2-[(1R,3S,4S)-4-ethenyl-4-methyl-3-prop-1-en-2-ylcyclohexyl]-N,N-bis(pyridin-2-ylmethyl)prop-2-en-1-amine | 1037218-35-1

• 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-[(1R,3S,4S)-4-ethenyl-4-methyl-3-prop-1-en-2-ylcyclohexyl]-N,N-bis(pyridin-2-ylmethyl)prop-2-en-1-amine
• CAS: 1037218-35-1
• 化学式: C₂₇H₃₅N₃
• 分子量: 401.595
• InChiKey: ZDMZXKSGBFBSJS-DURWQBQJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  29
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  13-chloro-β-elemene 、 二甲基吡啶胺 在 sodium hydroxide 作用下， 以 乙腈 为溶剂， 以87%的产率得到2-[(1R,3S,4S)-4-ethenyl-4-methyl-3-prop-1-en-2-ylcyclohexyl]-N,N-bis(pyridin-2-ylmethyl)prop-2-en-1-amine
  参考文献：
  名称：

  Synthesis and radiolabelling of Re(CO)₃-β-elemene derivatives as potential therapeutic radiopharmaceuticals

  摘要：

  β-榄香烯，(1S, 2S, 4R)-(-)-(1-甲基-1-乙烯基-2,4-二异亚丙烯基环己烷)是一种中草药抗癌剂。研究人员合成了三种新型 Re(CO)3-β 烯衍生物，包括含有 N,N,N三叉配体和三羰基铼的放射性共轭物（络合物 12、13、14）。红外光谱（IR）、1H-NMR 和 HRMS 对它们的结构进行了表征。三种衍生物（复合物 15、16、17）都获得了良好的放射性收率（90%以上）和 Re-188 放射性化学纯度（95%以上）。用 WST-1 方法评估了非放射性 β-烯-Re(CO)3 衍生物对 Lewis 肺癌细胞和 HeLa 细胞系的抗增殖活性。结果表明，与母体化合物 β-榄香烯相比，其 IC50 值大大降低。β-榄香烯三羰基铼共轭物的合成和放射性合成为寻找一种新的β-榄香烯放射性药物提供了可能。Copyright © 2009 John Wiley & Sons, Ltd. All Rights Reserved.

  DOI：

  10.1002/jlcr.1580

文献信息

• Synthesis and radiolabelling of Re(CO)₃-<i>β</i>-elemene derivatives as potential therapeutic radiopharmaceuticals
  作者：Yunfeng Ren、Yanhong Sun、Kangmin Cheng、Guifeng Liu、Yumei Shen

  DOI：10.1002/jlcr.1580

  日期：2009.5.15

  β-Elemene, (1S, 2S, 4R)-(−)-(1-methy-1-vinyl-2,4-diisopropenyl cyclohexane) is an anticancer agent from the Traditional Chinese Herb Medicinal. Three novel Re(CO)3-β-elemene derivatives including their radioactive conjugates containing N,N,N tridentate ligands and tricarbonyl rhenium (complex 12, 13, 14) were synthesized. Their structures were characterized by infrared (IR), 1H-NMR and HRMS. Good radioactive yield (above 90%) and radioactive chemical purity with Re-188 (above 95%) were obtained for all of the three derivatives (complex 15, 16, 17). The antiproliferative activity of non-radioactive β-elemene-Re(CO)3 derivatives on Lewis lung cancer cells and HeLa cell lines were evaluated by WST-1 methods. The result shows substantial decrease in IC50 values compared with the parent compound β-elemene. The synthesis and radiosynthesis of β-elemene tricarbonyl rhenium conjugates provide the possibility to find a new kind of potential radiopharmaceuticals on β-elemene. Copyright © 2009 John Wiley & Sons, Ltd.

  β-榄香烯，(1S, 2S, 4R)-(-)-(1-甲基-1-乙烯基-2,4-二异亚丙烯基环己烷)是一种中草药抗癌剂。研究人员合成了三种新型 Re(CO)3-β 烯衍生物，包括含有 N,N,N三叉配体和三羰基铼的放射性共轭物（络合物 12、13、14）。红外光谱（IR）、1H-NMR 和 HRMS 对它们的结构进行了表征。三种衍生物（复合物 15、16、17）都获得了良好的放射性收率（90%以上）和 Re-188 放射性化学纯度（95%以上）。用 WST-1 方法评估了非放射性 β-烯-Re(CO)3 衍生物对 Lewis 肺癌细胞和 HeLa 细胞系的抗增殖活性。结果表明，与母体化合物 β-榄香烯相比，其 IC50 值大大降低。β-榄香烯三羰基铼共轭物的合成和放射性合成为寻找一种新的β-榄香烯放射性药物提供了可能。Copyright © 2009 John Wiley & Sons, Ltd. All Rights Reserved.
• Synthesis and in vitro anti-proliferative activity of β-elemene monosubstituted derivatives in HeLa cells mediated through arrest of cell cycle at the G1 phase
  作者：Yanhong Sun、Guifeng Liu、Yuangqing Zhang、Hua Zhu、Yunfeng Ren、Yu-Mei Shen

  DOI：10.1016/j.bmc.2008.12.040

  日期：2009.2

  beta-Elemene monosubstituted amine, ether and rhenium coordinated complex were synthesized. Their structures were characterized by IR, H-1 NMR, C-13 NMR, HRMS or EA. Their IC50 on HeLa cell lines, cell cycle and protein expression of G(1) phase (Cyclin D-1, Rb, P-Rb) were detected respectively by the method of WST-1, Flow Cytometry and Western Blot. The Results showed that the in vitro anti-proliferative activity of beta-elemene monosubstituted amine and Re(CO)(3)-beta-elemene derivatives in human cervix epitheloid carcinoma HeLa cells were improved significantly compared with both of ether derivatives and parent beta-belemene. These derivatives could reduce Rb phosphorylation and cyclin D1 protein expression to arrest the cell cycle at G1 phase. (C) 2008 Elsevier Ltd. All rights reserved.