| Identification | Back Directory | [Name]
2'-Deoxy-2'-fluoroguanosine | [CAS]
78842-13-4 | [Synonyms]
2'-FdG
2'-F-2'-dG
2'-deoxy-2'-fluoroguanosine
2'-Fluoro -2'-deoxyguanosine
Guanosine,2'-deoxy-2'-fluoro-
2'-Deoxy-2'-fluoroguanosine USP/EP/BP
2-amino-9-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one | [EINECS(EC#)]
1806241-263-5 | [Molecular Formula]
C10H12FN5O4 | [MDL Number]
MFCD00923832 | [MOL File]
78842-13-4.mol | [Molecular Weight]
285.23 |
| Chemical Properties | Back Directory | [Melting point ]
262-264 °C(Solv: water (7732-18-5)) | [density ]
2.17±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [solubility ]
DMSO : 50 mg/mL (175.30 mM) | [form ]
Powder | [pka]
9?+-.0.20(Predicted) | [color ]
White to Off-white | [InChI]
InChI=1S/C10H12FN5O4/c11-4-6(18)3(1-17)20-9(4)16-2-13-5-7(16)14-10(12)15-8(5)19/h2-4,6,9,17-18H,1H2,(H3,12,14,15,19)/t3-,4-,6-,9-/m1/s1 | [InChIKey]
UXUZARPLRQRNNX-DXTOWSMRSA-N | [SMILES]
OC[C@H]1O[C@@H](N2C3=C(C(NC(=N3)N)=O)N=C2)[C@H](F)[C@@H]1O |
| Hazard Information | Back Directory | [Uses]
2'-Deoxy-2'-fluoroguanosine(CAS:78842-13-4), can be used as powerful tool for structural manipulation of G-quadruplexes. It is also a influenza viral polymerase inhibitor like Ribavirin (R414475), used as a antiviral drug against avian (H5N1) influenza virus.
| [Definition]
2'-Deoxy-2'-fluoroguanosine is an analog of guanosine that inhibits the viral life cycle. It is a competitive inhibitor of the viral transcriptase enzyme, which prevents RNA synthesis and subsequent protein synthesis. 2'-Deoxy-2'-fluoroguanosine has been shown to inhibit the growth of wild-type viruses in cell culture and to be effective against resistant mutants in cell culture. This drug has also been shown to inhibit the replication of herpes simplex virus type 1 (HSV-1) and influenza virus type A/WSN/33 (H1N1) in cell culture, as well as inhibiting the production of rna from these viruses.
| [Synthesis]
The synthesis of 2'-deoxy-2'-fluoroguanosine was accomplished using tetraisopropyldisiloxanyl (TPDS) protected 9-beta-D-arabinofuranosylguanine as starting material, and conversion to the intermediate diisobutyryl-arabinofuranosylguanosine. Deprotection of the TPDS group, was followed by protection of the hydroxyl group with THP to give diisobutyryl di-THP protected arabinofuranosylguanine. Selective O-deacylation and triflation was followed by treatment of the crude product with fluoride, then deprotection of the THP groups. | [References]
[1] M. Ikehara, J. Imura. “Studies on Nucleosides and Nucleotides. LXXXVII. Purine Cyclonucleosides. XLII. Synthesis of 2’-Deoxy-2’-fluoroguanosine.” Chemical & pharmaceutical bulletin 22 1 (1981): 1034–1038.
[2] G V Zaitseva. “Chemical and enzymatic synthesis and antiviral properties of 2’-deoxy-2’-fluoroguanosine.” Nucleosides & nucleotides 18 4–5 (1999): 687–8.
[3] M Tisdale. “Inhibition of influenza virus transcription by 2’-deoxy-2’-fluoroguanosine.” Antimicrobial Agents and Chemotherapy 39 11 (1995): 2454–8. |
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