6-(3-ethylureido)-4-(4-methylpiperazin-1-yl)nicotinic acid | 1623159-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 6-(3-ethylureido)-4-(4-methylpiperazin-1-yl)nicotinic acid
• CAS: 1623159-93-2
• 化学式: C₁₄H₂₁N₅O₃
• 分子量: 307.352
• InChiKey: KUXCPILOKLEOKH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  97.8
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-氨基吡啶 、 6-(3-ethylureido)-4-(4-methylpiperazin-1-yl)nicotinic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.25h， 以41%的产率得到6-(3-ethylureido)-4-(4-methylpiperazin-1-yl)-N-(pyridin-3-yl)nicotinamide
  参考文献：
  名称：

  Pyridine-3-carboxamide-6-yl-ureas as novel inhibitors of bacterial DNA gyrase: Structure based design, synthesis, SAR and antimicrobial activity

  摘要：

  The development of antibacterial drugs based on novel chemotypes is essential to the future management of serious drug resistant infections. We herein report the design, synthesis and SAR of a novel series of N-ethylurea inhibitors based on a pyridine-3-carboxamide scaffold targeting the ATPase sub-unit of DNA gyrase. Consideration of structural aspects of the GyrB ATPase site has aided the development of this series resulting in derivatives that demonstrate excellent enzyme inhibitory activity coupled to potent Gram positive antibacterial efficacy. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.025
• 作为产物：
  描述：

  4,6-二羟基烟酸乙酯 在 potassium tert-butylate 、 palladium diacetate 、 三乙胺 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 、 sodium hydroxide 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 乙醇 、 水 为溶剂， 反应 11.5h， 生成 6-(3-ethylureido)-4-(4-methylpiperazin-1-yl)nicotinic acid
  参考文献：
  名称：

  Pyridine-3-carboxamide-6-yl-ureas as novel inhibitors of bacterial DNA gyrase: Structure based design, synthesis, SAR and antimicrobial activity

  摘要：

  The development of antibacterial drugs based on novel chemotypes is essential to the future management of serious drug resistant infections. We herein report the design, synthesis and SAR of a novel series of N-ethylurea inhibitors based on a pyridine-3-carboxamide scaffold targeting the ATPase sub-unit of DNA gyrase. Consideration of structural aspects of the GyrB ATPase site has aided the development of this series resulting in derivatives that demonstrate excellent enzyme inhibitory activity coupled to potent Gram positive antibacterial efficacy. (c) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.08.025