1-cyclopropyl-6-fluoro-8-methoxy-7-{3-[N-methyl-N-(2-isatin-1-ylethyl)amino]piperidin-1-yl}-1,4-dihydro-4-oxoquinoline-3-carboxylic acid | 1236145-62-2

• 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-{3-[N-methyl-N-(2-isatin-1-ylethyl)amino]piperidin-1-yl}-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
• 英文别名: 1-Cyclopropyl-7-[3-[2-(2,3-dioxoindol-1-yl)ethyl-methylamino]piperidin-1-yl]-6-fluoro-8-methoxy-4-oxoquinoline-3-carboxylic acid
• CAS: 1236145-62-2
• 化学式: C₃₀H₃₁FN₄O₆
• 分子量: 562.598
• InChiKey: SBOSKNYPGKQOHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-cyclopropyl-6-fluoro-8-methoxy-7-{3-[N-methyl-N-(2-isatin-1-ylethyl)amino]piperidin-1-yl}-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 在 盐酸羟胺 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 以85%的产率得到1-cyclopropyl-6-fluoro-7-{3-[N-methyl-N-(2-(isatin-1-yl-β-hydroxyimino)ethyl)amino]piperidin-1-yl}-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and in vitro antimycobacterial activity of balofloxacin ethylene isatin derivatives

  摘要：

  A series of novel balofloxacin ethylene isatin derivatives with remarkable improvement in lipophilicity, as compared to the parent compound balofloxacin, were designed, synthesized and characterized by H-1 NMR, MS and HRMS. These derivatives were initially evaluated for their in vitro antimycobacterial activity against M. phlei CMCC 93201 and M. smegmatis CMCC 93202. Compounds 3b, 3d, 3g-j and 3l were chosen for further evaluation their in vitro activity against MTB 09710 clinical isolate, and then compounds 3h and 3g against MTB H37Rv ATCC 27294. All of the synthesized compounds were less active than balofloxacin against M. phlei CMCC 93201 and M. smegmatis CMCC 93202, but compounds 3g-j (MIC: <0.5-8 mu g/mL) were more potent than balofloxacin (MIC: 16 mu g/mL) against MTB 09710. In particular, compound 3h (MIC: 0.25- < 0.5 mu g/mL) was found to be comparable to moxifloxacin. and >= 32 fold more potent than balofloxacin against MTB 09710 and MTB H37Rv ATCC 27294. The results demonstrated that the lipophilicity of the tested compounds was not the sole parameter affecting antimycobacterial activity, as well as the potential and importance of developing new fluoroquinolone derivatives against mycobacterial infections. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.027
• 作为产物：
  描述：

  1-(2-溴乙基)-1H-吲哚-2,3-二酮 、 巴罗沙星 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 以59%的产率得到1-cyclopropyl-6-fluoro-8-methoxy-7-{3-[N-methyl-N-(2-isatin-1-ylethyl)amino]piperidin-1-yl}-1,4-dihydro-4-oxoquinoline-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and in vitro antimycobacterial activity of balofloxacin ethylene isatin derivatives

  摘要：

  A series of novel balofloxacin ethylene isatin derivatives with remarkable improvement in lipophilicity, as compared to the parent compound balofloxacin, were designed, synthesized and characterized by H-1 NMR, MS and HRMS. These derivatives were initially evaluated for their in vitro antimycobacterial activity against M. phlei CMCC 93201 and M. smegmatis CMCC 93202. Compounds 3b, 3d, 3g-j and 3l were chosen for further evaluation their in vitro activity against MTB 09710 clinical isolate, and then compounds 3h and 3g against MTB H37Rv ATCC 27294. All of the synthesized compounds were less active than balofloxacin against M. phlei CMCC 93201 and M. smegmatis CMCC 93202, but compounds 3g-j (MIC: <0.5-8 mu g/mL) were more potent than balofloxacin (MIC: 16 mu g/mL) against MTB 09710. In particular, compound 3h (MIC: 0.25- < 0.5 mu g/mL) was found to be comparable to moxifloxacin. and >= 32 fold more potent than balofloxacin against MTB 09710 and MTB H37Rv ATCC 27294. The results demonstrated that the lipophilicity of the tested compounds was not the sole parameter affecting antimycobacterial activity, as well as the potential and importance of developing new fluoroquinolone derivatives against mycobacterial infections. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.04.027

文献信息

• Synthesis and in vitro antimycobacterial activity of balofloxacin ethylene isatin derivatives
  作者：Lian-Shun Feng、Ming-Liang Liu、Bo Wang、Yun Chai、Xue-Qin Hao、Shuai Meng、Hui-Yuan Guo

  DOI：10.1016/j.ejmech.2010.04.027

  日期：2010.8

  A series of novel balofloxacin ethylene isatin derivatives with remarkable improvement in lipophilicity, as compared to the parent compound balofloxacin, were designed, synthesized and characterized by H-1 NMR, MS and HRMS. These derivatives were initially evaluated for their in vitro antimycobacterial activity against M. phlei CMCC 93201 and M. smegmatis CMCC 93202. Compounds 3b, 3d, 3g-j and 3l were chosen for further evaluation their in vitro activity against MTB 09710 clinical isolate, and then compounds 3h and 3g against MTB H37Rv ATCC 27294. All of the synthesized compounds were less active than balofloxacin against M. phlei CMCC 93201 and M. smegmatis CMCC 93202, but compounds 3g-j (MIC: <0.5-8 mu g/mL) were more potent than balofloxacin (MIC: 16 mu g/mL) against MTB 09710. In particular, compound 3h (MIC: 0.25- < 0.5 mu g/mL) was found to be comparable to moxifloxacin. and >= 32 fold more potent than balofloxacin against MTB 09710 and MTB H37Rv ATCC 27294. The results demonstrated that the lipophilicity of the tested compounds was not the sole parameter affecting antimycobacterial activity, as well as the potential and importance of developing new fluoroquinolone derivatives against mycobacterial infections. (C) 2010 Elsevier Masson SAS. All rights reserved.