2'-Deoxy-2'-fluoroguanosine

한글명:2'-Deoxy-2'-fluoroguanosine

카스 번호78842-13-4

상품명:2'-Deoxy-2'-fluoroguanosine

CBNumberCB51231453

분자식C10H12FN5O4

포뮬러 무게285.23

MOL 파일78842-13-4.mol

화학적 성질

녹는점	262-264 °C(Solv: water (7732-18-5))
밀도	2.17±0.1 g/cm3(Predicted)
저장 조건	2-8°C(protect from light)
용해도	DMSO : 50 mg/mL (175.30 mM)
산도 계수 (pKa)	9?+-.0.20(Predicted)
물리적 상태	가루
색상	흰색에서 황백색까지
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

위험 및 안전 성명

HS 번호

2934999090

그림문자(GHS)

2'-Deoxy-2'-fluoroguanosine 화학적 특성, 용도, 생산

용도
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.
정의
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.
참고 문헌
[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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