1-cylopropyl-7-(1,4-dioxa-8-aza-spiro[4,5]dec-8-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid | 848070-83-7

• 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: 1-cylopropyl-7-(1,4-dioxa-8-aza-spiro[4,5]dec-8-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-7-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-6-fluoro-8-methoxy-4-oxo-quinoline-3-carboxylic acid；1-cyclopropyl-7-(1,4-dioxa-8-azaspiro[4.5]decan-8-yl)-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
• CAS: 848070-83-7
• 化学式: C₂₁H₂₃FN₂O₆
• 分子量: 418.422
• InChiKey: UJALCXRMXIMOLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  88.5
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-哌啶酮缩乙二醇 、 1-环丙基-6,7-二氟-1,4-二氢-8-甲氧基-4-氧代-3-喹啉羧酸 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 0.03h， 以73%的产率得到1-cylopropyl-7-(1,4-dioxa-8-aza-spiro[4,5]dec-8-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and antimycobacterial evaluation of newer 1-cyclopropyl-1,4-dihydro-6-fluoro-7-(substituted secondary amino)-8-methoxy-5-(sub)-4-oxoquinoline-3-carboxylic acids

  摘要：

  Thirty-four newer 1-cyclopropyl-1,4-dihydro-6-fluoro-7-(substituted secondary amino)-8-methoxy-5-(sub)-4-oxoquinoline-3-carboxylic acids were synthesized from 1,2,3,4-tetrafluoro benzene and evaluated for in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MT13), multi-drug resistant M. tuberculosis (MDR-TB) and Mycobacterium sinegmatis (MC2) and also tested for the ability to inhibit the supercoiling activity of DNA gyrase. Among the synthesized compounds, 7-(1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydroisoquinolin-2(1H)-yl)-1-cyclopropy1-6-fluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylic acid (13n) was found to be the most active compound in vitro with MIC of 0.16 and 0.33 mu M against MT13 and MDR-TB, respectively. In the in vivo animal model 13n decreased the bacterial load in lung and spleen tissues with 2.54 and 2.92 - log 10 protections, respectively, at the dose of 50 mg/kg body weight. Compound 13n also inhibited the supercoiling activity of mycobacterial DNA gyrase with IC50 of 30.0 mu g/ml. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.050

文献信息

• Antibacterial agents
  申请人：Ellsworth Lee Edmund

  公开号：US20050096278A1

  公开（公告）日：2005-05-05

  Compounds of formula I, II, III, IV, IV, and VI and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula I as well as pharmaceutically acceptable compositions comprising compounds of formula I. Compounds of formula I as disclosed herein can be used in a variety of applications including use as antibacterial agents.

  本文披露了I、II、III、IV、V和VI式化合物的制备方法。还披露了制备公式I的生物活性化合物的方法，以及包括公式I化合物的药学上可接受的组合物的方法。本文所披露的公式I化合物可用于各种应用，包括用作抗菌剂。
• [EN] QUINOLONE ANTIBACTERIAL AGENTS<br/>[FR] AGENTS ANTIBACTERIENS A BASE DE QUINOLONE
  申请人：WARNER LAMBERT CO

  公开号：WO2005026145A2

  公开（公告）日：2005-03-24

  Compounds of formula (I, II, III, IV, V, and VI) and methods for their preparation are disclosed. Further disclosed are methods of making biologically active compounds of formula (I) as well as pharmaceutically acceptable compositions comprising compounds of formula (I). Compounds of formula (I) as disclosed herein can be used in a variety of applications including use as antibacterial agents.
• Synthesis and antimycobacterial evaluation of newer 1-cyclopropyl-1,4-dihydro-6-fluoro-7-(substituted secondary amino)-8-methoxy-5-(sub)-4-oxoquinoline-3-carboxylic acids
  作者：Palaniappan Senthilkumar、Murugesan Dinakaran、Debjani Banerjee、Ruth Vandana Devakaram、Perumal Yogeeswari、Arnab China、Valakunja Nagaraja、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2007.11.050

  日期：2008.3

  Thirty-four newer 1-cyclopropyl-1,4-dihydro-6-fluoro-7-(substituted secondary amino)-8-methoxy-5-(sub)-4-oxoquinoline-3-carboxylic acids were synthesized from 1,2,3,4-tetrafluoro benzene and evaluated for in vitro and in vivo antimycobacterial activities against Mycobacterium tuberculosis H37Rv (MT13), multi-drug resistant M. tuberculosis (MDR-TB) and Mycobacterium sinegmatis (MC2) and also tested for the ability to inhibit the supercoiling activity of DNA gyrase. Among the synthesized compounds, 7-(1-(4-methoxybenzyl)-3,4,5,6,7,8-hexahydroisoquinolin-2(1H)-yl)-1-cyclopropy1-6-fluoro-1,4-dihydro-8-methoxy-5-nitro-4-oxoquinoline-3-carboxylic acid (13n) was found to be the most active compound in vitro with MIC of 0.16 and 0.33 mu M against MT13 and MDR-TB, respectively. In the in vivo animal model 13n decreased the bacterial load in lung and spleen tissues with 2.54 and 2.92 - log 10 protections, respectively, at the dose of 50 mg/kg body weight. Compound 13n also inhibited the supercoiling activity of mycobacterial DNA gyrase with IC50 of 30.0 mu g/ml. (C) 2007 Elsevier Ltd. All rights reserved.