benzoic acid-4-cholesterylcarbamate | 402717-34-4

• 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: benzoic acid-4-cholesterylcarbamate
• 英文别名: 4-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxycarbonylamino]benzoic acid
• CAS: 402717-34-4
• 化学式: C₃₅H₅₁NO₄
• 分子量: 549.794
• InChiKey: PPHRDLHLCJIZJN-QDAKNDIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10
• 重原子数：
  40
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  75.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  胆固醇甲酰氯 、 对氨基苯甲酸 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以74%的产率得到benzoic acid-4-cholesterylcarbamate
  参考文献：
  名称：

  Cholesteryl-(l-Lactic Acid)_n̄ Building Blocks for Self-Assembling Biomaterials

  摘要：

  The synthesis and properties of a novel set of building blocks for the preparation of self-assembling biomaterials are described. These molecules consist of a relatively short oligo(L-lactic acid)((n) over bar) segment ((n) over bar = 10-40) that is substituted with a cholesterol moiety as an end group and in some cases has a second biofunctional substituent at its other terminus. The cholesterol moiety not only serves to induce liquid crystalline properties and drive the self-assembly of these oligomers, but also is expected to have an effect on the interaction of cells with these materials. The cholesteryl-(L-lactic acid)((n) over bar) (CLA((n) over bar)) oligomers form thermotropic liquid crystals and self-assemble into lamellar structures consisting of interdigitated bilayers. In addition, the CLA((n) over bar) oligomers can be homogeneously blended with poly(L-lactic acid), thereby offering the possibility to improve the cell interaction properties of this common surgical biomaterial. Furthermore, the secondary alcohol terminus of the CLA((n) over bar) oligomers allows the opportunity to introduce additional bioactive substituents such as cholesterol, indomethacin (an antiinflammatory drug), and pyrene and rhodamine B (which can act as fluorescent labels for bioimaging purposes) and various alpha-amino acids. These biofunctional CLA((n) over bar) oligomers can also be homogeneously mixed with the unsubstituted CLA((n) over bar) oligomers and thus could enable a further noncovalent functionalization of self-assembling biomaterials.

  DOI：

  10.1021/ma010907x