1-[(2E)-3,7-dimethylocta-2,6-dienyl]-4-[2-[6-[2-[4-[(2E)-3,7-dimethylocta-2,6-dienyl]piperazin-1-yl]ethyl]-5-oxahexacyclo[5.4.1.02,6.03,10.04,8.09,12]dodecan-4-yl]ethyl]piperazine | 1156536-67-2

• 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-[(2E)-3,7-dimethylocta-2,6-dienyl]-4-[2-[6-[2-[4-[(2E)-3,7-dimethylocta-2,6-dienyl]piperazin-1-yl]ethyl]-5-oxahexacyclo[5.4.1.02,6.03,10.04,8.09,12]dodecan-4-yl]ethyl]piperazine
• CAS: 1156536-67-2
• 化学式: C₄₃H₆₈N₄O
• 分子量: 657.039
• InChiKey: QQRLFYWNRLYXNU-YGUJLFRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  48
• 可旋转键数：
  16
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  22.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-geranylpiperazine 、 2-[6-[2-(4-methylphenyl)sulfonyloxyethyl]-5-oxahexacyclo[5.4.1.02,6.03,10.04,8.09,12]dodecan-4-yl]ethyl 4-methylbenzenesulfonate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 96.0h， 以71%的产率得到1-[(2E)-3,7-dimethylocta-2,6-dienyl]-4-[2-[6-[2-[4-[(2E)-3,7-dimethylocta-2,6-dienyl]piperazin-1-yl]ethyl]-5-oxahexacyclo[5.4.1.02,6.03,10.04,8.09,12]dodecan-4-yl]ethyl]piperazine
  参考文献：
  名称：

  Pentacyclo-undecane derived cyclic tetra-amines: Synthesis and evaluation as potent anti-tuberculosis agents

  摘要：

  As part of an ongoing effort to develop highly potent anti-tuberculosis agents, fourteen pentacycloundecane (PCU) tetra-amine compounds were synthesized and screened for their in vitro anti-mycobacterial activity against two TB strains, H37Rv and XDR 194 [an extensively drug-resistant strain of tuberculosis]. Using the broth macrodilution method, nitrofuranylamide based compounds (6a and 6b) showed almost similar activities against the H37Rv strain of Mycobacterium tuberculosis when compared with the control drug, ethambutol. N-Geranyl piperazine PCU (8a) and trans-trans farnesyl piperazine PCU (8b) were 3.2 and 3.7 times more potent than commercially available ethambutol. Both isoprenyl PCU tetra-amine derivatives and N-decyl piperazine PCU (9a) were highly active against the XDR 194 strain of tuberculosis with MICs in the range of 0.63-3.02 mu M. Cytotoxicities (IC50) of isoprenyl based compounds (8a, 8b) and compound 9a were tested on a mammalian cell line [MDBK (Madin Darby bovine kidney epithelium)] with values of 30, 24 and 25 mu M respectively. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.07.015