3-hydroxytridecan-4-one

• 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: 3-hydroxytridecan-4-one
• 化学式: C₁₃H₂₆O₂
• 分子量: 214.348
• InChiKey: OWRHIIOUJRCXDH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  15
• 可旋转键数：
  10
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-hydroxytridecan-4-one 在 sodium tetrahydroborate 、 硫酸 作用下， 以 甲醇 为溶剂， 以56%的产率得到3,4-tridecanediol
  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
• 作为产物：
  描述：

  癸醛 、 丙醛 在 3-苄基羟乙基甲基噻唑氯化锂 三乙胺 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 4-hydroxytridecan-3-one 、 3-hydroxytridecan-4-one
  参考文献：
  名称：

  脂肪醛的交叉丙烯酰缩合

  摘要：

  通过噻唑鎓催化的两种不同的未受阻醛缩合，使用 1 摩尔当量的一种醛与 3 摩尔当量的另一种醛，可以有效地制备交叉 acyloins。通过用氧化铋 (III) 或 Dess-Martin periodinane 氧化得到 1,2-二酮，然后用羟胺处理得到肟，转化为相应的非对称 1,2-二肟。

  DOI：

  10.1002/1099-0690(200107)2001:14<2623::aid-ejoc2623>3.0.co;2-1

文献信息

• [EN] HETEROCYCLE ANALOGS OF CAI-1 AS AGONISTS OF QUORUM SENSING IN VIBRIO<br/>[FR] ANALOGUES HÉTÉROCYCLIQUES DE CAI-1 EN TANT QU'AGONISTES DE LA DÉTECTION DU QUORUM CHEZ VIBRIO
  申请人：UNIV PRINCETON

  公开号：WO2015026796A1

  公开（公告）日：2015-02-26

  A structurally distinct and potent series of synthetic small molecule activators of Vibrio cholerae quorum sensing have been chemically synthesized. The small molecule activators reduce virulence in V. cholerae. Acyl pyrrole molecules displayed strong potency and stability, particularly l-(1H-pyrrol-3-yl)decan-l-one.

  一系列结构独特且强效的合成小分子活化剂已经化学合成，用于强化霍乱弧菌的群体感应。这些小分子活化剂降低了霍乱弧菌的毒力。酰基吡咯分子表现出很强的效力和稳定性，尤其是l-(1H-吡咯-3-基)癸酮。
• BROAD SPECTRUM PRO-QUORUM-SENSING MOLECULES AS INHIBITORS OF VIRULENCE IN VIBRIOS
  申请人：THE TRUSTEES OF PRINCETON UNIVERSITY

  公开号：US20150126474A1

  公开（公告）日：2015-05-07

  Using a whole-cell high-throughput screen, eleven molecules were identified that activate V. cholerae quorum sensing (QS). Eight molecules are receptor agonists and three molecules are antagonists of LuxO, the central NtrC-type response regulator that controls the global V. cholerae QS cascade. Pro-QS molecules are used for the development of novel anti-infectives.

  使用全细胞高通量筛选，鉴定出了11种分子，可以激活V. cholerae的群体感应（QS）。其中8种分子是受体激动剂，3种分子是LuxO的拮抗剂，LuxO是控制全局V. cholerae QS级联反应的中央NtrC型响应调节器。Pro-QS分子可用于开发新型抗感染药物。
• HETEROCYCLE ANALOGS OF CAI-1 AS AGONISTS OF QUORUM SENSING IN VIBRIO
  申请人：BASSLER Bonnie L.

  公开号：US20160200678A1

  公开（公告）日：2016-07-14

  A structurally distinct and potent series of synthetic small molecule activators of Vibrio cholerae quorum sensing have been chemically synthesized. The small molecule activators reduce virulence in V. cholerae . Acyl pyrrole molecules displayed strong potency and stability, particularly 1-(1H-pyrrol-3-yl)decan-1-one.

  一种结构独特且有效的合成小分子激活剂系列已经化学合成，可以激活霍乱弧菌的感应系统。这些小分子激活剂可以减少霍乱弧菌的毒力。酰基吡咯分子表现出强大的效力和稳定性，特别是1-(1H-吡咯-3-基)癸酮。
• Heterocycle analogs of CAI-1 as agonists of quorum sensing in vibrio
  申请人：The Trustees of Princeton University

  公开号：US10285978B2

  公开（公告）日：2019-05-14

  A structurally distinct and potent series of synthetic small molecule activators of Vibrio cholerae quorum sensing have been chemically synthesized. The small molecule activators reduce virulence in V. cholerae. Acyl pyrrole molecules displayed strong potency and stability, particularly 1-(1H-pyrrol-3-yl)decan-1-one.

  我们用化学方法合成了一系列结构独特、效力强大的霍乱弧菌法定人数感应合成小分子激活剂。这些小分子激活剂降低了霍乱弧菌的毒力。酰基吡咯分子显示出很强的效力和稳定性，尤其是 1-（1H-吡咯-3-基）癸-1-酮。
• Processes and host cells for genome, pathway, and biomolecular engineering
  申请人：enEvolv, Inc.

  公开号：US10370654B2

  公开（公告）日：2019-08-06

  The present disclosure provides compositions and methods for genomic engineering.

  本公开提供了基因组工程的组合物和方法。