1-Cyclopropyl-6-fluoro-8-methoxy-7-thiomorpholino-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | 114213-99-9

• 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: 1-Cyclopropyl-6-fluoro-8-methoxy-7-thiomorpholino-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-thiomorpholino-quinoline-3-carboxylic acid；1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-7-thiomorpholin-4-ylquinoline-3-carboxylic acid
• CAS: 114213-99-9
• 化学式: C₁₈H₁₉FN₂O₄S
• 分子量: 378.424
• InChiKey: NMSDGCWERWFJQZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  95.4
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-环丙基-6,7-二氟-1,4-二氢-8-甲氧基-4-氧代-3-喹啉羧酸 生成 1-Cyclopropyl-6-fluoro-8-methoxy-7-thiomorpholino-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  IVATA, MASAYUKI;KIMURA, FUMIO;FUDZIVARA, JOSIMI;KATSUBEH, TEHTSUDZI

  摘要：

  DOI：

文献信息

• Quinoline-3-carboxylic acid derivatives, their preparation and use
  申请人：Sankyo Company Limited

  公开号：EP0241206A2

  公开（公告）日：1987-10-14

  Compounds of formula (I): (in which R1 is alkoxy, R is alkyl, haloalkyl, alkylammo, cycloalkyl or optionally substituted phenyl, X is chlorine or fluorine and Y is selected from certain specific heterocycles) have excellent antibacterial activity. They may be prepared by introducing the group represented by Y into the corresponding compound in which Y is replaced by a halogen atom.

  式(I)化合物： (其中 R1 为烷氧基，R 为烷基、卤代烷基、烷基酰胺基、环烷基或任选取代的苯基，X 为氯或氟，Y 选自某些特定杂环）具有极佳的抗菌活性。它们可以通过将 Y 所代表的基团引入相应的化合物中来制备，其中 Y 被卤素原子取代。
• 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.
• IVATA, MASAYUKI;KIMURA, FUMIO;FUDZIVARA, JOSIMI;KATSUBEH, TEHTSUDZI
  作者：IVATA, MASAYUKI、KIMURA, FUMIO、FUDZIVARA, JOSIMI、KATSUBEH, TEHTSUDZI

  DOI：——

  日期：——
• US4997943A
  申请人：——

  公开号：US4997943A

  公开（公告）日：1991-03-05