9-((3aR,4R,6R,6aR)-6-((6-chloropyrimidin-4-ylamino)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-1H-purin-6(9H)-one | 1271789-81-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-((3aR,4R,6R,6aR)-6-((6-chloropyrimidin-4-ylamino)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-1H-purin-6(9H)-one
• CAS: 1271789-81-1
• 化学式: C₁₇H₁₈ClN₇O₄
• 分子量: 419.827
• InChiKey: GUGSFKGQRGIDLE-KWDXPJCYSA-N

物化性质

• 熔点：
  114-115 °C
• 沸点：
  733.0±70.0 °C(Predicted)
• 密度：
  1.80±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.09
• 重原子数：
  29.0
• 可旋转键数：
  4.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  129.07
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  9-((3aR,4R,6R,6aR)-6-((6-chloropyrimidin-4-ylamino)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-1H-purin-6(9H)-one 在 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二乙二醇二甲醚 、 水 为溶剂， 反应 0.66h， 生成 9-((2R,3R,4S,5R)-5-((6-(dimethylamino)pyrimidin-4-ylamino)methyl)-3,4-dihydroxy-tetrahydrofuran-2-yl)-1H-purin-6(9H)-one
  参考文献：
  名称：

  Synthesis and antitumor activity of novel ribonucleosides with C-5 OH replaced by a diaminopyrimidinyl group

  摘要：

  A series of novel ribonucleosides with C-5 OH replaced by a diaminopyrimidinyl group were synthesized by successively nucleophilic substitutions of 5'-deoxy-5'-amino-ribonucleosides with 2,4-dichloropyrimidine and then with various fatty amines under microwave irradiation. Their anticancer activities in vitro were preliminarily evaluated. Compounds 7a and 8a only exhibited anticancer activity against A549 cell line with the IC50 values of 10.73 and 10.99 mu M, respectively. In addition, 7h and 8h showed potent activities against both A549 and Hela cell lines with the IC50 values of 12.71, 8.55 and 8.44, 5.55 mu M, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.069
• 作为产物：
  描述：

  4,6-二氯嘧啶 、 5'-amino-5'-deoxy-2',3'-isopropylidene-inosine 在 N,N-二异丙基乙胺 作用下， 以 正丁醇 为溶剂， 反应 3.0h， 以72%的产率得到9-((3aR,4R,6R,6aR)-6-((6-chloropyrimidin-4-ylamino)methyl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)-1H-purin-6(9H)-one
  参考文献：
  名称：

  Synthesis and antitumor activity of novel ribonucleosides with C-5 OH replaced by a diaminopyrimidinyl group

  摘要：

  A series of novel ribonucleosides with C-5 OH replaced by a diaminopyrimidinyl group were synthesized by successively nucleophilic substitutions of 5'-deoxy-5'-amino-ribonucleosides with 2,4-dichloropyrimidine and then with various fatty amines under microwave irradiation. Their anticancer activities in vitro were preliminarily evaluated. Compounds 7a and 8a only exhibited anticancer activity against A549 cell line with the IC50 values of 10.73 and 10.99 mu M, respectively. In addition, 7h and 8h showed potent activities against both A549 and Hela cell lines with the IC50 values of 12.71, 8.55 and 8.44, 5.55 mu M, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.069