N6-Cyclopropylmethyladenosine | 36397-00-9

• 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: N6-Cyclopropylmethyladenosine
• 英文别名: N-(Cyclopropylmethyl)adenosine；(2R,3R,4S,5R)-2-[6-(cyclopropylmethylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 36397-00-9
• 化学式: C₁₄H₁₉N₅O₄
• 分子量: 321.336
• InChiKey: LLDGSWFLUWHPQB-IDTAVKCVSA-N

物化性质

• 沸点：
  672.1±65.0 °C(Predicted)
• 密度：
  1.86±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  6-N-2',3',5'-tri-O-tetraacetyladenosine 在 正丙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 24.0h， 生成 N6-Cyclopropylmethyladenosine
  参考文献：
  名称：

  Chemical modification of the plant isoprenoid cytokinin N6-isopentenyladenosine yields a selective inhibitor of human enterovirus 71 replication

  摘要：

  In this study, we demonstrate that N-6-isopentenyladenosine, which essentially is a plant cytokinin-like compound, exerts a potent and selective antiviral effect on the replication of human enterovirus 71 with an EC50 of 1.0 +/- 0.2 mu M and a selectivity index (SI) of 5.7. The synthesis of analogs with modification of the N-6-position did not result in a lower EC50 value. However, in particular with the synthesis of N6-(5hexene-2-yne-1-yl)adenosine (EC50 = 43 +/- 1.5 mu M), the selectivity index was significantly increased: because of a reduction in the adverse effect of this compound on the host cells, an SI > 101 could be calculated. With this study, we for the first time provide proof that a compound class that is based on the plant cytokinin skeleton offers an interesting starting point for the development of novel antivirals against mammalian viruses, in the present context in particular against enterovirus 71. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.11.048

文献信息

• N6-Alkyladenosines: Synthesis and evaluation of in vitro anticancer activity
  作者：Roberta Ottria、Silvana Casati、Erika Baldoli、Jeanette A.M. Maier、Pierangela Ciuffreda

  DOI：10.1016/j.bmc.2010.09.030

  日期：2010.12

  between structure and biological activity of iPA. The structures of the compounds were confirmed by standard studies of 1H NMR, MS and elemental analysis. These molecules were then evaluated for their anti-proliferative activity on bladder cancer cells. We found that some of these compounds possess anti-proliferative activity but have no effect on cell invasion and metalloprotease activity.

  合成了一系列在N 6位上不同取代的腺苷类似物，以继续我们对iPA的结构与生物学活性之间关系的研究。化合物的结构通过1 H NMR，MS和元素分析的标准研究确认。然后评估这些分子对膀胱癌细胞的抗增殖活性。我们发现其中一些化合物具有抗增殖活性，但对细胞侵袭和金属蛋白酶活性没有影响。