1-[2-(4-fluorophenyl)tricyclo[3.3.1.1^3,7]dec-2-yl]piperazine maleate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-[2-(4-fluorophenyl)tricyclo[3.3.1.1^3,7]dec-2-yl]piperazine maleate
• 英文别名: (Z)-but-2-enedioic acid;1-[2-(4-fluorophenyl)-2-adamantyl]piperazine
• 化学式: C₄H₄O₄*C₂₀H₂₇FN₂
• 分子量: 430.52
• InChiKey: FDVDFDJOFOKYKF-BTJKTKAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.09
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  89.9
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  溴乙酰氯 、 1-[2-(4-fluorophenyl)tricyclo[3.3.1.1^3,7]dec-2-yl]piperazine maleate 在 potassium carbonate 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Novel 1-(2-aryl-2-adamantyl)piperazine derivatives with antiproliferative activity

  摘要：

  Novel 1-(2-aryl-2-adamantyl)piperazine derivatives have been synthesized and evaluated in vitro for their antitumor properties against HeLa cervical carcinoma, MDA MB 231 breast cancer, MIA PaCa2 pancreatic cancer, and NCI H1975 non-small cell lung cancer. The parent piperazine 6 was found to exhibit a reasonable activity toward the HeLa and MDA MB 231 tumor cell lines (IC50=9.2 and 8.4 mu M, respectively). Concurrent benzene ring C4-fluorination and piperidine acetylation of the piperazino NH of compound 6 resulted in the most active compound 13 of the series in both of the above cell lines (IC50=8.4 and 6.8 mu M, respectively). Noticeably, compounds 6 and 13 exhibited a significantly low cytotoxicity level over the normal human cells HUVEC (Human Umbilical Vein Endothelial Cells) and NHDF (Normal Human Dermal Fibroblasts). (C) 2015 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2015.02.021
• 作为产物：
  描述：

  2-chloro-2-(4'-fluorophenyl)adamantane 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 20.0~105.0 ℃ 、344.75 kPa 条件下， 反应 13.33h， 生成 1-[2-(4-fluorophenyl)tricyclo[3.3.1.1^3,7]dec-2-yl]piperazine maleate
  参考文献：
  名称：

  Novel 1-(2-aryl-2-adamantyl)piperazine derivatives with antiproliferative activity

  摘要：

  Novel 1-(2-aryl-2-adamantyl)piperazine derivatives have been synthesized and evaluated in vitro for their antitumor properties against HeLa cervical carcinoma, MDA MB 231 breast cancer, MIA PaCa2 pancreatic cancer, and NCI H1975 non-small cell lung cancer. The parent piperazine 6 was found to exhibit a reasonable activity toward the HeLa and MDA MB 231 tumor cell lines (IC50=9.2 and 8.4 mu M, respectively). Concurrent benzene ring C4-fluorination and piperidine acetylation of the piperazino NH of compound 6 resulted in the most active compound 13 of the series in both of the above cell lines (IC50=8.4 and 6.8 mu M, respectively). Noticeably, compounds 6 and 13 exhibited a significantly low cytotoxicity level over the normal human cells HUVEC (Human Umbilical Vein Endothelial Cells) and NHDF (Normal Human Dermal Fibroblasts). (C) 2015 Published by Elsevier Masson SAS.

  DOI：

  10.1016/j.ejmech.2015.02.021

文献信息

• Novel 1-(2-aryl-2-adamantyl)piperazine derivatives with antiproliferative activity
  作者：Christos Fytas、Grigoris Zoidis、Andrew Tsotinis、George Fytas、Mohsin A. Khan、Samar Akhtar、Khondaker M. Rahman、David E. Thurston

  DOI：10.1016/j.ejmech.2015.02.021

  日期：2015.3

  Novel 1-(2-aryl-2-adamantyl)piperazine derivatives have been synthesized and evaluated in vitro for their antitumor properties against HeLa cervical carcinoma, MDA MB 231 breast cancer, MIA PaCa2 pancreatic cancer, and NCI H1975 non-small cell lung cancer. The parent piperazine 6 was found to exhibit a reasonable activity toward the HeLa and MDA MB 231 tumor cell lines (IC50=9.2 and 8.4 mu M, respectively). Concurrent benzene ring C4-fluorination and piperidine acetylation of the piperazino NH of compound 6 resulted in the most active compound 13 of the series in both of the above cell lines (IC50=8.4 and 6.8 mu M, respectively). Noticeably, compounds 6 and 13 exhibited a significantly low cytotoxicity level over the normal human cells HUVEC (Human Umbilical Vein Endothelial Cells) and NHDF (Normal Human Dermal Fibroblasts). (C) 2015 Published by Elsevier Masson SAS.