3'-fluoro-3'-deoxyadenosine Chemical Properties

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)

form 

Solid

color 

White to off-white

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

3'-fluoro-3'-deoxyadenosine Usage And Synthesis

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.