10-deacetoxy-10-[2-(o-nitrophenylselenyl)ethyl]-7-O-triethylsilylbaccatin III | 325735-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 10-deacetoxy-10-[2-(o-nitrophenylselenyl)ethyl]-7-O-triethylsilylbaccatin III
• CAS: 325735-50-0
• 化学式: C₄₄H₅₉NO₁₁SeSi
• 分子量: 884.998
• InChiKey: XLERNSMAVGYUHT-RDVSHKRFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  58.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  171.73
• 氢给体数：
  2.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  10-deacetoxy-10-[2-(o-nitrophenylselenyl)ethyl]-7-O-triethylsilylbaccatin III 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 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
• 作为产物：
  描述：

  2-硝基苯基丝氰酸酯 、 10-deacetoxy-10-hydroxypropyl-7-O-triethylsilylbaccatin III 在 三丁基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以73%的产率得到10-deacetoxy-10-[2-(o-nitrophenylselenyl)ethyl]-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