N-[(1S,2S)-2-hydroxycyclohexyl]-3-oxododecanamide | 886755-19-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(1S,2S)-2-hydroxycyclohexyl]-3-oxododecanamide
• 英文别名: 3-Oxo-dodecanoic acid ((1S,2S)-2-hydroxy-cyclohexyl)-amide
• CAS: 886755-19-7
• 化学式: C₁₈H₃₃NO₃
• 分子量: 311.465
• InChiKey: UMKKAXTZUXAHLX-IRXDYDNUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-[(1S,2S)-2-hydroxycyclohexyl]-3-oxododecanamide 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 以20%的产率得到decanoic acid (2-oxo-cyclohexyl)-amide
  参考文献：
  名称：

  Synthesis and stability of small molecule probes for Pseudomonas aeruginosa quorum sensing modulation

  摘要：

  人类病原体铜绿假单胞菌（Pseudomonas aeruginosa）利用N-丁酰基-L-高丝氨酸内酯（BHL）和N-(3-氧代十二烷基)-L-高丝氨酸内酯（OdDHL）作为小分子细胞间信号，这种现象被称为群体感应（Quorum sensing，QS）。QS调节剂能有效减弱铜绿假单胞菌的毒力，因此，它们有可能成为一类新型抗菌剂。在生理条件下，BHL和OdDHL中的内酯环会发生水解，且水解速率快于α-手性中心的消旋化。设计并合成了非水解、非消旋的类似物（小分子探针），用酮基取代了内酯环。研究发现，除非在β-酮胺基之间进行二氟化，否则OdDHL类似物相对不稳定，易于分解。对一种非水解的环己酮类似物的稳定性研究显示，α-手性中心的消旋化相对较慢。该类似物的检测结果表明，L-异构体可能是铜绿假单胞菌和沙雷氏菌ATCC39006株中QS自诱导活性的原因。

  DOI：

  10.1039/b412802h

文献信息

• Combinatorial libraries of autoinducer analogs, autoinducer agonists and antagonists, and methods of use thereof
  申请人：——

  公开号：US20040115732A1

  公开（公告）日：2004-06-17

  The present invention relates to solid phase or solution phase combinatorial libraries of autoinducer analogs. The present invention also relates to autoinducer agonists and antagonists. In addition, the present invention relates to methods for identifying autoinducer agonists and antagonists, as well as methods for regulating the activity of an autoinducer receptor, regulating biofilm formation, regulating growth or virulence of an organism in a subject, inhibiting the quorum sensing mechanism of an organism, and treating an infection in a subject caused by an organism possessing a quorum sensing mechanism which use the autoinducer analogs of the present invention.

  本发明涉及自感应剂类似物的固相或溶液相组合库。本发明还涉及自感应剂和拮抗剂。此外，本发明还涉及识别自感应剂和拮抗剂的方法，以及调节自感应受体的活性、调节生物膜形成、调节生物体在主体中的生长或毒力、抑制生物体的群体感应机制，并使用本发明的自感应剂类似物治疗由具有群体感应机制的生物体引起的主体感染。
• COMBINATORIAL LIBRARIES OF AUTOINDUCER ANALOGS, AUTOINDUCER AGONISTS AND ANTAGONISTS, AND METHODS OF USE THEREOF
  申请人：SUGA Hiroaki

  公开号：US20080027115A1

  公开（公告）日：2008-01-31

  The present invention relates to solid phase or solution phase combinatorial libraries of autoinducer analogs. The present invention also relates to autoinducer agonists and antagonists. In addition, the present invention relates to methods for identifying autoinducer agonists and antagonists, as well as methods for regulating the activity of an autoinducer receptor, regulating biofilm formation, regulating growth or virulence of an organism in a subject, inhibiting the quorum sensing mechanism of an organism, and treating an infection in a subject caused by an organism possessing a quorum sensing mechanism which use the autoinducer analogs of the present invention.

  本发明涉及自感应物类似物的固相或溶液相组合库。本发明还涉及自感应物激动剂和拮抗剂。此外，本发明还涉及识别自感应物激动剂和拮抗剂的方法，以及调节自感应物受体活性、调节生物膜形成、调节在受体中生物体的生长或毒力、抑制生物体的群体感应机制、以及使用本发明的自感应物类似物治疗由具有群体感应机制的生物体引起的受体感染的方法。
• ANALOGUES OF N-ACYL-HOMOSERINE LACTONES AND PHARMACEUTICAL COMPOSITION COMPRISING SAME
  申请人：SORBONNE UNIVERSITE

  公开号：US20220411397A1

  公开（公告）日：2022-12-29

  The present invention relates to analogues of N-acyl homoserine lactones (AHLs) and pharmaceutical compositions comprising same. The invention also relates to their use in the treatment of inflammatory diseases of the epithelium.
• US7498292B2
  申请人：——

  公开号：US7498292B2

  公开（公告）日：2009-03-03
• [EN] COMBINATORIAL LIBRARIES OF AUTOINDUCER ANALOGS, AUTOINDUCER AGONISTS AND ANTAGONISTS, AND METHODS OF USE THEREOF<br/>[FR] BIBLIOTHEQUES COMBINATOIRES D'ANALOGUES AUTOINDUCTEURS, D'AGONISTES ET D'ANTAGONISTES AUTOINDUCTEURS, ET LEURS PROCEDES D'UTILISATION
  申请人：UNIV NEW YORK STATE RES FOUND

  公开号：WO2004016213A2

  公开（公告）日：2004-02-26

  The present invention relates to solid phase or solution phase combinatorial libraries of autoinducer analogs. The present invention also relates to autoinducer agonists and antagonists. In addition, the present invention relates to methods for identifying autoinducer agonists and antagonists, as well as methods for regulating the activity of an autoinducer receptor, regulating biofilm formation, regulating growth or virulence of an organism in a subject, inhibiting the quorum sensing mechanism of an organism, and treating an infection in a subject caused by an organism possessing a quorum sensing mechanism which use the autoinducer analogs of the present invention.