5-(5-bromo-2-hydroxybenzylidene)-2-thioxoimidazolidin-4-one

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-(5-bromo-2-hydroxybenzylidene)-2-thioxoimidazolidin-4-one
• 英文别名: 5-[(5-Bromo-2-hydroxyphenyl)methylidene]-2-sulfanylideneimidazolidin-4-one
• 化学式: C₁₀H₇BrN₂O₂S
• 分子量: 299.148
• InChiKey: SEOSGSHCDDALFE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  93.4
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-硫代乙内酰脲 、 5-溴水杨醛 在 哌啶 作用下， 以 乙醇 为溶剂， 以67%的产率得到5-(5-bromo-2-hydroxybenzylidene)-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  Structure–activity relationship studies of c-di-AMP synthase inhibitor, bromophenol-thiohydantoin

  摘要：

  C-di-AMP, a bacterial second messenger, regulates various processes in Gram-positive bacteria and mycobacteria. Small molecule inhibitors of c-di-AMP metabolic enzymes could affect bacterial growth and viability. A medium throughput screening identified bromophenol-thiohydantoin (BTH) as the first inhibitor of c-di-AMP synthase, DisA. Herein, we performed SAR studies of bromophenol-thiohydantoin to identify the salient features on BTH that are important for DisA inhibition. Seemingly minor substitution changes (e.g., aromatic bromo to chloro substitutions) resulted in dramatic changes in ligand potency. Bromophenol TH is specific for c-di-AMP synthase and did not inhibit RocR (c-di-GMP PDE), YybT (c-di-AMP PDE) or WspR (c-di-GMP synthase). (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.073

文献信息

• Structure–activity relationship studies of c-di-AMP synthase inhibitor, bromophenol-thiohydantoin
  作者：Yue Zheng、Jie Zhou、Stefan M. Cooper、Clement Opoku-Temeng、Amanda Moreira De Brito、Herman O. Sintim

  DOI：10.1016/j.tet.2015.10.073

  日期：2016.6

  C-di-AMP, a bacterial second messenger, regulates various processes in Gram-positive bacteria and mycobacteria. Small molecule inhibitors of c-di-AMP metabolic enzymes could affect bacterial growth and viability. A medium throughput screening identified bromophenol-thiohydantoin (BTH) as the first inhibitor of c-di-AMP synthase, DisA. Herein, we performed SAR studies of bromophenol-thiohydantoin to identify the salient features on BTH that are important for DisA inhibition. Seemingly minor substitution changes (e.g., aromatic bromo to chloro substitutions) resulted in dramatic changes in ligand potency. Bromophenol TH is specific for c-di-AMP synthase and did not inhibit RocR (c-di-GMP PDE), YybT (c-di-AMP PDE) or WspR (c-di-GMP synthase). (C) 2015 Elsevier Ltd. All rights reserved.