2',3'-O-isopropylidene-5'-O-[N-(Boc-L-prolyl)sulfamoyl]-8-oxoadenosine | 864500-82-3

• 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: 2',3'-O-isopropylidene-5'-O-[N-(Boc-L-prolyl)sulfamoyl]-8-oxoadenosine
• CAS: 864500-82-3
• 化学式: C₂₃H₃₃N₇O₁₀S
• 分子量: 599.622
• InChiKey: MHKJKCYFGLSCHT-QTOWJTHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  41.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  219.29
• 氢给体数：
  3.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2',3'-O-isopropylidene-5'-O-[N-(Boc-L-prolyl)sulfamoyl]-8-oxoadenosine 在 甲酸 作用下， 反应 12.0h， 以59%的产率得到5'-O-[N-(L-prolyl)sulfamoyl]-8-oxoadenosine
  参考文献：
  名称：

  Synthesis and Biological Properties of New Phosmidosine Analogs Having anN-Acylsulfamate Linkage

  摘要：

  A new phosmidosine analog 10, in which the proline and 8-oxoadenosine moieties were linked by an N -acyl sulfamate linkage, was successfully synthesized by the sulfamoylation of an 8-oxoadenosine derivative 5 followed by coupling with an L-proline derivative 8. An L-alanine-substituted derivative 13 and its derivative 14 without the alanyl residue were also synthesized. The morphological reversion activity of these synthetic compounds in v-src(ts) NRK cells and their antitumor activity in L1210 and KB cells were studied. As the result, neither L-proline- nor L-alanine-substituted phosmidosine analogs 10 and 13 showed any antitumor activity. Contrary to these results, the derivative 14 lacking the amino acid residue showed potent antitumor activities against cancer cells.

  DOI：

  10.1080/15257770600686360
• 作为产物：
  描述：

  2',3'-O-isopropylidene-8-oxoadenosine 在 氨基磺酰氯 、 sodium hydride 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙二醇二甲醚 、 乙腈 为溶剂， 反应 14.0h， 生成 2',3'-O-isopropylidene-5'-O-[N-(Boc-L-prolyl)sulfamoyl]-8-oxoadenosine
  参考文献：
  名称：

  Synthesis and Biological Properties of New Phosmidosine Analogs Having anN-Acylsulfamate Linkage

  摘要：

  A new phosmidosine analog 10, in which the proline and 8-oxoadenosine moieties were linked by an N -acyl sulfamate linkage, was successfully synthesized by the sulfamoylation of an 8-oxoadenosine derivative 5 followed by coupling with an L-proline derivative 8. An L-alanine-substituted derivative 13 and its derivative 14 without the alanyl residue were also synthesized. The morphological reversion activity of these synthetic compounds in v-src(ts) NRK cells and their antitumor activity in L1210 and KB cells were studied. As the result, neither L-proline- nor L-alanine-substituted phosmidosine analogs 10 and 13 showed any antitumor activity. Contrary to these results, the derivative 14 lacking the amino acid residue showed potent antitumor activities against cancer cells.

  DOI：

  10.1080/15257770600686360