(3R,4S)-1-tert-butoxycarbonyl-3-[(triethylsilyl)oxy]-4-(furan-2-yl)-3-methyl-azetidinone | 496918-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酰胺类
• 英文名称: (3R,4S)-1-tert-butoxycarbonyl-3-[(triethylsilyl)oxy]-4-(furan-2-yl)-3-methyl-azetidinone
• 英文别名: tert-butyl (2S,3R)-2-(furan-2-yl)-3-methyl-4-oxo-3-triethylsilyloxyazetidine-1-carboxylate
• CAS: 496918-71-9
• 化学式: C₁₉H₃₁NO₅Si
• 分子量: 381.544
• InChiKey: OGZMOQRNYKWTKC-HNAYVOBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.88
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  69
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3R,4S)-1-tert-butoxycarbonyl-3-[(triethylsilyl)oxy]-4-(furan-2-yl)-3-methyl-azetidinone 在 吡啶 、 氢氟酸 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 6.17h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3R)-3-(furan-2-yl)-2-hydroxy-2-methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2‘-Methyl Taxoids Derived from Baccatin III and 14β-OH-Baccatin III 1,14-Carbonate

  摘要：

  A series of 2'-methyl taxoids were synthesized and essayed for growth inhibition experiments conducted in human ovarian cancer cell line A2780wt and its counterparts A2780cis, A2780tax, and A2780adr, resistant to cisplatin, paclitaxel, and doxorubicin, respectively, to test the effect of this substituent on the antitumor activity. Additional experiments were performed on MCF-7 human breast cancer cell line and MCF7-R resistant to doxorubicin. In several cases these taxoids were more active than paclitaxel showing subnanomolar IC50 values.

  DOI：

  10.1021/jm034146v
• 作为产物：
  描述：

  (furan-2-ylmethylene)(trimethylsilanyl)amine 在 咪唑 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成 (3R,4S)-1-tert-butoxycarbonyl-3-[(triethylsilyl)oxy]-4-(furan-2-yl)-3-methyl-azetidinone
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2‘-Methyl Taxoids Derived from Baccatin III and 14β-OH-Baccatin III 1,14-Carbonate

  摘要：

  A series of 2'-methyl taxoids were synthesized and essayed for growth inhibition experiments conducted in human ovarian cancer cell line A2780wt and its counterparts A2780cis, A2780tax, and A2780adr, resistant to cisplatin, paclitaxel, and doxorubicin, respectively, to test the effect of this substituent on the antitumor activity. Additional experiments were performed on MCF-7 human breast cancer cell line and MCF7-R resistant to doxorubicin. In several cases these taxoids were more active than paclitaxel showing subnanomolar IC50 values.

  DOI：

  10.1021/jm034146v

文献信息

• Synthesis and Biological Evaluation of 2‘-Methyl Taxoids Derived from Baccatin III and 14β-OH-Baccatin III 1,14-Carbonate
  作者：Arturo Battaglia、Ralph J. Bernacki、Carlo Bertucci、Ezio Bombardelli、Samanta Cimitan、Cristiano Ferlini、Gabriele Fontana、Andrea Guerrini、Antonella Riva

  DOI：10.1021/jm034146v

  日期：2003.11.1

  A series of 2'-methyl taxoids were synthesized and essayed for growth inhibition experiments conducted in human ovarian cancer cell line A2780wt and its counterparts A2780cis, A2780tax, and A2780adr, resistant to cisplatin, paclitaxel, and doxorubicin, respectively, to test the effect of this substituent on the antitumor activity. Additional experiments were performed on MCF-7 human breast cancer cell line and MCF7-R resistant to doxorubicin. In several cases these taxoids were more active than paclitaxel showing subnanomolar IC50 values.