40656-71-1 Usage
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.
Check Digit Verification of cas no
The CAS Registry Mumber 40656-71-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 4,0,6,5 and 6 respectively; the second part has 2 digits, 7 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 40656-71:
(7*4)+(6*0)+(5*6)+(4*5)+(3*6)+(2*7)+(1*1)=111
111 % 10 = 1
So 40656-71-1 is a valid CAS Registry Number.
InChI:InChI=1/C11H13ClN4O4/c12-6-1-4-7(10(13)15-6)14-3-16(4)11-9(19)8(18)5(2-17)20-11/h1,3,5,8-9,11,17-19H,2H2,(H2,13,15)
40656-71-1Relevant articles and documents
A convenient route for the synthesis of 3-deazaspongosine
Bande, Omprakash,Herdewijn, Piet
, p. 231 - 236 (2014/01/06)
The first chemical synthesis of the 3-deazaspongosine nucleoside is described, starting from commercially available 4-amino-2,6-dichloropyridine. The key step is the introduction of required functional groups at the 2 and 6 positions of the 4-amino-3-nitropyridine without any conflict in the synthesis of nucleobase. Regioselective nucleophilic substitution with allyl alkoxide at the 2 position of 4-amino-2,6-dimethoxypyridine, followed by sequential deallylation and chlorination led to the desired 2-chloro derivative. Ring closure of the 3,4-diaminopyridine and stereoselective glycosylation of the imidazo[4,5-c]pyridine with tetraacetate-protected ribofuranose gave only the N9-β-isomer. A final nucleophilic displacement of the 6-chloride by hydrazine followed by reduction with Raney Nickel gave the desired 3-deazaspongosine. The synthesis of 3-deazaspongosine by the stereoselective glycosylation of imidazo[4,5-c]pyridine with tetraacetate-protected ribofuranose is described. The key step is the synthesis of the nucleobase starting from 2,6-dimethoxy-3-nitropyridin-4-amine by introducing the required functional groups at the 2 and 6 positions through the regioselective addition of allyl alcohol. Copyright
