8-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-8-oxo-N-(5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)octanamide | 1402993-90-1

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 8-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-8-oxo-N-(5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)octanamide
• 英文别名: 8-(4-hydroxy-6-methyl-2-oxopyran-3-yl)-8-oxo-N-(5-oxo-4H-dithiolo[4,3-b]pyrrol-6-yl)octanamide
• CAS: 1402993-90-1
• 化学式: C₁₉H₂₀N₂O₆S₂
• 分子量: 436.51
• InChiKey: JNWWJFCESBXCBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  29
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  172
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  8-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-8-oxo-N-(5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)octanamide 在 potassium peroxymonosulfate 作用下， 以 水 、 丙酮 为溶剂， 反应 0.5h， 以40%的产率得到N-(2,2-dioxido-5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)-8-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-8-oxooctanamide
  参考文献：
  名称：

  Novel Hybrid-Type Antimicrobial Agents Targeting the Switch Region of Bacterial RNA Polymerase

  摘要：

  The bacterial RNA polymerase (RNAP) is an ideal target for the development of antimicrobial agents against drug-resistant bacteria. Especially, the switch region within RNAP has been considered as an attractive binding site for drug discovery. Here, we designed and synthesized a series of novel hybrid-type inhibitors of bacterial RNAP. The antimicrobial activities were evaluated using a paper disk diffusion assay, and selected derivatives were tested to determine their MIC values. The hybrid-type antimicrobial agent 29 showed inhibitory activity against Escherichia coli RNAP. The molecular docking study suggested that the RNAP switch region would be the binding site of 29.

  DOI：

  10.1021/ml300350p
• 作为产物：
  描述：

  辛二酸单甲酯 在 4-二甲氨基吡啶 、 草酰氯 、 三乙胺 、 lithium hydroxide 、 N,N'-二异丙基碳二亚胺 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 24.5h， 生成 8-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-8-oxo-N-(5-oxo-4,5-dihydro-[1,2]dithiolo[4,3-b]pyrrol-6-yl)octanamide
  参考文献：
  名称：

  Novel Hybrid-Type Antimicrobial Agents Targeting the Switch Region of Bacterial RNA Polymerase

  摘要：

  The bacterial RNA polymerase (RNAP) is an ideal target for the development of antimicrobial agents against drug-resistant bacteria. Especially, the switch region within RNAP has been considered as an attractive binding site for drug discovery. Here, we designed and synthesized a series of novel hybrid-type inhibitors of bacterial RNAP. The antimicrobial activities were evaluated using a paper disk diffusion assay, and selected derivatives were tested to determine their MIC values. The hybrid-type antimicrobial agent 29 showed inhibitory activity against Escherichia coli RNAP. The molecular docking study suggested that the RNAP switch region would be the binding site of 29.

  DOI：

  10.1021/ml300350p