393711
2′,3′-Dideoxy-3′-fluorouridine
95%
Synonym(s):
3′-Fluoro-2′,3′-dideoxyuridine
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About This Item
Empirical Formula (Hill Notation):
C9H11FN2O4
CAS Number:
Molecular Weight:
230.19
UNSPSC Code:
12352100
NACRES:
NA.22
PubChem Substance ID:
EC Number:
415-360-8
Beilstein/REAXYS Number:
6064366
MDL number:
InChI key
BKIUEHLYJFLWPK-SHYZEUOFSA-N
InChI
1S/C9H11FN2O4/c10-5-3-8(16-6(5)4-13)12-2-1-7(14)11-9(12)15/h1-2,5-6,8,13H,3-4H2,(H,11,14,15)/t5-,6+,8+/m0/s1
SMILES string
OC[C@H]1O[C@H](C[C@@H]1F)N2C=CC(=O)NC2=O
assay
95%
optical activity
[α]20/D +10.5°, c = 0.5 in 1 M NaOH
mp
184-188 °C (lit.)
General description
2′,3′-Dideoxy-3′-fluorouridine (3′-fluoro-2′,3′-dideoxyuridine, FddUrd) is a fluorinated pyrimidine nucleoside analog of uridine. It has been studied extensively for its potential use as an antiviral agent against HIV.
Application
2′,3′-Dideoxy-3′-fluorouridine can be used as a starting material in the synthesis of:
- 3′-fluoro 2′,3′-dideoxynucleoside analogs for in vitro antiviral activity studies.
- 3′-fluoro deoxyuridine monophosphate analogs as potential anti parasites.
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E De Clercq
Chemioterapia : international journal of the Mediterranean Society of Chemotherapy, 7(6), 357-364 (1988-12-01)
Several steps in the replicative cycle of human immunodeficiency virus (HIV) could be envisaged as targets for anti-AIDS drugs. The anionic compound PMEA [9-(2-phosphonyl-methoxyethyl)adenine], the 2'3'-dideoxynucleoside analogues D4T (2',3-deidehydro-2',3'-dideoxythymidine), AzddUrd 3'-azido-2',3'-dideoxyuridine), FddUrd (3'-fluoro-2',3-dideoxyuridine), AzddDAPR (3'-azido-2',3'-dideoxy-2,6' diaminopurine riboside) and the sulfated
Deoxyuridine triphosphate nucleotidohydrolase as a potential antiparasitic drug target
Nguyen C, et al.
Journal of Medicinal Chemistry, 48(19), 5942-5954 (2005)
J Balzarini et al.
Molecular pharmacology, 35(5), 571-577 (1989-05-01)
The novel 5-chloro-, 5-bromo-, and 5-iodo-derivatives of 3'-fluoro-2',3'-dideoxyuridine (FddUrd), designated FddCIUrd, FddBrUrd, and FddIUrd, respectively, have been synthesized and evaluated for their antiretrovirus activity against human immunodeficiency virus (HIV) and murine Moloney sarcoma virus. All three 5-halogeno-FddUrd analogues inhibited HIV-1
Naveen C Srivastav et al.
Bioorganic & medicinal chemistry, 18(21), 7542-7547 (2010-09-28)
Chronic infections with hepatitis B virus (HBV) and hepatitis C virus (HCV) lead to serious liver diseases worldwide. Co-infection with HBV and HCV is very common and is associated with increased risk of liver pathogenesis, liver cancer, and liver failure.
Hiyama T
Organofluorine Compounds: Chemistry and Applications, 153-153 null
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