8-(4-phenylpiperazin-1-yl)octyl 2-[(5R,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoate | 1365733-25-0

• 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: 8-(4-phenylpiperazin-1-yl)octyl 2-[(5R,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoate
• CAS: 1365733-25-0
• 化学式: C₃₃H₄₈N₂O₃
• 分子量: 520.756
• InChiKey: PFJGQZIBNINLHB-PUFWETDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  38
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  一枝蒿酮酸 在 苄基三乙基氯化铵 、 potassium carbonate 、 sodium hydroxide 作用下， 以 氯仿 、 水 、 乙腈 为溶剂， 生成 8-(4-phenylpiperazin-1-yl)octyl 2-[(5R,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoate
  参考文献：
  名称：

  Synthesis and anti-influenza activity of aminoalkyl rupestonates

  摘要：

  A series of aminoalkyl rupestonates were designed and synthesized by reacting rupestonic acid with 1,omega-dibromoalkanes, followed by amination. All of the new compounds were bioassayed in vitro to determine their activities against influenza A (H3N2, H1N1) and B viruses. The results showed that compounds 5a-5g, which each contain a 1H-1,2,4-triazolyl moiety, were found to be the most potent set of compounds. Compound 5g was demonstrated to possess the highest inhibitory activity against influenza H3N2 and H1N1, with IC50 values of 0.97 and 0.42 mu M, respectively. Our results also indicated that compounds 2g, 3g, 4g and 5g, which contain ten-CH2-unit spacers between the rupestonic acid and amino functional groups, were the most potent inhibitors of influenza H1N1 among the synthesized compounds. Unfortunately, most of the synthesized compounds did not show an obvious activity against influenza B; the only exceptions were compounds 5d and 5f, which had IC50 values of 17.3 and 3.2 mu M, respectively. Compounds 4g and 5g were potent inhibitors of influenza H1N1, and they might be potentially developed as new lead anti-influenza virus compounds. Further studies of the mechanism of action are underway. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.01.056

文献信息

• Synthesis and anti-influenza activity of aminoalkyl rupestonates
  作者：Jiangyu Zhao、Haji Akber Aisa

  DOI：10.1016/j.bmcl.2012.01.056

  日期：2012.3

  A series of aminoalkyl rupestonates were designed and synthesized by reacting rupestonic acid with 1,omega-dibromoalkanes, followed by amination. All of the new compounds were bioassayed in vitro to determine their activities against influenza A (H3N2, H1N1) and B viruses. The results showed that compounds 5a-5g, which each contain a 1H-1,2,4-triazolyl moiety, were found to be the most potent set of compounds. Compound 5g was demonstrated to possess the highest inhibitory activity against influenza H3N2 and H1N1, with IC50 values of 0.97 and 0.42 mu M, respectively. Our results also indicated that compounds 2g, 3g, 4g and 5g, which contain ten-CH2-unit spacers between the rupestonic acid and amino functional groups, were the most potent inhibitors of influenza H1N1 among the synthesized compounds. Unfortunately, most of the synthesized compounds did not show an obvious activity against influenza B; the only exceptions were compounds 5d and 5f, which had IC50 values of 17.3 and 3.2 mu M, respectively. Compounds 4g and 5g were potent inhibitors of influenza H1N1, and they might be potentially developed as new lead anti-influenza virus compounds. Further studies of the mechanism of action are underway. (C) 2012 Elsevier Ltd. All rights reserved.