Isopentenyladenosine

White to off-white crystalline powder

N(6)-(Delta(2)-isopentenyl)adenosine is a nucleoside analogue in which adenosine has been modified by substitution at the 6-amino nitrogen by a Delta(2)-isopentenyl group. It has a role as an antineoplastic agent, a plant growth regulator and a plant metabolite. It is a nucleoside analogue and a N-ribosyl-N(6)-isopentenyladenine. It derives from an adenosine.|Ipa has been used in trials studying the treatment of Nausea and Surgical Site Infection.|N(6)-[delta(3)-isopentenyl]adenosine. Isopentenyl derivative of adenosine which is a member of the cytokinin family of plant growth regulators.

Synthesis of N6-Isopentenyl-ATP (00901011044) (2253) (2254) N6-Isopentenyl-ATP (237): A solution of N6-isopentenyl-adenosine 236 (146.0 mg, 0.44 mmol; applied heat to make it soluble) and proton sponge (139.95 mg, 0.65 mmol, 1.5 equiv.) in trimethyl phosphate (1.5 mL) was stirred for 10.0 minutes at 0 C. Phosphorus oxychloride (60.8 muL, 0.65 mmol, 2.0 equiv.) was added dropwise to the solution and it was then kept stirring for 2.0 hours under N2 atmosphere. A mixture of tributylamine (414.0 muL, 1.74 mmol, 4.0 equiv.) and bis(tributylammonium) pyrophosphate (716.60 mg, 1.30 mmol, 3.0 equiv.) in acetonitrile (2.5 mL) was added at once. After -25 minutes, the reaction was quenched with 0.2 M TEAB buffer (17.0 mL) and the clear solution was stirred at room temperature for an hour. LCMS analysis indicated the formation of the corresponding triphosphate. The reaction mixture was then lyophilized overnight. The crude reaction mixture was purified by anion exchange followed by HPLC (Waters, Phenomenex C18 reverse-phase preparative column, 250 x 21.2 mm, 10.0 micron; gradient (1 percent): 100 percent A for 3.0 min, then 1percent B/min, A = 100 mM TEAA buffer, B = ACN; flow rate: 10.0 mL/min; retention time: 28.0-31.0 min). Fractions containing the desired were pooled together and lyophilized to yield the N6-isopentenyl-adenosine-TP (60) as a tetrakis(triethylammonium salt) (23.3 mg, 9.32 percent, based on epsilon268 = 15, 000.0 Lmol-1cm-1). UVmax = 268 nm; MS: m/e 573.90 (M-H).xample 73. Synthesis of N -Isopentenyl-ATP (00901011044) Isopentenyl-ATP (237): A solution of N -isopentenyl-adenosine 236 (146.0 mg, 0.44 mmol; applied at to make it soluble) and proton sponge (139.95 mg, 0.65 mmol, 1 .5 equiv.) in trimethyl phosphate 5 ml_) was stirred for 1 0.0 minutes at 0 C. Phosphorus oxychloride (60.8 muIota_, 0.65 mmol, 2.0 uiv.) was added dropwise to the solution and it was then kept stirring for 2.0 hours under N2mosphere. A mixture of tributylamine (414.0 muIota_, 1 .74 mmol, 4.0 equiv.) and bis(tributylammonium) ophosphate (716.60 mg, 1 .30 mmol, 3.0 equiv.) in acetonitrile (2.5 ml_) was added at once. After 5 minutes, the reaction was quenched with 0.2 M TEAB buffer (17.0 ml_) and the clear solution was red at room temperature for an hour. LCMS analysis indicated the formation of the corresponding hosphate. The reaction mixture was then lyophilized overnight. The crude reaction mixture was ified by anion exchange followed by H PLC (Waters, Phenomenex C18 reverse-phase preparative umn, 250 x 21 .2 mm, 10.0 micron; gradient (1 percent): 1 00 percent A for 3.0 min, then 1 percent B/min, A = 1 00M TEAA buffer, B = ACN ; flow rate: 1 0.0 mL/min; retention time: 28.0-31 .0 min). Fractions ntaining the desired were pooled together and lyophilized to yield the N6-isopentenyl-adenosine-TP ) as a tetrakis(triethylammonium salt) (23.3 mg, 9.32 percent, based on C268 = 15, 000.0 Lmor1cm'1). max = 268 nm; MS: m/e 573.90 (M-H).

N6-Isopentenyladenosine has antiproliferative activity on MCF-7 breast cancer cells.

Molecular Weight:335.36
XLogP3:1.1
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:5
Exact Mass:335.15935417
Monoisotopic Mass:335.15935417
Topological Polar Surface Area:126
Heavy Atom Count:24
Complexity:461
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes