3'-dephenyl-3'-(2-methylprop-1-enyl)-7-(3-methyldisulfanylpropanoyl)-10-propanoyl-2'-triisopropylsilyldocetaxel | 485801-35-2

• 英文名称: 3'-dephenyl-3'-(2-methylprop-1-enyl)-7-(3-methyldisulfanylpropanoyl)-10-propanoyl-2'-triisopropylsilyldocetaxel
• 英文别名: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1-hydroxy-10,14,17,17-tetramethyl-9-[3-(methyldisulfanyl)propanoyloxy]-15-[(2R,3S)-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-tri(propan-2-yl)silyloxyhex-4-enoyl]oxy-11-oxo-12-propanoyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
• CAS: 485801-35-2
• 化学式: C₅₇H₈₅NO₁₆S₂Si
• 分子量: 1132.52
• InChiKey: QBXSHQFQMNDVOC-DNQRLQICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.97
• 重原子数：
  77
• 可旋转键数：
  27
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  276
• 氢给体数：
  2
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  3'-dephenyl-3'-(2-methylprop-1-enyl)-7-(3-methyldisulfanylpropanoyl)-10-propanoyl-2'-triisopropylsilyldocetaxel 在 氟化氢吡啶 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以86%的产率得到[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1-hydroxy-15-[(2R,3S)-2-hydroxy-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]hex-4-enoyl]oxy-10,14,17,17-tetramethyl-9-[3-(methyldisulfanyl)propanoyloxy]-11-oxo-12-propanoyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Tumor-Specific Novel Taxoid−Monoclonal Antibody Conjugates

  摘要：

  Taxoids: bearing methyldisulfanyl(alkanoyl) groups for taxoid-antibody immunoconjugates were designed, synthesized and their activities evaluated. A highly cytotoxic C-10 methyldisuffanylpropanoyl taxoid was conjugated to monoclonal antibodies recognizing the epidermal growth factor receptor (EGFR) expressed in human squamous cancers. These conjugates were shown to possess remarkable target-specific antitumor activity in vivo against EGFR-expressing A431 tumor xenografts in severe combined immune deficiency mice, resulting in complete inhibition of tumor growth in all the treated mice.

  DOI：

  10.1021/jm025540g
• 作为产物：
  描述：

  [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1-hydroxy-10,14,17,17-tetramethyl-15-[(2R,3S)-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]-2-tri(propan-2-yl)silyloxyhex-4-enoyl]oxy-11-oxo-12-propanoyloxy-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate 在 4-二甲氨基吡啶 盐酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 3'-dephenyl-3'-(2-methylprop-1-enyl)-7-(3-methyldisulfanylpropanoyl)-10-propanoyl-2'-triisopropylsilyldocetaxel
  参考文献：
  名称：

  Tumor-Specific Novel Taxoid−Monoclonal Antibody Conjugates

  摘要：

  Taxoids: bearing methyldisulfanyl(alkanoyl) groups for taxoid-antibody immunoconjugates were designed, synthesized and their activities evaluated. A highly cytotoxic C-10 methyldisuffanylpropanoyl taxoid was conjugated to monoclonal antibodies recognizing the epidermal growth factor receptor (EGFR) expressed in human squamous cancers. These conjugates were shown to possess remarkable target-specific antitumor activity in vivo against EGFR-expressing A431 tumor xenografts in severe combined immune deficiency mice, resulting in complete inhibition of tumor growth in all the treated mice.

  DOI：

  10.1021/jm025540g