2'-O-{N-methyl-N-[4-(allyl β-D-glucopyranosiduronate)-3-nitrobenzyloxycarbonyl]-2-aminoethyl}oxycarbonylpaclitaxel | 901778-62-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 2'-O-{N-methyl-N-[4-(allyl β-D-glucopyranosiduronate)-3-nitrobenzyloxycarbonyl]-2-aminoethyl}oxycarbonylpaclitaxel
• CAS: 901778-62-9
• 化学式: C₆₈H₇₅N₃O₂₇
• 分子量: 1366.35
• InChiKey: XUWNYTBUGJRBSJ-KKHVHXFXSA-N

反应信息

• 作为反应物：
  描述：

  2'-O-{N-methyl-N-[4-(allyl β-D-glucopyranosiduronate)-3-nitrobenzyloxycarbonyl]-2-aminoethyl}oxycarbonylpaclitaxel 在 四(三苯基膦)钯 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以80%的产率得到2'-O-{N-methyl-N-[4-(β-D-glucopyranosiduronate)-3-nitrobenzyloxycarbonyl]-2-aminoethyl}oxycarbonylpaclitaxel
  参考文献：
  名称：

  New Taxol® (paclitaxel) prodrugs designed for ADEPT and PMT strategies in cancer chemotherapy

  摘要：

  Two new glucuronide paclitaxel prodrugs have been synthesized. Linked to the 2'-OH of the drug by a carbonate function, they include a self-immolative spacer bearing an arylnitro or arylamino group between the drug and the glucuronic acid residue. Both prodrugs were well detoxified and easily cleaved in the presence of beta-D-glucuronidase with fast removal of the spacer, releasing paclitaxel. The arylamino spacer-containing prodrug, more stable than the corresponding nitro analogue, was selected for further studies.

  DOI：

  10.1016/j.bmc.2006.03.002
• 作为产物：
  描述：

  2'-O-{N-methyl-N-[4-(allyl (2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosid)uronate)-3-nitrobenzyloxycarbonyl]-2-aminoethyl}oxycarbonylpaclitaxel 在 吡啶 、 氟化氢吡啶 作用下， 反应 26.0h， 以75%的产率得到2'-O-{N-methyl-N-[4-(allyl β-D-glucopyranosiduronate)-3-nitrobenzyloxycarbonyl]-2-aminoethyl}oxycarbonylpaclitaxel
  参考文献：
  名称：

  New Taxol® (paclitaxel) prodrugs designed for ADEPT and PMT strategies in cancer chemotherapy

  摘要：

  Two new glucuronide paclitaxel prodrugs have been synthesized. Linked to the 2'-OH of the drug by a carbonate function, they include a self-immolative spacer bearing an arylnitro or arylamino group between the drug and the glucuronic acid residue. Both prodrugs were well detoxified and easily cleaved in the presence of beta-D-glucuronidase with fast removal of the spacer, releasing paclitaxel. The arylamino spacer-containing prodrug, more stable than the corresponding nitro analogue, was selected for further studies.

  DOI：

  10.1016/j.bmc.2006.03.002