2-Fluoroadenosine
|
|
|
- CAS-Nr.
- 146-78-1
- Englisch Name:
- 2-Fluoroadenosine
- Synonyma:
- 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
- Summenformel:
- C10H12FN5O4
- Molgewicht:
- 285.23
- MOL-Datei:
- 146-78-1.mol
|
2-Fluoroadenosine Eigenschaften
- Schmelzpunkt:
- 240 °C (D)(lit.)
- Siedepunkt:
- 747.3±70.0 °C(Predicted)
- Dichte
- 2.17±0.1 g/cm3(Predicted)
- Brechungsindex
- -72 ° (C=0.1, EtOH)
- storage temp.
- Keep in dark place,Sealed in dry,Room Temperature
- Löslichkeit
- DMSO (Slightly, Sonicated), Methanol (Slightly, Heated, Sonicated)
- Aggregatzustand
- Solid
- pka
- 13.05±0.70(Predicted)
- Farbe
- 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 Datenbank
- 146-78-1(CAS DataBase Reference)
Sicherheit
- Risiko- und Sicherheitserklärung
- Gefahreninformationscode (GHS)
| Kennzeichnung gefährlicher |
Xn |
|
|
| R-Sätze: |
22-36/37/38 |
|
|
| S-Sätze: |
26 |
|
|
| WGK Germany |
3 |
|
|
| RTECS-Nr. |
AU7386000 |
|
|
| HS Code |
29349990 |
|
|
| Toxizität |
mouse,LD10,unreported,1000ug/kg (1mg/kg),Progress in Medical Chemistry. Vol. 7, Pg. 69, 1970. |
|
|
| Bildanzeige (GHS) |
|
| Alarmwort |
Warnung |
| Gefahrenhinweise |
| Code |
Gefahrenhinweise |
Gefahrenklasse |
Abteilung |
Alarmwort |
Symbol |
P-Code |
| H302 |
Gesundheitsschädlich bei Verschlucken. |
Akute Toxizität oral |
Kategorie 4 |
Warnung |
|
P264, P270, P301+P312, P330, P501 |
| H315 |
Verursacht Hautreizungen. |
Hautreizung |
Kategorie 2 |
Warnung |
|
P264, P280, P302+P352, P321,P332+P313, P362 |
| H319 |
Verursacht schwere Augenreizung. |
Schwere Augenreizung |
Kategorie 2 |
Warnung |
|
P264, P280, P305+P351+P338,P337+P313P |
| H335 |
Kann die Atemwege reizen. |
Spezifische Zielorgan-Toxizität (einmalige Exposition) |
Kategorie 3 (Atemwegsreizung) |
Warnung |
|
|
|
| Sicherheit |
| P261 |
Einatmen von Staub vermeiden. |
| P264 |
Nach Gebrauch gründlich waschen. |
| P264 |
Nach Gebrauch gründlich waschen. |
| P270 |
Bei Gebrauch nicht essen, trinken oder rauchen. |
| P301+P312 |
BEI VERSCHLUCKEN: Bei Unwohlsein GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen. |
| P302+P352 |
BEI BERÜHRUNG MIT DER HAUT: Mit viel Wasser/... (Hersteller kann, falls zweckmäßig, ein Reinigungsmittel angeben oder, wenn Wasser eindeutig ungeeignet ist, ein alternatives Mittel empfehlen) waschen. |
| P305+P351+P338 |
BEI KONTAKT MIT DEN AUGEN: Einige Minuten lang behutsam mit Wasser spülen. Eventuell vorhandene Kontaktlinsen nach Möglichkeit entfernen. Weiter spülen. |
|
2-Fluoroadenosine Chemische Eigenschaften,Einsatz,Produktion Methoden
R-Sätze Betriebsanweisung:
R22:Gesundheitsschädlich beim Verschlucken.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
S-Sätze Betriebsanweisung:
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
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.
Verwenden
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.
Biologische Funktion
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].
Synthese
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.
2-Fluoroadenosine Upstream-Materialien And Downstream Produkte
Upstream-Materialien
Downstream Produkte
2-Fluoroadenosine Anbieter Lieferant Produzent Hersteller Vertrieb Händler.
Global( 204)Lieferanten
146-78-1()Verwandte Suche:
- 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
- (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-far
- 2-fas
- 2-fluoro-adenosin
- Adenosine, 2-fluoro-
- 2-Fluoroadenosine>
- 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
