N-(trans-trans-farnesyl)piperazine | 55436-89-0

• 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: N-(trans-trans-farnesyl)piperazine
• 英文别名: 1-(3,7,11-Trimethyl-2,6,10-dodecatrienyl)piperazine；1-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]piperazine
• CAS: 55436-89-0
• 化学式: C₁₉H₃₄N₂
• 分子量: 290.492
• InChiKey: LUESRGDNECYQIC-ZYCAGONGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  N-(trans-trans-farnesyl)piperazine 、 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63%的产率得到1-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]-4-[2-[6-[2-[4-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]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
• 作为产物：
  描述：

  哌嗪 、 反,反-法呢基溴 以 二氯甲烷 为溶剂， 反应 24.75h， 以65%的产率得到N-(trans-trans-farnesyl)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

文献信息

• US4213985A
  申请人：——

  公开号：US4213985A

  公开（公告）日：1980-07-22
• 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.