4-N-[1,1',2-tris-nor-squalenoyl] 1-β-D-arabinofuranosylcytosine | 915978-85-7

• 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: 4-N-[1,1',2-tris-nor-squalenoyl] 1-β-D-arabinofuranosylcytosine
• 英文别名: 4-N-[(4E,8E,12E,16E)-4,8,13,17,21-pentamethyl-4,8,12,16,20-docosapentaenoyl] 1-β-D-arabinofuranosylcytosine
• CAS: 915978-85-7
• 化学式: C₃₆H₅₅N₃O₆
• 分子量: 625.849
• InChiKey: MWVGYQKDTSFGSN-LZCZMJEWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  45.0
• 可旋转键数：
  18.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  133.91
• 氢给体数：
  4.0
• 氢受体数：
  8.0

反应信息

• 作为产物：
  描述：

  4,8,13,17,21-五甲基-4,8,12,16,20-二十二碳五烯酸 、 阿糖胞苷 在 氯甲酸乙酯 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.33h， 以56%的产率得到4-N-[1,1',2-tris-nor-squalenoyl] 1-β-D-arabinofuranosylcytosine
  参考文献：
  名称：

  Synthesis of n-squalenoyl cytarabine and evaluation of its affinity with phospholipid bilayers and monolayers

  摘要：

  Cytarabine (1-beta-D-arabinofuranosylcytosine, Ara-C), a pyrimidine nucleoside analogue, is an attractive therapeutic agent for the treatment of both acute and chronic myeloblastic leukemias. 1,1',2-tris-nor-Squalene acid (squaleneCOOH) has been conjugated to cytarabine with the formation of the squalenoyl-cytarabine prodrug, in order to improve the drug lipophilicity and, consequently, the affinity towards the environment of biological membranes, as well as of lipophilic carriers.The interaction of cytarabine and its prodrug with dimyristoylphosphatidylcholine (DMPC) multilamellar vesicles and monolayers has been studied by the differential scanning calorimetry and the Langmuir-Blodgett techniques. The interaction has been evaluated considering the effect of the compounds on the DMPC MLV and monolayers behaviour. The aim was to have information on the interaction of the drug and the prodrug with the biological membranes and on the possibility to use liposomes as carriers for the prodrug. The results showed an improved affinity of the prodrug with MLV and monolayers with respect to the free drug. (c) 2011 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.ijpharm.2010.12.038