2-Fluoroadenosine

ChemicalBook > CAS DataBase List > 2-Fluoroadenosine

2-Fluoroadenosine

Product Name: 2-Fluoroadenosine
CAS No.: 146-78-1
Chemical Name: 2-Fluoroadenosine
Synonyms: 2-fas;2-far;nsc30605;2-Fluorodenosine;2-FLUOROADENOSINE;2-fluoro-adenosin;Adenosine, 2-fluoro-;2-Fluoroadenosine>2-Fluoroadenosine USP/EP/BP;2-FLUOROADENOSINE(FLUDARABINE INTERMEDIATE)
CBNumber: CB6306915
Molecular Formula: C10H12FN5O4
Formula Weight: 285.23
MOL File: 146-78-1.mol

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2-Fluoroadenosine Property

Melting point:: 240 °C (D)(lit.)
Boiling point:: 747.3±70.0 °C(Predicted)
Density: 2.17±0.1 g/cm3(Predicted)
refractive index: -72 ° (C=0.1, EtOH)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
solubility: DMSO (Slightly, Sonicated), Methanol (Slightly, Heated, Sonicated)
form: Solid
pka: 13.05±0.70(Predicted)
color: Off-White
InChI: InChI=1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6-,9-/m1/s1
InChIKey: HBUBKKRHXORPQB-UUOKFMHZSA-N
SMILES: OC[C@H]1O[C@@H](N2C3C(=C(N=C(F)N=3)N)N=C2)[C@H](O)[C@@H]1O
CAS DataBase Reference: 146-78-1(CAS DataBase Reference)

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Safety

Hazard Codes: Xn
Risk Statements: 22-36/37/38
Safety Statements: 26
WGK Germany: 3
RTECS: AU7386000
HS Code: 29349990
Toxicity: mouse,LD10,unreported,1000ug/kg (1mg/kg),Progress in Medical Chemistry. Vol. 7, Pg. 69, 1970.

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 656402
Product name: 2-Fluoroadenosine
Purity: 97%
Packaging: 250mg
Price: $85.2
Updated: 2024/03/01

Sigma-Aldrich

Product number: 656402
Product name: 2-Fluoroadenosine
Purity: 97%
Packaging: 1g
Price: $679
Updated: 2024/03/01

TCI Chemical

Product number: F0656
Product name: 2-Fluoroadenosine
Purity: >96.0%(HPLC)(T)
Packaging: 1g
Price: $283
Updated: 2024/03/01

TCI Chemical

Product number: F0656
Product name: 2-Fluoroadenosine
Purity: >96.0%(HPLC)(T)
Packaging: 200mg
Price: $71
Updated: 2024/03/01

Alfa Aesar

Product number: H27412
Product name: 2-Fluoroadenosine, 97%
Packaging: 250mg
Price: $150
Updated: 2021/12/16

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2-Fluoroadenosine Chemical Properties,Usage,Production

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.

Definition

ChEBI: 2-fluoroadenosine is a member of adenosines and an organofluorine compound.

Biological Functions

2-Fluoroadenosine (F-Ado) was synthesized by Montgomery and his co-workers. This compound has been found to suppress the growth of H.Ep. No. 2 cells growing in culture. Bennett and Smithers have shown that in the same cells, the synthesis of 5-phosphoribosylamine was markedly inhibited by both 2- fluoroadenine and F-Ado. The compound was found to inhibit the incorporation of variously labeled precursors into ribonucleic acid in whole Ehrlich ascites cells. Upon incubation with ascites cells, the nucleoside was readily converted to the 5’-mono-, 5’-di-, and 5’-triphosphates.In addition, striking potentiation of the inhibition of human platelet aggregation by combinations of forskolin with PGE 1 or F-Ado [1-2].

Synthesis

A novel method for the introduction of fluorine in the purine 2-position is described and employed in the synthesis of a potential antimycobacterial compound. Also 2-fluoroadenosine has been synthesized for the first time from adenosine with perbenzoylated 2-nitroadenosine as a key intermediate. Mild reaction conditions are employed and few synthetic steps are required. The novel synthesis of fluoroadenosine can be regarded as a formal synthesis of the antileukemic drug fludarabine phosphate.
[1] MORTEN BR?NDVANG L. G. A Novel Method for the Introduction of Fluorine into the Purine 2-Position: Synthesis of 2-Fluoroadenosine and a Formal Synthesis of the Antileukemic Drug Fludarabine[J]. Synthesis-Stuttgart, 2006, 87 1: 2993-2995. DOI:10.1055/S-2006-942544.

References

[1] H T Shigeura. “Metabolism of 2-fluoroadenosine by Ehrlich ascites cells.” Archives of biochemistry and biophysics 111 3 (1965): 713–9.
[2] Kailash C. Agarwal, Robert E. Parks Jr. “Synergistic inhibition of platelet aggregation by forskolin plus PGE1 or 2-fluoroadenosine: Effects 2′,5′-dideoxyadenosine and 5′-methylthioadenosine.” Biochemical pharmacology 31 22 (1982): Pages 3713-3716.

2-Fluoroadenosine Preparation Products And Raw materials

Raw materials

Preparation Products

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View Lastest Price from 2-Fluoroadenosine manufacturers

Honest Joy Holdings Limited

Product: 2-Fluoroadenosine 146-78-1
Price: US $0.00/KG
Min. Order: 1KG
Purity: 99.3%
Supply Ability: 100 tons
Release date: 2022-02-21

Career Henan Chemical Co

Product: 2-Fluoroadenosine 146-78-1
Price: US $7.00/KG
Min. Order: 1KG
Purity: 99%
Supply Ability: 100kg
Release date: 2018-12-24

146-78-1, 2-FluoroadenosineRelated Search:

2-Fluoro-2',3',5'-triacetoxyadenosine 2-Fluoroadenosine 2-Fluoropurine 2-Fluoroadenine Fludarabine 2',3'-Dideoxy-2'-fluoroadenosine 5'-O-Sulfamoyl-4'-fluoroadenosine 2'-AMINO-2'-DEOXY-2-FLUOROADENOSINE 8-FLUOROADENOSINE 2'-DEOXY-2-FLUOROADENOSINE 2-FLUOROPYRIMIDINE 3’,5’-Di-O-acetyl-2-fluoro-2’-O-trifluoro-methanesulfonyladenosine 2-Amino-2',3'-dideoxy-3'-fluoroadenosine 3'-AMINO-2',3'-DIDEOXY-2-FLUOROADENOSINE 2'-deoxy-2'-fluoroadenosine 5'-diphosphate 2-FLUORO-3'-DEOXYADENOSINE 5'-Deoxy-2-fluoroadenosine 4',5'-didehydro-5'-deoxy-5'-fluoroadenosine

2-far

2-fas

2-fluoro-adenosin

6-amino-2-fluoro-9-beta-d-ribofuranosyl-purin

6-amino-2-fluoro-9-beta-d-ribofuranosylpurine

nsc30605

2-FLUOROADENOSINE

2-FLUOROADENOSINE(FLUDARABINE INTERMEDIATE)

2-Fluorodenosine

2-Fluoro-9-β-D-ribofuranosyl-9H-purin-6-amine

Adenosine, 2-fluoro-

(2R,3R,4S,5R)-2-(6-aMino-2-fluoro-9H-purin-9-yl)-5-(hydroxyMethyl)oxolane-3,4-diol

(2R,3R,4S,5R)-2-(6-AMino-2-fluoro-9H-purin-9-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol

2-Fluoroadenosine&gt

2-Fluoroadenosine USP/EP/BP

(2R,3R,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

146-78-1

145-78-1

C10H12FN5O4

Oligonucleotide Synthesis

Nucleosides

Specialty Synthesis

Biochemistry

Nucleosides and their analogs

Nucleosides, Nucleotides & Related Reagents

Nucleosides

Oligonucleotide Synthesis

Specialty Synthesis

Miscellaneous Biochemicals

API intermediates