| Identification | Back Directory | [Name]
4-Amino-6-chloro-1--D-ribofuranosylimidazo[4,5-c]pyridine | [CAS]
40656-71-1 | [Synonyms]
NSC 158900
2-chloro-3-Deazaadenosine
6-Amino-2-chloro-9-(b-D-ribofuranosyl)purine
4-Amino-6-chloro-1--D-ribofuranosylimidazo[4,5-c]pyridine
6-Chloro-1-β-D-ribofuranosyl-1H-iMidazo[4,5-c]pyridin-4-aMine | [Molecular Formula]
C11H13ClN4O4 | [MDL Number]
MFCD00005734 | [MOL File]
40656-71-1.mol | [Molecular Weight]
300.698 |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [Melting point ]
223-225°C | [Boiling point ]
694.6±65.0 °C(Predicted) | [density ]
2.02±0.1 g/cm3(Predicted) | [storage temp. ]
Refrigerator | [solubility ]
DMSO, Methanol | [form ]
Solid | [pka]
13.18±0.70(Predicted) | [color ]
Off-White to Beige |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Solid | [Uses]
Adenosine analog | [Biological Activity]
2-chloro-3-deazaadenosine, a stable analog of adenosine, is an agonist for adenosine receptors [1].adenosine receptors are members of g-protein-coupled receptors (gpcrs). extracellular adenosine acts as a local modulator with a generally cytoprotective function in the body. extracellular adenosine has been implicated in increasing the ratio of oxygen supply to demand, protecting against ischaemic damage by cell conditioning, triggering anti-inflammatory responses and the promotion of angiogenesis [2]. | [in vitro]
the ki values of 2-chloro-3-deazaadenosine for a1, a2a, a2b, and a3 receptors were 0.3, 0.08, 25.5, and 1.9 μm, respectively [1]. 2-chloroadenosine (25 μm) increased activity of platelet adenylate cyclase to about 150–160% of the control value. higher concentrations of 2-chloroadenosine showed less effect above 100 μm [3]. | [in vivo]
in the rat with delayed ischaemic damage, iterative focal injections of 2-chloroadenosine protected against selective hippocampal ca1 loss [4]. | [References]
[1] linden j, thai t, figler h, et al. characterization of human a2b adenosine receptors: radioligand binding, western blotting, and coupling to gqin human embryonic kidney 293 cells and hmc-1 mast cells[j]. molecular pharmacology, 1999, 56(4): 705-713.
[2] jacobson k a, gao z g. adenosine receptors as therapeutic targets[j]. nature reviews drug discovery, 2006, 5(3): 247-264.
[3] haslam r j, lynham j a. activation and inhibition of blood platelet adenylate cyclase by adenosine or by 2-chloroadenosine[j]. life sciences, 1972, 11(23): 1143-1154.
[4] evans m c, swan j h, meldrum b s. an adenosine analogue, 2-chloroadenosine, protects against long term development of ischaemic cell loss in the rat hippocampus[j]. neuroscience letters, 1987, 83(3): 287-292. |
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