1-[2-CHLORO-6-[[(3-IODOPHENYL)METHYL]AMINO]-9H-PURIN-9-YL]-1-DEOXY-N-METHYL-BETA-D-RIBOFURANURONAMIDE

Namodenoson (CF-102) is a selective A3 adenosine receptor agonist (Ki = 0.33 nM). Displays 2500- and 1400-fold selectivity over A1 and A2A receptors respectively.

CF-102 has been used in trials studying the treatment of Chronic Hepatitis C and Hepatocellular Carcinoma.|Namodenoson is an orally bioavailable, synthetic, highly selective adenosine A3 receptor (A3AR) agonist with potential antineoplastic activity. Namodenoson selectively binds to and activates the cell surface-expressed A3AR, deregulating Wnt and NF-kB signal transduction pathways downstream, which may result in apoptosis of A3AR-expressing tumor cells. A3AR, a G protein-coupled receptor, is highly expressed on the cell surfaces of various solid tumor cell types, including hepatocellular carcinoma (HCC) cells, and plays an important role in cellular proliferation.

The intermediate compound (15 g, 26.89 mmol) prepared in Step 3Acetonitrile-water (130 mL, 1: 1)It was dissolved in a solution(Di acetoxy iodo) benzene(19 g, 59.16 mmol)And 2, 2, 6, 6-tetramethyl-1-piperidinyl oxyl (840 mg, 5.37mmol) toIt was added dropwise and then stirred at room temperature for 4 hours.After confirmation of the completion of the reaction the reaction solution was concentrated under reduced pressure to give the acid intermediate, without purification.Acid intermediate thus obtained (15 g, 26.23 mmol)In absolute ethanol (500mL) in a stream of nitrogenA dissolved and then cooled to 0 thionyl chloride (9.52 mL, 131.17 mmol)It was added dropwise slowly and then stirred at room temperature for 12 hours.After confirmation of the completion of the reaction the reaction solution was concentrated under reduced pressure to give the intermediate ethyl ester without purification.This was added dropwise to the resulting ethyl ester intermediate (15.5 g, 25.84 mmol), methylamine (750 mL, 2 N THF solution) then stirred at room temperature for 12 hours.Concentrated under reduced pressure and then check the completion of the reaction, and then separating the obtained residue was purified by column chromatography to intermediate compound (2S, 5R) -5- (2- chloro-6- (3-iodo-benzylamino) -9H- purine 9-yl) -N- methyl-3, 4-dihydroxy-2-carboxamide in tetrahydrofuran (5 g, to give a 31.80percent)

2-Cl-IB-MECA acts as an A3 adenosine receptor-selective nucleoside.

Molecular Weight:544.7
XLogP3:1.9
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:544.01228
Monoisotopic Mass:544.01228
Topological Polar Surface Area:134
Heavy Atom Count:30
Complexity:623
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes