6-(3-methyl-butylamino)-9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]purine | 1238220-52-4

• 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: 6-(3-methyl-butylamino)-9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]purine
• 英文别名: 2-[2-[6-(3-Methylbutylamino)purin-9-yl]ethyl]propane-1,3-diol
• CAS: 1238220-52-4
• 化学式: C₁₅H₂₅N₅O₂
• 分子量: 307.396
• InChiKey: DDRXXGFGPMVMMX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  22
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  96.1
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-(3-methyl-butylamino)-9-[(2,2-dimethyl-1,3-dioxan-5-yl)ethyl]purine 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 6-(3-methyl-butylamino)-9-[4-hydroxy-3-(hydroxymethyl)but-1-yl]purine
  参考文献：
  名称：

  Novel Isopentenyladenosine Analogues: Synthesis, Characterization, and Evaluation of Antiproliferative Activity on Bladder Carcinoma Cells

  摘要：

  Isopentenyladenosine (iPA), a member of the cytokinin family of plant hormones, exerts a marked antiproliferative activity on some leukemic and epithelial cancer cell lines. To characterize the molecular moieties required for the in vitro antitumor activity of the molecule and to obtain cytostatic iPA derivatives potentially useful as chemotherapeutic agents, N9-acyclic analogues have been synthesized using regioselective Mitsunobu reaction and characterized by elemental analyses, H-1 and C-13 NMR. These compounds were analyzed for their activity on human bladder cancer cell lines. In this study, we report that iPA inhibited the proliferation but not the migration of human bladder cancer cells, while the newly synthesized analogues revealed no significant cytostatic activity apart from the compound with a saturated double bond of the isopentenyl chain. These results indicate that the integrity of the ribose ring is required for the cytostatic activity of iPA.

  DOI：

  10.1080/15257770903155550

文献信息

• Novel Isopentenyladenosine Analogues: Synthesis, Characterization, and Evaluation of Antiproliferative Activity on Bladder Carcinoma Cells
  作者：Roberta Ottria、Silvana Casati、Jeanette A. M. Maier、Massimo Mariotti、Pierangela Ciuffreda

  DOI：10.1080/15257770903155550

  日期：2009.9.11

  Isopentenyladenosine (iPA), a member of the cytokinin family of plant hormones, exerts a marked antiproliferative activity on some leukemic and epithelial cancer cell lines. To characterize the molecular moieties required for the in vitro antitumor activity of the molecule and to obtain cytostatic iPA derivatives potentially useful as chemotherapeutic agents, N9-acyclic analogues have been synthesized using regioselective Mitsunobu reaction and characterized by elemental analyses, H-1 and C-13 NMR. These compounds were analyzed for their activity on human bladder cancer cell lines. In this study, we report that iPA inhibited the proliferation but not the migration of human bladder cancer cells, while the newly synthesized analogues revealed no significant cytostatic activity apart from the compound with a saturated double bond of the isopentenyl chain. These results indicate that the integrity of the ribose ring is required for the cytostatic activity of iPA.