4-chloro-6-(3-ethylureido)nicotinic acid | 1623160-15-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-chloro-6-(3-ethylureido)nicotinic acid
• CAS: 1623160-15-5
• 化学式: C₉H₁₀ClN₃O₃
• 分子量: 243.65
• InChiKey: PYTLJBBDUJMBLX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  91.32
• 氢给体数：
  3.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-chloro-6-(3-ethylureido)nicotinic acid 在 吡啶 、 盐酸 、 1-丙基磷酸酐 作用下， 以 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 34.0h， 生成 6-(3-ethylureido)-4-(3-hydroxyphenylamino)-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：

  ethyl 4-chloro-6-(3-ethylureido)nicotinate 在 sodium hydroxide 作用下， 反应 16.0h， 以83%的产率得到4-chloro-6-(3-ethylureido)nicotinic acid
  参考文献：
  名称：

  New insights into the binding mode of pyridine-3-carboxamide inhibitors of E. coli DNA gyrase

  摘要：

  Previously we have reported on a series of pyridine-3-carboxamide inhibitors of DNA gyrase and DNA topoisomerase IV that were designed using a computational de novo design approach and which showed promising antibacterial properties. Herein we describe the synthesis of additional examples from this series aimed specifically at DNA gyrase, along with crystal structures confirming the predicted mode of binding and in vitro ADME data which describe the drug-likeness of these compounds.

  DOI：

  10.1016/j.bmc.2019.06.015