2-Fluoroadenosine

Base Information

• Chemical Name: 2-Fluoroadenosine
• CAS No.: 146-78-1
• Molecular Formula: C10H12FN5O4
• Molecular Weight: 285.235
• Hs Code.: 29349990
• European Community (EC) Number: 633-923-8
• UNII: 0S67290CRJ
• DSSTox Substance ID: DTXSID70163252
• Nikkaji Number: J73.405E
• Wikidata: Q27095228
• Pharos Ligand ID: B6J1S2X7G7PH
• Metabolomics Workbench ID: 56347
• ChEMBL ID: CHEMBL290077
• Mol file: 146-78-1.mol

Synonyms:2-fluoroadenosine

Chemical Property of 2-Fluoroadenosine

Chemical Property:

• Appearance/Colour: white powder
• Melting Point: 240 °C
• Refractive Index: -72 ° (C=0.1, EtOH)
• Boiling Point: 747.303 °C at 760 mmHg
• PKA: 13.05±0.70(Predicted)
• Flash Point: 405.755 °C
• PSA: 139.54000
• Density: 2.176 g/cm³
• LogP: -1.25970
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly, Heated, Sonicated)
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 285.08733204
• Heavy Atom Count: 20
• Complexity: 367

Purity/Quality:

99% ^*data from raw suppliers

2-Fluoroadenosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)CO)O)O)F)N
• Isomeric SMILES: C1=NC2=C(N=C(N=C2N1[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O)F)N
• Description: 2-Fluoroadenosine (F-Ado) was developed at Southern Research Institute in 1957 as a potential anticancer drug. 2-Fluoroadenosine is not deaminated by adenosine deaminase but metabolized to triphosphate as shown in vitro. The drug was also shown to be a potent inhibitor of lymphocyte-mediated cytolysis.
• Uses: 2-Fluoroadenosine is a fluorinated analog of Adenoside nucleotide. It is used as an intermediate for the drug fludarabine. Fludarabine is a purine analogue and antineoplastic agent. It is a chemotherapy medication used in the treatment of leukemia and lymphoma.

Technology Process of 2-Fluoroadenosine

There total 36 articles about 2-Fluoroadenosine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

2-fluoro-9-(2,3,5-tri-o-benzyl-beta-D-arabinofuranosyl)adenine (24649-69-2) → Fludarabine (146-78-1,19768-92-4,21679-14-1,21679-15-2)

Guidance literature:

2-fluoro-9-(2,3,5-tri-o-benzyl-beta-D-arabinofuranosyl)adenine; With palladium 10% on activated carbon; ammonium formate; In methanol; water; at 25 - 75 ℃; Inert atmosphere;

In water; at 90 - 95 ℃;

DOI:10.1021/op3000509

Reference yield: 93.0%

2-fluoro-9-(3,5-di-O-benzoyl-β-D-arabinofuranosyl)adenine → Fludarabine (146-78-1,19768-92-4,21679-14-1,21679-15-2)

Guidance literature:

With methanol; ammonia; at 0 - 40 ℃; for 6h; Autoclave;

DOI:10.1055/s-0039-1690732

Reference yield: 92.0%

araU (3083-77-0) + 2-fluoroadenosine (146-78-1) → Fludarabine (146-78-1,19768-92-4,21679-14-1,21679-15-2)

Guidance literature:

With uridine phosphorylase; disodium hydrogen arsenate heptahydrate; Escherichia coli purine nucleoside phosphorylase; In aq. phosphate buffer; at 52 ℃; pH=7; Enzymatic reaction;

DOI:10.1134/S1068162016040105

upstream raw materials:

adenosine-2-amine

2-fluoro-6-N,N-dibenzoyl-9-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine

2-nitro-pentabenzoyl adenosine

N⁶,N⁶,2',3',5'-pentabenzoyl-β-D-adenosine

Downstream raw materials:

2-fluoroadenine

O¹-Phosphono-α-D-arabinofuranose

α-D-ribofuranosyl-1-phosphate

2-fluoro-2'-deoxyadenosine

Refernces

• 1、 Nóbile, Matías,Médici, Rosario,Terreni, Marco,Lewkowicz, Elizabeth S.,Iribarren, Adolfo M.. "Use of Citrobacter koseri whole cells for the production of arabinonucleosides: A larger scale approach". . p. 2182 - 2188. Retrieved 2012.
• 2、 Konstantinova,Fateev,Miroshnikov. "The arsenolysis reaction in the biotechnological method of synthesis of modified purine β-D-arabinonucleosides". . p. 372 - 380. Retrieved 2016.
• 3、 Bai, Jiang,Ding, Haixin,Liu, Jiang,Ouyang, Wenliang,Shen, Chunyang,Xiao, Qiang. "Practical Synthesis of Fludarabine and Nelarabine". . p. 417 - 423. Retrieved 2020.
• 4、 Taran,Verevkina,Feofanov,Miroshnikov. "Enzymatic transglycosylation of natural and modified nucleosides by immobilized thermostable nucleoside phosphorylases from Geobacillus stearothermophilus". . p. 739 - 745. Retrieved 2009.
• 5、 Kaspar, Felix,Giessmann, Robert T.,Neubauer, Peter,Wagner, Anke,Gimpel, Matthias. "Thermodynamic Reaction Control of Nucleoside Phosphorolysis". supporting information. p. 867 - 876. Retrieved 2020/01/24.