134379-77-4

Usage

Uses

Used in HIV Treatment:
Dexelvucitabine is used as an antiviral agent for the treatment of HIV-1 and HIV-2 infection. It acts as a nucleoside reverse transcriptase inhibitor, which helps to inhibit the replication of the virus and reduce the viral load in the body.
However, due to its potential to cause damage to the pancreas, the drug was discontinued, and alternative treatments are now used for HIV management.

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+/m0/s1

Upstream product

• 219989-60-3 Benzoic acid (2S,5R)-5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydro-furan-2-ylmethyl ester 
• 221156-15-6 β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine 
• 869383-89-1 4-methoxybenzoic acid 5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydrofuran-2-ylmethyl ester 
• 869496-59-3 1,4-anhydro-3',5'-di-p-methoxybenzoyloxy-2-deoxy-D-threo-pent-1-enitol 
• 869383-87-9 1,2-O-isopropylidene-3,5-di-O-p-methoxybenzoyl-α-D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 221156-13-4 β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-5-fluoro-2'-(phenylselenenyl)cytidine 
• 6893-67-0 1,2-O-isopropylidene-3,5-di-O-benzoyl-α-D-xylofuranose 
• 532-20-7 D-xylofuranose 
• 191538-87-1 C₁₉H₁₆O₅ 
• 219989-63-6 C₂₃H₁₉FIN₃O₆ 
• 316-46-1 5-fluorouridine 

Downstream Products

• 98-00-0 (2-furyl)methyl alcohol 
• 2022-85-7 Flucytosine 

Relevant academic research and scientific papers

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 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.