ethyl 1-cyclopropyl-6-fluoro-8-nitro-4-oxo-7-phenyl-1,4-dihydroquinoline-3-carboxylate | 1247019-53-9

• 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: ethyl 1-cyclopropyl-6-fluoro-8-nitro-4-oxo-7-phenyl-1,4-dihydroquinoline-3-carboxylate
• CAS: 1247019-53-9
• 化学式: C₂₁H₁₇FN₂O₅
• 分子量: 396.375
• InChiKey: RSKCOKSVPLKLFY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.23
• 重原子数：
  29.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  91.44
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 1-cyclopropyl-6-fluoro-8-nitro-4-oxo-7-phenyl-1,4-dihydroquinoline-3-carboxylate 在 亚磷酸三乙酯 作用下， 反应 1.75h， 以36%的产率得到ethyl 1-cyclopropyl-6-fluoro-4-oxo-4,11-dihydro-1H-pyrido[2,3-a]carbazole-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of tetracyclic fluoroquinolones as antibacterial and anticancer agents

  摘要：

  A simple and efficient synthesis of 6-fluoro-4-oxopyrido[2,3-a] carbazole-3-carboxylic acids (13a-e) and a structurally related 6-fluoro-4-oxothieno[2 ',3 ': 4,5] pyrrolo[3,2-h] quinoline (13f) was achieved via Stille arylation of 7-chloro-6-fluoro-8-nitro-4-oxoquinoline-3-carboxylate and a subsequent microwave-assisted phosphite-mediated Cadogan reaction. The new compounds were tested for their in vitro antimicrobial and antiproliferative activity. The ability of 13a-f to inhibit the activity of DNA gyrase and topoisomerase IV was also investigated. The thieno isostere (13f) emerged as the most active antibacterial, while the 9-fluoro derivative (13e) was the most potent against multidrug-resistant staphylococci. Compounds 13a, 13c-f displayed growth inhibition against MCF-7 breast tumor and A549 non-small cell lung cancer cells coupled with an absence of cytotoxicity toward normal human-derm fibroblasts (HuDe). Compound 13e was the most active anticancer against MCF-7 cells, with greater potency than ellipticine (IC50 0.8 and 1.6 mu M, respectively). The most active compounds in this series show promise as dual acting anticancer and antibacterial chemotherapeutics. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.098
• 作为产物：
  描述：

  三甲基(苯基)锡 、 ethyl 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylate 在 palladium diacetate 、 cesium fluoride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以45%的产率得到ethyl 1-cyclopropyl-6-fluoro-8-nitro-4-oxo-7-phenyl-1,4-dihydroquinoline-3-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of tetracyclic fluoroquinolones as antibacterial and anticancer agents

  摘要：

  A simple and efficient synthesis of 6-fluoro-4-oxopyrido[2,3-a] carbazole-3-carboxylic acids (13a-e) and a structurally related 6-fluoro-4-oxothieno[2 ',3 ': 4,5] pyrrolo[3,2-h] quinoline (13f) was achieved via Stille arylation of 7-chloro-6-fluoro-8-nitro-4-oxoquinoline-3-carboxylate and a subsequent microwave-assisted phosphite-mediated Cadogan reaction. The new compounds were tested for their in vitro antimicrobial and antiproliferative activity. The ability of 13a-f to inhibit the activity of DNA gyrase and topoisomerase IV was also investigated. The thieno isostere (13f) emerged as the most active antibacterial, while the 9-fluoro derivative (13e) was the most potent against multidrug-resistant staphylococci. Compounds 13a, 13c-f displayed growth inhibition against MCF-7 breast tumor and A549 non-small cell lung cancer cells coupled with an absence of cytotoxicity toward normal human-derm fibroblasts (HuDe). Compound 13e was the most active anticancer against MCF-7 cells, with greater potency than ellipticine (IC50 0.8 and 1.6 mu M, respectively). The most active compounds in this series show promise as dual acting anticancer and antibacterial chemotherapeutics. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.098

文献信息

• A new efficient route to 7-aryl-6-fluoro-8-nitroquinolones as potent antibacterial agents
  作者：Salah A. Al-Trawneh、Mustafa M. El-Abadelah、Mohammad M. Al-Abadleh、Franca Zani、Matteo Incerti、Paola Vicini

  DOI：10.1016/j.ejmech.2014.08.065

  日期：2014.10

  A series of 7-aryl-6-fluoro-8-nitroquinolones (6a-e) were synthesized through a novel, simple and clean synthetic procedure, through a Suzuki-Miyaura reaction. The target compounds were evaluated in vitro for their antimicrobial properties against bacterial and fungal strains. All of them showed antibacterial activity higher than the activity of ciprofloxacin, both towards Gram positive Bacillus subtilis and Staphylococcus aureus, and Gram negative Haemophilus influenzae strains. Compound 6d, containing the trisubstituted 7-aryl moiety, emerged as the most active quinolone derivative with MIC values ranging from 0.00007 mu g/mL to 0.015 mu g/mL. (C) 2014 Elsevier Masson SAS. All rights reserved.