10-acetyl-2-debenzoyl-2-(3-methyldisulfanylbenzoyl)-3'-dephenyl-3'-(2-methylprop-1-enyl)-7-triethylsilyl-2'-triisopropylsilyldocetaxel | 485801-55-6

• 英文名称: 10-acetyl-2-debenzoyl-2-(3-methyldisulfanylbenzoyl)-3'-dephenyl-3'-(2-methylprop-1-enyl)-7-triethylsilyl-2'-triisopropylsilyldocetaxel
• 英文别名: [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-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-9-triethylsilyloxy-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 3-(methyldisulfanyl)benzoate
• CAS: 485801-55-6
• 化学式: C₅₉H₉₃NO₁₅S₂Si₂
• 分子量: 1176.69
• InChiKey: RRCATSKIZKDFDQ-YSTFSKQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.02
• 重原子数：
  79
• 可旋转键数：
  27
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  259
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  10-acetyl-2-debenzoyl-2-(3-methyldisulfanylbenzoyl)-3'-dephenyl-3'-(2-methylprop-1-enyl)-7-triethylsilyl-2'-triisopropylsilyldocetaxel 在 氟化氢吡啶 作用下， 以 乙腈 为溶剂， 以98%的产率得到[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-1,9-dihydroxy-15-[(2R,3S)-2-hydroxy-5-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]hex-4-enoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 3-(methyldisulfanyl)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：

  10-acetyl-3'-dephenyl-3'-(2-methylprop-1-enyl)-7-triethylsilyl-2'-triisopropylsilyldocetaxel 在 4-二甲氨基吡啶 甲醇 、 苄基三甲基氢氧化铵 、 N,N'-二异丙基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 10-acetyl-2-debenzoyl-2-(3-methyldisulfanylbenzoyl)-3'-dephenyl-3'-(2-methylprop-1-enyl)-7-triethylsilyl-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