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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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2-Fluoroadenosine Suppliers

J & K SCIENTIFIC LTD.
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010-82848833 400-666-7788
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86-10-82849933
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jkinfo@jkchemical.com
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China
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Meryer (Shanghai) Chemical Technology Co., Ltd.
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400-6106006
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021-67582001/03/05
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saleschina@alfa-asia.com
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Energy Chemical
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View Lastest Price from 2-Fluoroadenosine manufacturers

Zibo Hangyu Biotechnology Development Co., Ltd
Product
2-Fluoroadenosine 146-78-1
Price
US $150.00-470.00/mg
Min. Order
500mg
Purity
99%
Supply Ability
50
Release date
2024-07-12
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:


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  • 146-78-1
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  • C10H12FN5O4
  • Oligonucleotide Synthesis
  • Nucleosides
  • Specialty Synthesis
  • Biochemistry
  • Nucleosides and their analogs
  • Nucleosides, Nucleotides & Related Reagents
  • Nucleosides
  • Oligonucleotide Synthesis
  • Specialty Synthesis
  • Miscellaneous Biochemicals
  • API intermediates