(Z)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)-N-(4-(3-(4-nitrophenyl)acryloyl)phenyl)acetamide | 1456929-09-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: (Z)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)-N-(4-(3-(4-nitrophenyl)acryloyl)phenyl)acetamide
• 英文别名: 2-[[5-(3-nitrophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl]-N-[4-[(Z)-3-(4-nitrophenyl)prop-2-enoyl]phenyl]acetamide
• CAS: 1456929-09-1
• 化学式: C₂₅H₁₇N₅O₇S
• 分子量: 531.505
• InChiKey: CUFLNSLBJNKYRO-MLPAPPSSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  202
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  5-(3-硝基苯基)-1,3,4-噁二唑-2-硫醇 在 氯化亚砜 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 8.0h， 生成 (Z)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)-N-(4-(3-(4-nitrophenyl)acryloyl)phenyl)acetamide
  参考文献：
  名称：

  Synthesis and antimicrobial evaluation of 1,3,4-oxadiazole-based chalcone derivatives

  摘要：

  A series of chalcones-bearing 1,3,4-oxadiazole derivatives was synthesized as novel bio-active antimicrobial agents against multidrug-resistant bacteria and fungi. The lead compounds (Z)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)-N-(4-(3-(aryl)acryloyl)phenyl)acetamides 5a-n were synthesized via acid-catalyzed aldol condensation (SOCl2) by reacting N-(4-acetylphenyl)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)acetamide (4) with differently substituted aldehydes. Compound (4) was obtained by reacting 5-(3-nitrophenyl)-1,3,4-oxadiazole-2-thiol (2) with N-(4-acetylphenyl)-2-chloroacetamide (3) in the presence of K2CO3. The intermediates (2) and (3) were synthesized simultaneously from 3-nitrobenzohydrazide (1) and 4-aminoacetophenone, respectively. The formation of intermediates and targeted compounds were confirmed for their structure by means of various spectral-analytical techniques like IR, H-1 NMR, C-13 NMR, elemental analysis, and mass spectra. Antimicrobial properties of all the synthesized compounds have been evaluated against broad panel of bacteria and fungi.

  DOI：

  10.1007/s00044-013-0791-1

文献信息

• Synthesis and antimicrobial evaluation of 1,3,4-oxadiazole-based chalcone derivatives
  作者：Deepkumar Joshi、Kalpesh Suryakant Parikh

  DOI：10.1007/s00044-013-0791-1

  日期：2014.4

  A series of chalcones-bearing 1,3,4-oxadiazole derivatives was synthesized as novel bio-active antimicrobial agents against multidrug-resistant bacteria and fungi. The lead compounds (Z)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)-N-(4-(3-(aryl)acryloyl)phenyl)acetamides 5a-n were synthesized via acid-catalyzed aldol condensation (SOCl2) by reacting N-(4-acetylphenyl)-2-(5-(3-nitrophenyl)-1,3,4-oxadiazol-2-ylthio)acetamide (4) with differently substituted aldehydes. Compound (4) was obtained by reacting 5-(3-nitrophenyl)-1,3,4-oxadiazole-2-thiol (2) with N-(4-acetylphenyl)-2-chloroacetamide (3) in the presence of K2CO3. The intermediates (2) and (3) were synthesized simultaneously from 3-nitrobenzohydrazide (1) and 4-aminoacetophenone, respectively. The formation of intermediates and targeted compounds were confirmed for their structure by means of various spectral-analytical techniques like IR, H-1 NMR, C-13 NMR, elemental analysis, and mass spectra. Antimicrobial properties of all the synthesized compounds have been evaluated against broad panel of bacteria and fungi.