134379-77-4

Basic information

• Product Name: Dexelvucitabine
• Synonyms: Dexelvucitabine;2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine;4-AMINO-5-FLUORO-1-[(2R,5S)-5-(HYDROXYMETHYL)-2,5-DIHYDROFURAN-2-YL]PYRIMIDIN-2(1H)-ONE;Cytidine,2',3'-didehydro-2',3'-dideoxy-5-fluoro-;INCB 8721;RA 131423;Reverset;YZ 817
• CAS NO: 134379-77-4
• Molecular Formula: C9H10 F N3 O3
• Molecular Weight: 227.19
• Mol File: 134379-77-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 394.9°Cat760mmHg
• Flash Point: 192.6°C
• Appearance: /
• Density: 1.66g/cm³
• Vapor Pressure: 7.15E-08mmHg at 25°C
• Refractive Index: 1.665
• PKA: 14.28±0.10(Predicted)
• CAS DataBase Reference: Dexelvucitabine(CAS DataBase Reference)
• NIST Chemistry Reference: Dexelvucitabine(134379-77-4)
• EPA Substance Registry System: Dexelvucitabine(134379-77-4)

Safety Data

• Hazardous Substances Data: 134379-77-4(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 134379-77-4 differently. You can refer to the following data:
1. Treatment of HIV-1 and HIV-2 infection.
2. Dexelvucitabine is a nucleoside reverse transcriptase inhibitor (NRTI) which had the potential to inhibit HIV-1 replication. The drug was discontinued due to evidence that it causes damage to the pancreas.

Brand name

Reverset (Incyte).

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

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

Downstream Products

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

Relevant articles and documents

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

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.