Ethyl 3-(diethylamino)-2-(2,4,5-trifluorobenzoyl)acrylate | 1364518-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Ethyl 3-(diethylamino)-2-(2,4,5-trifluorobenzoyl)acrylate
• 英文别名: ethyl 3-(diethylamino)-2-(2,4,5-trifluorobenzoyl)prop-2-enoate
• CAS: 1364518-39-7
• 化学式: C₁₆H₁₈F₃NO₃
• 分子量: 329.319
• InChiKey: GGNMPFWHBZGVHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ethyl 3-(diethylamino)-2-(2,4,5-trifluorobenzoyl)acrylate 在 三氟化硼乙醚 、 potassium carbonate 、 三乙胺 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 80.0h， 生成 7-(3-Carboxypiperazin-1-yl)-1-cyclopropyl-6-fluoro-4-oxo-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of gatifloxacin derivatives and their biological activities against Mycobacterium leprae and Mycobacterium tuberculosis

  摘要：

  Novel 3'-piperazinyl derivatives of the 8-hydrogeno and 8-methoxy-6-fluoro-1-cyclopropyl-4quinolone-3-carboxylic acid scaffolds were designed, synthesized and characterized by H-1, C-13 and F-19 NMR, and HRMS. The activity of these derivatives against pathogenic mycobacteria (M. leprae and M. tuberculosis), wild-type (WT) strains or strains harboring mutations implicated in quinolone resistance, were determined by measuring drug concentrations inhibiting cell growth (MIC) and/or DNA supercoiling by DNA gyrase (IC50), or inducing 25% DNA cleavage by DNA gyrase (CC25). Compound 4 (with a methoxy in R-8 and a secondary carbamate in R-3') and compound 5 (with a hydrogen in R-8 and an ethyl ester in R-3') displayed biological activities close to those of ofloxacin but inferior to those of gatifloxacin and moxifloxacin against M. tuberculosis and M. leprae WT DNA gyrases, whereas all of the compounds were less active in inhibiting M. tuberculosis growth and M. leprae mutant DNA gyrases. Since R-3' substitutions have been poorly investigated previously, our results may help to design new quinolone derivatives in the future. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.12.011
• 作为产物：
  描述：

  丙炔酸乙酯 在 三乙胺 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 29.0h， 生成 Ethyl 3-(diethylamino)-2-(2,4,5-trifluorobenzoyl)acrylate
  参考文献：
  名称：

  Synthesis of Novel Ciprofloxacin-Based Hybrid Molecules toward Potent Antimalarial Activity

  摘要：

  Antimalarial drug resistance is a serious obstacle in the persistent quest to eradicate malaria. There is a need for potent chemical agents that are able to act on drug-resistant Plasmodium falciparum populations at reasonable concentrations without any related toxicity to the host. By rational drug design, we envisaged to address this issue by generating a novel hybrid drug possessing two pharmacophores that can act on two unique and independent targets within the cell. We synthesized a new class of ciprofloxacinbased hybrid molecules, which have been integrated with acridine, quinolone, sulphonamide, and cinnamoyl pharmacophores (1-4). We realized a potent chloroquinolone-ciprofloxacin-based antimalarial hybrid (2, CQ-CFX) whose mechanism of action is unlike that of its parent molecules indicating a unique biological target. CQ-CFX is not only potent against CQ-resistant and susceptible strains of Plasmodium falciparum at low nanomolar concentrations (IC50 values are 63.17 +/- 1.2 nM and 25.52 +/- 4.45 nM, respectively) but is also not toxic to mammalian and bacterial systems up to 20 mu M and 1 mu M, respectively.

  DOI：

  10.1021/acsmedchemlett.0c00196