- Synthesis and anti-HIV activity of triazolo-fused 3′,5′-cyclic nucleoside analogues derived from an intramolecular Huisgen 1,3-dipolar cycloaddition
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Triazolo-fused 3′,5′-cyclic nucleoside analogues were synthesized by an intramolecular 1,3-dipolar cycloaddition of nucleoside-derived azido-alkynes in a regio- and stereospecific manner. The thymine nucleoside base in these target compounds was transform
- Sun, Jingbo,Liu, Xinyu,Li, Hongming,Duan, Ronghui,Wu, Jinchang
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p. 772 - 779
(2012/06/16)
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- Solid-Phase Synthesis of Dipeptide-Conjugated Nucleosides and Their Interaction with RNA
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Dipeptide-conjugated nucleosides were efficiently synthesized from the intermediates of 3′-amino-3′-deoxy-nucleosides by using the solid-phase synthetic strategy with HOBt/HBTU (1-hydroxy-1H-benzotriazole/2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluoroborate) as the coupling reagents (Schemes 1-3). CD Spectra and thermal melting studies showed that the synthesized hydrophobic dipeptide-thymidine and -uridine derivatives 8a-8d, 13a-d, and 18 had a mild affinity with the polyA · polyU duplex and could induce the change of RNA conformation. The results also implied that the interaction of conjugates with RNA might be related to the sugar pucker conformation of the nucleoside.
- Dong, Guimin,Zhang, Liangren,Zhang, Lihe
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p. 3516 - 3524
(2007/10/03)
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- A novel synthesis of AZT
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A novel synthesis of AZT has been achieved from two commercial available products acetaldehyde and D-mannitol. The originality of the synthesis consists of using the powerful monovinylogation reagent, the 2-lithio-1-trimethylsiloxyethylene, and to introduce the thymine moiety and to build the furanose ring in the same and last step.
- Gauthier, Christine,Ramondenc, Yvan,Plé, Gérard
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p. 7513 - 7517
(2007/10/03)
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- Selective deformylation of an α,β-unsaturated sugar aldehyde in a very short synthesis of 3'-azido-3'-deoxythimidine (AZT) and its stereoisomers
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(2E,4S)-5-Acetoxy-4-formyloxy-2-pentenal (2) prepared in one step from tri-O-acetyl-d-glucal was selectively deformylated to give the α,β-unsaturated aldehyde 3 with an unprotected hydroxy group at C-4. Michael-type addition reaction of hydrazoic acid to 3 followed by acylation at C-1 gave a 1:1 mixture of the erythro- and threo-isomers of 5-O-acetyl-3-azido-1-O-(4-biphenylcarbonyl)-2,3-dideoxypentofuranoses 4 and 5. They were used as substrates for nucleoside coupling with silylated thymine to give all four D-isomers of 3'-azido-3'-deoxythymidine 6-9.
- Wengel,Pedersen
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p. 451 - 454
(2007/10/02)
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- 3'-Substituted 2',3'-Dideoxynucleoside Analogues as Potential Anti-HIV (HTLV-III/LAV) Agents
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A series of 2',3'-unsaturated and 3'-substituted 2',3'-dideoxynucleoside analogues of purines and pyrimidines have been synthesized and evaluated for their inhibitory activity against human immunodeficiency virus (HIV).The 2',3'-unsaturated analogues of 2',3'-dideoxycytidine (ddeCyd) and 2',3'-dideoxythymidine (ddeThd), 3'-azido-2',3'-dideoxythymidine (AzddThd), 3'-fluoro-2',3'-dideoxythymidine, 2',3'-dideoxycytidine (ddCyd), and 2',3'-dideoxyadenosine (ddAdo) emerged as the most potent inhibitors of HIV-induced cytopathogenicity in the human T lymphocyte cell lines ATH8 and MT4.In ATH8 cells ddCyd, ddeCyd, and ddAdo had the highest therapeutic index whereas in MT4 cells AzddThd, ddThd, ddCyd, and ddAdo were the most selective.Derivatives from ddThd in which the substituent group was linked to the 3'-carbon atom via a thio, sulfonyl, or oxygen bridge were far less inhibitory to HIV than was AzddThd.
- Herdewijn, Piet,Balzarini, Jan,Clerq, Erik De,Pauwels, Rudi,Baba, Masanori,et al.
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p. 1270 - 1278
(2007/10/02)
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- Nucleosides. 115. Reaction of 3'-O-Mesylthymidine. Formation of 1-(3-Azido-2,3-dideoxy-β-D-threo-pentofuranosyl)thymine and Its Conversion into 6,3'-Imino-1-(2,3-dideoxy-β-D-threo-pentofuranosyl)thymine
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Treatment of 5'-O-trityl-3'-O-mesylthymidine (3) with NaN3 in DMF at reflux gave 5'-O-trityl-3'-azido-3'-deoxythymidine (5) and 6,3'-imino-1-(5-O-trityl-3-deoxy-β-D-threo-pentofuranosyl)thymine (8).Compound 8 was formed from the 3'-azido-threo-pentofuranosylthymine derivative 6.A mechanism is proposed for the formation of 8 from 6.Also, the 6,5'-imino-bridged thymidine 18 was prepared.Conformational features of these imino-bridged nucleosides are discussed.
- Matsuda, Akira,Watanabe, Kyoichi A.,Fox, Jack J.
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p. 3274 - 3278
(2007/10/02)
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