181785-84-2

Basic information

• Product Name: 4-amino-5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one
• Synonyms: 4-amino-5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one;4-Amino-1-[(2S,5R)-2,5-dihydro-5-(hydroxymethyl)-2-furanyl]-5-fluoro-2(1H)-pyrimidinone;ACH 126443;Elvucitabine;L-Fd 4C;.beta.-L-2',3'-Didehydro-2',3'-dideoxy-5-fluorocytidine;.beta.-L-Fd4c;Aids060327
• CAS NO: 181785-84-2
• Molecular Formula: C9H10FN3O3
• Molecular Weight: 227.19
• Product Categories: Chemical Amines;Amines;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Amines, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 181785-84-2.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 394.9°C at 760 mmHg
• Flash Point: 192.6°C
• Appearance: /
• Density: 1.66g/cm³
• Vapor Pressure: 7.15E-08mmHg at 25°C
• Refractive Index: 1.665
• PKA: 14.28±0.10(Predicted)
• CAS DataBase Reference: 4-amino-5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-amino-5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one(181785-84-2)
• EPA Substance Registry System: 4-amino-5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2-one(181785-84-2)

Safety Data

• Hazardous Substances Data: 181785-84-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 181785-84-2 differently. You can refer to the following data:
1. A novel antiviral agent
2. A novel antiviral agent.

InChI:InChI=1/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/t5-,7+/m1/s1

Upstream product

• 202119-57-1 methyl L-lyxofuranoside 
• 532-20-7 L-lyxofuranose 
• 1382683-49-9 2',3'-dideoxy-5-fluoro-5'-O-(tbutyldiphenylsilyl)-α-L-cytidine 
• 1382683-45-5 1-[5-O-(t-butyldiphenylsilyl)-α-L-lyxofuranosyl]-5-fluorocytosine 
• 1382683-43-3 1-(α-L-Lyxofuranosyl)-5-fluorocytosine 
• 1382683-41-1 1-(2,3,5-tri-O-acetyl-α-L-lyxofuranosyl)-5-fluorocytosine 
• 1382683-39-7 C₁₂H₁₈O₈ 
• 219989-63-6 C₂₃H₁₉FIN₃O₆ 
• 221156-13-4 β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-dideoxy-5-fluoro-2'-(phenylselenenyl)cytidine 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 869383-87-9 1,2-O-isopropylidene-3,5-di-O-p-methoxybenzoyl-α-D-xylofuranose 
• 869496-59-3 1,4-anhydro-3',5'-di-p-methoxybenzoyloxy-2-deoxy-D-threo-pent-1-enitol 
• 869383-89-1 4-methoxybenzoic acid 5-(4-amino-5-fluoro-2-oxo-2H-pyrimidin-1-yl)-2,5-dihydrofuran-2-ylmethyl ester 
• 221156-15-6 β-D-5'-O-(tert-butyldiphenylsilyl)-2',3'-didehydro-2',3'-dideoxy-5-fluorocytidine 

Relevant articles and documents

Total synthesis of α-elvucitabine

(Chemical Equation Presented) Total synthesis of α-elvucitabine was achieved in 26% overall yield by a concise nine-step procedure starting from L-lyxose, with trimethylsilyl trifluoromethaneoulfonate (TMSOTf)-mediated stereocontrolled α-N-glycosidation and olefination through Barton-McCombie deoxygenation being the key steps, and the stereochemistry of the product was determined by nuclear Overhauser effect spectroscopy. Copyright Taylor & Francis Group, LLC.

METHOD FOR SYNTHESIZING β-L-FLUORO-2′,3′DIDEHYDROCYTIDINE (β-L-FD4C)

The invention provided a method of synthesizing β -L-5-fluoro-2′,3′-dideoxy-2′,3′-didehydrocytidine (β -L-FD4C). The method allows for large-scale production of β -L-FD4C in an efficient, cost-efficient, and environmentally sound manner.

Synthesis and biological evaluation of 2',3'-didehydro-2',3'-dideoxy-5- fluorocytidine (D4FC) analogues: Discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase

The discovery of a novel cytosine nucleoside, β-D-2',3'-didehydro- 2',3'-dideoxy-5-fluorocytidine (D-D4FC), as a potent antihuman immunodeficiency virus (HIV) agent led us to synthesize a series of analogues and derivatives of β-D-D4FC that could be more selective and also possess increased glycosidic bond stability. The synthesized D-D4FC analogues were evaluated for anti-HIV-1 activity, anticancer activity, and cytotoxicity in various cells. The biological data demonstrated that the 5-substitution of β-D-D4FC with bromine (6c) and iodine (6d) resulted in the loss of antiviral activity, and the α-D anomer (7a) of D-D4FC was also devoid of activity. The 5-fluorouracil analogues (6b and 7b) of D-D4FC were less potent and more cytotoxic than the parent compound, whereas the β-L-D4FU (11) showed both potent anti-HIV-1 activity and cytotoxicity. N4- and 5'-O-acyl derivatives (17, 15a-c) of β-D-D4FC exhibited comparable antiviral activity to β-D- D4FC. In contrast, the N4-isopropyl derivative (20) of β-D-D4FC was not active against HIV-1, even at 100 μM. The carbocyclic analogues (26a,b) of D4FC demonstrated weak activity against HIV-1 and no toxicity in various cells. The triphosphates (27a,b) of the carbocyclic nucleosides demonstrated potent inhibitory activity against recombinant HIV-1 reverse transcriptase at submicromolar concentrations. Of the compounds tested as potential anticancer agents, β-D-, α-D-, and β-L-D4FU (6b, 7b, 11) showed inhibitory activity against rat glioma and modest activity against human lung carcinoma, lymphoblastoid, and skin melanoma cells.