181785-84-2

Usage

Uses

Different sources of media describe the Uses of 181785-84-2 differently. You can refer to the following data:
1. A novel antiviral agent
2. A novel antiviral agent.

InChI:InChI=1/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/t5-,7+/m1/s1

Upstream product

• 31615-99-3 3',5'-dibenzoyl-2'-deoxy-β-L-uridine 
• 612805-65-9 C₁₇H₁₆FN₃O₄ 
• 221156-15-6 β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 316-46-1 5-fluorouridine 
• 1382683-39-7 C₁₂H₁₈O₈ 
• 1382683-41-1 1-(2,3,5-tri-O-acetyl-α-L-lyxofuranosyl)-5-fluorocytosine 
• 1382683-43-3 1-(α-L-Lyxofuranosyl)-5-fluorocytosine 
• 1382683-45-5 1-[5-O-(t-butyldiphenylsilyl)-α-L-lyxofuranosyl]-5-fluorocytosine 
• 1382683-49-9 2',3'-dideoxy-5-fluoro-5'-O-(tbutyldiphenylsilyl)-α-L-cytidine 
• 532-20-7 L-lyxofuranose 
• 202119-57-1 methyl L-lyxofuranoside 
• 219989-63-6 C₂₃H₁₉FIN₃O₆ 
• 532-20-7 D-xylofuranose 

Relevant academic research and scientific papers

Total synthesis of α-elvucitabine

(Chemical Equation Presented) Total synthesis of α-elvucitabine was achieved in 26% overall yield by a concise nine-step procedure starting from L-lyxose, with trimethylsilyl trifluoromethaneoulfonate (TMSOTf)-mediated stereocontrolled α-N-glycosidation and olefination through Barton-McCombie deoxygenation being the key steps, and the stereochemistry of the product was determined by nuclear Overhauser effect spectroscopy. Copyright Taylor & Francis Group, LLC.

Synthesis of D-D4FC, a biologically active nucleoside via an unprecedented palladium mediated Ferrier rearrangement-type glycosidation with an aromatization prone xylo-furanoid glycal

D-D4FC (1) is an anti-HIV agent currently under phase II clinical trial (Pharmaset Inc). Its molecular architecture is suitable for a Ferrier rearrangement kind of operation on a furanoid glycal to fix the position of the double bond and the relative ster

METHOD FOR SYNTHESIZING β-L-FLUORO-2′,3′DIDEHYDROCYTIDINE (β-L-FD4C)

The invention provided a method of synthesizing β -L-5-fluoro-2′,3′-dideoxy-2′,3′-didehydrocytidine (β -L-FD4C). The method allows for large-scale production of β -L-FD4C in an efficient, cost-efficient, and environmentally sound manner.

Method for the synthesis of 2',3'-dideoxy-2',3'-didehydronucleosides

The present invention is an efficient synthetic route to 2′,3′-dideoxy-2′,3 ′-didehydro-nucleosides from available precursors with the option of introducing functionality as needed, such as, the 2′,3′-dideoxy and 2′- or 3′-deoxyribo-nucleoside analogs as well as additional derivatives obtained by subsequent functional group manipulations. Briefly, the present invention discloses a method for the preparation of β-D and β-L-2′,3′-dideoxy-2′,3′-didehydro-nucleosides starting from appropriately substituted ribonucleosides in two, optionally three steps: Step (1) a haloacylation, such as haloacetylation, and in particular, bromoacetylation; Step (2) a reductive elimination; and optionally, Step (3) a deprotection. The haloacylation of step (1) can form the 2′-acyl-3′-halonucleoside, the 3′-acyl-2′-halonucleoside, or a mixture thereof.

Synthesis and biological evaluation of 2',3'-didehydro-2',3'-dideoxy-5- fluorocytidine (D4FC) analogues: Discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase

The discovery of a novel cytosine nucleoside, β-D-2',3'-didehydro- 2',3'-dideoxy-5-fluorocytidine (D-D4FC), as a potent antihuman immunodeficiency virus (HIV) agent led us to synthesize a series of analogues and derivatives of β-D-D4FC that could be more selective and also possess increased glycosidic bond stability. The synthesized D-D4FC analogues were evaluated for anti-HIV-1 activity, anticancer activity, and cytotoxicity in various cells. The biological data demonstrated that the 5-substitution of β-D-D4FC with bromine (6c) and iodine (6d) resulted in the loss of antiviral activity, and the α-D anomer (7a) of D-D4FC was also devoid of activity. The 5-fluorouracil analogues (6b and 7b) of D-D4FC were less potent and more cytotoxic than the parent compound, whereas the β-L-D4FU (11) showed both potent anti-HIV-1 activity and cytotoxicity. N4- and 5'-O-acyl derivatives (17, 15a-c) of β-D-D4FC exhibited comparable antiviral activity to β-D- D4FC. In contrast, the N4-isopropyl derivative (20) of β-D-D4FC was not active against HIV-1, even at 100 μM. The carbocyclic analogues (26a,b) of D4FC demonstrated weak activity against HIV-1 and no toxicity in various cells. The triphosphates (27a,b) of the carbocyclic nucleosides demonstrated potent inhibitory activity against recombinant HIV-1 reverse transcriptase at submicromolar concentrations. Of the compounds tested as potential anticancer agents, β-D-, α-D-, and β-L-D4FU (6b, 7b, 11) showed inhibitory activity against rat glioma and modest activity against human lung carcinoma, lymphoblastoid, and skin melanoma cells.

Synthesis and comparative evaluation of two antiviral agents: β-L- Fd4C and β-D-Fd4C

The synthesis of β-D-Fd4C was achieved in a stereoselective fashion from D-xylose. The antiviral activity and cytotoxicity of β-D-Fd4C was compared with that of β-L-Fd4C and 3TC (Lamivudine). Of the three agents compared, β-L-Fd4C was found to be the most potent antiviral agent.

Stereoselective syntheses of β-L-FD4C and β-L-FddC

Stereocontrolled syntheses of two potent antiviral agents, β-L-FD4C and β-L-FddC, were accomplished both in 10-step sequences, with an overall yield of 27% and 25%, respectively. It is worthwhile to mention that the introduction of a phenylseleno moiety to the C-2α position of the lactone 4 can now be performed in a stereocontrolled fashion, providing the key intermediate 5α in 75% yield.