1,8,9,10,11,11-hexachloro-4,5-(exo)cis-dihydroxy-2,3-7,6-endo-2,1-7,8-exotetracyclo[6.2.1.1^3,6.0^2,7]dodec-9-ene | 30460-74-3

• 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: 1,8,9,10,11,11-hexachloro-4,5-(exo)cis-dihydroxy-2,3-7,6-endo-2,1-7,8-exotetracyclo[6.2.1.1^3,6.0^2,7]dodec-9-ene
• 英文别名: cis-aldrin diol；cis-Dihydroaldrindiol；(1S,2S,3R,4R,5S,6S,7R,8R)-1,8,9,10,11,11-hexachlorotetracyclo[6.2.1.13,6.02,7]dodec-9-ene-4,5-diol
• CAS: 30460-74-3
• 化学式: C₁₂H₁₀Cl₆O₂
• 分子量: 398.928
• InChiKey: NWRDBJRTQVHAKR-PICURKEMSA-N

物化性质

• 沸点：
  455.1±45.0 °C(Predicted)
• 密度：
  1.86±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  aldrin 在 吡啶 、 四氧化锇 、 甘露醇 、 potassium hydroxide 作用下， 以 乙醚 、 二氯甲烷 、 水 为溶剂， 以90%的产率得到1,8,9,10,11,11-hexachloro-4,5-(exo)cis-dihydroxy-2,3-7,6-endo-2,1-7,8-exotetracyclo[6.2.1.1^3,6.0^2,7]dodec-9-ene
  参考文献：
  名称：

  Cellular Localization of Dieldrin and Structure–Activity Relationship of Dieldrin Analogues in Dopaminergic Cells

  摘要：

  The incidence of Parkinson's disease (PD) correlates with environmental exposure to pesticides, such as the organochlorine insecticide, dieldrin. Previous studies found an increased concentration of the pesticide in the striatal region of the brains of PD patients and also that dieldrin adversely affects cellular processes associated with PD. These processes include mitochondrial function and reactive oxygen species production. However, the mechanism and specific cellular targets responsible for dieldrin-mediated cellular dysfunction and the structural components of dieldrin contributing to its toxicity (toxicophore) have not been fully defined. In order to identify the toxicophore of dieldrin, a structure-activity approach was used, with the toxicity profiles of numerous analogues of dieldrin (including aldrin, endrin, and cis-aldrin diol) assessed in PC6-3 cells. The MTT and lactate dehydrogenase (LDH) assays were used to monitor cell viability and membrane permeability after treatment with each compound. Cellular assays monitoring ROS production and extracellular dopamine metabolite levels were also used. Structure and stereochemistry for dieldrin were found to be very important for toxicity and other end points measured. Small changes in structure for dieldrin (e.g., comparison to the stereoisomer endrin) yielded significant differences in toxicity. Interestingly, the cis-diol metabolite of dieldrin was found to be significantly more toxic than the parent compound. Disruption of dopamine catabolism yielded elevated levels of the neurotoxin, 3,4-dihydroicyphenylacetaldehyde, for many organochlorines. Comparisons of the toxicity profiles for each dieldrin analogue indicated a structure-specific effect important for elucidating the mechanisms of dieldrin neurotoxicity.

  DOI：

  10.1021/tx300458b