1-(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)-3-(4-methoxyphenyl)thiourea | 1623153-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)-3-(4-methoxyphenyl)thiourea
• 英文别名: 1-[1-[2-(7-Methoxy-2-oxo-1,5-naphthyridin-1-yl)ethyl]piperidin-4-yl]-3-(4-methoxyphenyl)thiourea；1-[1-[2-(7-methoxy-2-oxo-1,5-naphthyridin-1-yl)ethyl]piperidin-4-yl]-3-(4-methoxyphenyl)thiourea
• CAS: 1623153-75-2
• 化学式: C₂₄H₂₉N₅O₃S
• 分子量: 467.592
• InChiKey: SSVMNUJXPQPUIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  tert-butyl (1-(2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)carbamate 在 盐酸 、 三乙胺 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 1-(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl)-3-(4-methoxyphenyl)thiourea
  参考文献：
  名称：

  Extending the N-linked aminopiperidine class to the mycobacterial gyrase domain: Pharmacophore mapping from known antibacterial leads

  摘要：

  Bacterial DNA gyrase is a well-established and clinically validated target to develop novel antibacterial. Our effort was designated to search for synthetically better compounds with possibility of hit to lead development. With this as objective, a series of 1-(2-(4-aminopiperidin-1-yl)ethyl)-1,5-naphthyridin-2(1H)-one derivatives were designed by molecular hybridization strategy and synthesized following nine step reaction to yield activity in low nanomolar range and commendable antibacterial activities. Compound 1-(4-fluorophenyl)-3-(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl) urea (35) emerged as the most promising inhibitor with an IC50 of 78 nM against Mycobacterium tuberculosis DNA gyrase enzyme, with MTB MIC of 0.62 mu M, and not cytotoxic at 50 mu M in eukaryotic cell line. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.018

文献信息

• Extending the N-linked aminopiperidine class to the mycobacterial gyrase domain: Pharmacophore mapping from known antibacterial leads
  作者：Karyakulam Andrews Bobesh、Janupally Renuka、Variam Ullas Jeankumar、Singh Kakan Shruti、Jonnalagadda Padma Sridevi、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.ejmech.2014.08.018

  日期：2014.10

  Bacterial DNA gyrase is a well-established and clinically validated target to develop novel antibacterial. Our effort was designated to search for synthetically better compounds with possibility of hit to lead development. With this as objective, a series of 1-(2-(4-aminopiperidin-1-yl)ethyl)-1,5-naphthyridin-2(1H)-one derivatives were designed by molecular hybridization strategy and synthesized following nine step reaction to yield activity in low nanomolar range and commendable antibacterial activities. Compound 1-(4-fluorophenyl)-3-(1-(2-(7-methoxy-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl)piperidin-4-yl) urea (35) emerged as the most promising inhibitor with an IC50 of 78 nM against Mycobacterium tuberculosis DNA gyrase enzyme, with MTB MIC of 0.62 mu M, and not cytotoxic at 50 mu M in eukaryotic cell line. (C) 2014 Elsevier Masson SAS. All rights reserved.