N-[4-(cholest-5-en-3β-yloxycarbonyl)butyl]morpholine | 403507-48-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: N-[4-(cholest-5-en-3β-yloxycarbonyl)butyl]morpholine
• 英文别名: N-(4-cholesteryloxycarbonylbutyl)morpholine
• CAS: 403507-48-2
• 化学式: C₃₆H₆₁NO₃
• 分子量: 555.885
• InChiKey: LUBKJMNWRZFBTM-MKQVXYPISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.44
• 重原子数：
  40.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  38.77
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  哌嗪 、 N-[4-(cholest-5-en-3β-yloxycarbonyl)butyl]morpholine 在 sodium iodide 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 反应 3.0h， 以67%的产率得到N-(4-cholesteryloxycarbonylbutyl)piperazine
  参考文献：
  名称：

  摘要：

  A number of cationic derivatives of cholesterol containing polar residues of N-methylimidazole, pyridine, N-methylmorpholine, and 4-N,N-dimethyaminopyridine were synthesized by the interaction of the corresponding heterocyclic bases with cholesterol 5-bromopentanoate followed by the treatment with methyl iodide in the case of tertiary amines. In addition, N-(4-cholesteryloxycarbonylbutyl)piperazine was obtained for the preparation of pH-sensitive liposomes.

  DOI：

  10.1023/a:1012996921113
• 作为产物：
  描述：

  胆固醇 在 吡啶 、 sodium iodide 作用下， 以 氯仿 、 二甲基亚砜 为溶剂， 反应 58.0h， 生成 N-[4-(cholest-5-en-3β-yloxycarbonyl)butyl]morpholine
  参考文献：
  名称：

  摘要：

  A number of cationic derivatives of cholesterol containing polar residues of N-methylimidazole, pyridine, N-methylmorpholine, and 4-N,N-dimethyaminopyridine were synthesized by the interaction of the corresponding heterocyclic bases with cholesterol 5-bromopentanoate followed by the treatment with methyl iodide in the case of tertiary amines. In addition, N-(4-cholesteryloxycarbonylbutyl)piperazine was obtained for the preparation of pH-sensitive liposomes.

  DOI：

  10.1023/a:1012996921113

文献信息

• Facile synthesis of carbon-11-labeled cholesterol-based cationic lipids as new potential PET probes for imaging of gene delivery in cancer
  作者：Mingzhang Gao、Min Wang、Kathy D. Miller、George W. Sledge、Gary D. Hutchins、Qi-Huang Zheng

  DOI：10.1016/j.steroids.2010.04.009

  日期：2010.10

  gene delivery in cancer. The [(11)C-methyl]quaternary amine target tracers, N-[(11)C]methyl-N-[4-(cholest-5-en-3beta-yloxycarbonyl)butyl]pyrrolidinium iodide ([(11)C]4a), N-[(11)C]methyl-N'-[4-(cholest-5-en-3beta-yloxycarbonyl)butyl]imidazolium iodide ([(11)C]4b), N-[(11)C]methyl-N-[4-(cholest-5-en-3beta-yloxycarbonyl)butyl]piperidinium iodide ([(11)C]4c), N-[(11)C]methyl-N-[4-(cholest-5-en-3beta-yl

  基于基因传递的基因治疗是治疗各种人类疾病（如癌症）的有前途的策略。阳离子脂质代表重要的合成基因递送系统之一。人们对使用生物医学成像技术正电子发射断层扫描 (PET) 进行基因治疗的成像非常感兴趣。碳 11 标记的基于胆固醇的阳离子脂质首先被设计和合成为新的潜在 PET 探针，用于癌症基因传递的成像。[(11)C-甲基]季胺目标示踪剂，N-[(11)C]甲基-N-[4-(cholest-5-en-3β-yloxycarbonyl)丁基]吡咯烷鎓碘化物([(11)C ]4a), N-[(11)C] 甲基-N'-[4-(cholest-5-en-3beta-yloxycarbonyl) 丁基] 咪唑鎓碘化物 ([(11)C]4b), N-[(11) )C]甲基-N-[4-(cholest-5-en-3β-yloxycarbonyl)丁基]哌啶鎓碘化物([(11)C]4c)，
• Novel Cholesterol-Based Cationic Lipids for Gene Delivery
  作者：Darya A. Medvedeva、Mikhail A. Maslov、Roman N. Serikov、Nina G. Morozova、Galina A. Serebrenikova、Dmitry V. Sheglov、Alexander V. Latyshev、Valentin V. Vlassov、Marina A. Zenkova

  DOI：10.1021/jm901022t

  日期：2009.11.12

  Gene therapy based on gene delivery is a promising strategy for the treatment of human disease. Here we present data oil structure/biological activity of new biodegradable cholesterol-based cationic lipids with various heterocyclic cationic head groups and linker types. Enhanced accumulation of nucleic acids in the cells mediated by the lipids was demonstrated by fluorescent microscopy and flow cytometry. Light scattering and atomic force microscopy were used to find structure/transfection activity correlations for the lipids. We found that the ability of the lipids to stimulate intracellular accumulation of the oligodeoxyribonucleotides and plasmid DNA correlates well with their ability to form in solution lipid/NA complexes of sizes that do not exceed 100 nm. Screening of the lipids revealed the most promising transfection agents both in terms of low toxicity and efficient delivery: cholesterol-based lipids with positively charged pyridine and methyl imidazole head groups and either the ester or carbamate linker.