1-hydroxy-1-(3,4-dihydroxyphenyl)undecan-2-one | 1351299-07-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-hydroxy-1-(3,4-dihydroxyphenyl)undecan-2-one
• 英文别名: 1-(3,4-Dihydroxyphenyl)-1-hydroxyundecan-2-one
• CAS: 1351299-07-4
• 化学式: C₁₇H₂₆O₄
• 分子量: 294.391
• InChiKey: FJWMFUZMNKISGS-UHFFFAOYSA-N

物化性质

• 沸点：
  467.7±40.0 °C(predicted)
• 密度：
  1.119±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3,4-二(叔-丁基二甲基硅烷基氧基)苯甲醛 在 N-氯代丁二酰亚胺 、 正丁基锂 、 四丁基氟化铵 、 水 、 silver nitrate 作用下， 以 四氢呋喃 、 正己烷 、 乙腈 为溶剂， 反应 16.25h， 生成 1-hydroxy-1-(3,4-dihydroxyphenyl)undecan-2-one
  参考文献：
  名称：

  Small molecule probes of the receptor binding site in the Vibrio cholerae CAI-1 quorum sensing circuit

  摘要：

  Based on modification of separate structural features of the Vibrio cholerae quorum sensing signal, (S)-3-hydroxytridecan-4-one (CAI-1), three focused compound libraries have been synthesized and evaluated for biological activity. Modifications to the acyl tail and alpha-hydroxy ketone typically provided agonists with activities correlated to tail length and conservative changes to the hydroxy ketone. Among the molecules identified within this collection of agonists is Am-CAI-1 (B11), which is among the most potent agonists reported to date with an EC50 of 0.21 mu M. Modifications to the ethyl side chain delivered molecules with both agonist and antagonist activity, including m-OH-Ph-CAI-1 (C13) which is the most potent antagonist reported to date with an IC50 of 36 mu M. The molecules described in this manuscript are anticipated to serve as valuable tools in the study of quorum sensing in Vibrio cholerae and provide new leads in the development of an antivirulence therapy against this human pathogen. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.09.021

文献信息

• Small molecule probes of the receptor binding site in the Vibrio cholerae CAI-1 quorum sensing circuit
  作者：Megan E. Bolitho、Lark J. Perez、Matthew J. Koch、Wai-Leung Ng、Bonnie L. Bassler、Martin F. Semmelhack

  DOI：10.1016/j.bmc.2011.09.021

  日期：2011.11

  Based on modification of separate structural features of the Vibrio cholerae quorum sensing signal, (S)-3-hydroxytridecan-4-one (CAI-1), three focused compound libraries have been synthesized and evaluated for biological activity. Modifications to the acyl tail and alpha-hydroxy ketone typically provided agonists with activities correlated to tail length and conservative changes to the hydroxy ketone. Among the molecules identified within this collection of agonists is Am-CAI-1 (B11), which is among the most potent agonists reported to date with an EC50 of 0.21 mu M. Modifications to the ethyl side chain delivered molecules with both agonist and antagonist activity, including m-OH-Ph-CAI-1 (C13) which is the most potent antagonist reported to date with an IC50 of 36 mu M. The molecules described in this manuscript are anticipated to serve as valuable tools in the study of quorum sensing in Vibrio cholerae and provide new leads in the development of an antivirulence therapy against this human pathogen. (C) 2011 Elsevier Ltd. All rights reserved.