8S-dihydroplexaurolone | 1349902-92-6

• 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: 8S-dihydroplexaurolone
• 英文别名: (1R,3R,4R,8S,11R,12R)-6-ketocembra-15(17)-ene-3,11-diol；(3R,4R,6R,9R,10R,13S)-4,10-dihydroxy-3,9,13-trimethyl-6-prop-1-en-2-ylcyclotetradecan-1-one
• CAS: 1349902-92-6
• 化学式: C₂₀H₃₆O₃
• 分子量: 324.504
• InChiKey: DDBLDAGSFDWDCS-CETRPMQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8S-dihydroplexaurolone 在 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以86.6%的产率得到(+)-1R,3R,4R,8S,11R,12R-3,6-oxa-cembra-15(17)-en-6,11-diol
  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

• Absolute stereochemistry of antifouling cembranoid epimers at C-8 from the Caribbean octocoral Pseudoplexaura flagellosa. Revised structures of plexaurolones
  作者：Edisson Tello、Leonardo Castellanos、Catalina Arevalo-Ferro、Jaime Rodríguez、Carlos Jiménez、Carmenza Duque

  DOI：10.1016/j.tet.2011.09.094

  日期：2011.11

  7, and 8 have been reported previously, their structures and NMR assignments are revised, completed or corrected. The structures of these compounds were established on the basis of detailed analysis of their spectroscopic data. Furthermore, the relative configurations of compounds 1–3 and 7 were confirmed by single-crystal X-ray diffraction. The absolute configurations of compounds 1–8 were determined

  在C-8（八个西松烷差向异构体1 - 8）从哥伦比亚加勒比海octocoral的有机提取物中分离Pseudoplexaura flagellosa。化合物2，4，和6报道首次。尽管化合物1，3，5，7，和8之前已经报道，它们的结构和NMR分配被修改，完成或校正。这些化合物的结构是在对其光谱数据进行详细分析的基础上确定的。此外，化合物的相对构型1 - 3通过单晶X射线衍射确认了图7和图7。化合物1 – 8的绝对构型是使用改良的Mosher方法和明确的化学相互转化方法确定的。使用群体感应的抑制（QSI）生物膜抑制生物测定其防污性能和评价结果表明，化合物3，6，和7具有针对优异的QSI活性紫色色杆菌，如通过抑制生产紫色杆菌素颜料的测量，而没有与它的增长的干扰。此外，化合物3，5，6，和8表现出抑制生物膜的成熟而不会干扰铜绿假单胞菌，哈维弧菌和金黄色葡萄球菌的生长。这是关于cembranoids作为细菌生物膜抑制剂和干扰C
• 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.