2'-Deoxy-2'-fluoroguanosine
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- CAS-Nr.
- 78842-13-4
- Englisch Name:
- 2'-Deoxy-2'-fluoroguanosine
- Synonyma:
- 2'-F-G;2'-FdG;2'-F-2'-dG;2'-F-2'-dG;2'-Fluoro-2'-dG;Guanosine Impurity 9;2'-F-2'-deoxyguanosine;2'-F-2'-deoxyguanosine;2'-Deoxy-2'-fuoroguanosine;2'-deoxy-2'-fluoroguanosine
- CBNumber:
- CB51231453
- Summenformel:
- C10H12FN5O4
- Molgewicht:
- 285.23
- MOL-Datei:
- 78842-13-4.mol
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2'-Deoxy-2'-fluoroguanosine Eigenschaften
- Schmelzpunkt:
- 262-264 °C(Solv: water (7732-18-5))
- Dichte
- 2.17±0.1 g/cm3(Predicted)
- storage temp.
- 2-8°C(protect from light)
- L?slichkeit
- DMSO : 50 mg/mL (175.30 mM)
- pka
- 9?+-.0.20(Predicted)
- Aggregatzustand
- Powder
- Farbe
- 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
Sicherheit
- Risiko- und Sicherheitserkl?rung
- Gefahreninformationscode (GHS)
| Bildanzeige (GHS) |
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| Alarmwort |
Warnung |
| Gefahrenhinweise |
| Code |
Gefahrenhinweise |
Gefahrenklasse |
Abteilung |
Alarmwort |
Symbol |
P-Code |
| H302 |
Gesundheitssch?dlich bei Verschlucken. |
Akute Toxizit?t oral |
Kategorie 4 |
Warnung |
![GHS hazard pictograms]() src="/GHS07.jpg" width="20" height="20" /> |
P264, P270, P301+P312, P330, P501 |
| H315 |
Verursacht Hautreizungen. |
Hautreizung |
Kategorie 2 |
Warnung |
![GHS hazard pictograms]() src="/GHS07.jpg" width="20" height="20" /> |
P264, P280, P302+P352, P321,P332+P313, P362 |
| H319 |
Verursacht schwere Augenreizung. |
Schwere Augenreizung |
Kategorie 2 |
Warnung |
![GHS hazard pictograms]() src="/GHS07.jpg" width="20" height="20" /> |
P264, P280, P305+P351+P338,P337+P313P |
| H335 |
Kann die Atemwege reizen. |
Spezifische Zielorgan-Toxizit?t (einmalige Exposition) |
Kategorie 3 (Atemwegsreizung) |
Warnung |
![GHS hazard pictograms]() src="/GHS07.jpg" width="20" height="20" /> |
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| Sicherheit |
| P261 |
Einatmen von Staub vermeiden. |
| P304+P340 |
BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen. |
| P305+P351+P338 |
BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach M?glichkeit entfernen. Weiter spülen. |
| P405 |
Unter Verschluss aufbewahren. |
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2'-Deoxy-2'-fluoroguanosine Chemische Eigenschaften,Einsatz,Produktion Methoden
Verwenden
2''-Deoxy-2''-fluoroguanosine, 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.
Synthese
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.
Einzelnachweise
[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.
2'-Deoxy-2'-fluoroguanosine Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
2'-Deoxy-2'-fluoroguanosine Anbieter Lieferant Produzent Hersteller Vertrieb H?ndler.
Global( 190)Lieferanten
78842-13-4()Verwandte Suche:
- 2'-deoxy-2'-fluoroguanosine
- 2'-FdG
- 2'-Fluoro -2'-deoxyguanosine
- 2'-F-2'-dG
- Guanosine,2'-deoxy-2'-fluoro-
- 2-amino-9-[(2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H-purin-6-one
- 2'-Deoxy-2'-fluoroguanosine USP/EP/BP
- 2'-F-G
- 2'-F-2'-deoxyguanosine
- nucleoside,strains,tract,Influenza Virus,Inhibitor,analog,fever,nasal,inhibit,virus,influenza,upper,2′Deoxy2′fluoroguanosine,2′ Deoxy 2′ fluoroguanosine,respiratory,inflammation
- 2-Amino-9-((2R,3R,4R,5R)-3-fluoro-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1,9-dihydro-6H-purin-6-one
- 2'-Fluoro-2'-Deoxyguanosine (FdG)
- 2'-Fluoro-2'-deoxyguanosine
- 2'-Deoxy-2'-fluoroguanosine
- 2'-Deoxy-2'-fuoroguanosine
- 2'-F-2'-deoxyguanosine
- 2'-F-2'-dG
- Guanosine Impurity 9
- 2'-Fluoro-2'-dG
- 78842-13-4
- 78842-23-4
- Nucleosides
- Modified（deoxy）nucleoside
- Nucleosides-2'-F Nucleosides
