9-[(5’R)-β-hexofuranosyl]-6-O-methylpurine | 1261280-76-5

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-[(5’R)-β-hexofuranosyl]-6-O-methylpurine
• 英文别名: 9-β-D-allofuranosyl-6-chloropurine；(2R,3R,4S,5R)-2-(6-chloropurin-9-yl)-5-[(1R)-1,2-dihydroxyethyl]oxolane-3,4-diol
• CAS: 1261280-76-5
• 化学式: C₁₁H₁₃ClN₄O₅
• 分子量: 316.701
• InChiKey: OUOLKZYURUSZPG-RWONEVQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  9-[(5’R)-β-hexofuranosyl]-6-O-methylpurine 在 N,O-双三甲硅基乙酰胺 、 水 、 对甲苯磺酸 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 甲苯 为溶剂， 反应 10.0h， 生成 9-(6-deoxy-6-diethylphosphono-2,3-O-isopropylidene-β-D-ribo-(5S)-hexofuranosyl)-6-O-methylpurine
  参考文献：
  名称：

  An Alternative Pathway to Ribonucleoside β-Hydroxyphosphonate Analogues and Related Prodrugs

  摘要：

  Nucleoside beta-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5'-nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reduction of beta-ketophosphonate intermediate. Herein, an original synthesis of these compounds using nucleoside epoxide intermediates, containing either a pyrimidine or a purine as nucleobase, was explored and allowed the direct synthesis of the corresponding bis S-acyl-2-thioethyl (SATE) prodrugs.

  DOI：

  10.1021/ol402143y
• 作为产物：
  描述：

  1,2,3,5,6-penta-O-acetyl-(α,β)-D-allofuranose 在 四氯化锡 、 potassium carbonate 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 9-[(5’R)-β-hexofuranosyl]-6-O-methylpurine
  参考文献：
  名称：

  An Alternative Pathway to Ribonucleoside β-Hydroxyphosphonate Analogues and Related Prodrugs

  摘要：

  Nucleoside beta-(S)-hydroxyphosphonate analogues have recently proven to be interesting bioactive compounds as 5'-nucleotidase inhibitors. These derivatives were obtained in a pyrimidine series through an ex-chiral pool pathway or the stereoselective reduction of beta-ketophosphonate intermediate. Herein, an original synthesis of these compounds using nucleoside epoxide intermediates, containing either a pyrimidine or a purine as nucleobase, was explored and allowed the direct synthesis of the corresponding bis S-acyl-2-thioethyl (SATE) prodrugs.

  DOI：

  10.1021/ol402143y

文献信息

• Synthesis and cytostatic activity of purine nucleosides derivatives of allofuranose
  作者：Pedro Besada、Tamara Costas、Marta Teijeira、Carmen Terán

  DOI：10.1016/j.ejmech.2010.09.046

  日期：2010.12

  Several new purine nucleosides derivatives of allofuranose were prepared according to Vorbrüggen method, starting from 1,2,5,6-di-O-isopropylidene-α-d-allofuranose and using 1,2,3,5,6-pentaacetoxy-β-d-allofuranose as key intermediate. The synthesized allofuranosyl nucleosides, as well as some acetyl derivatives, were evaluated for their cytotoxicity in vitro in three human cancer cell lines (MCF-7

  根据Vorbrüggen方法，从1,2,5,6-二-O-异亚丙基-α - d-铝呋喃糖开始，并使用1,2,3,5,6-五乙酰氧基-β制备了几种新的异呋喃糖嘌呤核苷衍生物。- ð -allofuranose作为关键中间体。在三种人类癌细胞系（MCF-7，Hela-229和HL-60）中，对合成的异呋喃糖基核苷以及一些乙酰基衍生物的体外细胞毒性进行了评估。在研究的化合物中，9-（2,3,5,6-四-O-乙酰基-β - d-氟呋喃糖基）-2,6-二氯嘌呤（9）是所评估的三种细胞系中最有效的一种，是其对顺铂相似的HL-60细胞的活性。