3'-O-tert-butyldimethylsilyldeoxyadenosine 5'-[ethyl N-(N-trityl-L-prolyl)phosphoroamidate] | 778510-90-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3'-O-tert-butyldimethylsilyldeoxyadenosine 5'-[ethyl N-(N-trityl-L-prolyl)phosphoroamidate]
• CAS: 778510-90-0
• 化学式: C₄₂H₅₄N₇O₆PSi
• 分子量: 811.993
• InChiKey: SOGOVOWSPPRAKD-IGDPAMPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.82
• 重原子数：
  57.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  155.95
• 氢给体数：
  2.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  3'-O-tert-butyldimethylsilyldeoxyadenosine 5'-[ethyl N-(N-trityl-L-prolyl)phosphoroamidate] 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 ((S)-1-Trityl-pyrrolidine-2-carbonyl)-phosphoramidic acid (2R,3S,5R)-5-(6-amino-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester ethyl ester
  参考文献：
  名称：

  Structure–activity relationship of phosmidosine: importance of the 7,8-dihydro-8-oxoadenosine residue for antitumor activity

  摘要：

  To study the structure-activity relationship of phosmidosine, a variety of phosmidosine derivatives 9a-g were synthesized by condensation of N-diisopropyl N'-(N-tritylprolyl)phosphorodiamidite 6 with appropriately protected nucleoside derivatives 7a-g. As the result, replacement of the 7,8-diliydro-8-oxoadenine base by adenine and 6-N-acetyladenine did not affect the antitumor activity. However, phosmidosine derivatives containing uracil, cytosine, and guanine in place of the 7,8-dibydro-8-oxoadenine base did not show significant activity. A plausible explanation for the selective expression of phosmidosine compared with that of phosmidosine analogs having other amino acids in place of proline is also discussed. These results suggest that phosmidosine serves as an inhibitor of prolyl adenosine 5'-phosphate (prolyl-AMP) to inhibit the peptide synthesis in cancer-related cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.021
• 作为产物：
  描述：

  3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 、 ethyl N,N-diisopropyl-N'-(N-trityl-L-prolyl)phosphorodiamidite 在 1-甲基-5-巯基-1H-四氮唑 、 叔丁基过氧化氢 作用下， 以 乙腈 、 癸烷 为溶剂， 反应 0.34h， 以58%的产率得到3'-O-tert-butyldimethylsilyldeoxyadenosine 5'-[ethyl N-(N-trityl-L-prolyl)phosphoroamidate]
  参考文献：
  名称：

  Structure–activity relationship of phosmidosine: importance of the 7,8-dihydro-8-oxoadenosine residue for antitumor activity

  摘要：

  To study the structure-activity relationship of phosmidosine, a variety of phosmidosine derivatives 9a-g were synthesized by condensation of N-diisopropyl N'-(N-tritylprolyl)phosphorodiamidite 6 with appropriately protected nucleoside derivatives 7a-g. As the result, replacement of the 7,8-diliydro-8-oxoadenine base by adenine and 6-N-acetyladenine did not affect the antitumor activity. However, phosmidosine derivatives containing uracil, cytosine, and guanine in place of the 7,8-dibydro-8-oxoadenine base did not show significant activity. A plausible explanation for the selective expression of phosmidosine compared with that of phosmidosine analogs having other amino acids in place of proline is also discussed. These results suggest that phosmidosine serves as an inhibitor of prolyl adenosine 5'-phosphate (prolyl-AMP) to inhibit the peptide synthesis in cancer-related cells. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.07.021