cholesteryl hydrazinecarboxylate | 539792-23-9

• 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: cholesteryl hydrazinecarboxylate
• 英文别名: 3β-[N-(hydrazino)carbamoyl]cholesterol
• CAS: 539792-23-9
• 化学式: C₂₈H₄₈N₂O₂
• 分子量: 444.701
• InChiKey: YBXRLGPSORAJGZ-JDTILAPWSA-N

物化性质

• 熔点：
  225-227 °C(Solv: chloroform (67-66-3); methanol (67-56-1))
• 沸点：
  556.1±20.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.0
• 重原子数：
  32.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  64.35
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  cholesteryl hydrazinecarboxylate 、 4-马来酰亚胺基丁酸-N-琥珀酰亚胺酯 以 氯仿 为溶剂， 以85%的产率得到3β-[N-(hydrazino-γ-maleimidobutyryl)carbamoyl]cholesterol
  参考文献：
  名称：

  Effect of Poly(ethylene glycol) Spacer on Peptide-Decorated Hepatocellular Carcinoma-Targeted Lipoplexes <I>In Vitro</I>

  摘要：

  肝细胞癌（HCC）是癌症相关死亡的主要原因，在乙型肝炎高发地区尤为普遍。传统治疗方法主要限于外科手术和经导管化学栓塞。然而，噬菌体展示文库的生物筛选已经发现了极具选择性的HCC靶向肽，这些肽可与阳离子脂质体结合，以非病毒方式将治疗性DNA输送到受影响的细胞，从而为开发新的基因治疗手段奠定了基础。在这项研究中，一种半胱氨酸化的HCC趋化肽通过一种新型膜内嵌马来酰亚胺胆固醇衍生物3β-[N-(肼基-γ-马来酰亚胺丁酰基)-氨基甲酰]胆固醇（Chol-Mal）或中间聚（乙二醇）间隔元素，直接与阳离子脂质体结合，其中包含细胞因子3β-[N-(N′-,N′-二甲基氨基丙基氨基)-氨基甲酰]-胆固醇（Chol-T）和二油磷脂酰乙醇胺。研究人员研究了亲水性聚合物对人类肝癌细胞系HepG2中靶向脂质复合物介导的基因传递的影响。结果表明，两种系统都能结合DNA并以相同的效率转染该细胞系，而人类胚胎肾细胞HEK293中的转基因表达水平较低，与HepG2细胞中的竞争性测定和用杂肽修饰的脂质复合物所达到

  DOI：

  10.1166/jnn.2015.9825
• 作为产物：
  描述：

  胆固醇甲酰氯 在 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 cholesteryl hydrazinecarboxylate
  参考文献：
  名称：

  New triangular steroid-based A(LS)₃ type gelators for selective fluoride sensing application

  摘要：

  一种新系列的三角形类固醇基A(LS)₃型凝胶剂已经开发出来，展现出选择性的氟离子感应能力。这些凝胶剂的凝胶化、自组装和阴离子感应性质可以通过系统地改变它们的分子结构来控制。

  DOI：

  10.1039/c4ra03070b

文献信息

• Preparation of substituted semicarbazides from corresponding amines and hydrazines via phenyl carbamates
  作者：Rebecca Hron、Branko S. Jursic

  DOI：10.1016/j.tetlet.2014.01.052

  日期：2014.2

  A simple synthetic procedure for the conversion of amines and hydrazines into substituted semicarbazides was developed. The initial condensation between the desired amine and phenyl chloroformate into phenyl carbamate is followed by the addition of hydrazine under basic conditions. The reaction is tolerable to a variety of functional groups, with mild conditions and high percent yields.

  开发了一种简单的合成方法，用于将胺和肼转化为取代的氨基脲。所需的胺和氯甲酸苯酯之间最初的缩合成氨基甲酸苯酯，然后在碱性条件下加入肼。该反应可耐受各种官能团，条件温和，收率高。
• Charge-Transfer-Assisted Supramolecular 1 D Nanofibers through a Cholesteric Structure-Directing Agent: Self-Assembly Design for Supramolecular Optoelectronic Materials
  作者：Thunga Madhu Babu、Edamana Prasad

  DOI：10.1002/chem.201502275

  日期：2015.8.17

  cholesterol unit resulted in the formation of a conducting material (1.9472×10−4 S Cm−1) due to the formation of 1 D nanofibers. X‐ray diffraction, IR, and atomic force microscopic (AFM) techniques were used to establish the mechanism of the self‐assembly of the multicomponent gels. Results indicate efficient charge transfer in the 1 D nanofibers, assisted by hydrogen bonding.

  自组装的芘丁酸（PBA）和2,4,7-三硝基-9- ħ被吡啶联胆固醇单元引导芴-9-酮（TNF）产生了一个导电材料的形成（1.9472×10 -4  S Cm -1）由于形成了1 D纳米纤维。X射线衍射，IR和原子力显微镜（AFM）技术用于建立多组分凝胶自组装的机理。结果表明，在氢键的辅助下，一维纳米纤维中的电荷有效转移。
• Cholesteryl derivatives as phase-selective gelators at room temperature
  作者：Min Xue、Di Gao、Kaiqiang Liu、Junxia Peng、Yu Fang

  DOI：10.1016/j.tet.2009.02.056

  日期：2009.4

  One cholesterol-based ALS and two dimeric cholesterol-based A(LS)(2) low-molecular-mass organic gelators (LMOGs) containing phthaloyl, isophthaloyl, and terephthaloyl moieties, respectively, were prepared. Gelation test revealed that 2 and 3 are more efficient gelators than 1. Interestingly, 2 and 3 can gel several solvents spontaneously at room temperature and these gels posses thixotropic properties as revealed by theological studies. More interestingly, 2 and 3 show selective gelation of the solvents from their mixtures with water. The network structures of some gels were investigated by SEM measurements, and the molecular packing mode of the LMOGs in the gel was studied by XRD analysis. Temperature-and concentration-dependent H-1 NMR measurements revealed that hydrogen bonding between the gelator molecules is an important driving force for the gel formation. (C) 2009 Elsevier Ltd. All rights reserved.