy-6-D-xylofuranosyl)adenine or 9-(3-amino-3-deoxy-D-xylofuranosyl)adenine. The oligonucleotides were synthesized by the phosphotriester method with triisopropylbenzenesulfonyl-chloride in the presence of N-methylimidazole as the condensing agent. The p-nitrophenylethyl group was used as the protecting group for the 2′-hydroxylfunction .(carbonate), the internucleotide linkage (phosphate ester) and the exocyclic amino groups of the heterocyclic base (carbamate). Bis(p-nitrophenylethy1)phosphoromonochloridate was used to phosphorylate the 5′-hy-droxyl group. All these blocking groups were removed with DBU in pyridine. 相似文献
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Abdalla Elsayed A. Hassan Satoshi Shuto Akira Matsuda 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):197-211
Abstract Reaction of 2′-deoxy-2′-methylidene-5′-O-trityluridine (1) with diethylamino-sulfur trifluoride (DAST) in CH2Cl2 resulted in the formation of a mixture of (3′R)-2′,3′-dideoxy-3′-fluoro-2′-methylidene derivative 3 and 2′,3′-didehydro-2′,3′-dideoxy-2′-fluoromethyl derivative 4 (3:4 = 1:1.5) in 65% yield. A similar treatment of 1-(2-deoxy-2-methylidene-5-O-trityl-β-D-threo-pentofuranosyl)uracil (19) with DAST in CH2Cl2 afforded (3′S)-2′,3′-dideoxy-3′-fluoro-2′-methylidene derivatives 20 and 4 in 38% and 17% yields respectively. Transformation of the uracil nucleosides 4, 12, and 20 into cytosines followed by deprotection furnished the corresponding cytidine derivatives 29, 18, and 25, respectively. The corresponding thymidine congener 27 was also synthesized in a similar manner. All of the newly synthesized nucleosides were evaluated for their inhibitory activities against HIV and for their antiproliferative activities against L1210 and KB cells. 相似文献