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147058-39-7 | 2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-[(2S,5R)-tetrahydro-5-(hydroxymethyl)-2-furanyl]-
CAS No: 147058-39-7 Catalog No: AG001EL0 MDL No:
Product Description
Catalog Number:
AG001EL0
Chemical Name:
2(1H)-Pyrimidinone, 4-amino-5-fluoro-1-[(2S,5R)-tetrahydro-5-(hydroxymethyl)-2-furanyl]-
CAS Number:
147058-39-7
Molecular Formula:
C9H12FN3O3
Molecular Weight:
229.2083
IUPAC Name:
4-amino-5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
InChI:
InChI=1S/C9H12FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h3,5,7,14H,1-2,4H2,(H2,11,12,15)/t5-,7+/m1/s1
InChI Key:
QBEIABZPRBJOFU-VDTYLAMSSA-N
SMILES:
Nc1nc(=O)n(cc1F)[C@@H]1CC[C@@H](O1)CO
Properties
Complexity:
369
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
2
Defined Bond Stereocenter Count:
0
Exact Mass:
229.086g/mol
Formal Charge:
0
Heavy Atom Count:
16
Hydrogen Bond Acceptor Count:
4
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
229.211g/mol
Monoisotopic Mass:
229.086g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
88.2A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.1
Literature
| Title | Journal |
|---|---|
| Antiviral L-nucleosides specific for hepatitis B virus infection. | Antimicrobial agents and chemotherapy 20010101 |
| Anti-HBV specific beta-L-2'-deoxynucleosides. | Nucleosides, nucleotides & nucleic acids 20010101 |
| Antiviral beta-L-nucleosides specific for hepatitis B virus infection. | Antiviral chemistry & chemotherapy 20010101 |
| Synthesis and biological evaluation of a series of 2'-fluorinated-2',3'-dideoxy-2',3'-didehydro-(L)-nucleosides. | Bioorganic & medicinal chemistry letters 19980707 |
| Metabolism of 2',3'-dideoxy-2',3'-didehydro-beta-L(-)-5-fluorocytidine and its activity in combination with clinically approved anti-human immunodeficiency virus beta-D(+) nucleoside analogs in vitro. | Antimicrobial agents and chemotherapy 19980701 |
| Identification of BMS-200475 as a potent and selective inhibitor of hepatitis B virus. | Antimicrobial agents and chemotherapy 19970701 |
| Design and synthesis of 2',3'-dideoxy-2',3'-didehydro-beta-L-cytidine (beta-L-d4C) and 2',3'-dideoxy 2',3'-didehydro-beta-L-5-fluorocytidine (beta-L-Fd4C), two exceptionally potent inhibitors of human hepatitis B virus (HBV) and potent inhibitors of human immunodeficiency virus (HIV) in vitro. | Journal of medicinal chemistry 19960426 |
| Favorable interaction of beta-L(-) nucleoside analogues with clinically approved anti-HIV nucleoside analogues for the treatment of human immunodeficiency virus. | Biochemical pharmacology 19960322 |
| Immunomodulatory and antiviral activities of 2',3'-dideoxy-beta-L-cytidine and 2',3'-dideoxy-beta-L-5-fluorocytidine. | Immunopharmacology and immunotoxicology 19950201 |
| Inhibition of human immunodeficiency virus type 1 reverse transcriptase by the 5'-triphosphate beta enantiomers of cytidine analogs. | Antimicrobial agents and chemotherapy 19941001 |
| Anti-human immunodeficiency virus activities of the beta-L enantiomer of 2',3'-dideoxycytidine and its 5-fluoro derivative in vitro. | Antimicrobial agents and chemotherapy 19940601 |
| Influence of stereochemistry on antiviral activities and resistance profiles of dideoxycytidine nucleosides. | Antimicrobial agents and chemotherapy 19940401 |
| Synthesis and biological evaluation of 2',3'-dideoxy-L-pyrimidine nucleosides as potential antiviral agents against human immunodeficiency virus (HIV) and hepatitis B virus (HBV). | Journal of medicinal chemistry 19940318 |
| Antiviral activity of 2',3'-dideoxy-beta-L-5-fluorocytidine (beta-L-FddC) and 2',3'-dideoxy-beta-L-cytidine (beta-L-ddC) against hepatitis B virus and human immunodeficiency virus type 1 in vitro. | Biochemical pharmacology 19940120 |
| Enantiomeric 2',3'-dideoxycytidine derivatives are potent human immunodeficiency virus inhibitors in cell cultures. | Comptes rendus de l'Academie des sciences. Serie III, Sciences de la vie 19940101 |
| Chemistry and anti-HIV properties of 2'-fluoro-2',3'-dideoxyarabinofuranosylpyrimidines. | Journal of medicinal chemistry 19920612 |
| Efficacies of antiherpesvirus nucleosides against two strains of herpes simplex virus type 1 in Vero and human embryo lung fibroblast cells. | Antimicrobial agents and chemotherapy 19880701 |
| Potential anti-AIDS drugs. 2',3'-Dideoxycytidine analogues. | Journal of medicinal chemistry 19870501 |
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