1-Chloro-6-methoxy-3,4-dihydronaphthalene-2-carbonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 1-Chloro-6-methoxy-3,4-dihydronaphthalene-2-carbonitrile
• 化学式: C₁₂H₁₀ClNO
• 分子量: 219.671
• InChiKey: ODWSKMQERAECFT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  33
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-Chloro-6-methoxy-3,4-dihydronaphthalene-2-carbonitrile 在 sodium sulphite nonahydrate 、 三乙胺 、 potassium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 7.5h， 生成 (S)-3-(3-(1-carboxy-2-phenylethyl)ureido)-7-methoxy-4,5-dihydronaphtho[1,2-b]thiophene-2-carboxylic acid
  参考文献：
  名称：

  Exploring the chemical space of ureidothiophene-2-carboxylic acids as inhibitors of the quorum sensing enzyme PqsD from Pseudomonas aeruginosa

  摘要：

  Pseudomonas aeruginosa employs a quorum sensing (QS) communication system that makes use of small diffusible molecules. Among other effects, the QS system coordinates the formation of biofilm which decisively contributes to difficulties in the therapy of Pseudomonas infections. The present work deals with the structure-activity exploration of ureidothiophene-2-carboxylic acids as inhibitors of PqsD, a key enzyme in the biosynthetic pathway of signal molecules in the Pseudomonas QS system. We describe an improvement of the inhibitory activity by successfully combining features from two different PqsD inhibitor classes. Furthermore the functional groups, which are responsible for the inhibitory potency, were identified. Moreover, the inability of the new inhibitors, to prevent signal molecule formation in whole cell assays, is discussed. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.007
• 作为产物：
  描述：

  N,N-二甲基甲酰胺 、 6-甲氧基-1-萘满酮 在 三氯氧磷 、 盐酸羟胺 作用下， 反应 1.25h， 生成 1-Chloro-6-methoxy-3,4-dihydronaphthalene-2-carbonitrile
  参考文献：
  名称：

  Exploring the chemical space of ureidothiophene-2-carboxylic acids as inhibitors of the quorum sensing enzyme PqsD from Pseudomonas aeruginosa

  摘要：

  Pseudomonas aeruginosa employs a quorum sensing (QS) communication system that makes use of small diffusible molecules. Among other effects, the QS system coordinates the formation of biofilm which decisively contributes to difficulties in the therapy of Pseudomonas infections. The present work deals with the structure-activity exploration of ureidothiophene-2-carboxylic acids as inhibitors of PqsD, a key enzyme in the biosynthetic pathway of signal molecules in the Pseudomonas QS system. We describe an improvement of the inhibitory activity by successfully combining features from two different PqsD inhibitor classes. Furthermore the functional groups, which are responsible for the inhibitory potency, were identified. Moreover, the inability of the new inhibitors, to prevent signal molecule formation in whole cell assays, is discussed. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.007