1,4-dihydro-1-(4-fluorophenyl)-7-(1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydroisoquinolin-2(1H)-yl)-6-nitro-4-oxoquinoline-3-carboxylic acid | 1119087-78-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: 1,4-dihydro-1-(4-fluorophenyl)-7-(1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydroisoquinolin-2(1H)-yl)-6-nitro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 1-(4-fluorophenyl)-7-[1-[(4-methoxyphenyl)methyl]-3,4,5,6,7,8-hexahydro-1H-isoquinolin-2-yl]-6-nitro-4-oxo-quinoline-3-carboxylic acid；1-(4-fluorophenyl)-7-[1-[(4-methoxyphenyl)methyl]-3,4,5,6,7,8-hexahydro-1H-isoquinolin-2-yl]-6-nitro-4-oxoquinoline-3-carboxylic acid
• CAS: 1119087-78-3
• 化学式: C₃₃H₃₀FN₃O₆
• 分子量: 583.616
• InChiKey: ONVZWNVAUIFNBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  7-chloro-1-(4-fluorophenyl)-1,4-dihydro-6-nitro-4-oxoquinoline-3-carboxylic acid 、 1,2,3,4,5,6,7,8-八氢-1-[(4-甲氧基苯基)甲基]异喹啉 以 二甲基亚砜 为溶剂， 以76%的产率得到1,4-dihydro-1-(4-fluorophenyl)-7-(1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydroisoquinolin-2(1H)-yl)-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