(E)-1,8-dinitro-p-menthane | 58940-69-5

• 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: (E)-1,8-dinitro-p-menthane
• CAS: 58940-69-5
• 化学式: C₁₀H₁₈N₂O₄
• 分子量: 230.264
• InChiKey: LYCLFSQGNXXOON-CZMCAQCFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.27
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.28
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (E)-1,8-dinitro-p-menthane 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 70.0 ℃ 、101.33 kPa 条件下， 反应 64.33h， 生成 N1,N8-bis<3-(o-allylphenoxy)-2-hydroxypropyl>-(E)-1,8-diamino-p-menthane
  参考文献：
  名称：

  Alkylating .beta.-blockers: activity of isomeric bromoacetyl alprenolol menthanes

  摘要：

  An affinity label for beta-adrenoceptors, N-(bromoacetyl)-N'-[3-(o-allylphenoxy)-2-hydroxypropyl]-1,8-dia min o-p-menthane, has been extensively used in the form of a mixture of four isomers. In the present study, all four isomers were isolated, their structures elucidated, and their interactions with beta-adrenoceptors characterized. The isomer with the aromatic (pharmacophore) group on carbon 1 of p-menthane and with the Z configuration (Z-1) predominates in the mixture and has the highest affinity for beta-adrenoceptors of rat heart (KD = 3 X 10(-8) M) and lungs (KD = 2 X 10(-8) M). This isomer acts as a ligand that binds irreversibly at the drug binding site of the receptor (i.e., after treatment and extensive washing of the membrane preparation, the concentration of the receptors is decreased in a dose-dependent manner), while binding characteristics of the remaining receptors are not changed. The corresponding E diastereomer (E-1) also binds irreversibly to the drug binding site of the receptor. The isomer with the aromatic group on carbon 8 and the Z configuration (Z-8) modifies the receptor noticeably only at higher concentrations and then on a site apparently different from the drug-binding site, i.e., affinity of receptors after the treatment and washing is changed. The corresponding E diastereomer (E-8) modified both the drug-binding and alternative binding site. The results suggest that there is some flexibility in the conformation of the beta-adrenoceptor that enables pairs of ligands, differing by axial or equatorial positions of critical groups, to alkylate the receptor in an analogous manner.

  DOI：

  10.1021/jm00149a028