共查询到20条相似文献,搜索用时 15 毫秒
1.
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
2.
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
3.
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
4.
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
5.
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
6.
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
7.
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
8.
《Nucleosides, nucleotides & nucleic acids》2013,32(5-8):891-894
Abstract The synthesis and anti-HBV and anti-HIV activity of a number of 2′,3′-dideoxy-2′-fluoro-3′-C-hydroxymethyl-β-D-arabinofuranosyl pyrimidine nucleosides are reported. 相似文献
9.
L. De Napoli A. Messere D. Montesarchio G. Piccialli C. Santacroce 《Nucleosides, nucleotides & nucleic acids》2013,32(8):1719-1728
Abstract Reaction of 5′-0-(4,4′-dimethoxytriphenylmethyl)-3′-deoxythy-midine with triphenylphosphine/carbon tetrachloride, followed by deprotection of the 5′-hydroxyl group, afforded the 4-chloro derivative 3 from which some 4-substituted pyrimidin-2(1H)one-2′, 3′-dideoxyribosides were obtained by nucleo-philic substitution under very mild conditions. 相似文献
10.
M. Camplo N. Mourier J-C Chermann J-L Kraus 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):879-880
Abstract The syntheses and biological evaluation of polyaminated 2′,3′-dideoxy-3′-thiacytidine have been performed. A new lead was found to increase the in vitro antiviral potency (syncitia formation on MT-4 cell line) of two order magnitude greater than the parent nucleoside drug. Moreover, the in vitro activity on HIV macrophages was found to be more than 3 log greater than the activity of the parent drug 1. 相似文献
11.
Vincent Roy Aleksandr Obikhod Hong-Wang Zhang Steven J. Coats Brian D. Herman Nicolas Sluis-Cremer 《Nucleosides, nucleotides & nucleic acids》2013,32(4):264-270
A series of hitherto unknown 3′-α-[1,2,3]-substituted triazolo-2′,3′-dideoxypyrimidine nucleoside analogues of the anti-HIV 3′-azido-3′-deoxythymidine (AZT) were synthesized through catalyzed alkyne-azide 1,3-dipolar cycloaddition (Huisgen reaction). Those 3′-[1,2,3]-triazolo analogues bearing an azido alkyl chain were evaluated for their anti-HIV activity against HIV-1 in primary human lymphocytes as well as for their cytotoxicity in different cells. None of them inhibit HIV replication (EC50 > 20 μM); two of them were converted to their triphosphate form to evaluate their HIV-RT inhibition. 相似文献
12.
13.
Abstract Various 2′, 3′ -dideoxy and carbocyclic pyrimidine nucleosides, and their corresponding 3-(3-oxoprop-1-enyl) derivatives, have been synthesized and evaluated against murine L1210 and P388 leukemias and Sarcoma 180 and human CCRF-CEM lymphoblastic leukemia. Among the compounds tested, 3-(3-oxoprop-1-enyl)-3′ -fluoro-3′ -deoxythymidine (17), 3-(3-oxoprop-1-enyl)-3′ -azido-3′ -deoxythymidine (15) and 3-(3-oxoprop-1-eny!)-(+)-1-[(lα, 3β, 4α)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]-5-methyl-2,4 (lH,3H)pyrimidinedione (6) were found to be the most active with ED50, values of 0.5,0.2,0.1, and 0.3 μM; 1.2, 0.5,1.0 and 1.0 μM; and 0.8,0.7,1.5, and 3.0μM, respectively. Our preliminary findings indicate that the 3-(3-oxoprop-1-enyl) derivative of carbocyclic thymidine is approximately 7 times more active than the 3-(3-oxoprop-1-enyl) derivative of carbocyclic thymine riboside against L1210 leukemia cells in vitro, with ED50 values of 0.8 μM and 5.5 μM, respectively. These findings suggest that the cytotoxicity of these compounds not only is dependent upon the 3-(3-oxoprop-1-enyl)-substituted group, but also may vary with the sugar moiety. 相似文献
14.
15.
Magnus Björsne Björn Classon Inger Kers Bertil Samuelsson Ingemar Kvarnström 《Nucleosides, nucleotides & nucleic acids》2013,32(3-5):283-286
Abstract Some 2′,3′-dideoxy-3′, 4′-dihydroxymethyl nucleoside analogues have been synthesised starting from diacetone-D-glucose. The 3-C-hydroxymethyl group was introduced by selective hydroboration-oxidation of the 3-C-methylene derivative. The 4-C-hydroxymethyl group was obtained by an aldol condensation followed by in situ cross Canizzaro reduction. Glycosylation using silylated pyrimidine bases furnished the 2′,3′-dideoxy-3′,4′-dihydroxymethyl nucleoside analogues. 相似文献
16.
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
17.
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
18.
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
19.
Åsa Lundquist Ingemar Kvarnström Stefan C. T. Svensson Björn Classon Bertil Samuelsson 《Nucleosides, nucleotides & nucleic acids》2013,32(7):1493-1502
Abstract The synthesis of 3′,4′-bishydroxymethyl-2′,3′,4′-trideoxy pentopyranosyl derivatives of thymine, uracil, cytosine, and adenine is described. trans-(3S,4S)-Bis(methoxycarbonyl)cyclopentanone (3) was converted to 1-O-acetyl-3,4-C-bis[(tert-butyldiphenylsiloxy)methyl]-2,3,4-trideoxy-α,β-L-threo-pentopyranose (6), which was subsequently condensed with the silylated purine and pyrimidine bases. 相似文献
20.
L. A. Agrofoglio F. Girard F. Fleury S. Léonce 《Nucleosides, nucleotides & nucleic acids》2013,32(4-5):599-600
Abstract The preparation of 5′-thioalkyl, sulfoxide and sulfone pyrimidine nucleosides is [4–11] is described. The key steps of this synthesis are the nucleophilic displacements of a chlorine by a thioalkyl sodium salt or the direct introduction of the thioalkyl group under Mitsunobu conditions. 相似文献