1748-04-5Relevant articles and documents
Inhibition of tyrosyl-DNA phosphodiesterase 1 by lipophilic pyrimidine nucleosides
Chernyshova, Irina A.,Drenichev, Mikhail S.,Dyrkheeva, Nadezhda S.,Ilina, Ekaterina S.,Ivanov, Georgy A.,Lavrik, Olga I.,Mikhailov, Sergey N.,Oslovsky, Vladimir E.,Zakharenko, Alexandra L.
, (2020)
Inhibition of DNA repair enzymes tyrosyl-DNA phosphodiesterase 1 and poly(ADP-ribose) polymerases 1 and 2 in the presence of pyrimidine nucleoside derivatives was studied here. New effective Tdp1 inhibitors were found in a series of nucleoside derivatives possessing 2′,3′,5′-tri-O-benzoyl-d-ribofuranose and 5-substituted uracil moieties and have half-maximal inhibitory concentrations (IC50) in the lower micromolar and submicromolar range. 2′,3′,5′-Tri-Obenzoyl- 5-iodouridinemanifested the strongest inhibitory effect on Tdp1 (IC50 = 0.6 μM). Adecrease in the number of benzoic acid residues led to a marked decline in the inhibitory activity, and pyrimidine nucleosides lacking lipophilic groups (uridine, 5-fluorouridine, 5-chlorouridine, 5-bromouridine, 5-iodouridine, and ribothymidine) did not cause noticeable inhibition of Tdp1 (IC50 > 50 μM). No PARP1/2 inhibitors were found among the studied compounds (residual activity in the presence of 1mMsubstances was 50-100%). Several O-benzoylated uridine and cytidine derivatives strengthened the action of topotecan on HeLa cervical cancer cells.
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Vorbrueggen,Bennua
, p. 1339 (1978)
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Tin(II) Chloride Catalyzed Synthesis of β-D-Ribonucleosides
Mukaiyama, Teruaki,Matsutani, Takafumi,Shimomura, Naoyuki
, p. 2089 - 2092 (1994)
Several β-D-ribonucleosides are stereoselectively synthesized in high yields from methyl 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl carbonate and trimethylsilylated nucleoside bases such as pertrimethylsilylated uracil and adenine under mild conditions by using a catalytic amount of tin(II) chloride, a weak Lewis acid.
NIS/TMSOTf-Promoted Glycosidation of Glycosyl ortho-Hexynylbenzoates for Versatile Synthesis of O-Glycosides and Nucleosides
Liu, Rongkun,Hua, Qingting,Lou, Qixin,Wang, Jiazhe,Li, Xiaona,Ma, Zhi,Yang, You
, p. 4763 - 4778 (2021/04/06)
Glycosidation plays a pivotal role in the synthesis of O-glycosides and nucleosides that mediate a diverse range of biological processes. However, efficient glycosidation approach for the synthesis of both O-glycosides and nucleosides remains challenging in terms of glycosidation yields, mild reaction conditions, readily available glycosyl donors, and cheap promoters. Here, we report a versatile N-iodosuccinimide/trimethylsilyl triflate (NIS/TMSOTf)-promoted glycosidation approach with glycosyl ortho-hexynylbenzoates as donors for the highly efficient synthesis of O-glycosides and nucleosides. The glycosidation approach highlights the merits of mild reaction conditions, cheap promoters, extremely wide substrate scope, and good to excellent yields. Notably, the glycosidation approach performs very well in the construction of a series of challenging O- and N-glycosidic linkages. The glycosidation approach is then applied to the efficient synthesis of oligosaccharides via the one-pot strategy and the stepwise strategy. On the basis of the isolation and characterization of the departure species derived from the leaving group, a plausible mechanism of NIS/TMSOTf-promoted glycosidation of glycosyl ortho-hexynylbenzoates is proposed.
3-methyl uridine and 4-methyl cytidine nucleoside compound, synthetic method and its pharmaceutical use
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Paragraph 0021; 0032, (2016/10/08)
The invention discloses a 3-methyluridine and 4-methylcytidine nucleosides compound and a synthesis method and pharmaceutical application thereof, belonging to the field of medicinal chemistry. The compound has a structural formula as shown in the specification. The compound has the effects of simultaneously modifying sugar rings and basic groups, increasing the activity of the compound and reducing the toxicity, provides a good application prospect for development of like medicines and can be applied to preparation of anti-HBV (Hepatitis B virus) medicines. The synthesis method is simple and feasible and provides conditions for mass synthesis of the compound.
