[2'R,3'S]-10-allyl-13-O-(3-tert-butoxycarbonylamino-2-O-triethylsilyl-3-phenylisoserinyl)-10-deacetoxy-7-O-triethylsilylbaccatin III | 325735-44-2

• 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'R,3'S]-10-allyl-13-O-(3-tert-butoxycarbonylamino-2-O-triethylsilyl-3-phenylisoserinyl)-10-deacetoxy-7-O-triethylsilylbaccatin III
• CAS: 325735-44-2
• 化学式: C₅₈H₈₅NO₁₃Si₂
• 分子量: 1060.48
• InChiKey: YDTYSRARMZQFDB-YSRWMIRKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.15
• 重原子数：
  74.0
• 可旋转键数：
  20.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  182.22
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  [2'R,3'S]-10-allyl-13-O-(3-tert-butoxycarbonylamino-2-O-triethylsilyl-3-phenylisoserinyl)-10-deacetoxy-7-O-triethylsilylbaccatin III 在 四氧化锇 、 N-甲基吲哚酮 、 sodium cyanoborohydride 、 氟化氢吡啶 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 水 为溶剂， 反应 26.0h， 生成 [2'R,3'S]-13-O-(3-tert-butoxycarbonylamino-3-phenylisoserinyl)-10-deacetoxy-10-[2-(1-homopiperidinyl)ethyl]baccatin III
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Non-Prodrug Water-soluble Taxoid: 10-C-Aminoalkylated Docetaxel Analogs

  摘要：

  To develop non-prodrugs of taxoids possessing satisfactory stability in vivo, high water solubility and potent antitumor activity, we prepared several 10-C-sec-aminoalkylated docetaxel analogs and evaluated their cytotoxicity against mouse leukemia and human tumor cell lines. These analogs were synthesized from a 10-deacetoxy-10-C-formylethyl baccatin derivative. Among these analogs, the 10-C-morpholinoethyl and 10-C-morpholinomethyl analogs exhibited cytotoxicity comparable or superior to that of docetaxel.

  DOI：

  10.3987/com-00-9051
• 作为产物：
  描述：

  10-deacetoxy-10-(3-methylthiopropyl)-7-O-triethylsilylbaccatin III 在 sodium periodate 、 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 水 、 邻二氯苯 为溶剂， 反应 8.0h， 生成 [2'R,3'S]-10-allyl-13-O-(3-tert-butoxycarbonylamino-2-O-triethylsilyl-3-phenylisoserinyl)-10-deacetoxy-7-O-triethylsilylbaccatin III
  参考文献：
  名称：

  Synthesis and Antitumor Activity of Non-Prodrug Water-soluble Taxoid: 10-C-Aminoalkylated Docetaxel Analogs

  摘要：

  To develop non-prodrugs of taxoids possessing satisfactory stability in vivo, high water solubility and potent antitumor activity, we prepared several 10-C-sec-aminoalkylated docetaxel analogs and evaluated their cytotoxicity against mouse leukemia and human tumor cell lines. These analogs were synthesized from a 10-deacetoxy-10-C-formylethyl baccatin derivative. Among these analogs, the 10-C-morpholinoethyl and 10-C-morpholinomethyl analogs exhibited cytotoxicity comparable or superior to that of docetaxel.

  DOI：

  10.3987/com-00-9051