4105-38-8Relevant articles and documents
Anomalous interaction of tri-acyl ester derivatives of uridine nucleoside with a l-α-dimyristoylphosphatidylcholine biomembrane model: a differential scanning calorimetry study
Berrío Escobar, Jhon Fernando,Márquez Fernández, Diana Margarita,Giordani, Cristiano,Castelli, Francesco,Sarpietro, Maria Grazia
, p. 329 - 337 (2019)
Objectives: Uridine was conjugated with fatty acids to improve the drug lipophilicity and the interaction with phospholipid bilayers. Methods: The esterification reaction using carbodiimides compounds as coupling agents and a nucleophilic catalyst allowed us to synthesize tri-acyl ester derivatives of uridine with fatty acids. Analysis of molecular interactions between these tri-acyl ester derivatives and l-α-dimyristoylphosphatidylcholine (DMPC) multilamellar vesicles (MLV) – as a mammalian cell membrane model – have been performed by differential scanning calorimetry (DSC). Key findings: The DSC thermograms suggest that nucleoside and uridine triacetate softly interact with phospholipidic multilamellar vesicles which are predominantly located between the polar phase, whereas the tri-acyl ester derivatives with fatty acids (myristic and stearic acids) present a strongly interaction with the DMPC bilayer due to the nucleoside and aliphatic chains parts which are oriented towards the polar and lipophilic phases of the phospholipidic bilayer, respectively. However, the effects caused by the tri-myristoyl uridine and tri-stearoyl uridine are different. Conclusions: We show how the structural changes of uridine modulate the calorimetric behaviour of DMPC shedding light on their affinity with the phospholipidic biomembrane model.
NMR studies show monomeric 5-fluorouridine forms base pairs of increased stability compared with uridine in non-aqueous solvents
Gmeiner,Anderson,Sahasrabudhe
, p. 2329 - 2344 (1994)
The binding constants and geometries for nucleoside base pairs involving 5-fluorouridine (FUr) and adenosine were determined by 1H, 13C, and 19F NMR to better understand how FUr may perturb RNA structure. 5FU:A base pairs are more stable than U:A base pairs.
Chemoenzymatic synthesis of Park's nucleotide: toward the development of high-throughput screening for MraY inhibitors
Kurosu, Michio,Mahapatra, Sebabrata,Narayanasamy, Prabagaran,Crick, Dean C.
, p. 799 - 803 (2007)
An efficient chemoenzymatic synthesis of UDP-N-acetylmuramyl-l-alanyl-γ-d-glutamyl-meso-diaminopimelyl-d-alanyl-d-alanine (Park's nucleotide) is reported. UDP-MurNAc is efficiently synthesized by a minimum number of protecting strategies. One-pot amino ac
Optimized synthesis of [3-15N]-labeled uridine phosphoramidites
Baral, Bharat,Kumar, Pawan,Anderson, Brooke A.,?stergaard, Michael E.,Sharma, Pawan K.,Hrdlicka, Patrick J.
, p. 5850 - 5852 (2009)
A short and high-yielding synthetic route to [3-15N]-labeled uridine phosphoramidite 1 (26% overall yield from uridine) has been developed. This will enable automated synthesis of isotopically labeled RNA strands and facilitate their use in str
Cyclic sulfates as synthetic equivalents of α-epoxynucleosides
Serra, Carme,Farras, Jaume,Vilarrasa, Jaume
, p. 9111 - 9113 (1999)
A stable sulfate derivative of N-nitrouridine has been obtained for the first time; it shows synthetic advantages in relation to its α-epoxide counterpart. A new iodide-mediated denitration reaction is reported.
Anti-hepatitis B virus compound as well as preparation method and application thereof
-
Paragraph 0025-0028, (2021/06/22)
The invention provides an anti-hepatitis B virus compound and a preparation method and application thereof, the compound is 4-thiouridine isobutyrate, the molecular formula is C13H18N2O6S, and the structural formula is shown in the specification. The compound provided by the invention can effectively inhibit the activity of hepatitis B virus, can be used as a substitute drug for lamivudine and telbivudine, solves the problem of drug resistance of lamivudine and the like in the aspect of resisting hepatitis B virus, is high in drug effect, low in toxicity and low in price, and provides a direction for development of drugs for treating hepatitis B. In addition, the invention discloses a preparation method of the compound 4-thiouridine isobutyrate, and the preparation method is mild in condition, easy to synthesize and suitable for industrial production.
Transglycosylation in the Modification and Isotope Labeling of Pyrimidine Nucleosides
Gong, Yong,Chen, Lu,Zhang, Wei,Salter, Rhys
supporting information, p. 5577 - 5581 (2020/07/24)
Transglycosylation of pyrimidine nucleosides is demonstrated in a one-pot synthesis of uridine derivatives under microwave irradiation. Inductive activation of 2′,3′,5′-tri-O-acetyl uridine with a 5-nitro group produces a more-reactive glycosyl donor. Under optimized Vorbrüggen conditions, the 5-nitrouridine facilitates a reversible nucleobase exchange with a series of 5-substituted uracils. The protocol is also exemplified in a gram-scale reaction under thermal heating. The strategy provides easy access to isotopically labeled uridine.
Stereoselective Synthesis of Highly Functionalized Arabinosyl Nucleosides through Application of an N-Nitro Protecting Group
Hilko, David H.,Bornaghi, Laurent F.,Poulsen, Sally-Ann
supporting information, p. 11944 - 11955 (2018/09/25)
2′-Deoxy-2′,5-disubstituted arabinosyl uridine derivatives bearing a halogen (Cl, Br or I) at C2′ and an ethynyl group at C5 have been synthesized in 6 steps from 2′,3′,5′-tri-O-acetyl-5-iodo-uridine in overall yields of 61% (compound 3, Cl), 47% (compound 4, Br), and 19% (compound 5, I). Stabilization of a 2′-O-triflyl leaving group intermediate to overcome spontaneous intramolecular 2,2′-anhydro uridine formation was pivotal to the synthesis. Specifically, to favor SN2 reaction with a halogen nucleophile over intramolecular cyclization, the nucleophilicity of O-2 oxygen was reduced by incorporation of an adjacent electron withdrawing nitro substituent at N-3. The introduction of the 3-N-nitro group proceeded rapidly (nitronium trifluoroacetate, 1 min) and in quantitative yield. A one-pot method to remove the 3-N-nitro group by reductive nitration (zinc metal in acetic acid, 5 min) and the silyl protecting groups of the alkyne and 3′,5′ hydroxyls (fluoride reagent, 16 h) was established as the final synthetic step. This application of the 3-N-nitro protecting group addresses the significant shortfalls of the conventional approach to synthesis of 2′ modified nucleosides, wherein condensation of a 2′ modified sugar fragment with a pyrimidine base provides poor stereocontrol of N-glycosylation, low yields and incompatibility with 2′ iodo sugars.
Concise synthesis and antibacterial evaluation of novel 3-(1,4-disubstituted-1,2,3-triazolyl)uridine nucleosides
Tachallait, Hamza,Bouyahya, Abdelhakim,Talha, Aicha,Bakri, Youssef,Dakka, Nadia,Demange, Luc,Benhida, Rachid,Bougrin, Khalid
, (2018/10/09)
We report herein a simple and efficient synthesis of a new series of antibacterial uridine nucleosides. The strategy involved a sequential silylation/N-glycosylation/N-propargylation procedure of uracil 1 for preparing the dipolarophile 5 in good yield. A series of novel uridine-[1,2,3]triazole nucleosides 6a–j were efficiently synthesized via the copper-catalyzed azide–alkyne cycloaddition (CuAAC) from dipolarophile 5 with different selected azides. The reactions were carried out under both conventional and ultrasonic irradiation conditions. In general, improvements were observed when reactions were carried out under sonication. Their antibacterial potential has been evaluated by means of a micro-dilution assay against either Gram-positive or Gram-negative bacteria. Compounds 6i and 6j have shown significant bactericidal activity against Staphylococcus aureus (MIC = 10 and 6 μM, respectively), and 6h against Escherichia coli (MIC = 8 μM). Moreover, antibacterial kinetic assays showed that 6i and 6j significantly reduced the S. aureus growth rate at the MIC concentration, after 6 h, compared to their deprotected analogs, 6k and 6l, respectively. Compound 6h also significantly reduced the growth of E. coli. These antibacterial effects may be related to the penetrating properties of these compounds, as revealed by the leakage of nucleic acids from the sensitive strains.
Effective synthesis of nucleosides utilizing O-acetyl-glycosyl chlorides as glycosyl donors in the absence of catalyst: Mechanism revision and application to silyl-hilbert-johnson reaction
Liang, Chengyuan,Ju, Weihui,Ding, Shunjun,Sun, Han,Mao, Gennian
, (2017/01/24)
An effective synthesis of nucleosides using glycosyl chlorides as glycosyl donors in the absence of Lewis acid has been developed. Glycosyl chlorides have been shown to be pivotal intermediates in the classical silyl-Hilbert-Johnson reaction. A possible mechanism that differs from the currently accepted mechanism advanced by Vorbrueggen has been proposed and verified by experiments. In practice, this catalyst-free method provides easy access to Capecitabine in high yield.
