2-[Benzyl-[2-[6-[2-[benzyl(2-hydroxyethyl)amino]ethyl]-5-oxahexacyclo[5.4.1.02,6.03,10.04,8.09,12]dodecan-4-yl]ethyl]amino]ethanol | 1093072-61-7

• 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: 2-[Benzyl-[2-[6-[2-[benzyl(2-hydroxyethyl)amino]ethyl]-5-oxahexacyclo[5.4.1.02,6.03,10.04,8.09,12]dodecan-4-yl]ethyl]amino]ethanol
• CAS: 1093072-61-7
• 化学式: C₃₃H₄₂N₂O₃
• 分子量: 514.708
• InChiKey: HDJMZWWBVRQRNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  56.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-苄基乙醇胺 、 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70%的产率得到2-[Benzyl-[2-[6-[2-[benzyl(2-hydroxyethyl)amino]ethyl]-5-oxahexacyclo[5.4.1.02,6.03,10.04,8.09,12]dodecan-4-yl]ethyl]amino]ethanol
  参考文献：
  名称：

  作为潜在抗结核药物的新型五环十一烷胺衍生物的合成和核磁共振分析

  摘要：

  报道了五种新型五环十一烷胺衍生物的合成和核磁共振分析。这些化合物是潜在的抗结核药物。1H 和 13C 光谱显示笼骨架的次甲基信号主要重叠，因此很难阐明这些化合物。重叠是由于笼子的羰基碳 (C-8/C-11) 的添加而发生的。二维核磁共振技术被证明是克服这个问题的有用工具。报道的所有化合物都是内消旋化合物，因此不仅简化了 NMR 结构解析，而且确实使之成为可能。版权所有 © 2008 John Wiley & Sons, Ltd.

  DOI：

  10.1002/mrc.2305

文献信息

• Synthesis and NMR elucidation of novel penta-cycloundecane amine derivatives as potential antituberculosis agents
  作者：Oluseye K. Onajole、Thavendran Govender、Maya Makatini、Hendrik G. Kruger

  DOI：10.1002/mrc.2305

  日期：2008.11

  The synthesis and NMR elucidation of five novel penta‐cycloundecane amine derivatives are reported. These compounds are potential antituberculosis agents. The 1H and 13C spectra showed major overlapping of methine signals of the cage skeleton making it extremely difficult to elucidate these compounds. The overlapping occurs as a result of the additions made to the carbonyl carbon (C‐8/C‐11) of the

  报道了五种新型五环十一烷胺衍生物的合成和核磁共振分析。这些化合物是潜在的抗结核药物。1H 和 13C 光谱显示笼骨架的次甲基信号主要重叠，因此很难阐明这些化合物。重叠是由于笼子的羰基碳 (C-8/C-11) 的添加而发生的。二维核磁共振技术被证明是克服这个问题的有用工具。报道的所有化合物都是内消旋化合物，因此不仅简化了 NMR 结构解析，而且确实使之成为可能。版权所有 © 2008 John Wiley & Sons, Ltd.
• Pentacyclo-undecane derived cyclic tetra-amines: Synthesis and evaluation as potent anti-tuberculosis agents
  作者：Oluseye K. Onajole、Karnishree Govender、Patrick Govender、Paul D. van Helden、Hendrik G. Kruger、Glenn E.M. Maguire、Karen Muthusamy、Manormoney Pillay、Ian Wiid、Thavendran Govender

  DOI：10.1016/j.ejmech.2009.07.015

  日期：2009.11

  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.