7-chloro-1-(4-fluorophenyl)-1,4-dihydro-6-nitro-4-oxoquinoline-3-carboxylic acid | 368839-20-7

• 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: 7-chloro-1-(4-fluorophenyl)-1,4-dihydro-6-nitro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 7-Chloro-1-(4-fluorophenyl)-6-nitro-4-oxoquinoline-3-carboxylic acid
• CAS: 368839-20-7
• 化学式: C₁₆H₈ClFN₂O₅
• 分子量: 362.701
• InChiKey: QFTVXRRNUNKJQR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-(1,4-苯并二烷-2-羰基)哌嗪 、 7-chloro-1-(4-fluorophenyl)-1,4-dihydro-6-nitro-4-oxoquinoline-3-carboxylic acid 以 二甲基亚砜 为溶剂， 以83%的产率得到7-(4-(2,3-dihydrobenzo[b][1,4]dioxin-2-ylcarbonyl)piperazin-1-yl)-1-(4-fluorophenyl)-1,4-dihydro-6-nitro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and antimycobacterial activities of novel 6-nitroquinolone-3-carboxylic acids

  摘要：

  Various 1-(substituted)-1,4-dihydro-6-nitro-4-oxo-7-(sub-secondary amino)-quinoline-3-carboxylic acids were synthesized from 2,4-dichlorobenzoic acid by six step synthesis. The compounds were evaluated for antimycobacterial in vitro and in vivo against Mycobacterium tuberculosis H37Rv (MTB), multi-drug resistant Mycobacterium tuberculosis (MDR-TB) and Mycobacterium smegmatis (MC2) and also tested for the ability to inhibit the supercoiling activity of DNA gyrase from M. smegmatis. Among the 48 synthesized compounds, 7-(4-((benzo[d][1,3]dioxol-5-yl)methyl)piperazin-1-yl)-1-cyclopropyl-1,4-dihydro-6-nitro-4-oxoquinotine-3-carboxylic acid (8c) was found to be the most active compound in vitro with MIC of 0.08 and 0.16 mu M against MTB and MDR-TB, respectively. In the in vivo animal model 8c decreased the bacterial load in lung and spleen tissues with 2.78 and 4.15-log 10 protections, respectively, at the dose of 50 mg/kg body weight. (C) 2008 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2008.02.031
• 作为产物：
  描述：

  ethyl ester of 3-dimethylamino-2-(5-nitro-2,4-dichlorobenzoyl)acrylic acid 在 盐酸 、 三乙胺 作用下， 以 乙醇 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.0h， 生成 7-chloro-1-(4-fluorophenyl)-1,4-dihydro-6-nitro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis of 1-substituted 6-nitro-4-oxo-1,4-dihydroquinoline-3-carboxylic acids as potential antimicrobial drugs

  摘要：

  DOI：

  10.1007/bf02464104