| Identification | Back Directory | [Name]
3'-fluoro-3'-deoxyadenosine | [CAS]
75059-22-2 | [Synonyms]
3'-F-3'-rA
3'-fluoro-3'-deoxyadenosine
Adenosine, 3'-deoxy-3'-fluoro-
(2R,3S,4S,5R)-2-(6-Amino-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol | [Molecular Formula]
C10H12FN5O3 | [MDL Number]
MFCD20134043 | [MOL File]
75059-22-2.mol | [Molecular Weight]
269.23 |
| Chemical Properties | Back Directory | [Melting point ]
211-212 °C | [Boiling point ]
628.6±65.0 °C(Predicted) | [density ]
2.01±0.1 g/cm3(Predicted) | [pka]
12.45±0.70(Predicted) | [InChI]
InChI=1S/C10H12FN5O3/c11-5-4(1-17)19-10(7(5)18)16-3-15-6-8(12)13-2-14-9(6)16/h2-5,7,10,17-18H,1H2,(H2,12,13,14)/t4-,5-,7-,10-/m1/s1 | [InChIKey]
QCDAWXDDXYQEJJ-QYYRPYCUSA-N | [SMILES]
OC[C@H]1O[C@@H](N2C3C(=C(N=CN=3)N)N=C2)[C@H](O)[C@@H]1F |
| Hazard Information | Back Directory | [Uses]
3'-deoxy-3'-fluoroadenosine can be used as pharmaceutical intermediates for pharmaceutical experimental research. | [Biological Activity]
3'-Fluoro-3'-deoxyadenosine was active against a broad range of viruses, encompassing both DNA viruses [pox (vaccinia)], single-stranded (+) RNA viruses [picorna (polio, Coxsackie B), toga (sindbis, Semliki Forest)] and double-stranded RNA viruses (reo). Its antiviral activity spectrum, 3'-fluoro-3'-deoxyadenosine, clearly differed from those adenosine analogs known as inhibitors of S-adenosylhomocysteine hydrolase. 3'-Fluoro-3'-deoxyadenosine also proved effective in vivo in inhibiting tail lesion formation in mice inoculated intravenously with vaccinia virus[1]. | [References]
[1] A. Van Aerschot. “Synthesis and antiviral activity evaluation of 3′-fluoro-3′-deoxyribonucleosides: broad-spectrum antiviral activity of 3′-fluoro-3′-deoxyadenosine.” Antiviral research 12 3 (1989): Pages 133-150. |
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