2-庚基-1,4-二氢-4-氧代-3-喹啉甲醛 | 402718-53-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 2-庚基-1,4-二氢-4-氧代-3-喹啉甲醛
• 英文名称: 3-formyl-2-heptyl-4-quinolone
• 英文别名: 2-Heptyl-4-oxo-1,4-dihydroquinoline-3-carbaldehyde；2-heptyl-4-oxo-1H-quinoline-3-carbaldehyde
• CAS: 402718-53-0
• 化学式: C₁₇H₂₁NO₂
• 分子量: 271.359
• InChiKey: YDGMJDFKESRTIZ-UHFFFAOYSA-N

物化性质

• 沸点：
  407.1±45.0 °C(Predicted)
• 密度：
  1.108

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933499090

反应信息

• 作为反应物：
  描述：

  2-庚基-1,4-二氢-4-氧代-3-喹啉甲醛 在 乙醇 、 双氧水 、 sodium hydroxide 作用下， 以29%的产率得到2-heptyl-3-hydroxy-4(1H)-quinolone
  参考文献：
  名称：

  HHQ的3-卤代类似物的合成，随后的交叉偶联和假单胞菌喹诺酮信号（PQS）的第一晶体结构

  摘要：

  2-芳基和2-烷基喹啉-4-酮及其N-取代的衍生物具有几种重要的生物学功能，例如假单胞菌喹诺酮信号（PQS）分子参与群体感应。在本文中，我们报告了其生物前体2-庚基-4-羟基喹啉（HHQ）和PQS可能的等排体的合成；C-3 Cl，Br和I类似物。碘化物的N-甲基化也是可行的，并且该化合物的有用性在Pd催化的交叉偶联反应中得到了证明，因此可以使用多种生物学上重要的分子。还包括PQS的第一晶体结构。

  DOI：

  10.1016/j.tetlet.2010.09.013
• 作为产物：
  描述：

  3-氧代癸酸甲酯 在 ammonium hydroxide 、 三氟乙酸 作用下， 以 二苯醚 、 水 、 乙酸乙酯 为溶剂， 反应 24.5h， 生成 2-庚基-1,4-二氢-4-氧代-3-喹啉甲醛
  参考文献：
  名称：

  Structure–function analysis of the C-3 position in analogues of microbial behavioural modulators HHQ and PQS

  摘要：

  2-庚基-3-羟基-4-喹啉（PQS）及其前体2-庚基-4-喹啉（HHQ）是重要的医院获得性感染病原体铜绿假单胞菌的关键信号分子。我们最近报道了这些分子在不同领域的影响，能够影响一系列微生物物种及人类致病酵母白色念珠菌的关键致病特征。这是首次对C-3位点进行针对性的化学衍生化研究，以探讨这些化合物在铜绿假单胞菌中生物活性的结构和分子特性，并且使用枯草芽孢杆菌作为适合的模型系统以研究物种之间行为的调节。

  DOI：

  10.1039/c2ob26823j

文献信息

• Synthetic quinolone signal analogues inhibiting the virulence factor elastase of Pseudomonas aeruginosa
  作者：Dávid Szamosvári、Valentin F. Reichle、Monica Jureschi、Thomas Böttcher

  DOI：10.1039/c6cc06295d

  日期：——

  We describe the synthesis of analogs of the Pseudomonas quinolone signal and the discovery of a potent inhibitor of the important virulence factor elastase of the human pathogenPseudomonas aeruginosa.

  我们描述了假单胞菌喹诺酮信号的类似物的合成，以及发现了对人类病原体假单胞菌的重要毒力因子弹性蛋白酶的有效抑制剂。
• Novel autoinducer molecules and uses therefor
  申请人：——

  公开号：US20020177715A1

  公开（公告）日：2002-11-28

  Novel bacterial quinolone signal molecules and, more particularly, pseudomonas quinolone signal (“PQS”) molecules, e.g., 2-heptyl-3-hydroxy-4-quinolone, and analogs and derivatives thereof are described. Therapeutic compositions containing the molecules, and therapeutic methods, methods of for regulating gene expression, methods for identifying modulators of the autoinducer molecules, and methods of modulating quorum sensing signalling in bacteria using the compounds of the invention are also described.

  描述了新型细菌喹诺酮信号分子，更具体地说是假单胞菌喹诺酮信号（“PQS”）分子，例如2-庚基-3-羟基-4-喹诺酮，以及其类似物和衍生物。还描述了含有这些分子的治疗组合物，治疗方法，调控基因表达的方法，识别自体诱导分子调节剂的方法，以及利用本发明中的化合物调节细菌中群体感知信号的方法。
• 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、—OCH3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，—OCH3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、—OCH3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。