N-(6-(4-(1H-tetrazol-5-yl)benzyl)-3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-2-chloro-5-(2-(2,2,2-trifluoroacetamido)ethoxy)benzamide | 1565758-96-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(6-(4-(1H-tetrazol-5-yl)benzyl)-3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-2-chloro-5-(2-(2,2,2-trifluoroacetamido)ethoxy)benzamide
• CAS: 1565758-96-4
• 化学式: C₂₇H₂₂ClF₃N₈O₃S
• 分子量: 631.038
• InChiKey: AYPHRLXIKSGRHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.32
• 重原子数：
  43.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  148.92
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  N-(6-(4-(1H-tetrazol-5-yl)benzyl)-3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-2-chloro-5-(2-(2,2,2-trifluoroacetamido)ethoxy)benzamide 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以64%的产率得到N-(6-(4-(1H-tetrazol-5-yl)benzyl)-3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-5-(2-aminoethoxy)-2-chlorobenzamide
  参考文献：
  名称：

  Design, synthesis and evaluation of second generation MurF inhibitors based on a cyanothiophene scaffold

  摘要：

  MurF ligase is a crucial enzyme that catalyses the ultimate intracellular step of bacterial peptidoglycan biosynthesis, and thus represents an attractive target for antibacterial drug discovery. We designed, synthesized and evaluated a new series of cyanothiophene-based inhibitors of MurF enzymes from Streptococcus pneumoniae and Escherichia colt. The target compounds had increased polarity compared to the first generation of inhibitors, with demonstrated enzyme inhibitory potencies in the low micromolar range. Furthermore, the best inhibitors displayed promising antibacterial activities against selected Gram-positive and Gram-negative strains. These results represent an important step towards the development of new antibacterial agents targeting peptidoglycan biosynthesis. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.031
• 作为产物：
  描述：

  2-(3-carboxy-4-chlorophenoxy)ethanammonium trifluoroacetate 在 吡啶 、 草酰氯 、 三乙酰氧基硼氢化钠 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 N-(6-(4-(1H-tetrazol-5-yl)benzyl)-3-cyano-4,5,6,7-tetrahydrothieno[2,3-c]pyridin-2-yl)-2-chloro-5-(2-(2,2,2-trifluoroacetamido)ethoxy)benzamide
  参考文献：
  名称：

  Design, synthesis and evaluation of second generation MurF inhibitors based on a cyanothiophene scaffold

  摘要：

  MurF ligase is a crucial enzyme that catalyses the ultimate intracellular step of bacterial peptidoglycan biosynthesis, and thus represents an attractive target for antibacterial drug discovery. We designed, synthesized and evaluated a new series of cyanothiophene-based inhibitors of MurF enzymes from Streptococcus pneumoniae and Escherichia colt. The target compounds had increased polarity compared to the first generation of inhibitors, with demonstrated enzyme inhibitory potencies in the low micromolar range. Furthermore, the best inhibitors displayed promising antibacterial activities against selected Gram-positive and Gram-negative strains. These results represent an important step towards the development of new antibacterial agents targeting peptidoglycan biosynthesis. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.031