2-(4-Bromophenyl)-N-(2-hydroxy-4-nitrophenyl)acetamide | 461031-55-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 2-(4-Bromophenyl)-N-(2-hydroxy-4-nitrophenyl)acetamide
• CAS: 461031-55-0
• 化学式: C₁₄H₁₁BrN₂O₄
• 分子量: 351.156
• InChiKey: POKGEWVGKSMPRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  95.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-Bromophenyl)-N-(2-hydroxy-4-nitrophenyl)acetamide 在 nickel dichloride 、 锌 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以44%的产率得到N-(4-amino-2-hydroxy-phenyl)-2-(4-bromo-phenyl)-acetamide
  参考文献：
  名称：

  Synthesis and biological evaluation of new N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamides and phenylacetamides as antimicrobial agents

  摘要：

  A new series of N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamide and phenylacetamide derivatives (la-In, 2a-2n) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Candida albicans, and their drug-resistant isolates. Microbiological results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms at MIC values between 500 and 1.95 mu g/ml. Benzamide derivative Id exhibited the greatest activity with MIC values of 1.95, 3.9, and 7.8 mu g/ml against drug-resistant B. subtilis, B. subtilis, and S. aureus, respectively. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.12.035
• 作为产物：
  描述：

  对溴苯乙酸 在 氯化亚砜 、 碳酸氢钠 作用下， 以 乙醚 、 苯 为溶剂， 反应 3.0h， 生成 2-(4-Bromophenyl)-N-(2-hydroxy-4-nitrophenyl)acetamide
  参考文献：
  名称：

  Synthesis and microbiological activity of some N-(2-hydroxy-4-substitutedphenyl)benzamides, phenylacetamides and furamides as the possible metabolites of antimicrobial active benzoxazoles

  摘要：

  The synthesis of some N-(2-hydroxy-4-substitutedphenyl)benzamides, phenylacetamides and furamides as the possible metabolites of benzoxazoles (II1-15) was performed in order to determine their in vitro antimicrobial activity against three Gram-positive bacteria, two Gram-negative bacteria and the fungus Candida albicans and their activities were compared with several control drugs. The compounds II11, II12, and II13 were found active at a MIC value of 12.5 mug/ml against the Gram-negative microorganism Pseudomonas aeruginosa. Most of the compounds show antibacterial activity at MIC a value of 25 mug/ml against the Gram-positive bacteria Staphylococcus aureus. For the antifungal activity against C. albicans, compound II10 was found more active than the other derivatives. The antimicrobial activity of some of these benzamides, phenylacetamides (II1 and II10) which are the possible metabolites of benzoxazoles, was also compared to their corresponding cyclic analogues III-IV. Compound II10 possesses two dilutions better antifungal activity than its cyclic analogue, benzoxazole IV, against C. albicans. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0014-827x(02)01226-0

文献信息

• Synthesis and microbiological activity of some N-(2-hydroxy-4-substitutedphenyl)benzamides, phenylacetamides and furamides as the possible metabolites of antimicrobial active benzoxazoles
  作者：Esin Akı-Şener、Kamuran K. Bingöl、Özlem Temiz-Arpacı、İsmail Yalçın、Nurten Altanlar

  DOI：10.1016/s0014-827x(02)01226-0

  日期：2002.5

  The synthesis of some N-(2-hydroxy-4-substitutedphenyl)benzamides, phenylacetamides and furamides as the possible metabolites of benzoxazoles (II1-15) was performed in order to determine their in vitro antimicrobial activity against three Gram-positive bacteria, two Gram-negative bacteria and the fungus Candida albicans and their activities were compared with several control drugs. The compounds II11, II12, and II13 were found active at a MIC value of 12.5 mug/ml against the Gram-negative microorganism Pseudomonas aeruginosa. Most of the compounds show antibacterial activity at MIC a value of 25 mug/ml against the Gram-positive bacteria Staphylococcus aureus. For the antifungal activity against C. albicans, compound II10 was found more active than the other derivatives. The antimicrobial activity of some of these benzamides, phenylacetamides (II1 and II10) which are the possible metabolites of benzoxazoles, was also compared to their corresponding cyclic analogues III-IV. Compound II10 possesses two dilutions better antifungal activity than its cyclic analogue, benzoxazole IV, against C. albicans. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.
• Synthesis and biological evaluation of new N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamides and phenylacetamides as antimicrobial agents
  作者：Tugba Ertan、Ilkay Yildiz、Semiha Ozkan、Ozlem Temiz-Arpaci、Fatma Kaynak、Ismail Yalcin、Esin Aki-Sener、Ufuk Abbasoglu

  DOI：10.1016/j.bmc.2006.12.035

  日期：2007.3

  A new series of N-(2-hydroxy-4(or 5)-nitro/aminophenyl)benzamide and phenylacetamide derivatives (la-In, 2a-2n) were synthesized and evaluated for antibacterial and antifungal activities against Staphylococcus aureus, Bacillus subtilis, Klebsiella pneumoniae, Pseudomonas aeruginosa, Escherichia coli, Candida albicans, and their drug-resistant isolates. Microbiological results indicated that the compounds possessed a broad spectrum of activity against the tested microorganisms at MIC values between 500 and 1.95 mu g/ml. Benzamide derivative Id exhibited the greatest activity with MIC values of 1.95, 3.9, and 7.8 mu g/ml against drug-resistant B. subtilis, B. subtilis, and S. aureus, respectively. (c) 2007 Elsevier Ltd. All rights reserved.