2'-Deoxy-2'-fluoroguanosine
![2'-Deoxy-2'-fluoroguanosine Structure](CAS/20180713/GIF/78842-13-4.gif)
- CAS No.
- 78842-13-4
- Chemical Name:
- 2'-Deoxy-2'-fluoroguanosine
- Synonyms
- 2'-F-G;2'-FdG;2'-F-2'-dG;2'-F-2'-dG;Guanosine Impurity 9;2'-F-2'-deoxyguanosine;2'-F-2'-deoxyguanosine;2'-Deoxy-2'-fuoroguanosine;2'-deoxy-2'-fluoroguanosine;2'-Fluoro-2'-deoxyguanosine
- CBNumber:
- CB51231453
- Molecular Formula:
- C10H12FN5O4
- Molecular Weight:
- 285.23
- MOL File:
- 78842-13-4.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/7/19 16:08:26
Melting point | 262-264 °C(Solv: water (7732-18-5)) |
---|---|
Density | 2.17±0.1 g/cm3(Predicted) |
storage temp. | 2-8°C(protect from light) |
solubility | DMSO : 50 mg/mL (175.30 mM) |
pka | 9?+-.0.20(Predicted) |
form | Powder |
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 |
SAFETY
Risk and Safety Statements
Symbol(GHS) | ![]() GHS07 |
---|---|
Signal word | Warning |
Hazard statements | H302-H315-H319-H335 |
Precautionary statements | P261-P280a-P304+P340-P305+P351+P338-P405-P501a |
HS Code | 2934999090 |
2'-Deoxy-2'-fluoroguanosine Chemical Properties,Uses,Production
Uses
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.
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.
2'-Deoxy-2'-fluoroguanosine Preparation Products And Raw materials
Raw materials
Preparation Products
Supplier | Tel | Country | ProdList | Advantage | Inquiry |
---|---|---|---|---|---|
A.J Chemicals | 91-9810153283 | New Delhi, India | 6124 | 58 | Inquiry |
CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
Yunbio Tech Co.,Ltd. | +86-010-60605551 +86-18046518538 | China | 321 | 58 | Inquiry |
Allbiosyn Biotechnology Co.,Ltd. | +8618666985712 | China | 286 | 58 | Inquiry |
Capot Chemical Co.,Ltd. | 571-85586718 +8613336195806 | China | 29798 | 60 | Inquiry |
Henan Tianfu Chemical Co.,Ltd. | +86-0371-55170693 +86-19937530512 | China | 21667 | 55 | Inquiry |
career henan chemical co | +86-0371-86658258 +8613203830695 | China | 29888 | 58 | Inquiry |
Shenzhen Nexconn Pharmatechs Ltd | +86-755-89396905 +86-15013857715 | China | 10311 | 58 | Inquiry |
BOC Sciences | +1-631-485-4226 | United States | 19553 | 58 | Inquiry |
Chongqing Chemdad Co., Ltd | +86-023-6139-8061 +86-86-13650506873 | China | 39916 | 58 | Inquiry |
Supplier | Advantage |
---|---|
A.J Chemicals | 58 |
CLEARSYNTH LABS LTD. | 58 |
Yunbio Tech Co.,Ltd. | 58 |
Allbiosyn Biotechnology Co.,Ltd. | 58 |
Capot Chemical Co.,Ltd. | 60 |
Henan Tianfu Chemical Co.,Ltd. | 55 |
career henan chemical co | 58 |
Shenzhen Nexconn Pharmatechs Ltd | 58 |
BOC Sciences | 58 |
Chongqing Chemdad Co., Ltd | 58 |
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