ChemicalBook--->CAS DataBase List--->6736-58-9

6736-58-9

6736-58-9 Structure

6736-58-9 Structure
IdentificationBack Directory
[Name]

3-DEAZAADENOSINE
[CAS]

6736-58-9
[Synonyms]

C3-Ado
NSC 167897
3-Deaza-rA
3-DEAZAADENOSINE
3-Deaza-D-adenosine
3-Deazaadenosine ,98%
1-β-D-Ribofuranosyl-1H-imidazo[4,5-c]pyridin-4-amine
4-Amino-1-(D-ribofuranosyl)-1H-imidazo(4,5)-pyridine
4-Amino-1-beta-D-ribofuranosyl-1H-imidazo[4,5-c]pyridine
1H-Imidazo4,5-cpyridin-4-amine, 1-.beta.-D-ribofuranosyl-
4-AMINO-1-[BETA-D-RIBOFURANOSYL]-1H-IMIDAZO[4,5]-PYRIDINE
(2R,3R,4S,5R)-2-(4-AMino-1H-iMidazo[4,5-c]pyridin-1-yl)-5-(hydroxyMethyl)tetrahydrofuran-3,4-diol
[Molecular Formula]

C11H14N4O4
[MDL Number]

MFCD00153951
[MOL File]

6736-58-9.mol
[Molecular Weight]

266.25
Chemical PropertiesBack Directory
[Description]

3-Deazaadenosine (3-DZA) is an inhibitor of SAH (Sadenosylhomocysteine) hydrolase (Ki = 3.9 μM). It has antiinflammatory properties, inhibiting leukocyte adhesion and chemotaxis, lymphocyte-mediated cytolysis, phagocytosis, degranulation, and NF-κB signaling. 3-DZA also has anti-viral and anti-bacterial activities.
[Appearance]

Bright Yellow Solid
[Melting point ]

228-229°C
[Boiling point ]

665.7±65.0 °C(Predicted)
[density ]

1.90±0.1 g/cm3 (20 ºC 760 Torr)
[storage temp. ]

2-8°C
[solubility ]

H2O: 10 mg/mL with heating to 60 °C
[form ]

Solid
[pka]

13.24±0.70(Predicted)
[color ]

White to Off-White
Hazard InformationBack Directory
[Chemical Properties]

Bright Yellow Solid
[Uses]

Possesses antiviral activity. It is an inhibitor of leukocyte adhesion to TNF-treated endothelial cells
[Biochem/physiol Actions]

Possesses antiviral activity inhibitor of leukocyte adhesion to TNF-treated endothelial cells.
[in vitro]

3-deazaadenosine showed inhibitory values against the ebo-z viruses, ebo, and marburg virus in various cell lines of primate (sw13, vero 76, frhl, llc-mk2, mrc-5, vero e6) and mouse (balb/3t3 clone a31) origin. 3-deazaadenosine at 2 μg/ml could reduce viral replication by 3 logs in a dose-dependent manner. however, there was no further inhibition even with a 100-fold increase in concentration [1].
[in vivo]

in vehicle control group, adult balb/c mice lethally infected with mouse-adapted ebola virus die 5-7 days after infection. in contrast, 3-deazaadenosine treatment initiated on day 0 or 1 led to a dose-dependent protection, with mortality completely prevented at doses around 0.7 mg/kg every 8 h. moreover, there was significant protection when 3-deazaadenosine treatment was begun on day 2, at which time, the spleen had an average titer of 2 × 106 pfu/g and the liver had 3 × 105 pfu/g virus. treatment with 3-aeazaadenosine at 2.2 mg/kg initiated on day 3 resulted in 40% survival [1].
[References]

[1] huggins, z. x. zhang and m. bray. antiretroviral drug therapy of filovirus infections: s-adenosylhomocysteine hydrolase inhibitors inhibit ebola virus in vitro and in a lethal mouse model. journal of infectious diseases 179 (1), s240-s247 (1999).
Safety DataBack Directory
[Safety Statements ]

24/25
[RIDADR ]

2811
[WGK Germany ]

3
[HazardClass ]

6.1(a)
[PackingGroup ]

II
[HS Code ]

29419090
Spectrum DetailBack Directory
[Spectrum Detail]

3-DEAZAADENOSINE(6736-58-9)MS
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