5-Iodotubercidin

5-Iodotubercidin is a potent adenosine kinase inhibitor with IC50 of 26 nM.

5-iodotubercidin is an organoiodine compound. It derives from a tubercidin.

A mixture of (2R, 3R, 4R, 5R)-2-(benzoyloxymethyl)-5-(4-chloro-5-iodo-7H- pyrrolo[2, 3-d]pyrimidin-7-yl)tetrahydrofuran-3, 4-diyl dibenzoate, (3.0 g, 4.1 mmol), and aqueous NH3 (45 ml) in 1, 4-dioxane (45 ml) was stirred at 80 °C for 16 h. LC-MS analysis indicated complete reaction. The mixture was concentrated to dryness. The residue was suspended in CHTri-benzoyl compound 42 (3.70 g, 5.31 mmol) was dissolved in a mixture of 53 mL of 1, 4-dioxane and 53 mL of 30percent aqueous NH4OH in a sealed tube. The tube was sealed and heated to 60 °C for 72 h before being cooled to rtand concentrated in vacuo to afford a brown oil. The oil was purified by flash chromatography (0–20percent MeOH/DCM)to give the triol 43Step 5. Step 5. 4-amino-5-iodo-7-(beta-D-ribofuranosyl)-7H-pyrrolo[2, 3-d]pyrimidine The nucleoside prepared as described above (155 mg, 0.38 mmol) was treated with liquid ammonia at 120 C. for 20 hours in the high pressure metal reactor. After evaporation of ammonia the residue was purified on silica gel with CH2Cl2/MeOH (30/1, 20/1, 15/1) as the eluents to yield the target compound as white powder (115 mg, 79%). 1H NMR (Acetone-d6): delta 8.10 (s, 1H), 7.59 (s, 1H), 6.37 (br s, 2H), 5.98 (d, 1H, J=6.5 Hz), 5.29 (br, 1H), 4.76 (m, 1H), 4.62 (br, 1H), 4.33 (br, 1H), 4.11 (m, 1H), 3.74 (m, 1H).

A potent and competitive inhibitor of ERK2, PKA, and ADK.

Molecular Weight:392.15
XLogP3:-0.7
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:2
Exact Mass:391.99815
Monoisotopic Mass:391.99815
Topological Polar Surface Area:127
Heavy Atom Count:20
Complexity:365
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes