2-bromoethyl 2-[(5R,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoate | 1365733-00-1

• 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-bromoethyl 2-[(5R,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoate
• CAS: 1365733-00-1
• 化学式: C₁₇H₂₃BrO₃
• 分子量: 355.272
• InChiKey: IUCROGWWIDLFII-GDLCADMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromoethyl 2-[(5R,8S,8aS)-3,8-dimethyl-2-oxo-4,5,6,7,8,8a-hexahydro-1H-azulen-5-yl]prop-2-enoate 在 silver nitrate 作用下， 以 乙腈 为溶剂， 以60%的产率得到C₁₇H₂₃NO₆
  参考文献：
  名称：

  Synthesis of Rupestonic Acid Derivatives with Antiviral Activity

  摘要：

  研究人员合成了一系列 23 种新的芦贝甾酸衍生物。研究了它们对甲型流感病毒（H3N2、H1N1）和乙型流感病毒的活性。化合物 2d 和 2g 对甲型流感病毒（H3N2）具有强效活性，IC50 值分别为 0.35 和 0.21 μM。化合物 5g（n = 10）是该系列中对 H3N2 和 H1N1 流感病毒最有效的化合物，其 IC50 值分别为 2.89 和 0.38 μM。合成的几种化合物对 B 型流感病毒的活性较弱，且毒性高于起始的芦贝糖醛酸。

  DOI：

  10.1007/s10600-017-1970-y
• 作为产物：
  描述：

  1,2-二溴乙烷 、 一枝蒿酮酸 在 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 氯仿 、 水 为溶剂， 以64%的产率得到2-bromoethyl 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.
• Synthesis of Rupestonic Acid Derivatives with Antiviral Activity
  作者：Jiangyu Zhao、Chao Niu、Gen Li、Haji Akber Aisa

  DOI：10.1007/s10600-017-1970-y

  日期：2017.3

  A series of 23 new rupestonic acid derivatives were synthesized. Their activities against influenza viruses A (H3N2, H1N1) and B were studied. Compounds 2d and 2g demonstrated potent activity against influenza virus A (H3N2) with IC50 values of 0.35 and 0.21 μM, respectively. Compound 5g (n = 10) was the most potent compound of this series against influenza viruses H3N2 and H1N1 with IC50 values of 2.89 and 0.38 μM. Several of the synthesized compounds were weakly active against influenza virus B and were more toxic than starting rupestonic acid.

  研究人员合成了一系列 23 种新的芦贝甾酸衍生物。研究了它们对甲型流感病毒（H3N2、H1N1）和乙型流感病毒的活性。化合物 2d 和 2g 对甲型流感病毒（H3N2）具有强效活性，IC50 值分别为 0.35 和 0.21 μM。化合物 5g（n = 10）是该系列中对 H3N2 和 H1N1 流感病毒最有效的化合物，其 IC50 值分别为 2.89 和 0.38 μM。合成的几种化合物对 B 型流感病毒的活性较弱，且毒性高于起始的芦贝糖醛酸。