2-debenzoyl-2-m-N3-benzoylcephalomannine | 959963-38-3

• 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-debenzoyl-2-m-N3-benzoylcephalomannine
• CAS: 959963-38-3
• 化学式: C₄₅H₅₂N₄O₁₄
• 分子量: 872.926
• InChiKey: OHSFSPLKGXCTIW-ATOQOJRGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.33
• 重原子数：
  63.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  270.05
• 氢给体数：
  4.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  2-debenzoyl-2-m-N3-benzoylcephalomannine 在 咪唑 、 一水合肼 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.17h， 生成 2'-O-(t-butyldimethylsilyl)-2-debenzoyl-2-m-N3-10-O-trimethylsilyl-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
• 作为产物：
  描述：

  2'-O-(t-butyldimethylsilyl)-7-O-(triethylsilyl)cephalomannine 在 吡啶 、 4-二甲氨基吡啶 、 氢氟酸 、 苄基三甲基氢氧化铵 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 二氯甲烷 、 水 、 甲苯 、 乙腈 为溶剂， 反应 87.5h， 生成 2-debenzoyl-2-m-N3-benzoylcephalomannine
  参考文献：
  名称：

  Isolation, identification, semi-synthesis of aziditaxel derivatives and their biological evaluation

  摘要：

  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.

  DOI：

  10.1080/10286020.2012.672322