2-((2-((4-(3H-imidazo[4,5-b]pyridin-2-yl)phenyl)amino)-2-oxoethyl)thio)acetic acid

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-((2-((4-(3H-imidazo[4,5-b]pyridin-2-yl)phenyl)amino)-2-oxoethyl)thio)acetic acid
• 英文别名: 2-[2-[4-(1H-imidazo[4,5-b]pyridin-2-yl)anilino]-2-oxoethyl]sulfanylacetic acid
• 化学式: C₁₆H₁₄N₄O₃S
• 分子量: 342.378
• InChiKey: DZEOFTATUHWECW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对氨基苯甲酸 在 Eaton’s reagent 、 1-丙基磷酸酐 、 三乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 生成 2-((2-((4-(3H-imidazo[4,5-b]pyridin-2-yl)phenyl)amino)-2-oxoethyl)thio)acetic acid
  参考文献：
  名称：

  Structure-guided design and development of novel benzimidazole class of compounds targeting DNA gyraseB enzyme of Staphylococcus aureus

  摘要：

  The gyraseB subunit of Staphylococcus aureus DNA gyrase is a well-established and validated target though less explored for the development of novel antimicrobial agents. Starting from the available structural information in PDB (3TTZ), we identified a novel series of benzimidazole used as inhibitors of DNA gyraseB with low micromolar inhibitory activity by employing structure-based drug design strategy. Subsequently, this chemical class of DNA gyrase inhibitors was extensively investigated biologically through in vitro assays, biofilm inhibition assays, cytotoxicity, and in vivo studies. The binding affinity of the most potent inhibitor 10 was further ascertained biophysically through differential scanning fluorimetry. Further, the most potent analogues did not show any signs of cardiotoxicity in Zebra fish ether-a-go-go-related gene (zERG), a major breakthrough among the previously reported cardiotoxic gyraseB inhibitors. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.09.008

文献信息

• Structure-guided design and development of novel benzimidazole class of compounds targeting DNA gyraseB enzyme of Staphylococcus aureus
  作者：Renuka Janupally、Variam Ullas Jeankumar、Karyakulam Andrews Bobesh、Vijay Soni、Parthiban Brindha Devi、Venkat Koushik Pulla、Priyanka Suryadevara、Keerthana Sharma Chennubhotla、Pushkar Kulkarni、Perumal Yogeeswari、Dharmarajan Sriram

  DOI：10.1016/j.bmc.2014.09.008

  日期：2014.11

  The gyraseB subunit of Staphylococcus aureus DNA gyrase is a well-established and validated target though less explored for the development of novel antimicrobial agents. Starting from the available structural information in PDB (3TTZ), we identified a novel series of benzimidazole used as inhibitors of DNA gyraseB with low micromolar inhibitory activity by employing structure-based drug design strategy. Subsequently, this chemical class of DNA gyrase inhibitors was extensively investigated biologically through in vitro assays, biofilm inhibition assays, cytotoxicity, and in vivo studies. The binding affinity of the most potent inhibitor 10 was further ascertained biophysically through differential scanning fluorimetry. Further, the most potent analogues did not show any signs of cardiotoxicity in Zebra fish ether-a-go-go-related gene (zERG), a major breakthrough among the previously reported cardiotoxic gyraseB inhibitors. (C) 2014 Elsevier Ltd. All rights reserved.