2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-10-Boc-7-methylaminocarbonyl-10-deacetylcephalomannine | 1329497-66-6

• 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-N3-10-Boc-7-methylaminocarbonyl-10-deacetylcephalomannine
• CAS: 1329497-66-6
• 化学式: C₅₆H₇₅N₅O₁₆Si
• 分子量: 1102.32
• InChiKey: WJEKISANVQAEOC-BKAXCJIQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.11
• 重原子数：
  78.0
• 可旋转键数：
  14.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  286.38
• 氢给体数：
  3.0
• 氢受体数：
  17.0

反应信息

• 作为反应物：
  描述：

  2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-10-Boc-7-methylaminocarbonyl-10-deacetylcephalomannine 在 吡啶 、 氢氟酸 、 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,12-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-9-(methylcarbamoyloxy)-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] 3-azidobenzoate
  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-N3-10-Boc-10-deacetylcephalomannine 在 4-二甲氨基吡啶 作用下， 以 异丙醇 、 甲苯 为溶剂， 反应 5.5h， 生成 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-10-Boc-7-methylaminocarbonyl-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