4-acetyl-[N'-(benzofuroxan-5-yl)methylene]benzohydrazide | 1160163-30-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-acetyl-[N'-(benzofuroxan-5-yl)methylene]benzohydrazide
• 英文别名: 4-acetyl-N-[(1-oxido-2,1,3-benzoxadiazol-1-ium-5-yl)methylideneamino]benzamide
• CAS: 1160163-30-3
• 化学式: C₁₆H₁₂N₄O₄
• 分子量: 324.296
• InChiKey: ICTATBHUOIZGJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.43
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  111.5
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  4-乙酰基苯甲酸酰肼 、 2,1,3-苯噁二唑-5-甲醛 1-氧化物 在 硫酸 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以87%的产率得到4-acetyl-[N'-(benzofuroxan-5-yl)methylene]benzohydrazide
  参考文献：
  名称：

  Design, synthesis, antimicrobial activity and molecular modeling studies of novel benzofuroxan derivatives against Staphylococcus aureus

  摘要：

  Molecular modi. cation is a quite promising strategy in the design and development of drug analogs with better bioavailability, higher intrinsic activity and less toxicity. In the search of new leads with potential antimicrobial activity, a new series of 14 4-substituted [N'-(benzofuroxan-5-yl) methylene] benzohydrazides, nifuroxazide derivatives, were synthesized and tested against standard and multidrug-resistant Staphylococcus aureus strains. The selection of the substituent groups was based on physicochemical properties, such as hydrophobicity and electronic effect. These properties were also evaluated through the lipophilic and electrostatic potential maps, respectively, considering the compounds with better biological pro. le. Twelve compounds exhibited similar bacteriostatic activity against standard and multidrug-resistant strains. The most active compound was the 4-CF3 substituted derivative, which presented a minimum inhibitory concentration (MIC) value of 14.6-13.1 mu g/mL, and a ClogP value of 1.87. The results highlight the benzofuroxan derivatives as potential leads for designing new future antimicrobial drug candidates. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.03.011