2-methyl-N′-((6-methyl-4-oxo-4H-chromen-3-yl)methylene)benzohydrazide | 1030534-25-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 2-methyl-N′-((6-methyl-4-oxo-4H-chromen-3-yl)methylene)benzohydrazide
• 英文别名: 2-methyl-N-[(6-methyl-4-oxochromen-3-yl)methylideneamino]benzamide
• CAS: 1030534-25-8
• 化学式: C₁₉H₁₆N₂O₃
• 分子量: 320.348
• InChiKey: ZGRMIECOICHCSY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  乙酸对甲酚酯 在 aluminum (III) chloride 、 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 12.0h， 生成 2-methyl-N′-((6-methyl-4-oxo-4H-chromen-3-yl)methylene)benzohydrazide
  参考文献：
  名称：

  Design and syntheses of novel N′-((4-oxo-4H-chromen-3-yl)methylene)benzohydrazide as inhibitors of cyanobacterial fructose-1,6-/sedoheptulose-1,7-bisphosphatase

  摘要：

  Cyanobacterial fructose-1,6-/sedoheptulose-1,7-bisphoshatase (Cy-FBP/SBPase) is an important target enzyme for finding inhibitors to solve harmful algal bloom (HAB). In this study, as potential inhibitors of Cy-FBP/SBPase, a series of novel chromone-connecting benzohydrazone compounds (Novel N'-((4-oxo-4H-chromen-3-yl) methylene) benzohydrazide) were designed and synthesized. Their inhibitory activities against Cy-FBP/SBPase were further examined in vitro. Some of these compounds, such as f6-f8, f11, f12 and f16, exhibit higher inhibitory activities (IC50 = 11.2-16.1 mu M), especially, the compound f7 was identified as the most potent inhibitor with IC50 value of 11.2 mu M. The probable binding-mode of compound f7 was further analyzed carefully by molecular docking methods. These results indicate that compound f7 could be used as a lead compound for further optimization and might have potential to be developed as a new algicide. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.04.003

文献信息

• Design and syntheses of novel N′-((4-oxo-4H-chromen-3-yl)methylene)benzohydrazide as inhibitors of cyanobacterial fructose-1,6-/sedoheptulose-1,7-bisphosphatase
  作者：Qi-Dong Tu、Ding Li、Yao Sun、Xin-Ya Han、Fan Yi、Yibamu Sha、Yan-Liang Ren、Ming-Wu Ding、Ling-Ling Feng、Jian Wan

  DOI：10.1016/j.bmc.2013.04.003

  日期：2013.6

  Cyanobacterial fructose-1,6-/sedoheptulose-1,7-bisphoshatase (Cy-FBP/SBPase) is an important target enzyme for finding inhibitors to solve harmful algal bloom (HAB). In this study, as potential inhibitors of Cy-FBP/SBPase, a series of novel chromone-connecting benzohydrazone compounds (Novel N'-((4-oxo-4H-chromen-3-yl) methylene) benzohydrazide) were designed and synthesized. Their inhibitory activities against Cy-FBP/SBPase were further examined in vitro. Some of these compounds, such as f6-f8, f11, f12 and f16, exhibit higher inhibitory activities (IC50 = 11.2-16.1 mu M), especially, the compound f7 was identified as the most potent inhibitor with IC50 value of 11.2 mu M. The probable binding-mode of compound f7 was further analyzed carefully by molecular docking methods. These results indicate that compound f7 could be used as a lead compound for further optimization and might have potential to be developed as a new algicide. (C) 2013 Elsevier Ltd. All rights reserved.