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75059-22-2

75059-22-2 | (2R,3S,4S,5R)-2-(6-Amino-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol

CAS No: 75059-22-2 Catalog No: AG005ELP MDL No:MFCD20134043

Product Description

Catalog Number:
AG005ELP
Chemical Name:
(2R,3S,4S,5R)-2-(6-Amino-9H-purin-9-yl)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-3-ol
CAS Number:
75059-22-2
Molecular Formula:
C10H12FN5O3
Molecular Weight:
269.2324
MDL Number:
MFCD20134043
IUPAC Name:
(2R,3S,4S,5R)-2-(6-aminopurin-9-yl)-4-fluoro-5-(hydroxymethyl)oxolan-3-ol
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
InChI Key:
QCDAWXDDXYQEJJ-QYYRPYCUSA-N
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1F)O)n1cnc2c1ncnc2N

Properties

Complexity:
338  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
269.092g/mol
Formal Charge:
0
Heavy Atom Count:
19  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
3  
Isotope Atom Count:
0
Molecular Weight:
269.236g/mol
Monoisotopic Mass:
269.092g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
119A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.6  

Literature

Title Journal
S-Adenosylhomocysteine hydrolase of the protozoan parasite Trichomonas vaginalis: potent inhibitory activity of 9-(2-deoxy-2-fluoro-β,D-arabinofuranosyl)adenine. Bioorganic & medicinal chemistry letters 20120615
Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase. Journal of medicinal chemistry 20040422
Phosphoramidate protides of 2',3'-dideoxy-3'-fluoroadenosine and related nucleosides with potent activity against HIV and HBV. Nucleosides, nucleotides & nucleic acids 20031001
Selective inhibition of arthropod-borne and arenaviruses in vitro by 3'-fluoro-3'-deoxyadenosine. Antiviral research 19920601
Synthesis and antiviral and cytostatic properties of 3'-deoxy-3'-fluoro- and 2'-azido-3'-fluoro-2',3'-dideoxy-D-ribofuranosides of natural heterocyclic bases. Journal of medicinal chemistry 19910701
Synthesis and antiviral activity evaluation of 3'-fluoro-3'-deoxyribonucleosides: broad-spectrum antiviral activity of 3'-fluoro-3'-deoxyadenosine. Antiviral research 19891001

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