4-bromo-[N'-(benzofuroxan-5-yl)methylene]benzohydrazide | 1160163-33-6

• 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: 4-bromo-[N'-(benzofuroxan-5-yl)methylene]benzohydrazide
• 英文别名: 4-bromo-N-[(1-oxido-2,1,3-benzoxadiazol-1-ium-5-yl)methylideneamino]benzamide
• CAS: 1160163-33-6
• 化学式: C₁₄H₉BrN₄O₃
• 分子量: 361.154
• InChiKey: RQDFVBHNXHXYRQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.99
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.43
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  4-溴苯甲酸 在 硫酸 、 一水合肼 、 溶剂黄146 作用下， 以 甲醇 、 水 为溶剂， 反应 5.17h， 生成 4-bromo-[N'-(benzofuroxan-5-yl)methylene]benzohydrazide
  参考文献：
  名称：

  Novel benzofuroxan derivatives against multidrug-resistant Staphylococcus aureus strains: Design using Topliss’ decision tree, synthesis and biological assay

  摘要：

  The aim of this study was the design of a set of benzofuroxan derivatives as antimicrobial agents exploring the physicochemical properties of the related substituents. Topliss' decision tree approach was applied to select the substituent groups. Hierarchical cluster analysis was also performed to emphasize natural clusters and patterns. The compounds were obtained using two synthetic approaches for reducing the synthetic steps as well as improving the yield. The minimal inhibitory concentration method was employed to evaluate the activity against multidrug-resistant Staphylococcus aureus strains. The most active compound was 4-nitro-3-(trifluoromethyl)[N'-(benzofuroxan-5-yl) methylene] benzhydrazide (MIC range 12.7-11.4 mu g/mL), pointing out that the antimicrobial activity was indeed influenced by the hydrophobic and electron-withdrawing property of the substituent groups 3-CF3 and 4-NO2, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.06.034

文献信息

• Design, synthesis, antimicrobial activity and molecular modeling studies of novel benzofuroxan derivatives against Staphylococcus aureus
  作者：Salomão Dória Jorge、Andrea Masunari、Carlota Oliveira Rangel-Yagui、Kerly Fernanda Mesquita Pasqualoto、Leoberto Costa Tavares

  DOI：10.1016/j.bmc.2009.03.011

  日期：2009.4

  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.
• Novel benzofuroxan derivatives against multidrug-resistant Staphylococcus aureus strains: Design using Topliss’ decision tree, synthesis and biological assay
  作者：Salomão Dória Jorge、Fanny Palace-Berl、Andrea Masunari、Cléber André Cechinel、Marina Ishii、Kerly Fernanda Mesquita Pasqualoto、Leoberto Costa Tavares

  DOI：10.1016/j.bmc.2011.06.034

  日期：2011.8

  The aim of this study was the design of a set of benzofuroxan derivatives as antimicrobial agents exploring the physicochemical properties of the related substituents. Topliss' decision tree approach was applied to select the substituent groups. Hierarchical cluster analysis was also performed to emphasize natural clusters and patterns. The compounds were obtained using two synthetic approaches for reducing the synthetic steps as well as improving the yield. The minimal inhibitory concentration method was employed to evaluate the activity against multidrug-resistant Staphylococcus aureus strains. The most active compound was 4-nitro-3-(trifluoromethyl)[N'-(benzofuroxan-5-yl) methylene] benzhydrazide (MIC range 12.7-11.4 mu g/mL), pointing out that the antimicrobial activity was indeed influenced by the hydrophobic and electron-withdrawing property of the substituent groups 3-CF3 and 4-NO2, respectively. (C) 2011 Elsevier Ltd. All rights reserved.