2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-benzoyl-10-deacetylcephalomannine | 1329497-59-7

• 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'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-benzoyl-10-deacetylcephalomannine
• CAS: 1329497-59-7
• 化学式: C₄₉H₆₄N₄O₁₃Si
• 分子量: 945.152
• InChiKey: UTOKETLFSVUZPZ-YSEYRGLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.79
• 重原子数：
  67.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  252.98
• 氢给体数：
  4.0
• 氢受体数：
  14.0

反应信息

• 作为反应物：
  描述：

  2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-benzoyl-10-deacetylcephalomannine 在 4-吡咯烷基吡啶 、 N,N'-二环己基碳二亚胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Effects of C7 substitutions in a high affinity microtubule-binding taxane on antitumor activity and drug transport

  摘要：

  Some C-7 modified analogs of 3, a taxane with high affinity for binding to microtubules, were prepared through multistep transformations. Most of the analogs, bearing less lipophilic C-7 substituents than propionyl in 3, exhibited comparable binding affinities to microtubules but less cytotoxicity against drug-sensitive as well as multidrug-resistant tumor cells overexpressing P-glycoprotein. In addition, these C7 modifications increased P-glycoprotein-mediated drug transport in both directions in a Caco-2 cell assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.034
• 作为产物：
  描述：

  2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-benzoylcephalomannine 在 一水合肼 作用下， 以 乙醇 、 水 为溶剂， 反应 10.0h， 以89%的产率得到2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-benzoyl-10-deacetylcephalomannine
  参考文献：
  名称：

  Effects of C7 substitutions in a high affinity microtubule-binding taxane on antitumor activity and drug transport

  摘要：

  Some C-7 modified analogs of 3, a taxane with high affinity for binding to microtubules, were prepared through multistep transformations. Most of the analogs, bearing less lipophilic C-7 substituents than propionyl in 3, exhibited comparable binding affinities to microtubules but less cytotoxicity against drug-sensitive as well as multidrug-resistant tumor cells overexpressing P-glycoprotein. In addition, these C7 modifications increased P-glycoprotein-mediated drug transport in both directions in a Caco-2 cell assay. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.06.034

文献信息

• Isolation, identification, semi-synthesis of aziditaxel derivatives and their biological evaluation
  作者：Shu-En Zhang、Jia-Yi Tao、Ying Zhao、Shao-Rong Wang、Di Zhou、Wei-Shuo Fang

  DOI：10.1080/10286020.2012.672322

  日期：2012.5

  Two new taxoids (5 and 6) were obtained by isolating impurities in aziditaxel, and their structures were characterized based on data analysis of H-1 NMR, C-13 NMR, HPLC-MS, and through comparison with literature. In order to test their cytotoxicities against human nonsmall lung cancer cell lines (A549), sufficient amounts of compounds 5 and 6 were obtained by semi-synthesis and both of them showed equipotent cytotoxiesty compared with taxol, docetaxel, and aziditaxel.