Novel arabinosyladenine derivatives
A technology of sugar adenine and derivatives, which is applied in the field of 2-substituted arabinose adenine derivatives, can solve the problems such as the inability to obtain strong antiviral effect and the inability to meet the requirements of ADA resistance.
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reference example 1
[0072] Synthesis of 9-(β-D-arabinofuranoyl)-2-methyladenine [comparison compound A]
[0073] Dissolve 1 gram of AICN arabinoside and 2 milliliters of acetonitrile in 50 milliliters of ammonia-saturated methanol at 0°C, and heat in an autoclave at 140°C for 16 hours. After the reaction, the solvent was distilled off, and the residue was purified by silica gel column separation and recrystallized with distilled water to obtain the reference compound (745 mg) as colorless needle crystals.
[0074] Melting point: 247-249°C
[0075] Mass: 282 (MH + )
[0076] 1H-NMR: 2.39 (1H, s) 3.64 (2H, m) 3.76 (1H, m) 4.12 (2H, m) 5.13 (1H, t, j = 4.9) 5.51 (1H, d, j = 4.4) 5.60 ( 1H, d, j = 4.9) 6.22 (1H, d, j = 4.9) 7.10 (2H, s) 8.09 (1H, s)
[0077] In the above reaction, the corresponding nitrile was used to replace the acetonitrile as the raw material compound, and other reactions were carried out in the same manner as in Reference Example 1 to obtain the reference compound B.
[0078...
reference example 2
[0083] Synthesis of 6-methylamino-9-(β-D-arabinosfuranyl)purine [Comparative Compound C]
[0084] 1 g N 6- Methyladenosine and 1.35 g of 1,3-dichlorotetraisopropyldisiloxane were dissolved in 20 ml of pyridine and stirred at room temperature for 2 hours. After the reaction was completed, the solvent was evaporated, and the residue was separated and purified by silica gel column, and recrystallized from ethyl acetate to obtain 1.9 grams of 6-methylamino-9-[3,5,-O-(tetraisopropyldisiloxane alkane-1,3-diyl)-β-D-ribofuranyl]purine. 100 mg of this compound was dissolved in 4 ml of acetic anhydride and 10 ml of dimethylsulfoxide (DMSO), and stirred at room temperature for 16 hours. After the reaction, the solvent was distilled off and dissolved in 20 ml of L(-)-5,6,7,8-tetrahydrofolate (THF). To this solution was added 50 mg of sodium borohydride and stirred for 30 minutes. Next, 2 mL of ethanol was added and stirred for another 1 hour. After adding a small amount of acetone to...
Embodiment 1
[0088] In the reaction of reference example 2, instead of raw material compound N 6 -Methyladenosine Use the corresponding adenosine derivatives, and the others are reacted in the same way as in Reference Example 2 to obtain compounds 1 and 2. 6-methylamino-9-(β-D-arabinosylfuranyl)-2- Butylpurine [Compound 1]
[0089] Melting point: 165-166°C
[0090] Mass: 319 (MH + )
[0091] Elemental Analysis: C 15 h 23 N 5 o 4 0.2H 2 o
[0092] Theoretical value: (C, 52.98; H, 6.91; N, 20.59); measured value: (C, 52.98; H, 6.74; N, 20.76)
[0093] 1 H-NMR: 0.91 (3H, t, j=7.6) 1.35 (2H, hex, j=7.6) 1.71 (2H, qui, j=7.6) 2.67 (2H, t, j=7.6) 2.95 (3H, s) 3.64 (2H, m) 3.76 (1H, m) 4.13 (2H, m) 5.09 (1H, t, j=5.5) 5.51 (1H, d, j=4.4) 5.61 (1H, d, j=5.5) 6.24 1H, d, j = 4.4) 7.50 (1H, s) 8.06 (1H, s)
[0094] 6-Methylamino-9-(β-D-arabinosfuranyl)-2-(1-butyn-1-yl)purine [compound 2]
[0095] Melting point: 243-246°C
[0096] Mass: 334 (MH + )
[0097] Elemental Analysis: C 14 ...
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