66503-47-7Relevant academic research and scientific papers
Synthesis and anti-HIV activity of triazolo-fused 3′,5′-cyclic nucleoside analogues derived from an intramolecular Huisgen 1,3-dipolar cycloaddition
Sun, Jingbo,Liu, Xinyu,Li, Hongming,Duan, Ronghui,Wu, Jinchang
experimental part, p. 772 - 779 (2012/06/16)
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
Solid-Phase Synthesis of Dipeptide-Conjugated Nucleosides and Their Interaction with RNA
Dong, Guimin,Zhang, Liangren,Zhang, Lihe
, p. 3516 - 3524 (2007/10/03)
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.
Synthesis and biological activity of 3'-azido- and 3'-amino substituted nucleoside analogs
Colla,Herdewijn,De Clercq,et al.
, p. 295 - 301 (2007/10/02)
The product distribution obtained in the reaction of 1-(5-0-trityl-0-mesyl-2-deoxy-β-D-erythro-pentofuranosyl)-2,4-(1H, 3H)-pyrimidinedione with lithium azide in N, N'-dimethylformamide at 100°C depends on the nature of the substituent in 5. The results may be explained by a difference in the acidity of the pyrimidinedione. The reaction of the more acidic nucleosides (X = I, F) appears to proceed preferentially through the 2,3'-anhydro intermediate, whereas for the less acidic products (X = H, CH3) direct nucleophilic displacement by the azide ion predominates. The different 3'-azidfo derivatives were reduced to 3'-amino compounds. All 3'-azido- and 3'-aminopyrimidine nucleosides were tested against herpes simplex virus, vaccinia and vesicular stomatitis virus and on murine L1210 cell growth. None of the substances exhibited significant activity.
One-Step Synthesis of 5'-Azido-nucleosides
Yamamoto, Isamu,Sekine, Mitsuo,Hata, Tsujiaki
, p. 306 - 310 (2007/10/02)
Regioselective azidation of unprotected or appropriately protected nucleosides was conducted by means of the reagent triphenylphosphine-carbon tetrabromide-lithium azide.By use of this reagent, 5'-azido-5'-deoxynucleosides were prepared conveniently in one step from nucleosides in high yields.Secondary hydroxy-groups of appropriately 5'-protected nucleosides were also converted by the reagent to azido-functions with complete inversion.
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
Matsuda, Akira,Watanabe, Kyoichi A.,Fox, Jack J.
, p. 3274 - 3278 (2007/10/02)
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.
