535087
2-Fluoroadenine
96%
Synonym(s):
2-Fluoro-7(9)H-purin-6-ylamine
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About This Item
Empirical Formula (Hill Notation):
C5H4FN5
CAS Number:
Molecular Weight:
153.12
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Recommended Products
Assay
96%
mp
>350 °C (lit.)
functional group
fluoro
SMILES string
Nc1[nH]c(F)nc2ncnc12
InChI
1S/C5H4FN5/c6-5-10-3(7)2-4(11-5)9-1-8-2/h1H,(H3,7,8,9,10,11)
InChI key
WKMPTBDYDNUJLF-UHFFFAOYSA-N
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Target Organs
Respiratory system
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Yukio Kitade et al.
Nucleic acids research. Supplement (2001), (3)(3), 5-6 (2003-09-27)
Carbocyclic and acyclic nucleosides possessing 2-fluoroadenine, such as 2-fluoronoraristeromycin (6) and 2-fluoro-9-[(2S,3R)-2,3,4-trihydroxy-butyl-1-yl]adenine (8), were synthesized and their inhibitory activities against human and Plasmodium falciparum recombinant SAH hydrolase were investigated.
P Huang et al.
Biochemical pharmacology, 36(18), 2945-2950 (1987-09-15)
2-Fluoroadenine (F-Ade) is a metabolite of 9-beta-D-arabinofuranosyl-2-fluoroadenine (F-ara-A) that may be involved in the development of toxic side effects from this anticancer drug. The liberation of F-Ade from F-ara-A has been examined in different biological systems. Extracts of Escherichia coli
D Voeks et al.
Gene therapy, 9(12), 759-768 (2002-06-01)
A gene-directed enzyme pro-drug therapy (GDEPT) based on purine nucleoside phosphorylase (PNP), that converts the prodrug, fludarabine to 2-fluoroadenine, has been described, but studies are limited compared with other GDEPTs. We investigated the in vitro and in vivo efficacies of
V I Avramis et al.
Biochemical and biophysical research communications, 113(1), 35-43 (1983-05-31)
Murine P388 cells incubated in vitro with the anticancer drug arabinosyl 2-fluoroadenine accumulate its 5'-triphosphate, F-araATP, as the major phosphorylated metabolite. A new chromatographically separate metabolite that accumulated to levels 10% of that of F-araATP was identified as 2-fluoro-ATP, by
Song Ye et al.
Nucleosides, nucleotides & nucleic acids, 22(10), 1899-1905 (2003-11-12)
A convenient synthesis of 2'-deoxy-2-fluoroadenosine from commercially available 2-fluoroadenine is described. The coupling reaction of silylated 2-fluoroadenine with phenyl 3,5-bis[O-(t-butyldimethylsilyl)]-2-deoxy-1-thio-D-erythro-pentofuranoside gave the corresponding 2-fluoro-2'-deoxyadenosine derivative (alpha/beta = 1:1) in good yield. The alpha- and beta-anomers were separated by chromatography, and
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