(2E,4E,6E,8E)-prop-2-yn-1-yl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate | 58508-30-8

• 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: (2E,4E,6E,8E)-prop-2-yn-1-yl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate
• 英文别名: vitamin A acid propargyl ester
• CAS: 58508-30-8
• 化学式: C₂₃H₃₀O₂
• 分子量: 338.49
• InChiKey: DUNQFULROOMZIM-FQNUCOOOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.69
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  26.3
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (2E,4E,6E,8E)-prop-2-yn-1-yl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate 、 1-azidooctane 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 水 、 叔丁醇 为溶剂， 反应 4.0h， 以67%的产率得到(2E,4E,6E,8E)-(1-octyl-1H-1,2,3-triazol-4-yl)methyl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate
  参考文献：
  名称：

  Promise of Retinoic Acid-Triazolyl Derivatives in Promoting Differentiation of Neuroblastoma Cells

  摘要：

  Retinoic acid induces differentiation in various types of cells including skeletal myoblasts and neuroblasts and maintains differentiation of epithelial cells. The present study demonstrates synthesis and screening of a library of retinoic acid-triazolyl derivatives for their differentiation potential on neuroblastoma cells. Click chemistry approach using copper (I)-catalyzed azide-alkyne cycloaddition was adopted for the preparation of these derivatives. The neurite outgrowth promoting potential of retinoic acid-triazolyl derivatives was studied on neuroblastoma cells. Morphological examination revealed that compounds 8a, 8e, 8f, and 8k, among the various derivatives screened, exhibited promising neurite-outgrowth inducing activity at a concentration of 10 mu M compared to undifferentiated and retinoic acid treated cells. Further on, to confirm this differentiation potential of these compounds, neuroblastoma cells were probed for expression of neuronal markers such as NF-H and NeuN. The results revealed a marked increase in the NF-H and NeuN protein expression when treated with 8a, 8e, 8f, and 8k compared to undifferentiated and retinoic acid treated cells. Thus, these compounds could act as potential leads in inducing neuronal differentiation for future studies.

  DOI：

  10.1021/acschemneuro.5b00267
• 作为产物：
  描述：

  维A酸 、 3-溴丙炔 在 caesium carbonate 作用下， 以 四氢呋喃 为溶剂， 以89%的产率得到(2E,4E,6E,8E)-prop-2-yn-1-yl 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoate
  参考文献：
  名称：

  Combating metastasis of breast cancer cells with a carboplatin analogue containing an all-trans retinoic acid ligand

  摘要：

  Pt-ATRA是一种含有全反式视黄酸衍生物配体的卡铂类似物，通过点击反应合成。Pt-ATRA具有双重功能，可以诱导细胞凋亡并抑制肿瘤转移。

  DOI：

  10.1039/d0dt00507j