共查询到20条相似文献,搜索用时 8 毫秒
1.
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
2.
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
3.
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
4.
Lea Messini Kamal N. Tiwari John A. Montgomery John A. Secrist III 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):683-685
Abstract Coupling of 1-O-acetyl-2-deoxy-3,5-di-O-toluoyl-4-thio-d-ribofuranose with 6-chloropurine and 2,6-dichloropurine gave a mixture of 9α and 9β anomers as major products. These anomers were separated and converted to 2′-deoxy-4′-thio analogues of adenosine, inosine, guanosine, 2-amino-adenosine, and 2-chloro adenosine as well as their α-anomers. 相似文献
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6.
Panagiotis Ioannidis Björn Classon Bertil Samuelsson Ingemar Kvarnström 《Nucleosides, nucleotides & nucleic acids》2013,32(6):1205-1218
Abstract Nucleoside analogues analogues1-(2′,3′-dideoxy-2′-C-hydroxymethyl-β-D-erythro-pentofuranos-yl)thymine (1), 2′,3′-dideoxy-2′-C-hydroxymethylcytidine (2), 2′,3′-dideoxy-2′-C-hydroxymethyladenosine (3), 1-(2′-C-azidomethyl-2′,3′-dideoxy-β-D-erythro-pento-furanosyl)thymine (4), 2′-C-azidomethyl-2′,3′-dideoxycytidine (5), and 2′3′-dideoxy-2′-C-methylcytidine (6) have been synthesized from (S)-4-hydroxymethyl-y-butyro-lactone (7) 相似文献
7.
《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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9.
Marianne Janson Lars Svansson Stefan C. T. Svensson Ingemar Kvarnström Björn Classon Bertil Samuelsson 《Nucleosides, nucleotides & nucleic acids》2013,32(10):1739-1747
Abstract The synthesis of some enantiomerically pure carbocyclic 2′,3′-dideoxy-3′-C-hydroxymethyl derivatives of adenine, inosine and guanine is described. The Mitsunobu reaction was used in the coupling procedure giving exclusively N9-coupling. The nucleosides were tested for inhibition of HIV multiplication in vitro and were found to be inactive in the assay. 相似文献
10.
Panagiotis Ioannidis Björn Classon Bertil Samuelssony Ingemar Kvarnström 《Nucleosides, nucleotides & nucleic acids》2013,32(8):865-877
Abstract 1-(2,3-Dideoxy-3-C-hydroxmethyl-β-D-threo-pentofuranosyl) -,1- (2,3-didehydro-2,3-dideoxy-3-C-hydroxymethyl-β-D-glycero- pentofuranosyl) -and 1-(3-C-azidomethyl-2,3-dideoxy-3-C-hydroxymethyl-β-D-glycero- pentofuranosyl)uracil, thymine and cytosine were synthesized and evaluated for anti-HIV activity. The synthetic strategy was based on an allylic alcohol transposition of the corresponding 3′-C-methylene-nucleoside analogues. 相似文献
11.
Synthesis of 2′-Deoxy-2′ -Fluoro-D-Arabinopyranopyranosyl Nucleosides and Their 3′,4′-Seco analogues
P. Herdewijn A. Van Aerschot R. Busson P. Claes E. De Clercq 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1525-1549
Abstract 2′-Deoxy-2′-fluoro-D-arabinopyranosyl nucleosides were synthesized by condensation of 1,3,4-tri-O-benzoyl-2-deoxy-2-fluoro-D-arabinopyranose with the appropriate silylated bases in the presence of trimethylsilyl triflate. Scission of the 3′,4′-bond by periodate oxidation followed by sodium borohydride reduction resulted in the formation of the 3′,4′-seco analogues of the 2′-deoxy-2′-fluoro-D-arabinofuranosyl nucleosides. 相似文献
12.
Muhammad Azymah Claude Chavis Marc Lucas Jean-Louis Imbach 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1371-1381
Abstract 1′, 2′-Seco-nucleoside derivatives of adenine, cytosine, guanine and thymine with a D or L-threitol side-chain configuration have been synthesized from D or L dimethyl tartarate respectively. Biological evaluation of the four enantiomeric pairs of nucleosides revealed they were inactive against various viruses in cell cultures. 相似文献
13.
Lars Svansson Ingemar Kvarnström Björn Classon Bertil Samuelsson 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1353-1366
Abstract The synthesis of 3′-C-fluoromethyl and 3′-C-azidomethyl nucleosides is reported. The 3′-C-fluoromethyl furanoside 4 was synthesized via fluoride ion induced displacement of the corresponding trifluoromethanesulfonate. The 3′-C-hydroxymethyl furanoside 3 was converted to the corresponding 3′-C-azidomethyl furanoside 6 using triphenylphosphine-carbon tetrabromide-lithium azide. The 3′-C-fluoromethyl furanoside derivative 5 and the 3′-C-azidomethyl furanoside derivative 7 were subsequently condensed with silylated purine and pyrimidine bases. Deblocking and separation of the anomers by chromatography afforded the α- and β-nucleoside analogues. The nucleosides were tested for inhibition of HIV multiplication in vitro and were found to be inactive in the assay. 相似文献
14.
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
15.
Abstract The best approach for the synthesis of1-(3-azido-2,3-dideoxy-β-D-erythro-pento-furanosyl)lumazine (5) and its 6,7-dimethyl- (4) and 6,7-diphenyl derivatives (3) has been found in the interconversion of the corresponding 1-(2-deoxy- β-threo-pentofuranosyl)-lumazines. Monomethoxytritylation at the 5′-position (1 7, 3 4, 4 9) followed by mesylation at the 3′-OH group and subsequent nucleophilic displacement by lithium azide afforded 1 9, 2 9 and 4 7 which were deprotected by acid treatment to give 3–5 in good yields. The syntheses of 1-(2,3-dideoxy-β-D-glycero-pentofuranosyl)-6,7-diphenyllumazine (6) and its 6,7-dimethyl derivative (7) were achieved from 1-(2-deoxy-β-D-erythro-pentofuranosyl)-6,7-diphenyllumazine and the corresponding 6,7-dimethyllumazine (2 6) via their 5′-O-p-toluoyl- (2 0, 3 0), and 3′-deoxy-3′-iodo derivatives (2 4, 3 1) to form, after radical dehalogenation and final deprotection, 6 and 7. The newly synthesized lumazine nucleosides have been characterized by elemental analyses, UV-and NMR spectra. 相似文献
16.
Biserka Kasnar Dean S. Wise Louis S. Kucera John C. Drach Leroy B. Townsend 《Nucleosides, nucleotides & nucleic acids》2013,32(1-3):459-479
Abstract The synthesis of 4-methoxy-, 4-amino-3-chloro-, and 4-amino-1-(2,3-dideoxy-B-D-glycero-pentofuranosyl)pyridazin-6-one nucleosides, 6,19 and 20 is described. The synthesis of 3,4-dichloropyridazin-6-one (10) was accomplished in 44% overall yield using bromomaleic anhydride (17) as the starting material. The condensation of the silylated base of 10 with the halogenose 12 in the presence of trimethylsilyl triflate as a catalyst afforded a mixture of3,4-dichloro-1-(3,5-di-O-p-toluoyl-2-deoxy-B-D-erythro-pentofuranosyl)pyrridazin-6-one (13) in 67% and its α-anomer 14 in 12% yield, respectively. A series of 3′-sulfonate esters were prepared to explore the synthesis of 3-chloro-4-hydroxy-1-(3-azido-2,3-dideoxy-B-D-erythro-pentofuranosyl) pyridazin-6-one (32) via 6,3-anhydronucleoside analogues. Compounds 15, 19 and 20 were evaluated against human immunodeficiency virus, human cytomegalovirus, and herpes simplex virus type 1 but were inactive. 相似文献
17.
Abstract The syntheses of 2′,3′-didehydro-2′,3′-dideoxyisoinosine (d4isoI, 4) as well as 7-deaza-2′,3′-didehydro-2′,3′-dideoxyisoinosine (d4c7isoI, 5) are described. Compounds 4 and 5 show both strong fluorescence. Compound 4 is oxidized by xanthine oxidase to give the corresponding xanthine 2′,3′-dideoxy-2′,3′-didehydronucleosides. A preparative chemo-enzymatic synthesis of 2′-deoxyxanthosine (3) is described. 相似文献
18.
Frank Seela Uwe Bindig Hansjürgen Driller Wilhelm Herdering Klaus Kaiser Andreas Kehne 《Nucleosides, nucleotides & nucleic acids》2013,32(1-2):11-23
Abstract The diastereoselective synthesis of several pyrrolo[2,3-d]- and pyrazolo[3,4-d]pyrimidine 2′-deoxy-ribofuranosides employing l-chloro-2-deoxy-3,5-di-0-(p-tolu-oyl)-a-D-erythropentofuranose and the nucleobase anion, generated by liquid-liquid or solid-liquid phase-transfer catalysis, is described. Appropriately protected phosphoramidites of 8-aza-7-deaza-2′-deoxyadenosine and 2′-deoxytubercidin were prepared and employed in solid-phase synthesis of palindromic DNA-fragments. The replacement of dA residues by deoxytubercidin within the Eco RI recognition site d(GAATTC) of the dodecamer d(GTAGAATTCTAC) gave evidence for purine N-7 binding to the endodeoxyribonuclease. The interpretation of similar experiments carried out on d(CGCGAATTCGCG) was obscured because of hairpin formation. 相似文献
19.
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
20.
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