8-propoxyquinoline-2-carboxylic acid | 1446747-07-4

• 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
• 英文名称: 8-propoxyquinoline-2-carboxylic acid
• 英文别名: 8-Propoxyquinoline-2-carboxylic acid
• CAS: 1446747-07-4
• 化学式: C₁₃H₁₃NO₃
• 分子量: 231.251
• InChiKey: NTZJFOQOARNHNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  59.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-propoxyquinoline-2-carboxylic acid 、 三乙二醇 在 硫酸 作用下， 以48.6%的产率得到(2-(2-(2-hydroxyethoxy)ethoxy)ethyl 8-propoxyquinoline-2-carboxylate)
  参考文献：
  名称：

  Colorimetric detection of Al(III) ions based on triethylene glycol appended 8-propyloxy quinoline ester

  摘要：

  A triethylene glycol modified quinoline ester (PQTEG) is synthesised, which acts as a colorimetric sensor for Al3+ ions with a detection limit of 8 x 10(-7) M in acetonitrile/water (95:5, v/v) solvent system. A visible, colour change from colourless to deep yellow was observed on binding of PQTEG with the metal ion. The unshared electron pairs of oxygen and nitrogen in triethylene glycol ester of quinoline provide a high binding affinity towards Al3+ and serves as the binding site. The metal binding was further confirmed from H-1 NMR studies and IR spectroscopic studies. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.05.134
• 作为产物：
  描述：

  2-甲基-8-丙氧基喹啉 在 selenium(IV) oxide 、 oxone 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 生成 8-propoxyquinoline-2-carboxylic acid
  参考文献：
  名称：

  Modified Fluoroquinolones as Antimicrobial Compounds Targeting Chlamydia trachomatis

  摘要：

  沙眼衣原体是最常见的性传播细菌感染和沙眼（一种眼部感染）的病因。未经治疗的感染会导致后遗症，如女性不育和异位妊娠以及失明。我们之前通过将金属螯合基团嫁接到氟喹诺酮环丙基环己酸上，增强了其对沙眼衣原体的抗菌活性。在本研究中，我们继续进行了这种药物改性，并获得了纳摩尔级别的活性分子(EC50)，可用于对抗这种病原体。这种活性增强促使我们评估了这类分子对其他致病菌的抗菌活性，如淋病奈瑟氏菌和ESKAPE菌群。结果表明，这种新型分子具有选择性地改善了对沙眼衣原体的活性，并展示了氟喹诺酮类抗菌药物的抗沙眼衣原体效果如何被增强。

  DOI：

  10.3390/ijms23126741

文献信息

• Colorimetric detection of Al(III) ions based on triethylene glycol appended 8-propyloxy quinoline ester
  作者：B. Jisha、M.R. Resmi、R.J. Maya、R. Luxmi Varma

  DOI：10.1016/j.tetlet.2013.05.134

  日期：2013.8

  A triethylene glycol modified quinoline ester (PQTEG) is synthesised, which acts as a colorimetric sensor for Al3+ ions with a detection limit of 8 x 10(-7) M in acetonitrile/water (95:5, v/v) solvent system. A visible, colour change from colourless to deep yellow was observed on binding of PQTEG with the metal ion. The unshared electron pairs of oxygen and nitrogen in triethylene glycol ester of quinoline provide a high binding affinity towards Al3+ and serves as the binding site. The metal binding was further confirmed from H-1 NMR studies and IR spectroscopic studies. (C) 2013 Elsevier Ltd. All rights reserved.
• Modified Fluoroquinolones as Antimicrobial Compounds Targeting Chlamydia trachomatis
  作者：Thi Huyen Vu、Erika Adhel、Katarina Vielfort、Ngûyet-Thanh Ha Duong、Guillaume Anquetin、Katy Jeannot、Philippe Verbeke、Sofia Hjalmar、Åsa Gylfe、Nawal Serradji

  DOI：10.3390/ijms23126741

  日期：——

  Chlamydia trachomatis causes the most common sexually transmitted bacterial infection and trachoma, an eye infection. Untreated infections can lead to sequelae, such as infertility and ectopic pregnancy in women and blindness. We previously enhanced the antichlamydial activity of the fluoroquinolone ciprofloxacin by grafting a metal chelating moiety onto it. In the present study, we pursued this pharmacomodulation and obtained nanomolar active molecules (EC50) against this pathogen. This gain in activity prompted us to evaluate the antibacterial activity of this family of molecules against other pathogenic bacteria, such as Neisseria gonorrhoeae and bacteria from the ESKAPE group. The results show that the novel molecules have selectively improved activity against C. trachomatis and demonstrate how the antichlamydial effect of fluoroquinolones can be enhanced.

  沙眼衣原体是最常见的性传播细菌感染和沙眼（一种眼部感染）的病因。未经治疗的感染会导致后遗症，如女性不育和异位妊娠以及失明。我们之前通过将金属螯合基团嫁接到氟喹诺酮环丙基环己酸上，增强了其对沙眼衣原体的抗菌活性。在本研究中，我们继续进行了这种药物改性，并获得了纳摩尔级别的活性分子(EC50)，可用于对抗这种病原体。这种活性增强促使我们评估了这类分子对其他致病菌的抗菌活性，如淋病奈瑟氏菌和ESKAPE菌群。结果表明，这种新型分子具有选择性地改善了对沙眼衣原体的活性，并展示了氟喹诺酮类抗菌药物的抗沙眼衣原体效果如何被增强。