Acetic acid (1R,2R,6S,10R,13R)-13-isopropenyl-2,6,10-trimethyl-4,9-dioxo-cyclotetradecyl ester | 75319-65-2

• 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: Acetic acid (1R,2R,6S,10R,13R)-13-isopropenyl-2,6,10-trimethyl-4,9-dioxo-cyclotetradecyl ester
• 英文别名: [(1R,2R,6S,10R,13R)-2,6,10-trimethyl-4,9-dioxo-13-prop-1-en-2-ylcyclotetradecyl] acetate
• CAS: 75319-65-2
• 化学式: C₂₂H₃₆O₄
• 分子量: 364.525
• InChiKey: IASAFXIPQZKOAE-GADAEZOWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酸酐 、 plexaurolone 在 吡啶 作用下， 生成 Acetic acid (1R,2R,6S,10R,13R)-13-isopropenyl-2,6,10-trimethyl-4,9-dioxo-cyclotetradecyl ester
  参考文献：
  名称：

  The structure and absolute configuration at low temperature of the acetate derivative of plexaurolone, a marine cembranoid

  摘要：

  DOI：

  10.1107/s0567740880007431

文献信息

• The structure and absolute configuration at low temperature of the acetate derivative of plexaurolone, a marine cembranoid
  作者：S. E. Ealick、D. van der Helm、R. A. Gross、A. J. Weinheimer、L. S. Ciereszko、R. E. Middlebrook

  DOI：10.1107/s0567740880007431

  日期：1980.8.1
• 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.