3-(苯基氨基)癸-2-烯酸乙酯 | 437755-74-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(苯基氨基)癸-2-烯酸乙酯
• 英文名称: Ethyl 3-anilino-2-decenoate
• 英文别名: ethyl 3-anilinodec-2-enoate
• CAS: 437755-74-3
• 化学式: C₁₈H₂₇NO₂
• 分子量: 289.418
• InChiKey: QBGFMRCYIAQYCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  21
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(苯基氨基)癸-2-烯酸乙酯 以 二苯醚 为溶剂， 反应 0.5h， 生成 2-庚基-4-喹啉酮
  参考文献：
  名称：

  Discovery of Antagonists of PqsR, a Key Player in 2-Alkyl-4-quinolone-Dependent Quorum Sensing in Pseudomonas aeruginosa

  摘要：

  The pqs quorum sensing communication system of Pseudomonas aeruginosa controls virulence factor production and is involved in biofilm formation, therefore playing an important role for pathogenicity. In order to attenuate P. aeruginosa pathogenicity, we followed a ligand-based drug design approach and synthesized a series of compounds targeting PqsR, the receptor of the pqs system. In vitro evaluation using a reporter gene assay in Escherichia coli led to the discovery of the first competitive PqsR antagonists, which are highly potent (K-d,K-app of compound 20: 7 nM). These antagonists are able to reduce the production of the virulence factor pyocyanin in P. aeruginosa. Our finding offers insights into the ligand-receptor interaction of PqsR and provides a promising starting point for further drug design.

  DOI：

  10.1016/j.chembiol.2012.01.015
• 作为产物：
  描述：

  3-羰基癸酸乙酯 、 苯胺 在 对甲苯磺酸 作用下， 以 正己烷 为溶剂， 反应 5.0h， 生成 3-(苯基氨基)癸-2-烯酸乙酯
  参考文献：
  名称：

  Discovery of Antagonists of PqsR, a Key Player in 2-Alkyl-4-quinolone-Dependent Quorum Sensing in Pseudomonas aeruginosa

  摘要：

  The pqs quorum sensing communication system of Pseudomonas aeruginosa controls virulence factor production and is involved in biofilm formation, therefore playing an important role for pathogenicity. In order to attenuate P. aeruginosa pathogenicity, we followed a ligand-based drug design approach and synthesized a series of compounds targeting PqsR, the receptor of the pqs system. In vitro evaluation using a reporter gene assay in Escherichia coli led to the discovery of the first competitive PqsR antagonists, which are highly potent (K-d,K-app of compound 20: 7 nM). These antagonists are able to reduce the production of the virulence factor pyocyanin in P. aeruginosa. Our finding offers insights into the ligand-receptor interaction of PqsR and provides a promising starting point for further drug design.

  DOI：

  10.1016/j.chembiol.2012.01.015

文献信息

• Synergistic compositions of n-acylhomoserine lactones and 4-quinolones
  申请人：——

  公开号：US20040198978A1

  公开（公告）日：2004-10-07

  A composition having immunosuppressant activity comprises at least one compound of the formula (I) in which R is an acyl group of the formula (II) wherein one of R 1 and R 2 is H and the other is selected from OR 4 , SR 4 and NHR 4 , wherein R 4 is H or 1-6C alkyl, or R 1 and R 2 together with the carbon atom to which they are joined form a keto group, and R 3 is a straight or branched chain, saturated or unsaturated aliphatic hydrocarbyl group containing from 8 to 11 carbon atoms and is optionally substituted by one or more substituent groups selected from halo, 1-6C alkoxy, carboxy, 1-6C alkoxycarbonyl and NR 5 R 6 wherein each of R 5 and R 6 is selected from H and 1-6C alkyl or R 5 and R 6 together with the N atom form a morpholino or piperazino group, or any enantiomer thereof; and at least one compound of the formula (III): wherein R 7 is a straight or branched chain, saturated or ethylenically-unsaturated aliphatic hydrocarbyl group containing from 1 to 18 carbon atoms which may optionally be substituted by one or more substituent groups selected from halo, 1-6C alkoxy, carboxy, 1-6C alkoxycarbonyl and NR 12 R 13 , wherein each of R 12 and R 13 is independently selected from H and 1-6C alkyl or R 12 and R 13 together with the N atom to which they are attached form a saturated heterocyclic group selected from piperidino, piperazino and morpholino; R 8 is a group selected from H, —OH, halo, —CHO, —CO 2 H and CONHR 14 wherein R 14 is H or a 1-6C alkyl; each of R 9 , R 10 and R 11 is independently selected from H, —CH 3 , —OCH 3 and halo; or a non-toxic pharmaceutically-acceptable salt thereof. The determined immunosuppressant activity of the composition is greater than the sum of the activities of the individual components of the composition when determined separately. 1

  具有免疫抑制活性的组合物包括公式（I）中至少一种化合物，其中R是公式（II）的酰基，其中R1和R2中的一个是H，另一个选自OR4，SR4和NHR4，其中R4是H或1-6C烷基，或者R1和R2与它们连接的碳原子形成酮基，R3是含有8至11个碳原子的直链或支链、饱和或不饱和的脂肪族羟基烷基，可选地被一个或多个取代基选自卤素，1-6C烷氧基，羧基，1-6C烷氧羰基和NR5R6取代，其中每个R5和R6选自H和1-6C烷基或R5和R6与N原子形成吗啉或哌嗪基团，或其任何对映体；以及公式（III）中的至少一种化合物：其中R7是含有1至18个碳原子的直链或支链、饱和或乙烯不饱和的脂肪族羟基烷基，可以选择地被一个或多个取代基选自卤素，1-6C烷氧基，羧基，1-6C烷氧羰基和NR12R13取代，其中每个R12和R13独立地选自H和1-6C烷基或R12和R13与它们附着的N原子形成选自哌啶基，哌嗪基和吗啉的饱和杂环基；R8是选自H，—OH，卤素，—CHO，—CO2H和CONHR14的基团，其中R14是H或1-6C烷基；每个R9、R10和R11独立地选自H、—CH3、—O 和卤素；或其非毒性药物可接受盐。当单独测定时，组合物的确定免疫抑制活性大于组合物各个组分的活性之和。
• Substituted-4-quinolones
  申请人：——

  公开号：US20040082579A1

  公开（公告）日：2004-04-29

  Substituted-4-quinolones of the formula (I): wherein R 1 is a straight or branched chain, saturated or ethylenically-unsaturated aliphatic hydrocarbyl group containing 1 to 18 carbon atoms which may optionally be substituted by one or more substituent groups selected from halo, 1-6C alkoxy, carboxy, 1-6C alkoxycarbonyl and NR 6 R 7 , wherein each of R 6 and R 7 is independently selected from H and 1-6C alkyl or R 6 and R 7 together with the N atom to which they are attached form a saturated heterocyclic group selected from piperidino, piperazino and morpholino. R 2 is a group selected from H, —OH, halo, —CHO, —CO 2 H and CONHR 8 wherein R 8 is H or a 1-6C alkyl; each of R 3 , R 4 and R 1 is independently selected form H, —CH 3 , —OCH 3 and halo; or a non-toxic pharmaceutically-acceptable salt thereof, have use in the manufacture of a medicament for the treatment of a disease of a living animal body, including a human, which disease is responsive to the activity of an immunosuppressant. The preferred compound of the formula 1 is 2-n-heptyl-3-hydroxy-4(1H)-quinolone.

  公式（I）中的取代-4-喹啉衍生物：其中R1是一种直链或支链，饱和或乙烯基不饱和的脂肪烃基，含1至18个碳原子，可以选择性地被一个或多个取代基取代，所述取代基选自卤素，1-6C烷氧基，羧基，1-6C烷氧羰基和NR6R7，其中每个R6和R7独立地选自H和1-6C烷基或R6和R7与它们连接的N原子一起形成从哌啶基，哌嗪基和吗啉基中选择的饱和杂环基。R2是选择自H，—OH，卤素，—CHO，—CO2H和CONHR8的基团，其中R8是H或1-6C烷基；R3，R4和R1中的每一个独立地选择自H，—CH3，—O 和卤素；或其非毒性药学上可接受的盐，在制造用于治疗对免疫抑制剂活性敏感的生物体的疾病的药物方面有用，包括人类。公式1的优选化合物是2-正庚基-3-羟基-4（1H）-喹啉。
• Synergistic compositions of N-acylhomoserine lactones and 4-quinolones
  申请人：The Secretary of State for Defense Science and Technology

  公开号：US07371779B2

  公开（公告）日：2008-05-13

  A composition having immunosuppressant activity comprises at least one compound of the formula (I) in which R is an acyl group of the formula (II) wherein one of R1 and R2 is H and the other is selected from OR4, SR4 and NHR4, wherein R4 is H or 1-6C alkyl, or R1 and R2 together with the carbon atom to which they are joined form a keto group, and R3 is a straight or branched chain, saturated or unsaturated aliphatic hydrocarbyl group containing from 8 to 11 carbon atoms and is optionally substituted by one or more substituent groups selected from halo, 1-6C alkoxy, carboxy, 1-6C alkoxycarbonyl and NR5R6 wherein each of R5 and R6 is selected from H and 1-6C alkyl or R5 and R6 together with the N atom form a morpholino or piperazino group, or any enantiomer thereof; and at least one compound of the formula (III): wherein R7 is a straight or branched chain, saturated or ethylenically-unsaturated aliphatic hydrocarbyl group containing from 1 to 18 carbon atoms which may optionally be substituted by one or more substituent groups selected from halo, 1-6C alkoxy, carboxy, 1-6C alkoxycarbonyl and NR12R13, wherein each of R12 and R13 is independently selected from H and 1-6C alkyl or R12 and R13 together with the N atom to which they are attached form a saturated heterocyclic group selected from piperidino, piperazino and morpholino; R8 is a group selected from H, —OH, halo, —CHO, —CO2H and CONHR14 wherein R14 is H or a 1-6C alkyl; each of R9, R10 and R11 is independently selected from H, —CH3, —OCH3 and halo; or a non-toxic pharmaceutically-acceptable salt thereof. The determined immunosuppressant activity of the composition is greater than the sum of the activities of the individual components of the composition when determined separately

  具有免疫抑制活性的组合物包括式(I)中至少一种化合物，其中R是式(II)的酰基，其中R1和R2中的一个为H，另一个选自OR4、SR4和NHR4，其中R4为H或1-6C烷基，或R1和R2与它们连接的碳原子形成酮基，R3是一种直链或支链、饱和或不饱和的脂肪族羟烃基，含有8-11个碳原子，并且可以被一个或多个取代基选自卤素、1-6C烷氧基、羧基、1-6C烷氧基羰基和NR5R6取代，其中每个R5和R6选自H和1-6C烷基，或R5和R6与N原子形成吗啡环或哌嗪环，或它们的任何对映异构体；和式(III)中的至少一种化合物：其中R7是一种直链或支链、饱和或乙烯基不饱和的脂肪族羟烃基，含有1-18个碳原子，可以选择地被一个或多个取代基选自卤素、1-6C烷氧基、羧基、1-6C烷氧基羰基和NR12R13取代，其中每个R12和R13独立地选自H和1-6C烷基，或R12和R13与它们附着的N原子形成选自哌啶、哌嗪和吗啡环的饱和杂环基；R8是选自H、—OH、卤素、—CHO、—CO2H和CONHR14的基团，其中R14是H或1-6C烷基；每个R9、R10和R11独立地选自H、—CH3、—O 和卤素；或其非毒性药学上可接受的盐。当单独测定时，组合物的确定的免疫抑制活性大于组合物各个成分的活性之和。