(-)-(1R,2S,7R,3E,8E,11E)-2,18-diacetoxycembra-3,8,11,15(17)-tetraen-7-ol | 1186654-86-3

• 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: (-)-(1R,2S,7R,3E,8E,11E)-2,18-diacetoxycembra-3,8,11,15(17)-tetraen-7-ol
• 英文别名: [(1E,3S,4R,7E,10E,12R)-3-acetyloxy-12-hydroxy-7,11-dimethyl-4-prop-1-en-2-ylcyclotetradeca-1,7,10-trien-1-yl]methyl acetate
• CAS: 1186654-86-3
• 化学式: C₂₄H₃₆O₅
• 分子量: 404.547
• InChiKey: VEMVDCAUWIBDLU-FUHDERAGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  72.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (-)-(1R,2S,7R,8R)-asperdiol acetate 在 吡啶 、 盐酸 、 碘 作用下， 以 氘代氯仿 、 异丙醇 为溶剂， 反应 60.0h， 生成 (-)-(1R,2S,7R,3E,8E,11E)-2,18-diacetoxycembra-3,8,11,15(17)-tetraen-7-ol 、 (-)-(1R,2S,7R,3E,8Z,11E)-2,18-diacetoxycembra-3,8,11,15(17)-tetraen-7-ol
  参考文献：
  名称：

  Synthesis of cembranoid analogues and evaluation of their potential as quorum sensing inhibitors

  摘要：

  Natural cembranoids have shown Quorum Sensing Inhibitory (QSI) activity, but their structure-function interactions are not well understood. Thirty-four cembranoid analogues were synthesized using six natural cembranoids (1-6) previously isolated from the Colombian Caribbean octocorals Eunicea knighti and Pseudoplexaura flagellosa as lead compounds. The analogues (7-40) obtained through the selected chemical transformations were tested in vitro against the QS systems of a Chromobacterium violaceum biosensor. Half of the cembranoid analogues assayed showed superior QSI activity to the lead compounds; three (8, 13, and 18) displayed remarkable potency up to three times higher than the natural compounds. Thereby, we have synthesized a pool of cembranoid QS inhibitors that can be used in concert with natural compounds to develop antipathogenic drugs and antifouling agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.10.022

文献信息

• Cembranoid Diterpenes from the Caribbean Sea Whip <i>Eunicea knighti</i>
  作者：Edisson Tello、Leonardo Castellanos、Catalina Arevalo-Ferro、Carmenza Duque

  DOI：10.1021/np9002492

  日期：2009.9.25

  Three new cembranoid diterpenes, knightol (1), knightol acetate (2), and knightal (3), along with the known asperdiol (4) and asperdiol acetate (5), were isolated as major compounds from the sea whip Eunicea knighti collected from the Colombian Caribbean. The structures and absolute configurations of 1−5 were determined on the basis of spectroscopic analyses and by a combination of chemical and NMR

  从海鞭Eunicea knighti收集的主要化合物中分离出了三个新的萜类二萜，knightol（1），乙酸knightol（2）和knightal（3），以及已知的曲霉酚（4）和乙酸曲霉二醇（5）。哥伦比亚加勒比海。的结构和绝对构型1 - 5分光分析的基础上，并通过化学和NMR方法的组合进行了测定，多重相关性在ROESY实验中观察到，并且使用经修改的莫舍方法。此外，五半个合成的化合物，6 - 10本文首次报道了天然化合物化学转化过程中获得的。测试了所有化合物对与严重结垢的表面相关的海洋细菌的抗菌活性，并筛选了抗群体感应（QS）活性。化合物1，3和8显示出对细菌分离显著的抗微生物活性，和1，3，7，和8表明通过生物发光抑制与生物传感器模型系统来测量优异的抗QS抑制活性。
• Synthesis of cembranoid analogues and evaluation of their potential as quorum sensing inhibitors
  作者：Edisson Tello、Leonardo Castellanos、Carmenza Duque

  DOI：10.1016/j.bmc.2012.10.022

  日期：2013.1

  Natural cembranoids have shown Quorum Sensing Inhibitory (QSI) activity, but their structure-function interactions are not well understood. Thirty-four cembranoid analogues were synthesized using six natural cembranoids (1-6) previously isolated from the Colombian Caribbean octocorals Eunicea knighti and Pseudoplexaura flagellosa as lead compounds. The analogues (7-40) obtained through the selected chemical transformations were tested in vitro against the QS systems of a Chromobacterium violaceum biosensor. Half of the cembranoid analogues assayed showed superior QSI activity to the lead compounds; three (8, 13, and 18) displayed remarkable potency up to three times higher than the natural compounds. Thereby, we have synthesized a pool of cembranoid QS inhibitors that can be used in concert with natural compounds to develop antipathogenic drugs and antifouling agents. (C) 2012 Elsevier Ltd. All rights reserved.