2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-10-Boc-7-imidazolylcarbonyl-10-deacetylcephalomannine | 1329497-65-5

• 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-imidazolylcarbonyl-10-deacetylcephalomannine
• CAS: 1329497-65-5
• 化学式: C₅₈H₇₄N₆O₁₆Si
• 分子量: 1139.34
• InChiKey: IGCRGESSTJSUSV-INOZVXDISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.64
• 重原子数：
  81.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  292.17
• 氢给体数：
  2.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-10-Boc-7-imidazolylcarbonyl-10-deacetylcephalomannine 在 吡啶 、 氢氟酸 、 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 、 异丙醇 、 乙腈 为溶剂， 反应 27.0h， 生成 [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-9-(dimethylcarbamoyloxy)-1,12-dihydroxy-15-[(2R,3S)-2-hydroxy-3-[[(E)-2-methylbut-2-enoyl]amino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-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-debenzoyl-2-m-N3-benzoylcephalomannine 在 咪唑 、 4-二甲氨基吡啶 、 cerium(III) chloride 、 一水合肼 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 33.17h， 生成 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-10-Boc-7-imidazolylcarbonyl-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